Descriptor: "POLE 3" - Searchworks@Jio Institute Digital Library Search Results

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53 results on '"POLE 3"'

1. Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives

Author: Xirui He, Huanhuan Song, Zefeng Zhao, Yongmin Zhang, Shaoping Wu, Xufei Chen, Tian Liu, Jing Xie, Xue Zhao, Xiaohui Zheng, Key Laboratory of Resource Biology and Biotechnology, Northwest University, Xi'an, Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)
Subjects: CNS agnets, POLE 3, Hematologic agents, Druggability, Antineoplastic Agents, Antiviral Agents, 01 natural sciences, Article, anti-inflammatory agents, 03 medical and health sciences, Drug Discovery, TMCA derivatives, [CHIM]Chemical Sciences, 030304 developmental biology, Pharmacology, 3,4,5-Trimethoxycinnamic acid, 0303 health sciences, Antitumor agents, Molecular Structure, 010405 organic chemistry, Drug discovery, Chemistry, Anti-Inflammatory Agents, Non-Steroidal, Organic Chemistry, Biological activity, General Medicine, Antimicrobial agents, Combinatorial chemistry, Anti-Bacterial Agents, 3. Good health, 0104 chemical sciences, GOBS, Cinnamates, Central Nervous System Agents, SAR
Abstract: TMCA (3,4,5-trimethoxycinnamic acid) ester and amide are privileged structural scaffolds in drug discovery which are widely distributed in natural products and consequently produced diverse therapeutically relevant pharmacological functions. Owing to the potential of TMCA ester and amide analogues as therapeutic agents, researches on chemical syntheses and modifications have been carried out to drug-like candidates with broad range of medicinal properties such as antitumor, antiviral, CNS (central nervous system) agents, antimicrobial, anti-inflammatory and hematologic agents for a long time. At the same time, SAR (structure-activity relationship) studies have draw greater attention among medicinal chemists, and many of the lead compounds were derived for various disease targets. However, there is an urgent need for the medicinal chemists to further exploit the precursor in developing chemical entities with promising bioactivity and druggability. This review concisely summarizes the synthesis and biological activity for TMCA ester and amide analogues. It also comprehensively reveals the relationship of significant biological activities along with SAR studies., Graphical abstract Image 1, Highlights • 3,4,5-Trimethoxycinnamic acid (TMCA) derivatives show applications in different pathophysiological conditions due to its privileged structural scaffolds. • Natural derived TMCA analogues and chemically modified TMCA ester and amide analogues and their bioactivities are focused in this review. Additionally, it also comprehensively summarized the relationship of significant biological activities along with SAR studies of synthetic TMCA derivatives.
Published: 2019

2. Total Synthesis of the Proposed Structure of Penasulfate A: <scp>l</scp>-Arabinose as a Source of Chirality

Author: Fei Ding, Yangguang Gao, Qiang Zhang, Zhou Cao, Yongmin Zhang, Rui Guo, Qingliang You, Jingjing Bi, Institute for Interdisciplinary Research, Jianghan University, Wuhan, PR China, Jianghan University [Whuan], Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Henan Normal University, Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: POLE 3, Longest linear sequence, Stereochemistry, Pharmaceutical Science, chemistry.chemical_element, Stereoisomerism, Alkenes, 01 natural sciences, Catalysis, Coupling reaction, Analytical Chemistry, Drug Discovery, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS, Pharmacology, Olefin fiber, Molecular Structure, 010405 organic chemistry, Chemistry, Fatty Acids, Organic Chemistry, Total synthesis, Arabinose, Copper, 0104 chemical sciences, GOBS, 010404 medicinal & biomolecular chemistry, Complementary and alternative medicine, Pipecolic Acids, Yield (chemistry), Molecular Medicine, Chirality (chemistry)
Abstract: The total synthesis of putative penasulfate A was effectively achieved by a convergent strategy with a longest linear sequence of 14 steps and overall yield of 8.6%. The highlights of our strategy involved an E-selective olefin cross-metathesis, Suzuki cross-coupling, and a copper(I)-catalyzed coupling reaction.
Published: 2019

3. Synthesis and structure-activity relationship studies of water-soluble β-cyclodextrin-glycyrrhetinic acid conjugates as potential anti-influenza virus agents

Author: Yongmin Zhang, Demin Zhou, Xiaojuan Yu, Sulong Xiao, Hongwei Jin, Lihe Zhang, Man Li, Shuobin Liang, State Key Laboratory of Natural and Biomimetic Drugs, Peking University [Beijing], Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: POLE 3, Stereochemistry, Chemistry Techniques, Synthetic, Antiviral Agents, 01 natural sciences, Article, Madin Darby Canine Kidney Cells, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, Dogs, Influenza A Virus, H1N1 Subtype, Drug Discovery, Glycyrrhetinic acid, Click reaction, [CHIM]Chemical Sciences, Cyclodextrin, Animals, Moiety, Structure–activity relationship, Cytotoxicity, 030304 developmental biology, Pharmacology, chemistry.chemical_classification, 0303 health sciences, Inhibitors, 010405 organic chemistry, Chemistry, beta-Cyclodextrins, Organic Chemistry, Water, General Medicine, 3. Good health, 0104 chemical sciences, GOBS, Solubility, Click chemistry, Influenza virus, Linker, Lead compound, Conjugate
Abstract: Glycyrrhetinic acid (GA) is a major constituent of the herb Glycyrrhiza glabra, and many of its derivatives demonstrate a broad spectrum of antiviral activities. In the current study, 18 water-soluble β-cyclodextrin (CD)-GA conjugates, in which GA was covalently coupled to the primary face of β-CD using 1,2,3-triazole moiety along with varying lengths of linker, were synthesized via copper-catalyzed azide-alkyl cycloaddition reaction. Benefited from the attached β-CD moiety, all these conjugates showed lower hydrophobicity (AlogP) compared with their parent compound GA. With the exception of per-O-methylated β-CD-GA conjugate (35), all other conjugates showed no significant cytotoxicity to MDCK cells, and these conjugates were then screened against A/WSN/33 (H1N1) virus using the cytopathic effect assay. The preliminary results indicated that six conjugates showed promising antiviral activity, and the C-3 and C-30 of GA could tolerate some modifications. Our findings suggested that GA could be used as a lead compound for the development of potential anti-influenza virus agents., Graphical abstract Image 1, Highlights • Triterpene natural products are proposed as a new class of compounds for blocking influenza virus entry. • A total of 18 β-cyclodextrin-glycyrrhetinic acid conjugates were designed and synthesized via click chemistry. • The structure-activity relationship of their anti-influenza A/WSN/33 (H1N1) viruses was summarized.
Published: 2019

4. Synthesis, structure activity relationship and in vitro anti-influenza virus activity of novel polyphenol-pentacyclic triterpene conjugates

Author: Haiwei Li, Shouxin Wang, Lihe Zhang, Renyang Xu, Man Li, Yongmin Zhang, Sulong Xiao, Demin Zhou, Central South University, Chinese Academy of Sciences [Changchun Branch] (CAS), State Key Laboratory of Natural and Biomimetic Drugs, Peking University [Beijing], Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: Models, Molecular, Oseltamivir, POLE 3, Hemagglutinin (influenza), Antiviral Agents, 01 natural sciences, Virus, Madin Darby Canine Kidney Cells, Inhibitory Concentration 50, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, Dogs, Influenza A Virus, H1N1 Subtype, Orthomyxoviridae Infections, Viral envelope, Drug Discovery, medicine, Animals, Humans, [CHIM]Chemical Sciences, Structure–activity relationship, 030304 developmental biology, Pharmacology, 0303 health sciences, Hemagglutination assay, biology, 010405 organic chemistry, Chemistry, Hemagglutination, Organic Chemistry, Polyphenols, General Medicine, Virus Internalization, In vitro, 3. Good health, 0104 chemical sciences, Entry inhibitor, GOBS, Biochemistry, biology.protein, Pentacyclic Triterpenes, medicine.drug
Abstract: It is urgently necessary to develop more effective anti-influenza agents due to the continuous emergence of drug-resistant strains of influenza virus. Our earlier studies have identified that certain pentacyclic triterpene derivatives are effective inhibitors of influenza virus infection. In the present study, a series of C-28 modified pentacyclic triterpene derivatives via conjugation with a series of polyphenols were synthesized, and their antiviral activities against influenza A/WSN/33 (H1N1) virus in MDCK (Madin-Darby canine kidney) cells were evaluated. Four compounds 23m, 23o, 23q and 23s displayed robust anti-influenza potency with averaged IC50 values at the low-micromole level, surpassing the potency of oseltamivir. In addition, the in vitro cytotoxic activity of the four conjugates against MDCK cells showed no toxicity at 100 μM. Further mechanism studies of compound 23s, one of the best representative conjugates with IC50 value of 5.80 μM and a selective index (SI) value of over 17.2, by hemagglutination inhibition (HI), surface plasmon resonance and molecular modeling indicated that this conjugate bound tightly to the viral envelope hemagglutinin (KD = 15.6 μM), thus blocking the invasion of influenza viruses into host cells.
Published: 2019

5. Total synthesis of wikstrol A and wikstrol B

Author: Ming Li, Xia Zhao, Zhi Gong, Yongmin Zhang, Sun Yuanyuan, Peng Yu, Yuna Huang, Qijun Wei, Kui Lu, Tianjin University of Science and Technology (TUST), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: POLE 3, 010405 organic chemistry, Stereochemistry, Organic Chemistry, Total synthesis, Sonogashira coupling, Halogenation, Regioselectivity, 01 natural sciences, Biochemistry, 0104 chemical sciences, GOBS, 010404 medicinal & biomolecular chemistry, chemistry.chemical_compound, Aldol reaction, chemistry, [CHIM]Chemical Sciences, Oxidative coupling of methane, Physical and Theoretical Chemistry, Sharpless asymmetric dihydroxylation, Derivative (chemistry)
Abstract: The first total synthesis of wikstrol A and wikstrol B was achieved via Sharpless asymmetric dihydroxylation, Sonogashira and rhodium-catalyzed oxidative coupling as key steps. , The first total synthesis of wikstrol A and wikstrol B was achieved by employing aldol reaction, Sharpless asymmetric dihydroxylation, regioselective iodination, Sonogashira coupling, and rhodium-catalyzed oxidative coupling as key steps. The structure of the key intermediate for wikstrol A was confirmed via its derivative by single-crystal X-ray analysis.
Published: 2019

6. β-Cyclodextrin-NHC-Gold(I) Complex (β-ICyD)AuCl: A Chiral Nanoreactor for Enantioselective and Substrate-Selective Alkoxycyclization Reactions

Author: Denis Lesage, Sylvain Roland, Kajetan Bijouard, Jorge Meijide Suárez, Matthieu Sollogoub, Etienne Derat, Louis Fensterbank, Olivia Bistri-Aslanoff, Nicolas Vanthuyne, Natalia del Rio, Pinglu Zhang, Mehdi Koohgard, Coralie Tugny, Virginie Mouriès-Mansuy, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Chimie Structurale Organique et Biologique (CSOB), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Méthodes et Application en Chimie Organique (MACO), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and ANR-17-CE07-0036,CaSPair,Paires de Lewis séparées par une cavité, une nouvelle plateforme pour la conversion catalytique de petites molécules(2017)
Subjects: POLE 3, POLE 1, Nanoreactor, cavity, 010402 general chemistry, 01 natural sciences, Catalysis, [CHIM]Chemical Sciences, Metrics & More Article Recommendations gold(I), chemistry.chemical_classification, cyclodextrins, Cyclodextrin, 010405 organic chemistry, Ligand, Chemistry, Enantioselective synthesis, selectivity, Substrate (chemistry), asymmetric catalysis, General Chemistry, Combinatorial chemistry, 0104 chemical sciences, 3. Good health, GOBS, Selectivity, MACO, CSOB
Abstract: International audience; NHC-capped β-cyclodextrin (β-ICyD) was used as a ligand for gold-catalyzed alkoxycyclization reactions. The cavity was found to be responsible for a triple selectivity: (i) the asymmetric shape of the cavity of β-ICyD induced highly stereoselective cyclizations, (ii) the shape of the interior favored the formation of a six-membered ring in the absence of a nucleophile, and finally, (iii) the encapsulation of the metal inside the cavity disfavored the addition of sterically hindered alcohols. Highly enantioselective and substrate-selective alkoxycyclizations of enynes are therefore promoted by the cavity-based molecular reactor (β-ICyD)AuCl.
Published: 2020

7. Tutorial: Ion Activation in Tandem Mass Spectrometry Using Ultra-High Resolition Spectroscopy

Author: Bayat, Parisa, Lesage, Denis, Cole, Richard B., Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Chimie Structurale Organique et Biologique (CSOB), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769)
Subjects: POLE 3, [CHIM]Chemical Sciences, CSOB
Published: 2020

8. Biomedical Applications of Glycoconjugates

Author: Yongmin Zhang, Fei Ding, Institute for Interdisciplinary Research, Jianghan University, Wuhan, PR China, Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: 0301 basic medicine, Glycan, POLE 3, Glycoconjugate, Cancer therapy, 02 engineering and technology, Computational biology, 03 medical and health sciences, Drug Delivery Systems, Drug Discovery, [CHIM]Chemical Sciences, Humans, Glycoproteins, Pharmacology, chemistry.chemical_classification, Binding Sites, biology, Chemistry, Glycopeptides, General Medicine, 021001 nanoscience & nanotechnology, 3. Good health, GOBS, 030104 developmental biology, Drug delivery, biology.protein, Glycolipids, 0210 nano-technology, Glycoconjugates
Abstract: Glycans expressed on the forefront surface of cells participate in many key biological processes via forming various glycoconjugates. The recognition of complex glycoconjugates as mediators of important biological processes has stimulated investigation into their therapeutic potential. As the increasing accessibility of glycoconjugates, it has been widely applied in the field of drug delivery. This review particularly refers to the constitutive glycoconjugates of receptor-mediated binding of glycoprotein, glycolipids and glycopeptides for cell-selective drug delivery, in order to broaden the future therapeutic scope of drug delivery system and effective cancer therapy.
Published: 2018

9. Structural analysis and antioxidant activity of the glycoside from Imperial Chrysanthemum

Author: Zhen-Yuan Zhu, Yun-Tang, Yong-Min Zhang, Li-Chao Pan, Tianjin University of Science and Technology (TUST), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: 0301 basic medicine, Antioxidant, POLE 3, Chrysanthemum, Surface Properties, medicine.medical_treatment, Clinical Biochemistry, Pharmaceutical Science, 02 engineering and technology, Biochemistry, High-performance liquid chromatography, Antioxidants, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, Column chromatography, Drug Discovery, medicine, [CHIM]Chemical Sciences, Monosaccharide, Thermal stability, Glycosides, Particle Size, Molecular Biology, chemistry.chemical_classification, Chromatography, Dose-Response Relationship, Drug, Molecular Structure, Silica gel, Organic Chemistry, Glycoside, Nuclear magnetic resonance spectroscopy, 021001 nanoscience & nanotechnology, GOBS, 030104 developmental biology, chemistry, Molecular Medicine, 0210 nano-technology
Abstract: A new glycoside, named as CG-1, was separated from Imperial Chrysanthemum with silica gel column chromatography. The purity was detected by TLC and HPLC. The crystal shape of CG-1 was consisting of a quadrangular and two rectangular pyramids. The analysis of DSC and TGA showed that the melting point of CG-1 crystal was 150.22 °C and had good thermal stability. The monosaccharide conformation analysis showed that it was d-glucose. The structure characteristics were compared by FT-IR, NMR spectroscopy and LC-MS and a molecular structure has been deduced which consistent with spectroscopic results. In vitro antioxidant results suggested that the glycoside extracted from Imperial Chrysanthemum could be effectively employed as natural antioxidant in health or functional food. This work is of significance to keep the antioxidant activity in the processing and application of Imperial Chrysanthemum.
Published: 2018

10. A chemically-responsive bis-acridinium receptor

Author: Lise-Marie Chamoreau, A. Gosset, Z. Xu, H.-P. Jacquot de Rouville, C. Perruchot, Valérie Heitz, François Maurel, S. Nowak, Guillaume Vives, Interfaces, Traitements, Organisation et Dynamique des Systèmes (ITODYS (UMR_7086)), Université Paris Diderot - Paris 7 (UPD7)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie de Strasbourg, and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
Subjects: POLE 3, 010405 organic chemistry, Chemistry, Solid-state, Triphenylene, macromolecular substances, General Chemistry, Methoxide, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, GOBS, chemistry.chemical_compound, Materials Chemistry, [CHIM]Chemical Sciences, Receptor
Abstract: A dicationic receptor based on two acridinium moieties linked by a triphenylene spacer was studied in solution and in the solid state. Recognition moieties, namely acridiniums, were exploited to evidence a host–guest response of the receptor with electron rich guests. Upon addition of methoxide anions, the formation of the bis-acridane form of the receptor was observed. The chemical responsiveness of the receptor to these anions inhibits its recognition properties towards π-donor guests. In addition, the reversibility of the chemical response was demonstrated under acidic conditions.
Published: 2018

11. Protective effect of gentiopicroside from Gentiana macrophylla Pall. in ethanol-induced gastric mucosal injury in mice

Author: Yang Yang, Bing Yin, Wenji Sun, Boling Qiao, Le Lv, Ziye Wang, Yongmin Zhang, Jiao He, Xin Wen, Li Zhang, Ziyang Chen, Minfeng Fang, Tianjin University of Science and Technology (TUST), Key Laboratory of Resource Biology and Biotechnology, Northwest University, Xi'an, Northwest University [Xi'an], Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Male, 0301 basic medicine, Necrosis, POLE 3, Iridoid Glucosides, Pharmacology, Mice, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, Epidermal growth factor, Oral administration, medicine, Gastric mucosa, Animals, [CHIM]Chemical Sciences, Gentiana, Stomach Ulcer, Ethanol, biology, business.industry, Stomach, Malondialdehyde, biology.organism_classification, 3. Good health, Gentiana macrophylla, Vascular endothelial growth factor, GOBS, 030104 developmental biology, medicine.anatomical_structure, chemistry, Gastric Mucosa, 030220 oncology & carcinogenesis, medicine.symptom, business
Abstract: Gentiopicroside isolated from gentiana macrophylla Pall. belongs to iridoid glycosides. This study aimed to evaluate the protective effect of gentiopicroside against ethanol-induced gastric mucosal injury in mice. Mice were proactively administrated with gentiopicroside by intragastric administration once a day for 3 consecutive days. On the 3rd day, gastric ulcer in mice was induced with 70% ethanol after the last intragastric administration. The stomach tissues were submitted for evaluation of the severity of gastric mucosal alterations. Gentiopicroside administrated orally ameliorated the severity of gastric mucosal alterations. Oral administration of gentiopicroside significantly increased heat shock protein-70 and glutathione levels and superoxide dismutase activity, normalized epidermal growth factor and vascular endothelial growth factor levels, and decreased the levels of tumour necrosis factor-α, interleukin-6 and malondialdehyde, and myeloperoxidase activity in gastric tissue. These findings demonstrated that gentiopicroside has protective effect against ethanol-induced gastric mucosal injury in mice through the improvements of antioxidative and anti-inflammatory effects, as well as up-regulation of heat shock protein-70 level and normalization of epidermal growth factor and vascular endothelial growth factor levels. The results presented in this study provide some evidence for the development of a novel antigastric ulcer agent.
Published: 2017

12. Large-Ring Cyclodextrins as Chiral Selectors for Enantiomeric Pharmaceuticals

Author: Franziska D. Zitzmann, Detlev Belder, Sebastian Thurmann, Yannick Krauke, Christian Sonnendecker, Andrea A. Robitzki, Wolfgang Zimmermann, Cédric Przybylski, Kate Monks, Nicole Heinke, Leipzig University, Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Universität Leipzig [Leipzig], and Institut für Analytische Chemie
Subjects: Spectrometry, Mass, Electrospray Ionization, POLE 3, Cell Survival, Complex formation, Supramolecular chemistry, Bacillus, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Catalysis, Cell Line, Bacterial Proteins, [CHIM]Chemical Sciences, Humans, Fragmentation (cell biology), Fluvastatin, chemistry.chemical_classification, Cyclodextrins, Chromatography, 010405 organic chemistry, 010401 analytical chemistry, Electrophoresis, Capillary, Stereoisomerism, General Chemistry, Reversed-phase chromatography, General Medicine, 3. Good health, 0104 chemical sciences, Mefloquine, Electrophoresis, Enzyme, chemistry, Pharmaceutical Preparations, Glucosyltransferases, Enantiomer, CSOB
Abstract: Large-ring cyclodextrins (CD) are cyclic glucans composed of 9 or more α-1,4-linked glucose units. They are minor side products of bacterial glucanotransferases (CGTases, EC 2.4.1.19) and have previously been available only in very small amounts for studies of their properties in supramolecular complex formation reactions. We engineered a CGTase to synthesize mainly large-ring CD facilitating their preparation in larger amounts. By reversed phase chromatography, we obtained single CD samples composed of 10 to 12 glucose units (CD10, CD11, and CD12) with a purity of >90 %. Their identity was confirmed by high resolution mass spectrometry and fragmentation analysis. We demonstrated the non-toxicity of CD10-CD12 for human cell lines by a cell proliferation assay and impedimetric monitoring. We then showed that CD10 and CD11 are efficient chiral selectors for the capillary electrophoretic separation of the enantiomeric pharmaceuticals fluvastatin, mefloquine, carvedilol, and primaquine.
Published: 2019

13. The Uncommon Strong Inhibition of α-Glucosidase by Multivalent Glycoclusters Based on Cyclodextrin Scaffolds

Author: Abed Bil, Takwa Khanchouche, Véronique Bonnet, José Kovensky, Cédric Przybylski, Urjwan Alali, David Mathiron, Rémi Beaulieu, Mohammed Benazza, Aurélie Vallin, Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Plateforme Analytique (PFA), Université de Picardie Jules Verne (UPJV), Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)
Subjects: POLE 3, medicine.medical_treatment, Saccharomyces cerevisiae, 010402 general chemistry, 01 natural sciences, Biochemistry, medicine, Monosaccharide, [CHIM]Chemical Sciences, Glycoside Hydrolase Inhibitors, Physical and Theoretical Chemistry, IC50, Acarbose, chemistry.chemical_classification, Cyclodextrins, Molecular Structure, Cyclodextrin, 010405 organic chemistry, Chemistry, Insulin, Organic Chemistry, Glycoside, alpha-Glucosidases, Combinatorial chemistry, 3. Good health, 0104 chemical sciences, Propargyl, Click chemistry, Click Chemistry, Glycoconjugates, CSOB, medicine.drug
Abstract: New inhibitors of α-glucosidase based on perglycosylated cyclodextrins were synthesized via click-chemistry and compared to acarbose. , The homeostasis disruption of d -glucose causes diabetes, a dramatic chronic disease worldwide. Type 1 diabetes is a successfully treatable form, where blood d -glucose is regulated by insulin treatment. In contrast type 2 diabetes, the non-insulin dependent kind, is problematic. The control of the d -glucose blood level via intestinal α- d -glucosidase inactivation can be achieved by using competitive inhibitors, such as iminosugars ( e.g. acarbose) or sulfonium sugar derivatives ( e.g. salacinol). Recently, an unprecedented result showed that multivalent diamond nanoparticles grafted with unmodified sugars displayed α-glucosidase inhibition at low micromolar concentrations. Herein we describe the synthesis of multivalent glycoclusters using cyclodextrins (CDs) as scaffolds and an assessment of their role as inhibitors of α- d -glucosidase. The glycoclusters were efficiently obtained from per-azido α, β and γ-CD derivatives and propargyl glycosides using click-chemistry under microwave irradiation. The methodology was successfully applied to various protected and non-protected propargylated monosaccharides, including both O - and S -glycosides, giving clear evidence of its versatility. The targeted 6- per -glycosylated CDs were isolated in moderate to excellent yields (30\textendash 90%) by silica gel chromatography. The results showed inhibition of α-glucosidase from Saccharomyces cerevisiae with IC 50 values in the 32\textendash 132 μM range, lower than that of acarbose (IC 50 = ∼250 μM), a well-known competitive inhibitor used in the clinical treatment of type 2 diabetes. Preliminary experiments suggest a mixed-type non-competitive inhibition mode for these new glycoclusters.
Published: 2019

14. 15 Silicates in Photocatalysis

Author: Cyril Ollivier, Christophe Lévêque, Louis Fensterbank, Vincent Corcé, Chemical Biology (CHEMBIO), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Méthodes et Application en Chimie Organique (MACO), and König, B.
Subjects: Materials science, CHEMBIO, Chemical engineering, POLE 3, POLE 1, Photocatalysis, [CHIM]Chemical Sciences, MACO, ComputingMilieux_MISCELLANEOUS, 3. Good health
Abstract: Bis(catecholato)silicates have emerged as robust alkyl radical sources under photocatalysis. This chapter describes the preparation of various silicates and their utilization under photocatalytic conditions for the formation of C–C and C–O bonds. The last section focuses on the use of silicates in photoredox/nickel dual catalysis.
Published: 2019

15. Synthesis of Azidosphingosine from D-Galactose or L-Arabinose

Author: Gao, Yangguang, Cao, Zhou, Han, Zhongxiang, Zhang, Qiang, Hu, Jie, Guo, Rui, He, Xianran, Ding, Fei, You, Qingliang, Zhang, Yongmin, Institute for Interdisciplinary Research, Jianghan University, Wuhan, PR China, Jianghan University [Whuan], Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: GOBS, POLE 3, 010405 organic chemistry, Chemistry, Stereochemistry, Organic Chemistry, [CHIM]Chemical Sciences, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences
Published: 2019

16. Design and Synthesis of a Novel Colorimetric Fluorescent Probe for the Selective Detection of Sulfur Dioxide in SH-SY5Y Neuroblastoma Cells and Its Applications in Traditional Chinese Medicines

Author: Jianli Li, Kangjia Sheng, Lili Yang, Junli Du, Mofan Liu, Shaoping Wu, Yongmin Zhang, Yaoyao Ning, Xiaoqing Wang, Xiaolu Li, Northwest University [Xi'an], Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: Detection limit, Fluorescence-lifetime imaging microscopy, Membrane permeability, POLE 3, chemistry.chemical_element, Environmental pollution, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Fluorescence, Sulfur, Combinatorial chemistry, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, GOBS, chemistry, Linear range, 13. Climate action, Materials Chemistry, [CHIM]Chemical Sciences, 0210 nano-technology, Sulfur dioxide
Abstract: A fast response time, low limit of detection and high fluorescence quantum yield probe DTCC was designed and synthesized to detect SO 2 derivatives based on coumarin-thiophene dye which was fused with a coumarin moiety and 2-thiophenecarboxaldehyde. , Sulfur fumigation has attracted extensive attention as one of the important post-harvest processing methods for some traditional Chinese medicines (TCMs) in the last decade. However, sulfur fumigation has recently emerged as a controversial topic due to its potential detrimental effects on the safety and efficacy of TCMs as some sulfur-fumigated TCMs contain numerous sulfur dioxide derivatives; moreover, high levels of sulfur dioxide derivatives can cause some diseases and dangerous environmental pollution. In this study, a DTCC probe with a fast response time, low limit of detection and a high fluorescence quantum yield was designed and synthesized to detect SO 2 derivatives based on the coumarin-thiophene dye, which was fused with a coumarin moiety and 2-thiophenecarboxaldehyde. The probe DTCC exhibited a fast response time (less than 10 s), satisfactory selectivity for SO 2 derivatives in the presence of other ROS and excellent sensitivity for SO 2 derivatives with a low limit of detection (0.23 μM) as well as a wide linear range (0\textendash 100 μM). Furthermore, the probe DTCC was successfully applied in fluorescence imaging in SH-SY5Y neuroblastoma cells with excellent membrane permeability and stability. It was also employed in monitoring the total SO 2 derivatives in several real TCM samples. These results illustrate that the probe DTCC has an excellent capability for monitoring SO 2 derivatives in living cells and real TCM samples.
Published: 2019

17. Structure Analysis and Anti-Fatigue Activity of a Polysaccharide from Lepidium Meyenii Walp

Author: Yongmin Zhang, Li-Chao Pan, Qiaoying Song, Hui-Qing Sun, Yun Tang, Zhen-Yuan Zhu, Tianjin University of Science and Technology (TUST), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: chemistry.chemical_classification, Chromatography, Structure analysis, Lepidium meyenii, POLE 3, 010405 organic chemistry, Organic Chemistry, Plant Science, Polysaccharide, 01 natural sciences, Biochemistry, 0104 chemical sciences, Analytical Chemistry, Hot water extraction, 010404 medicinal & biomolecular chemistry, GOBS, chemistry, Sephadex, [CHIM]Chemical Sciences
Abstract: A polysaccharide was obtained from Lepidium meyenii Walp by hot water extraction and purification by Millipore (100 kD) and Sephadex G-200. The content of polysaccharide was examined to be 89.9% with phenol-sulfuric acid method. Its average molecular weight was estimated to be 2.213 × 106 Da by High Performance Gel Permeation Chromatography (HPGPC). Monosaccharide analysis showed that the polysaccharide was composed of arabinose, mannose, glucose and galactose with the molar ratio of 2.134: 1: 2.78: 2.82. After Smith degradation, methylation, infrared spectroscopy and NMR, the primary structure of the polysaccharide was identified. The backbone of the polysaccharide was composed of →4)-β-D-Galp-(1→ and →4)-α-D-Galp-(1→, while the branches were comprised of →6)-β-D-Glup-(1→, →5)- β-D-Araf-(1→, →3,6)-α-D-Manp-(1→, →3)-α-D-Galp-(1→, and α-D-Glup-(1→. The anti-fatigue effect of the polysaccharide was evaluated using exhaustive swimming test and biochemical indexes. The results indicated the polysaccharide has anti-fatigue effect.
Published: 2019

18. CpeF Is the Bilin Lyase That Ligates the Doubly Linked Phycoerythrobilin on β-Phycoerythrin in the Cyanobacterium \emphFremyella\emph Diplosiphon

Author: Jacob P. Frick, David M. Kehoe, M. Nazim Boutaghou, Wendy M. Schluchter, Andrian Gutu, Jonathan A. Karty, Richard B. Cole, Carla V. Hernandez, Christina M. Kronfel, Leanora S. Hernandez, University of New Orleans, Department of Biology (Kehoe's Lab), Indiana University [Bloomington], Indiana University System-Indiana University System, Mass Spectrometry Facility, Indiana University System-Indiana University System-Department of Chemistry, Indiana University System, Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Department of Biological Sciences [New Orleans], The University of New Orleans, Dpt of Chemistry [New Orleans], and University of New Orleans, New Orleans
Subjects: 0301 basic medicine, 030102 biochemistry & molecular biology, biology, POLE 3, Protein subunit, Phycobiliprotein, Phycoerythrobilin, Cell Biology, Lyase, Biochemistry, CPEB, 03 medical and health sciences, chemistry.chemical_compound, 030104 developmental biology, chemistry, biology.protein, [CHIM]Chemical Sciences, Phycobilisome, Bilin, Molecular Biology, Phycoerythrin, CSOB
Abstract: Phycoerythrin (PE) is a green light–absorbing protein present in the light-harvesting complex of cyanobacteria and red algae. The spectral characteristics of PE are due to its prosthetic groups, or phycoerythrobilins (PEBs), that are covalently attached to the protein chain by specific bilin lyases. Only two PE lyases have been identified and characterized so far, and the other bilin lyases are unknown. Here, using in silico analyses, markerless deletion, biochemical assays with purified and recombinant proteins, and site-directed mutagenesis, we examined the role of a putative lyase-encoding gene, cpeF, in the cyanobacterium Fremyella diplosiphon. Analyzing the phenotype of the cpeF deletion, we found that cpeF is required for proper PE biogenesis, specifically for ligation of the doubly linked PEB to Cys-48/Cys-59 residues of the CpeB subunit of PE. We also show that in a heterologous host, CpeF can attach PEB to Cys-48/Cys-59 of CpeB, but only in the presence of the chaperone-like protein CpeZ. Additionally, we report that CpeF likely ligates the A ring of PEB to Cys-48 prior to the attachment of the D ring to Cys-59. We conclude that CpeF is the bilin lyase responsible for attachment of the doubly ligated PEB to Cys-48/Cys-59 of CpeB and together with other specific bilin lyases contributes to the post-translational modification and assembly of PE into mature light-harvesting complexes.
Published: 2019

19. Functionalized Cyclodextrins and Their Applications in Biodelivery

Author: Matthieu Sollogoub, Yongmin Zhang, Jiang Liu, Peng Yu, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Tianjin University of Science and Technology (TUST), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Key Laboratory of Resource Biology and Biotechnology, Northwest University, Xi'an, Liu, Yu and Chen, Yong and Zhang, and Heng-Yi
Subjects: GOBS, POLE 3, 010405 organic chemistry, Chemistry, [CHIM]Chemical Sciences, 010402 general chemistry, 01 natural sciences, ComputingMilieux_MISCELLANEOUS, 0104 chemical sciences
Abstract: International audience
Published: 2019

20. Identification of Postblast Residues by DART-High Resolution Mass Spectrometry Combined with Multivariate Statistical Analysis of the Kendrick Mass Defect

Author: Maxime C. Bridoux, Nolwenn Floch, Alexandre Sonnette, Gabriel Gaiffe, Richard B. Cole, Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), DAM Île-de-France (DAM/DIF), Direction des Applications Militaires (DAM), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Laboratoire Central de la Préfecture de Police, École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Dart, Kendrick mass, POLE 3, Chemistry, 010401 analytical chemistry, Analytical chemistry, 010402 general chemistry, Orbitrap, Mass spectrometry, 01 natural sciences, DART ion source, 0104 chemical sciences, Analytical Chemistry, law.invention, law, Mass spectrum, [CHIM]Chemical Sciences, Plastic explosive, computer, CSOB, Semtex, computer.programming_language
Abstract: The coupling of an atmospheric pressure ionization source (Direct Analysis in Real Time, DART) and a high-resolution mass spectrometer (Orbitrap) has enabled the rapid and efficient analysis of a variety of energetic formulations. This approach was used to generate mass spectra for 83 plastic explosives and polymer samples in less than 2 min per sample. To manually interpret and identify all of the constituent polymers and other interesting features in the acquired mass spectra is a tedious and time-consuming challenge. Instead, a methodology based on the systematic calculation of Kendrick mass defects (KMDs) was developed and implemented. Its application allowed the identification of the polymeric support present in each energetic formulation. The presence of polyisobutylene in PG2 has been confirmed thanks to this approach, and a mixture of polyisobutylene, polybutadiene, and polystyrene has been confirmed in the Semtex 10 formulation. The developed methodology has also permitted the observation of changes that occur to the polymeric composition of these formulations after a blast. It appears that the most adequate way to describe post blast polymer samples is that they are less oxygenated and, above all, more unsaturated than the original starting material. These conclusions were deduced with the aid of principal component analysis, which served to establish the main factors that differentiate the samples.
Published: 2019

21. New Insights into the Biological Activities of Chrysanthemum Morifolium: Natural Flavonoids Alleviate Diabetes by Targeting α-Glucosidase and the PTP-1B Signaling Pathway

Author: Chen Mingzhu, Hai-Feng Sun, Yujiao Ma, Zhang Mengdi, Hua Sun, Yinan Zhang, Kaili Wang, He Jiang, Yongmin Zhang, Zongxin Jin, Peng Yu, Hang Zheng, Tianjin University of Science and Technology (TUST), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: Male, POLE 3, Chrysanthemum, Flavonoid, Pharmacology, 01 natural sciences, Streptozocin, Diabetes Mellitus, Experimental, Mice, 03 medical and health sciences, chemistry.chemical_compound, Cricetulus, Cell Line, Tumor, Drug Discovery, Animals, Hypoglycemic Agents, [CHIM]Chemical Sciences, Glycoside Hydrolase Inhibitors, Protein kinase B, Triglycerides, ComputingMilieux_MISCELLANEOUS, 030304 developmental biology, Flavonoids, Protein Tyrosine Phosphatase, Non-Receptor Type 1, chemistry.chemical_classification, 0303 health sciences, biology, 010405 organic chemistry, Chrysanthemum morifolium, Organic Chemistry, General Medicine, Maltose, biology.organism_classification, Diosmetin, Rats, 0104 chemical sciences, GOBS, Cholesterol, Glucose, Enzyme, chemistry, Phosphorylation, Signal transduction, Signal Transduction
Abstract: As dual regulators, the PTP-1B signaling pathway and α-glucosidase slow glucose release and increase the degree of insulin sensitivity, representing a promising therapeutic target for type 2 diabetes. In this study, we systematically examined the in vivo and in vitro anti-diabetic activities of natural flavonoids 1–6 from Chrysanthemum morifolium. Flavonoids 1–6 increased glucose consumption-promoting activity and the phosphorylation of GSK-3β and Akt, and decreased PTP-1B protein level along with slightly inhibitory activity of the PTP-1B enzyme. Moreover, flavonoids 1–2 treatment induced insulin secretion in INS-1 cells. Besides, in vivo study revealed that flavonoids 2 and 5 demonstrated potent anti-hyperglycemic and anti-hyperlipidemic activity, and improved maltose and glucose tolerance. Although flavonoid 2 exhibited lower inhibitory activity against α-glucosidase in vitro, it could deglycosylated in vivo to diosmetin to function as an α-glucosidase inhibitor. Taken together, these results led to the identification of the natural flavonoids 1–6 from C. morifolium as dual regulators of α-glucosidase and the PTP-1B signaling pathway, suggesting their potential application as new oral anti-diabetic drugs or functional food ingredients.
Published: 2019

22. Facile Preparation and Characterization of Novel Oleanane-Type Triterpene Functionalized β-Cyclodextrin Conjugates

Author: Demin Zhou, Yingying Chen, Sulong Xiao, Fuxiang Ran, Yongmin Zhang, Man Li, Pingxuan Jiao, Shouxin Wang, Haiwei Li, Lihe Zhang, Shuobin Liang, Qianqian Gao, Dezhong Ji, State Key Laboratory of Natural and Biomimetic Drugs, Peking University [Beijing], Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Central South University, Chinese Academy of Sciences [Changchun Branch] (CAS), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: chemistry.chemical_classification, Cyclodextrin, POLE 3, Stereochemistry, 02 engineering and technology, General Chemistry, Carbon-13 NMR, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 3. Good health, 0104 chemical sciences, chemistry.chemical_compound, GOBS, chemistry, Triterpene, Amphiphile, Proton NMR, Click chemistry, [CHIM]Chemical Sciences, 0210 nano-technology, Oleanane, Oleanolic acid
Abstract: Oleanolic acid (OA) and echinocystic acid (EA), two naturally occurring pentacyclic oleanane triterpenes, are gaining increasing attention due to their promising pharmacological activities. Conjugation with amphiphilic α(β)-cyclodextrin (CD) via “click chemistry” can improve their solubility and anti-HCV entry potency. In the present work, four water-soluble β-CD-pentacyclic triterpene conjugates were designed and synthesized, in which OA and EA was coupled to one of the primary hydroxyl groups of β-CD via ester and amide bonds. The structures of the conjugates were unambiguously determined by 1H NMR, 13C NMR and HRMS or MALDI-TOF-MS. All the conjugates showed lower hydrophobicity (AlogP) than their parent compounds and no significant cytotoxicity was found to HL-60, A549, Hela and Bel-7402 cells at concentrations up to 10 μmol/L. Further anti-HCV entry activity and mechanism studies are under way in our laboratory.
Published: 2019

23. Characterization of Fluorinated Polymers by Atmospheric-Solid-Analysis-Probe High-Resolution Mass Spectrometry (ASAP/HRMS) Combined with Kendrick-Mass-Defect Analysis

Author: Maxime C. Bridoux, Gabriel Gaiffe, Richard B. Cole, Sabrina Lacpatia, Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), LCPP - laboratoire central de la préfecture de police, DAM Île-de-France (DAM/DIF), Direction des Applications Militaires (DAM), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, Kendrick mass, POLE 3, 010401 analytical chemistry, Analytical chemistry, chemistry.chemical_element, Polymer, 010402 general chemistry, Mass spectrometry, Orbitrap, 01 natural sciences, Polyvinylidene fluoride, 0104 chemical sciences, Analytical Chemistry, law.invention, chemistry.chemical_compound, chemistry, law, Fluorine, [CHIM]Chemical Sciences, Hexafluoropropylene, Chlorotrifluoroethylene, CSOB
Abstract: Fluorinated polymers are a diverse and important class of polymers with unique applications. However, characterization of fluorinated polymers by conventional mass spectrometric methods is challenging because (i) their high fluorine contents make them insoluble or only sparingly soluble in most common solvents and (ii) commonly used matrices employed for MALDI do not desorb or ionize them efficiently. In this work, atmospheric-solid-analysis-probe (ASAP) high-resolution orbitrap mass spectrometry (HRMS) was used as a new tool for the molecular characterization of various fluorinated polymers, including polyvinylidene fluoride (PVDF) and fluorinated copolymers containing PVDF and chlorotrifluoroethylene (KEL-F 800) or PVDF and hexafluoropropylene (Viton A and Tecnoflon). The major peaks of the observed distributions were assigned compositions, but the high number of species required the use of an alternative method to treat such complex data. Kendrick-mass defects (KMD) were calculated on the basis of the "common-to-all" vinylidene difluoride repeating unit. By plotting the KMD as a function of the nominal Kendrick masses (NKM), specific patterns based on homologous series emerged. Kendrick maps were therefore drawn to simplify the mass spectra and provide confident peak assignments through homologous-series recognition. A specific fingerprint for each polymer has been identified, and the ability to discern the four species present in a blend through KMD analysis was demonstrated.
Published: 2018

24. The chemical structure and anti-aging bioactivity of an acid polysaccharide obtained from rose buds

Author: Qiaoying Song, Hui-Qing Sun, Zhen-Yuan Zhu, Yong-Min Zhang, Yun Tang, Yao Liu, Tianjin University of Science and Technology (TUST), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: Aging, Magnetic Resonance Spectroscopy, POLE 3, Chemical structure, 02 engineering and technology, Flowers, Polysaccharide, Rosa, 01 natural sciences, chemistry.chemical_compound, Polysaccharides, Spectroscopy, Fourier Transform Infrared, Side chain, [CHIM]Chemical Sciences, Animals, chemistry.chemical_classification, 010405 organic chemistry, Plant Extracts, Diptera, Periodic acid, General Medicine, Nuclear magnetic resonance spectroscopy, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Congo red, GOBS, chemistry, Sephadex, Yield (chemistry), Female, 0210 nano-technology, Food Science, Nuclear chemistry
Abstract: An acid polysaccharide, named R-PL, was extracted from rose buds by hot water (80 °C) extraction and purified by Sephadex G-200. R-PL, extracted with a total yield of 1.90%, is a highly pure polysaccharide with a total sugar content of 92.51%. A single and symmetrically sharp peak in its high-performance gel-permeation chromatography (HPGPC) spectrum indicates that R-PL is a homogeneous polysaccharide with a molecular weight of 7.727 × 105 Da. Monosaccharide composition analysis shows that it consists of D-arabinose, D-xylose, D-glucose, D-galactose, D-galacturonic acid, and D-glucuronic acid with a molar ratio of 4.6 : 1.4 : 5.22 : 4.81 : 1 : 1.86. Structure analysis, such as FTIR spectroscopy, periodic acid oxidation, Smith degradation, methylation, and NMR analysis, reveals that R-PL has a backbone of →1)-α-D-Glcp-(6→ with side chains of →1)-β-D-Galp-(4,6→, →1)-β-D-Araf-(5→, →1)-α-D-Xylp-(4→, →1)-α-D-GlcpA-(2→ and →1)-α-D-GalpA-(4→. Its morphological characteristics were identified by Congo red experiments and scanning electron microscopy (SEM) analysis. The results show that R-PL does not have a triple-helical conformation in solution; its shape resembles twisted ribbons. Anti-oxidative and anti-aging analyses show that R-PL has significant antioxidant and anti-aging abilities in vivo.
Published: 2018

25. Revealing cooperative binding of polycationic cyclodextrins with DNA oligomers by capillary electrophoresis coupled to mass spectrometry

Author: Juan M. Benito, José M. García Fernández, Carmen Ortiz Mellet, Cédric Przybylski, Véronique Bonnet, Ministerio de Economía y Competitividad (España), Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla-Consejo Superior de Investigaciones Científicas [Madrid] (CSIC), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), and Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: POLE 3, Cooperative effects, DNA, Single-Stranded, dnaN, Gene delivery, 010402 general chemistry, Mass spectrometry, 01 natural sciences, Biochemistry, Mass Spectrometry, Polymerization, Analytical Chemistry, chemistry.chemical_compound, Capillary electrophoresis, [CHIM]Chemical Sciences, Environmental Chemistry, Hill number, Spectroscopy, Cyclodextrins, Drug Carriers, Chromatography, Base Sequence, 010405 organic chemistry, Oligonucleotide, Electrophoresis, Capillary, Cooperative binding, DNA, 0104 chemical sciences, Polycationic cyclodextrins, chemistry, CE-MS, Nucleic acid, CSOB
Abstract: Gene delivery is critical for the development of nucleic acid-based therapies against a range of severe diseases. The conception of non-viral (semi)synthetic vectors with low cytotoxicity and virus-like efficiency is gathering a lot of efforts, but it represents a fantastic challenge still far from accomplishment. Carbohydrate-based scaffolds offer interesting features towards this end, such as easy availability, relatively cheap cost, tuning properties and a good biocompatibility. The lack of analytical methods providing quantitative and qualitative data on their binding properties with oligonucleotides (DNA/RNA), with a minimal time and sample consumption, represents a limitation for these channels. Here, we attempted to fill the gap by hyphenation of capillary electrophoresis with mass spectrometry (CE-MS). This coupling strategy allows discriminating free and complexed DNA oligomers with cationic cyclodextrins (CDs), determining the stoichiometry where the highest observed is always DNA: n/3(CD), and unambiguously assigning the partners through m/z detection. Very reliable data were obtained with migration time within 5.5 (standard deviation < 0.5%) and 25 min (standard deviation < 1.1%) for UV and MS detection, respectively. Furthermore, varying the nitrogen/phosphorus ratio (N/P), key parameters relating to the thermodynamics e.g. the micro and macroscopic dissociation constants K and K, respectively (both in low μM range) and the Gibbs free energy ΔG (−16.3 to −26.9 kJ mol), and also the cooperativity as Hill number (nH between 0.98 and 15.75) of the supramolecular process can be delineated, providing a unique tool for the high throughput screening and selection of efficient gene delivery carriers., The authors thank Genopole-France and the Conseil Régional d’Ile-de-France and the Spanish Ministerio de Economia y Competitividad (MinECo, contract no. SAF2013-44021-R and CTQ2015-64425-C2-1-R).
Published: 2018

26. De Novo Design and Synthesis of a Novel Colorimetric Fluorescent Probe Based on Naphthalenone Scaffold for Selective Detection of Hypochlorite and Its Application in Living Cells

Author: Shaoping Wu, Jihong Cui, Yongmin Zhang, Jianli Li, Xiaoqing Wang, Yaoyao Ning, Chaoni Xiao, Yiwei Lu, Northwest University [Xi'an], Northwestern Polytechnical University [Xi'an] (NPU), Key Laboratory of Resource Biology and Biotechnology, Northwest University, Xi'an, Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Scaffold, Biocompatibility, POLE 3, Hypochlorite, 010402 general chemistry, 01 natural sciences, symbols.namesake, chemistry.chemical_compound, Stokes shift, Materials Chemistry, [CHIM]Chemical Sciences, Electrical and Electronic Engineering, Instrumentation, Detection limit, 010405 organic chemistry, Chemistry, Metals and Alloys, Condensed Matter Physics, Fluorescence, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, GOBS, Energy based, symbols, Biophysics, Titration
Abstract: It is extremely important and necessary to develop a highly sensitive and excellent selective fluorescence probe for detection of ClO− in living systems because the excess production of ClO− was related to a series of diseases. Herein, a novel turn-on colorimetric fluorescent probe ADT-MAM based on naphthalenone scaffold was successfully designed and synthesized for highly selective and sensitive detection of ClO− with fast response time, a large Stokes shift, low limit of detection and wide pH range in applications. Meanwhile, probe ADT-MAM allowed colorimetric detection of ClO− by naked eyes. Fluorescence titration experiments showed that the probe has an excellent linear relationship (R2 = 0.9949) and a low detection limit of 0.15 μM. HOMO-LUMO energy based on density functional theory (DFT) has been calculated in order to provide a better understanding of optical property for ADT-MAM and DTC. Moreover, the probe could be applied to sense exogenous imaging of ClO− in HeLa cells and A549 cells with negligible cytotoxicity, cell membrane permeability and good biocompatibility. The success of subcellular imaging suggested that such a novel probe ADT-MAM could be applied to further reveal essential biological functions and pathological roles of ClO− in extensive biological systems.
Published: 2018

27. A Systematic Tandem Mass Spectrometric Study of Anion Attachment for Improved Detection and Acidity Evaluation of Nitrogen-Rich Energetic Compounds

Author: Christine Costanza, Richard B. Cole, Maxime C. Bridoux, Gabriel Gaiffe, Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), DAM Île-de-France (DAM/DIF), Direction des Applications Militaires (DAM), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Laboratoire Central de la Préfecture de Police, École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: POLE 3, Electrospray ionization, 010401 analytical chemistry, Analytical chemistry, Pentaerythritol tetranitrate, 010402 general chemistry, Tandem mass spectrometry, 01 natural sciences, Dissociation (chemistry), 0104 chemical sciences, Adduct, Ion, chemistry.chemical_compound, Deprotonation, chemistry, Molecule, [CHIM]Chemical Sciences, CSOB, Spectroscopy
Abstract: The development of rapid, efficient, and reliable detection methods for the characterization of energetic compounds is of high importance to security forces concerned with terrorist threats. With a mass spectrometric approach, characteristic ions can be produced by attaching anions to analyte molecules in the negative ion mode of electrospray ionization mass spectrometry (ESI-MS). Under optimized conditions, formed anionic adducts can be detected with higher sensitivities as compared with the deprotonated molecules. Fundamental aspects pertaining to the formation of anionic adducts of 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX), 1,3,5-trinitro-1,3,5-triazinane (RDX), pentaerythritol tetranitrate (PETN), nitroglycerin (NG), and 1,3,5-trinitroso-1,3,5-triazinane energetic (R-salt) compounds using various anions have been systematically studied by ESI-MS and ESI tandem mass spectrometry (collision-induced dissociation) experiments. Bracketing method results show that the gas-phase acidities of PETN, RDX, and HMX fall between those of HF and acetic acid. Moreover, PETN and RDX are each less acidic than HMX in the gas phase. Nitroglycerin was found to be the most acidic among the nitrogen-rich explosives studied. The ensemble of bracketing results allows the construction of the following ranking of gas-phase acidities: PETN (1530-1458 kJ/mol) > RDX (approximately 1458 kJ/mol) > HMX (approximately 1433 kJ/mol) > nitroglycerin (1427-1327.8 kJ/mol).
Published: 2018

28. Low-Energy Collision-Induced Dissociation (Low-Energy CID), Collision-Induced Dissociation (CID), and Higher Energy Collision Dissociation (HCD) Mass Spectrometry for Structural Elucidation of Saccharides and Clarification of Their Dissolution Mechanism i

Author: Parisa Bayat, Denis Lesage, Richard B. Cole, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Chimie Structurale Organique et Biologique (CSOB), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769)
Subjects: chemistry.chemical_classification, Collision-induced dissociation, POLE 3, 010401 analytical chemistry, Glycosidic bond, 010402 general chemistry, Photochemistry, Mass spectrometry, 01 natural sciences, Dissociation (chemistry), 0104 chemical sciences, chemistry.chemical_compound, Reaction rate constant, chemistry, Fragmentation (mass spectrometry), Lithium chloride, [CHIM]Chemical Sciences, Dissolution, CSOB, Spectroscopy
Abstract: The dissolution mechanism of oligosaccharides in N,N-dimethylacetamide/lithium chloride (DMAc/LiCl), a solvent used for cellulose dissolution, and the capabilities of low-energy collision-induced dissociation (low-energy CID), collision-induced dissociation (CID), and higher energy collision dissociation (HCD) for structural analysis of carbohydrates were investigated. Comparing the spectra obtained using 3 techniques shows that, generally, when working with monolithiated sugars, CID spectra provide more structurally informative fragments, and glycosidic bond cleavage is the main pathway. However, when working with dilithiated sugars, HCD spectra can be more informative providing predominately cross-ring cleavage fragments. This is because HCD is a nonresonant activation technique, and it allows a higher amount of energy to be deposited in a short time, giving access to more endothermic decomposition pathways as well as consecutive fragmentations. The difference in preferred dissociation pathways of monolithiated and dilithiated sugars indicates that the presence of the second lithium strongly influences the relative rate constants for cross-ring cleavages vs glycosidic bond cleavages, and disfavors the latter. Regarding the dissolution mechanism of sugars in DMAc/LiCl, CID and HCD experiments on dilithiated and trilithiated sugars reveal that intensities of product ions containing 2 Li+ or 3 Li+ , respectively, are higher than those bearing only 1 Li+ . In addition, comparing the fragmentation spectra (both HCD and CID) of LiCl-adducted lithiated sugar and NaCl-adducted sodiated sugar shows that while, in the latter case, loss of NaCl is dominant, in the former case, loss of HCl occurs preferentially. The compiled evidence implies that there is a strong and direct interaction between lithium and the saccharide during the dissolution process in the DMAc/LiCl solvent system.
Published: 2018

29. Synthesis of NSAIDs\textendashSe Derivatives as Potent Anticancer Agents

Author: Liu, Lei, Li, Shaolei, LI, Xiaolong, Zhong, Min, Lu, Yin, Jiajie, Yang, Yongmin, Zhang, He, Xianran, Institute for Interdisciplinary Research, Jianghan University, Wuhan, PR China, Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Jianghan University [Whuan], Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)
Subjects: GOBS, POLE 3, [CHIM]Chemical Sciences
Published: 2018

30. Confinement of Metal-N-Heterocyclic Carbene Complexes to Control Reactivity in Catalytic Reactions

Author: Jorge Meijide Suárez, Matthieu Sollogoub, Sylvain Roland, Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)
Subjects: POLE 3, 010405 organic chemistry, Organic Chemistry, Substrate (chemistry), Regioselectivity, General Chemistry, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Catalysis, Product distribution, 0104 chemical sciences, Metal, chemistry.chemical_compound, GOBS, chemistry, visual_art, visual_art.visual_art_medium, [CHIM]Chemical Sciences, Reactivity (chemistry), Selectivity, Carbene
Abstract: Confinement of a metal complex is a promising way to induce reactivity modulation and selectivity. Combining this principle with the properties of N-heterocyclic carbenes (NHC) used as ligands is therefore of great interest. NHCs metal complexes have been encapsulated in polymeric structures (metal-organic frameworks, metal organic polymers and porous organic polymers), and in molecular containers (capsules, cages or cavitands). This confinement induced reactivity change, on and off switching of reactions, substrate selection, stereoselectivity, regioselectivity, and product distribution variation. The syntheses and the influence of confinement on reactivity will be discussed in this Minireview.
Published: 2018

31. Theranostic Applications of Antibody-Based Systems in Human Diseases

Author: Yongmin Zhang, Fei Ding, Xianran He, Yangguang Gao, Institute for Interdisciplinary Research, Jianghan University, Wuhan, PR China, Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Key Laboratory of Resource Biology and Biotechnology, and Northwest University, Xi'an
Subjects: 0301 basic medicine, Drug, Theranostic Nanomedicine, POLE 3, media_common.quotation_subject, Biomedical Engineering, Pharmaceutical Science, Medicine (miscellaneous), Bioengineering, Antibodies, Epitope, 03 medical and health sciences, Immune system, Humans, Medicine, [CHIM]Chemical Sciences, General Materials Science, media_common, biology, Effector, business.industry, Biological activity, Small molecule, 3. Good health, GOBS, 030104 developmental biology, Viruses, Immunology, biology.protein, Antibody, business
Abstract: Since antibodies are one of the most successful classes of biopharmaceuticals for cancer treatment, it is very important to discuss the functionality and biological activity of endogenous antibodies in the diagnosis and treatment of the diseases. Antibodies act on tumor cells in diverse ways, including engaging in antibody-dependent effector mechanisms, internalizing to deliver toxins, and displaying direct effects on cells. In this review, we outline three kinds of antibody-based therapeutic systems, namely Antibody-based Drug Conjugates (Ab-DCs), Antibody-based Recruiting Small Molecules (Ab-RSMs) and Carbohydrate Epitopes Recruiting Natural Antibodies (CERNA) for human disease treatment and imaging. These antibody-based therapeutic systems are able to strengthen the binding ability of antibodies with disease-relevant cells or viruses, leading to their immuno-mediated therapeutic responses and clearance. Research in these fields shows exciting potential at the junction of organic chemistry and immune-biology. Since the applications of antibodies are of great importance, it is necessary to functionalize antibodies or develop other antibody-based synthetic strategies to modulate the human immune system, and ultimately achieve the treatment of diseases.
Published: 2018

32. Characterization of Degradation Products of Macitentan under Various Stress Conditions Using Liquid Chromatography/Mass Spectrometry

Author: Sukanya Pandeti, Jean-Claude Tabet, Jagadeshwar Reddy Thota, Naga Veera Yerra, Pavankumar Pallerla, CSIR Indian Institute of Chemical Technology [Hyderabad] (IICT), Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Spectrometry, Mass, Electrospray Ionization, POLE 3, Endothelin A Receptor Antagonists, Electrospray ionization, Pharmaceutical formulation, Tandem mass spectrometry, Mass spectrometry, 01 natural sciences, Analytical Chemistry, 03 medical and health sciences, chemistry.chemical_compound, Hydrolysis, 0302 clinical medicine, Drug Stability, Liquid chromatography–mass spectrometry, Tandem Mass Spectrometry, Ammonium formate, [CHIM]Chemical Sciences, Spectroscopy, Chromatography, High Pressure Liquid, Sulfonamides, Chromatography, Photolysis, 010401 analytical chemistry, Organic Chemistry, 0104 chemical sciences, Endothelin B Receptor Antagonists, Pyrimidines, 030228 respiratory system, chemistry, Degradation (geology), Oxidation-Reduction, CSOB
Abstract: Rationale Stress testing of a drug candidate is an important step in the drug discovery and development process. The presence of degradation products in a drug affects the quality as well as the safety and efficacy of drug formulation. Hence, it is essential to develop an efficient analytical method which could be useful for the separation, identification and characterization of all possible degradation products (DPs) of a drug. Macitentan (MT) is an endothelin receptor antagonist (ERA) drug used to treat high blood pressure in the lungs. Comprehensive stress testing of MT was carried out as per ICH guidelines to understand the degradation profile of the drug. Methods MT was subjected to various stress conditions such as acidic, basic, neutral hydrolysis, oxidation, photolysis and thermal conditions; and the resulting degradation products were investigated using liquid chromatography/diode-array detection/electrospray ionization high-resolution mass spectrometry (LC/DAD/ESI-HRMS) and tandem mass spectrometry (MS/MS) techniques. An efficient and simple ultra-high-performance liquid chromatography (UHPLC) method has been developed using an Accucore C18 column (4.6 × 150 mm, 2.6 μm) using a gradient elution of 5 mM ammonium formate and acetonitrile as mobile phases. Results MT was found to degrade under acid and base hydrolysis stress conditions; whereas it was stable under oxidation, neutral hydrolysis, thermal and photolytic conditions. MT formed nine DPs (DP1 to DP9) and one DP (DP10) under acidic and basic hydrolytic conditions, respectively. All the degradation products (DP1 to DP10) were identified and characterized by LC/MS/MS in positive ion mode with accurate mass measurements. Conclusions MT was found to be labile under hydrolytic conditions. The structures of the DPs were characterized by appropriate mechanisms. The proposed method can be effectively used for the characterization of MT and its DPs.
Published: 2018

33. Synthesis and Guest Recognition of Switchable Pt-Salphen Based Molecular Tweezers

Author: Bernold Hasenknopf, Lorien Benda, Guillaume Vives, Benjamin Doistau, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Glycochimie Organique Biologique et Supramoléculaire (GOBS), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769)
Subjects: Models, Molecular, Materials science, POLE 3, molecular tweezers, Intercalation (chemistry), guest binding, Molecular Conformation, Pharmaceutical Science, Phenylenediamines, 010402 general chemistry, 01 natural sciences, Article, Analytical Chemistry, lcsh:QD241-441, chemistry.chemical_compound, lcsh:Organic chemistry, Drug Discovery, Tweezers, [CHIM]Chemical Sciences, Open form, platinum, Physical and Theoretical Chemistry, terpyridine, salphen, 010405 organic chemistry, Ligand, Spectrum Analysis, Organic Chemistry, Molecular machine, Coronene, 0104 chemical sciences, Crystallography, GOBS, chemistry, Chemistry (miscellaneous), Molecular Medicine, Terpyridine, Molecular tweezers
Abstract: Molecular tweezers are artificial receptors that have an open cavity generated by two recognition units pre-organized by a spacer. Switchable molecular tweezers, using a stimuli-responsive spacer, are particularly appealing as prototypes of the molecular machines that combine mechanical motion and allosteric recognition properties. In this present study, the synthesis of switchable molecular tweezers composed of a central terpyridine unit substituted in 4,4″ positions by two Pt(II)-salphen complexes is reported. The terpyridine ligand can be reversibly converted upon Zn(II) coordination from a free ‘U’-shaped closed form to a coordinated ‘W’ open form. This new substitution pattern enables a reverse control of the mechanical motion compared to the previously reported 6,6″ substituted terpyridine-based tweezers. Guest binding studies with aromatic guests showed an intercalation of coronene in the cavity created by the Pt-salphen moieties in the closed conformation. The formation of 1:1 host-guest complex was investigated by a combination of NMR studies and DFT calculations.
Published: 2018

34. Xylylene Clips for the Topology-Guided Control of the Inclusion and Self-Assembling Properties of Cyclodextrins

Author: Juan M. Benito, Carmen Ortiz Mellet, Cédric Przybylski, Francisco Mendicuti, Thais Carmona, José M. García Fernández, Tania Neva, University of Sevilla, Universidad de Alcalá - University of Alcalá (UAH), Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla-Consejo Superior de Investigaciones Científicas [Madrid] (CSIC), Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), European Commission, Universidad de Alcalá, Junta de Andalucía, Ministerio de Economía y Competitividad (España), and Universidad de Sevilla
Subjects: POLE 3, 010405 organic chemistry, Chemistry, Organic Chemistry, 010402 general chemistry, Topology, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Monomer, Planar, Self assembling, Ovoid, Moiety, [CHIM]Chemical Sciences, Xylylene, CSOB, Topology (chemistry)
Abstract: The topology of ß-cyclodextrin can be molded, from toroidal to ovoid basket-shaped, by the installation of an o- or m-xylylene moiety connecting two consecutive d-glucopyranosyl units through the secondary O-2(I) and O-3(II) positions. This strategy can be exploited advantageously to precast the cavity for preferential inclusion of globular or planar guests as well as to privilege dimeric or monomeric species in water solution., This study was supported by the Spanish Ministerio de Economía y Competitividad (contract numbers CTQ2015-64425-C2-1-R, CTQ2016-80600-P and SAF2016-76083-R), the Junta de Andalucía (contract number FQM2012-1467), the UAH (CCGP2017-EXP/027) and the European Regional Development Funds (FEDER and FSE). Technical assistance from the research support services of the University of Seville (CITIUS) is also acknowledged. T.N. acknowledges the Junta de Andalucía for a doctoral fellowship.
Published: 2018

35. Rapid Photoinduced Charge Injection into Covalent Polyoxometalate\textendash Bodipy Conjugates

Author: Black, Fiona A., Jacquart, Aurélie, Toupalas, Georgios, Alves, Sandra, Proust, Anna, Clark, Ian P., Gibson, Elizabeth A., Izzet, Guillaume, School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK., School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK. Code (UMR, EA, ...), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Chimie Structurale Organique et Biologique (CSOB), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Edifices PolyMétalliques (E-POM), Central Laser Facility (CLF), STFC Rutherford Appleton Laboratory (RAL), and Science and Technology Facilities Council (STFC)-Science and Technology Facilities Council (STFC)
Subjects: POLE 3, POLE 2, [CHIM]Chemical Sciences, E-POM, CSOB
Published: 2018

36. Positive and negative ion mode comparison for the determination of DNA/peptide noncovalent binding sites through the formation of 'three-body' noncovalent fragment ions

Author: Sandra Alves, Jean-Claude Tabet, Bessem Brahim, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Chimie Structurale Organique et Biologique (CSOB), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769)
Subjects: Spectrometry, Mass, Electrospray Ionization, POLE 3, Stereochemistry, Electrospray ionization, Peptide, 010402 general chemistry, 01 natural sciences, Dissociation (chemistry), Ion, chemistry.chemical_compound, Fragmentation (mass spectrometry), Physics::Atomic and Molecular Clusters, [CHIM]Chemical Sciences, Binding site, Nuclear Experiment, Spectroscopy, chemistry.chemical_classification, Ions, Quantitative Biology::Biomolecules, Binding Sites, 010401 analytical chemistry, General Medicine, DNA, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, chemistry, Peptides, CSOB, Single strand
Abstract: Gas-phase fragmentation of single strand DNA-peptide noncovalent complexes is investigated in positive and negative electrospray ionization modes.Collision-induced dissociation experiments, performed on the positively charged noncovalent complex precursor ions, have confirmed the trend previously observed in negative ion mode, i.e. a high stability of noncovalent complexes containing very basic peptidic residues (i.e. R K) and acidic nucleotide units (i.e. Thy units), certainly incoming from the existence of salt bridge interactions. Independent of the ion polarity, stable noncovalent complex precursor ions were found to dissociate preferentially through covalent bond cleavages of the partners without disrupting noncovalent interactions. The resulting DNA fragment ions were found to be still noncovalently linked to the peptides. Additionally, the losses of an internal nucleic fragment producing "three-body" noncovalent fragment ions were also observed in both ion polarities, demonstrating the spectacular salt bridge interaction stability. The identical fragmentation patterns (regardless of the relative fragment ion abundances) observed in both polarities have shown a common location of salt bridge interaction certainly preserved from solution. Nonetheless, most abundant noncovalent fragment ions (and particularly three-body ones) are observed from positively charged noncovalent complexes. Therefore, we assume that, independent of the preexisting salt bridge interaction and zwitterion structures, multiple covalent bond cleavages from single-stranded DNA/peptide complexes rely on an excess of positive charges in both electrospray ionization ion polarities.
Published: 2017

37. Silver perchlorate in the mobile phase for rapid separation and determination of a pair of positional isomers in Inula racemosa Hook.f. with RP-HPLC

Author: Yang Yang, Wenji Sun, Zhongliang Zhu, Yongmin Zhang, Rui Tu, Key Laboratory of Resource Biology and Biotechnology, Northwest University, Xi'an, Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, Analyte, Acetonitriles, POLE 3, Clinical Biochemistry, Biochemistry, Plant Roots, Analytical Chemistry, 03 medical and health sciences, chemistry.chemical_compound, Lactones, Isomerism, Phase (matter), Structural isomer, [CHIM]Chemical Sciences, Sesquiterpenes, Eudesmane, Acetonitrile, Chromatography, High Pressure Liquid, Chromatography, Reverse-Phase, Inula, Natural product, Chromatography, Perchlorates, biology, Plant Extracts, Inula racemosa, Silver Compounds, Cell Biology, General Medicine, biology.organism_classification, Silver perchlorate, GOBS, 030104 developmental biology, chemistry, Sesquiterpenes
Abstract: Alantolactone and isoalantolactone isolated from many species of plants are a pair of positional isomers of CC bond. Previously, alantolactone and isoalantolactone have been proved to be good lead compounds for future anticancer agent development. Similarity of their molecular structures increases the separation difficulty for these two isomers on a conventional C18 column. Silver perchlorate (AgClO4) as mobile phase additives with RP-HPLC for improving the separation was developed for rapid determination of the positional isomers in Inula racemosa Hook.f. The effects of the concentration of silver perchlorate on the separation of the analytes were investigated. The composition of acetonitrile and water containing 5.0% silver perchlorate in a 65:35 (v/v) ratio was used as mobile phase, in which they were well separated within a short period of time on the C18 column. The method was successfully applied to determine them in an extract of Inula racemosa Hook.f. root. Silver perchlorate in mobile phase can efficiently improve the separation of the positional isomers and could be applied to rapidly determinate their content in this plant.
Published: 2017

38. Inhibition of Influenza Virus Infection by Multivalent Pentacyclic Triterpene-Functionalized per- O -Methylated Cyclodextrin Conjugates

Author: Sulong Xiao, Xiaoshu Zhou, Kun Meng, Zhenyu Tian, Yongmin Zhang, Demin Zhou, Longlong Si, State Key Laboratory of Natural and Biomimetic Drugs, Peking University [Beijing], Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, POLE 3, Hemagglutinin (influenza), Hemagglutinin Glycoproteins, Influenza Virus, 010402 general chemistry, 01 natural sciences, Antiviral Agents, Virus, Madin Darby Canine Kidney Cells, 03 medical and health sciences, chemistry.chemical_compound, Dogs, Influenza A Virus, H1N1 Subtype, Orthomyxoviridae Infections, Viral entry, Drug Discovery, Influenza, Human, Animals, Humans, [CHIM]Chemical Sciences, IC50, Pharmacology, chemistry.chemical_classification, Cyclodextrins, Hemagglutination assay, Cyclodextrin, biology, Chemistry, Organic Chemistry, General Medicine, Virus Internalization, 0104 chemical sciences, 3. Good health, Sialic acid, Dissociation constant, GOBS, 030104 developmental biology, Biochemistry, biology.protein, Pentacyclic Triterpenes
Abstract: Multivalent ligands that exhibit high binding affinity to influenza hemagglutinin (HA) trimer can block the interaction of HA with its sialic acid receptor. In this study, a series of multivalent pentacyclic triterpene-functionalized per-O-methylated cyclodextrin (CD) derivatives were designed and synthesized using 1, 3-dipolar cycloaddition click reaction. A cell-based assay showed that three compounds (25, 28 and 31) exhibited strong inhibitory activity against influenza A/WSN/33 (H1N1) virus. Compound 28 showed the most potent anti-influenza activity with IC50 of 4.7 μM. The time-of-addition assay indicated that compound 28 inhibited the entry of influenza virus into host cell. Further hemagglutination inhibition (HI) and surface plasmon resonance (SPR) assays indicated that compound 28 tightly bound to influenza HA protein with a dissociation constant (KD) of 4.0 μM. Our results demonstrated a strategy of using per-O-methylated β-CD as a scaffold for designing multivalent compounds to disrupt influenza HA protein-host receptor protein interaction and thus block influenza virus entry into host cells.
Published: 2017

39. Synthesis and In Vitro Anti-Influenza Virus Evaluation of Novel Sialic Acid (C-5 and C-9)-Pentacyclic Triterpene Derivatives

Author: Xu Han, Demin Zhou, Man Li, Yongmin Zhang, Zibo Fan, Pingxuan Jiao, Jiaqi Sun, Zhenyu Tian, Yongying Shi, Shouxin Wang, Longlong Si, Fuxiang Ran, Sulong Xiao, State Key Laboratory of Natural and Biomimetic Drugs, Peking University [Beijing], Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, pentacyclic triterpene, POLE 3, Proton Magnetic Resonance Spectroscopy, Pharmaceutical Science, Hemagglutinin Glycoproteins, Influenza Virus, medicine.disease_cause, 01 natural sciences, influenza virus, Madin Darby Canine Kidney Cells, Analytical Chemistry, HeLa, chemistry.chemical_compound, structure-activity relationship (SAR), Influenza A Virus, H1N1 Subtype, Triterpene, Drug Discovery, Influenza A virus, Cytotoxicity, chemistry.chemical_classification, biology, sialic acid, 3. Good health, GOBS, Biochemistry, Chemistry (miscellaneous), Molecular Medicine, Spectrometry, Mass, Electrospray Ionization, Hemagglutinin (influenza), Antiviral Agents, Article, lcsh:QD241-441, 03 medical and health sciences, Dogs, lcsh:Organic chemistry, Cell Line, Tumor, medicine, Animals, Humans, [CHIM]Chemical Sciences, MTT assay, Carbon-13 Magnetic Resonance Spectroscopy, Physical and Theoretical Chemistry, 010405 organic chemistry, Organic Chemistry, biology.organism_classification, N-Acetylneuraminic Acid, Triterpenes, In vitro, 0104 chemical sciences, Sialic acid, 030104 developmental biology, chemistry, biology.protein
Abstract: The emergence of drug resistant variants of the influenza virus has led to a great need to identify novel and effective antiviral agents. In our previous study, a series of sialic acid (C-2 and C-4)-pentacyclic triterpene conjugates have been synthesized, and a five-fold more potent antiviral activity was observed when sialic acid was conjugated with pentacyclic triterpene via C-4 than C-2. It was here that we further reported the synthesis and anti-influenza activity of novel sialic acid (C-5 and C-9)-pentacyclic triterpene conjugates. Their structures were confirmed by ESI-HRMS, 1H-NMR, and 13C-NMR spectroscopic analyses. Two conjugates (26 and 42) showed strong cytotoxicity to MDCK cells in the CellTiter-Glo assay at a concentration of 100 μM. However, they showed no significant cytotoxicity to HL-60, Hela, and A549 cell lines in MTT assay under the concentration of 10 μM (except compound 42 showed weak cytotoxicity to HL-60 cell line (10 μM, ~53%)). Compounds 20, 28, 36, and 44 displayed weak potency to influenza A/WSN/33 (H1N1) virus (100 μM, ~20–30%), and no significant anti-influenza activity was found for the other conjugates. The data suggested that both the C-5 acetylamide and C-9 hydroxy of sialic acid were important for its binding with hemagglutinin during viral entry into host cells, while C-4 and C-2 hydroxy were not critical for the binding process and could be replaced with hydrophobic moieties. The research presented herein had significant implications for the design of novel antiviral inhibitors based on a sialic acid scaffold.
Published: 2017

40. Facile Preparation of a Symmetric Hexavalent Oleanolic Acid/per- O -Methylated α -Cyclodextrin Conjugate with Two Conformations in Solution and Unambiguous NMR Analysis

Author: Yongmin Zhang, Demin Zhou, Lihe Zhang, Kun Meng, Naixia Zhang, Zhenyu Tian, Sulong Xiao, Yanhong Shi, Hongwei Jin, Xuehui Liu, State Key Laboratory of Natural and Biomimetic Drugs, Peking University [Beijing], Shanghai Institute of Materia Medica, Chinese Academy of Sciences [Changchun Branch] (CAS), National Laboratory of Biomacromolecules [Pékin, Chine], CAS Center for Excellence in Biomacromolecules [Pékin, Chine], Institute of Biophysics [Pékin, Chine], Chinese Academy of Sciences [Beijing] (CAS)-Chinese Academy of Sciences [Beijing] (CAS)-Institute of Biophysics [Pékin, Chine], Chinese Academy of Sciences [Beijing] (CAS)-Chinese Academy of Sciences [Beijing] (CAS), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, Cyclodextrin, POLE 3, 010405 organic chemistry, Stereochemistry, Organic Chemistry, Fluorine-19 NMR, Carbon-13 NMR, 01 natural sciences, Biochemistry, 0104 chemical sciences, NMR spectra database, 03 medical and health sciences, chemistry.chemical_compound, GOBS, 0302 clinical medicine, chemistry, 030220 oncology & carcinogenesis, Drug Discovery, Proton NMR, [CHIM]Chemical Sciences, Oleanolic acid, Heteronuclear single quantum coherence spectroscopy, Conjugate
Abstract: A newly synthesized hexavalent oleanolic acid/per- O -methylated α -cyclodextrin conjugate shows significant differences in NMR spectra with previously synthesized analogs. Characterization of the product by 1 H NMR, 13 C NMR, COSY, HSQC, HMBC, TOCSY, NOE, and ROESY experiments were performed. Detailed investigations revealed that the compound has two conformations in solution and the ratio of them was 1:1. Further variable-temperature NMR study revealed that the two conformations were stable at temperature range of 273–323 K in CDCl 3 solution.
Published: 2017

41. Synthesis of Novel Pentacyclic Triterpene\textendashNeu5Ac2en Derivatives and Investigation of Their in Vitro Anti-Influenza Entry Activity

Author: Man Li, Zibo Fan, Demin Zhou, Shouxin Wang, Sulong Xiao, Jiaqi Sun, Yongmin Zhang, Yongying Shi, Longlong Si, Xu Han, State Key Laboratory of Natural and Biomimetic Drugs, Peking University [Beijing], Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, POLE 3, Stereochemistry, Pharmaceutical Science, Hemagglutinin (influenza), Stereoisomerism, Biochemistry, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, Triterpene, Drug Discovery, Peptide bond, [CHIM]Chemical Sciences, Pharmacology, chemistry.chemical_classification, Hemagglutination assay, biology, Organic Chemistry, 3. Good health, Sialic acid, GOBS, 030104 developmental biology, chemistry, 030220 oncology & carcinogenesis, biology.protein, Molecular Medicine, Pentacyclic Triterpenes, Neuraminidase
Abstract: Sialic acid derivatives, analogs, and their conjugates are important pharmacophores. Modification of the C-4 hydroxyl group of sialic acid can lead to derivatives, such as zanamivir, with potent anti-influenza activities. Herein, we described the synthesis of C-4-modified sialic acid derivatives via conjugation with naturally derived pentacyclic triterpenes, which are active ingredients of traditional Chinese medicine, and the evaluation of their in vitro anti-influenza virus activity in MDCK cells. Interestingly, a set of configurational isomers was obtained during the de-O-acetylation reaction of two pentacyclic triterpene-sialic acid conjugates under Zemplen conditions, and a mechanism was proposed. Owing to the attachment of the Neu5Ac2en moiety, all synthesized conjugates displayed lower hydrophobicity than their parent compounds. In comparison with ursane- and lupane-type triterpenes, oleanane-type triterpene-functionalized Neu5Ac2en conjugates were most promising. The insertion of a (1,2,3-triazol-4-yl)-methyl between the amide bond and Neu5Ac2en caused a substantial decrease in activity. Compound 15a exhibited the highest inhibitory activity (IC50 = 8.3 μM) and selectivity index (SI = 22.7). Further studies involving hemagglutination inhibition and neuraminidase inhibition suggested that compound 15a inhibited virus-induced hemagglutination with no effect on the enzymatic activity of neuraminidase, indicating that the antiviral activity appeared to be mediated via interaction with hemagglutinin at the initial stage of viral infection.
Published: 2017

42. Gastroprotective Effect of Aucubin against Ethanol-Induced Gastric Mucosal Injury in Mice

Author: Bing Yin, Wenji Sun, Yang Li, Xin Wen, Yongmin Zhang, Ye Zhao, Ziyang Chen, Jiao He, Yang Yang, Le Lv, Ziye Wang, Key Laboratory of Resource Biology and Biotechnology, Northwest University, Xi'an, Northwest University [Xi'an], Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, Male, POLE 3, Anti-Inflammatory Agents, Pharmacology, Ulcer index, medicine.disease_cause, Antioxidants, chemistry.chemical_compound, Mice, 0302 clinical medicine, Oral administration, Malondialdehyde, General Pharmacology, Toxicology and Pharmaceutics, biology, General Medicine, Glutathione, 3. Good health, Up-Regulation, Vascular endothelial growth factor, GOBS, medicine.anatomical_structure, 030220 oncology & carcinogenesis, Myeloperoxidase, Seeds, Cytokines, Iridoid Glucosides, General Biochemistry, Genetics and Molecular Biology, 03 medical and health sciences, Gastric mucosa, medicine, Animals, [CHIM]Chemical Sciences, HSP70 Heat-Shock Proteins, Stomach Ulcer, Aucubin, Peroxidase, Dose-Response Relationship, Drug, Ethanol, business.industry, Interleukin-6, Tumor Necrosis Factor-alpha, Eucommiaceae, Disease Models, Animal, Oxidative Stress, 030104 developmental biology, chemistry, Gastric Mucosa, biology.protein, business, Oxidative stress
Abstract: Aucubin, an iridoid glycoside, was isolated from seeds of Eucommia ulmoides Oliver. This study was aimed to evaluate the protective effect of aucubin against ethanol-induced gastric mucosal injury in mice.Mice were orally administrated with aucubin (20, 40 and 80mg/kg) for 3 consecutive days. On the 3rd day, the mice of gastric mucosal injury were induced with 70% ethanol after the last administration of aucubin. Gastric tissue of mice were submitted for evaluating the severity of gastric mucosal injury. The protective effect of aucubin was evaluated by the gastric ulcer index and histological examinations and determining the levels of inflammatory cytokines, oxidative stress and some gastric mucosal protection factors.Prophylactic oral administration of aucubin decreased gastric ulcer indexes and histological scores. A significant decrease of myeloperoxidase (MPO) activity and the levels of malondialdehyde (MDA), tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) were observed in aucubin administrated groups. In addition, mice administrated with aucubin increased glutathione (GSH) and heat shock protein-70 (HSP-70) levels and superoxide dismutase (SOD) activity, as well as normalized the levels of epidermal growth factor (EGF), vascular endothelial growth factor (VEGF) and cyclooxygenase-1 (COX-1) in gastric tissue of mice.The findings of this study demonstrated that aucubin shows protective effect against ethanol-induced acute gastric mucosal injury through its anti-inflammatory and anti-oxidant effects. Furthermore, aucubin enhanced gastric mucosal protection by up-regulation of HSP-70 level and normalization of EGF, VEGF and COX-1 levels.
Published: 2017

43. Secondary-Rim γ-Cyclodextrin Functionalization to Conjugate with C60: Improved Efficacy as Photosensitizer

Author: Xiaolei Zhu, Matthieu Sollogoub, Yongmin Zhang, Annamaria Quaranta, René V. Bensasson, Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), CEA Saclay, Département de Biologie Cellulaire et Moléculaire, Section de Bioénergétique, Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Molécules de Communication et Adaptation des Micro-organismes (MCAM), Muséum national d'Histoire naturelle (MNHN)-Centre National de la Recherche Scientifique (CNRS), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Aqueous solution, POLE 3, 010405 organic chemistry, Chemistry, Singlet oxygen, gamma-CD * secondary rim * C60 * aggregation * photosensitizer, Organic Chemistry, Quantum yield, General Chemistry, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, GOBS, Surface modification, [CHIM]Chemical Sciences, Photosensitizer, Order of magnitude, Demethylation, Conjugate
Abstract: DIBAL-H-mediated demethylation provides a novel method to access secondary-rim functionalized γ-cyclodextrin. 2A ,3B -Dihydroxyl-per-O-methylated-γ-cyclodextrin has been obtained, whose conjugation with C60 allows access to the most water-soluble C60 conjugate described so far. The water solubility of 0.12 m (550 mg mL-1 ) is 150 times higher than that of the native γ-CD/C60 complex. Its singlet oxygen (1 O2 ) quantum yield is 0.39, an increase of one to two orders of magnitude compared to that of α(β)CD-C60 conjugates.
Published: 2017

44. Synthesis and Anti-Oxidant Activity Evaluation of (±)-Anastatins A, B and Their Analogs

Author: Peng Yu, Guojun Pan, Yuou Teng, Kui Lu, Long Zhao, Xuehui Li, Su Chao, Yong-Min Zhang, Xuzhe Li, Meng Wu, Tianjin University of Science and Technology (TUST), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, Antioxidant, Double bond, POLE 3, Stereochemistry, medicine.medical_treatment, Apoptosis, PC12 Cells, 01 natural sciences, Antioxidants, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, Suzuki reaction, Drug Discovery, Aurone, medicine, Animals, [CHIM]Chemical Sciences, Benzofuran, Hydrogen peroxide, Flavonoids, Pharmacology, chemistry.chemical_classification, Dose-Response Relationship, Drug, Molecular Structure, 010405 organic chemistry, Organic Chemistry, Halogenation, Hydrogen Peroxide, General Medicine, Carbon-13 NMR, Rats, 0104 chemical sciences, GOBS, 030104 developmental biology, chemistry
Abstract: Two novel flavonoids (±)-Anastatins A and B as well as 14 analogs, which containing a benzofuran moiety, were synthesized by using halogenation, Suzuki coupling reaction and an oxidation/Oxa-Michael reaction cascade as the key steps. The structures of the new flavonoids were confirmed by 1 H NMR, 13 C NMR and HRMS. The antioxidant activities of them as well as the key intermediates were evaluated by ferric reducing antioxidant power (FRAP) assay and the active compounds were evaluated in the PC12 cell model of hydrogen peroxide (H 2 O 2 )-induced oxidative damage. SAR studies suggested that, for in vitro antioxidant activity, aurone derivatives showed better bioactivity than flavone counterparts. However, cyclization to benzofuran and connecting the two conjugated parts as a whole conjugated system by a double bond diminished the in vitro antioxidant activity. Among them, the most potent compound 24c was significantly decreased H 2 O 2 -caused cell injury. The apoptotic rate (Annexin V + ) of H 2 O 2 -damaged PC12 cells was 60.7% while that of the compound 24c -treated cells decreased to 5.9% and 4.1% at 10 μM and 100 μM respectively.
Published: 2017

45. Synthesis of 6-Hydroxyaurone Analogues and Evaluation of Their α-Glucosidase Inhibitory and Glucose Consumption-Promoting Activity: Development of Highly Active 5,6-Disubstituted Derivatives

Author: Runling Wang, Hua Sun, Kaili Wang, Dong Wang, Weina Ding, Robert H. Dodd, Yazhou Zhang, Kui Lu, Peng Yuan, Ying Ma, Xiaotong Song, Chen Mingzhu, Yongmin Zhang, Peng Yu, Tianjin University of Science and Technology (TUST), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
Subjects: POLE 3, Stereochemistry, Clinical Biochemistry, Substituent, Pharmaceutical Science, Saccharomyces cerevisiae, 010402 general chemistry, Inhibitory postsynaptic potential, 01 natural sciences, Biochemistry, chemistry.chemical_compound, Drug Discovery, medicine, Humans, Potency, [CHIM]Chemical Sciences, Glycoside Hydrolase Inhibitors, Molecular Biology, IC50, Benzofurans, Acarbose, 010405 organic chemistry, Aryl, Organic Chemistry, alpha-Glucosidases, Hep G2 Cells, In vitro, 0104 chemical sciences, Molecular Docking Simulation, GOBS, Glucose, chemistry, Docking (molecular), Molecular Medicine, medicine.drug
Abstract: A series of 6-hydroxyaurones and their analogues have been synthesized and evaluated for their in vitro α-glucosidase inhibitory and glucose consumption-promoting activity. These compounds exhibited varying degrees of α-glucosidase inhibitory activity, 11 of them showing higher potency than that of the control standard acarbose (IC50=50.30μM). Surprisingly, analogues devoid of a substituent at C-2 but having an aryl group at C-5 were found to be highly active (e.g., 7f, IC50=9.88μM). Docking analysis substantiated these findings. The kinetic analysis of compound 7f, the most potent α-glucosidase inhibitor of this study, revealed that it inhibited α-glucosidase in an irreversible and mixed competitive mode. In addition, compounds 7f and 10c exhibited significant glucose consumption promoting activity at 1μM.
Published: 2017

46. The Preparation of Three Selenium-Containing Cordyceps Militaris Polysaccharides: Characterization and Anti-Tumor Activities

Author: Fei Liu, Zhen-Yuan Zhu, Yong-Min Zhang, Xiaoli Sun, Hui Gao, Tianjin University of Science and Technology (TUST), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: POLE 3, chemistry.chemical_element, Antineoplastic Agents, 02 engineering and technology, Polysaccharide, 01 natural sciences, Biochemistry, chemistry.chemical_compound, Selenium, Structural Biology, Polysaccharides, Cordyceps militaris, Monosaccharide, Humans, [CHIM]Chemical Sciences, Molecular Biology, chemistry.chemical_classification, biology, 010405 organic chemistry, Monosaccharides, General Medicine, Nuclear magnetic resonance spectroscopy, Hep G2 Cells, 021001 nanoscience & nanotechnology, biology.organism_classification, In vitro, 0104 chemical sciences, Congo red, GOBS, chemistry, Cordyceps, 0210 nano-technology, Graphite furnace atomic absorption, Nuclear chemistry
Abstract: In the present work, three fractions of selenized Cordyceps militaris polysaccharides (SeCPS) named SeCPS- I, SeCPS- II and SeCPS- III were isolated and purified by ultra-filtration. Their selenium content were measured as 541.3, 863.7 and 623.3μg/g respectively by a graphite furnace atomic absorption spectroscopy. The monosaccharide comformation analysis showed that they were mainly consisted of D-Mannose, D-Glucose, and D-Galactose in mole ratios of 1:7.63:0.83, 1:1.34:0.31 and 1:3.77:0.41 respectively. Their structure characteristics were compared by IFR and NMR spectroscopy. Scanning electron microscopy (SEM) and Congo red (CR) spectrophotometric method were used to investigate their morphological characteristics and conformational transition. SeCPS-II showed the strongest anti-tumor effects judging from the result of in vitro anti-tumor assays against two tumor cell lines (hepatocellular carcinoma HepG-2 cells and lung adenocarcinom A549 cells).
Published: 2017

47. The Background to Electrospray

Author: Richard B. Cole, Bing Guan, University of New Orleans, Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Electrospray, History, POLE 3, William Henley, 02 engineering and technology, Jean-Antoine Nollet, Malcolm Dole, William Gilbert, Lord Kelvin, 01 natural sciences, Lord Rayleigh, William Thomson, 0103 physical sciences, Mass analyzer, Geoffrey Taylor, Harold Ransburg, [CHIM]Chemical Sciences, 010306 general physics, Literature, John Ellicott, business.industry, Environmental ethics, W. A. Macky, 021001 nanoscience & nanotechnology, Sir Thomas Browne, John Zeleny, Electrospray history, Electrostatic attraction, Electrospray development, Stephen Gray, John William Strutt, 0210 nano-technology, business, CSOB
Abstract: International audience; This article traces the development of electrospray back to its earliest beginnings. Many readers may be surprised to learn that descriptions of the electrostatic attraction of liquids to surfaces appear in the scientific literature as early as the year 1600, and that true electrospray experiments are documented to have been performed in the eighteenth century. Progress in the development of electrospray is detailed through these earliest observations and subsequent ingenious applications, mathematical descriptions, and, finally, coupling to mass analyzer instrumentation.
Published: 2016

48. Negative Ion MALDI Mass Spectrometry of Polyoxometalates (POMs): Mechanism of Singly Charged Anion Formation and Chemical Properties Evaluation

Author: Richard B. Cole, Jean E. Boulicault, Sandra Alves, Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Chimie Structurale Organique et Biologique (CSOB), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: POLE 3, Chemistry, 010401 analytical chemistry, Cationic polymerization, Analytical chemistry, 010402 general chemistry, Mass spectrometry, 01 natural sciences, 0104 chemical sciences, Adduct, Ion, Crystallography, Electron transfer, Fragmentation (mass spectrometry), Structural Biology, Mass spectrum, [CHIM]Chemical Sciences, Sample preparation, CSOB, Spectroscopy
Abstract: MALDI-MS has been developed for the negative ion mode analysis of polyoxometalates (POMs). Matrix optimization was performed using a variety of matrix compounds. A first group of matrixes offers MALDI mass spectra containing abundant intact singly charged anionic adduct ions, as well as abundant in-source fragmentations at elevated laser powers. A relative ranking of the ability to induce POM fragmentation is found to be: DAN > CHCA > CNA > DIT> HABA > DCTB > IAA. Matrixes of a second group provide poorer quality MALDI mass spectra without observable fragments. Sample preparation, including the testing of salt additives, was performed to optimize signals for a model POM, POMc12, the core structure of which bears four negative charges. The matrix 9-cyanoanthracene (CNA) provided the best signals corresponding to singly charged intact POMc12 anions. Decompositions of these intact anionic species were examined in detail, and it was concluded that hydrogen radical-induced mechanisms were not prevalent, but rather that the observed prompt fragments originate from transferred energy derived from initial electronic excitation of the CNA matrix. Moreover, in obtained MALDI mass spectra, clear evidence of electron transfer to analyte POM species was found: a manifestation of the POMs ability to readily capture electrons. The affinity of polyanionic POMc12 toward a variety of cations was evaluated and the following affinity ranking was established: Fe(3+) > Al(3+) > Li(+) > Ga(3+) > Co(2+) > Cr(3+) > Cu(2+) > [Mn(2+), Mg(2+)] > [Na(+), K(+)]. Thus, from the available cationic species, specific adducts are preferentially formed, and evidence is given that these higher affinity POM complexes are formed in the gas phase during the early stages of plume expansion. Graphical Abstract ᅟ.
Published: 2016

49. Carbohydrate\textendash Carbohydrate Interaction: From Hypothesis to Confirmation

Author: Zhang, Yanyan, Lu, Dan, Sollogoub, Matthieu, Zhang, Yongmin, Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: GOBS, animal structures, POLE 3, [CHIM]Chemical Sciences, psychological phenomena and processes, nervous system diseases
Abstract: International audience; Carbohydrates play important roles in a wide range of biological processes. Since the first hypothesis about carbohydrate\textendash carbohydrate interaction (CCI) was proposed by Hakomori et al., an increasing interest has been placed on CCI, using a variety of techniques. Based on all these studies, Lewisx\textendash Lewisx interaction (a typical CCI) has been now confirmed to be specific, homotypic, and mediated by the presence of divalent cations such as Ca2+. In this review, a detailed overview of the process from hypothesis to confirmation of carbohydrate\textendash carbohydrate interaction is summarized.
Published: 2016

50. Naphthoquinones from Onosma Paniculatum with Potential Anti-Inflammatory Activity

Author: Kai Luo, Yong-Min Zhang, Dan Liu, Rong-Tao Li, Miao Dong, Xuan-Qin Chen, Yan-Hong Li, Kunming University of Science and Technology (KMUST), Paris School of Business (PSB), HESAM Université - Communauté d'universités et d'établissements Hautes écoles Sorbonne Arts et métiers université (HESAM), Glycochimie Organique Biologique et Supramoléculaire (GOBS), Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: POLE 3, medicine.drug_class, Stereochemistry, Nitric oxide biosynthesis, Pharmaceutical Science, Onosma paniculatum, Nitric Oxide, 01 natural sciences, Plant Roots, Anti-inflammatory, Analytical Chemistry, chemistry.chemical_compound, Mice, Drug Discovery, medicine, Animals, [CHIM]Chemical Sciences, No production, IC50, RAW 264.7 Cells, Pharmacology, biology, 010405 organic chemistry, Chemistry, Organic Chemistry, Anti-Inflammatory Agents, Non-Steroidal, Boraginaceae, biology.organism_classification, Naphthoquinone, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, GOBS, Complementary and alternative medicine, Molecular Medicine, Drugs, Chinese Herbal, Naphthoquinones
Abstract: Four new naphthoquinones (1–4), including a dimeric one, shikometabolin G (1), together with six known ones (6–10), were isolated from the methanol extract of Onosma paniculatum. Their structures were established based on the analysis of NMR and MS spectroscopic data. All of the compounds were evaluated for inhibitory effects on NO production in murine macrophage RAW 264.7 cells. Compounds 2, 3, 5, 6, 7, 8, and 10 displayed good activity on the inhibition of NO production (IC50 = 0.4–16.5 µM), suggesting the potential property of anti-inflammation.
Published: 2016

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