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1. Chemography: Searching for Hidden Treasures

Author

Alexandre Varnek, Dmitriy M. Volochnyuk, Dragos Horvath, Gilles Marcou, Arkadii Lin, Yuliana Zabolotna, Chimie de la matière complexe (CMC), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chémoinformatique, Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institute of Organic Chemistry of NASU [Kyiv], and National Academy of Sciences of Ukraine (NASU)

Subjects
Engineering, 010304 chemical physics, business.industry, Chemistry, Pharmaceutical, General Chemical Engineering, General Chemistry, Library and Information Sciences, 01 natural sciences, 0104 chemical sciences, Computer Science Applications, World Wide Web, 010404 medicinal & biomolecular chemistry, 0103 physical sciences, business, [CHIM.CHEM]Chemical Sciences/Cheminformatics
Abstract

International audience; The days when medicinal chemistry was limited to a few series of compounds of therapeutic interest are long gone. Nowadays, no human may succeed to acquire a complete overview of more than a billion existing or feasible compounds within which the potential “blockbuster drugs” are well hidden and yet only a few mouse clicks away. To reach these “hidden treasures”, we adapted the generative topographic mapping method to enable efficient navigation through the chemical space, from a global overview to a structural pattern detection, covering, for the first time, the complete ZINC library of purchasable compounds, relative to 1.6 million biologically relevant ChEMBL molecules. About 40 000 hierarchical maps of the chemical space were constructed. Structural motifs inherent to only one library were identified. Roughly 20 000 off-market ChEMBL compound families represent incentives to enrich commercial catalogs. Alternatively, 125 000 ZINC-specific compound classes, absent in structure–activity bases, are novel paths to explore in medicinal chemistry. The complete list of these chemotypes can be downloaded using the link https://forms.gle/B6bUJj82t9EfmttV6.

Published
2020
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2. (Thia)calixarenephosphonic Acids as Potent Inhibitors of the Nucleic Acid Chaperone Activity of the HIV-1 Nucleocapsid Protein with a New Binding Mode and Multitarget Antiviral Activity

Author

Nicolas Humbert, Maurizio Botta, Federica Poggialini, Eleonore Real, Manuel Pires, Christian Boudier, Vitaly I. Kalchenko, Yves Mély, Alessia Giannini, Maurizio Zazzi, Carole Seguin-Devaux, Sarah Cianférani, S. O. Cherenok, Kamal Kant Sharma, Mattia Mori, Francesco Saladini, Thomas Botzanowski, Lesia Kovalenko, Olga A. Zaporozhets, Laboratoire de Bioimagerie et Pathologies (LBP), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Département Sciences Analytiques et Interactions Ioniques et Biomoléculaires (DSA-IPHC), Institut Pluridisciplinaire Hubert Curien (IPHC), Université de Strasbourg (UNISTRA)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Centre National de la Recherche Scientifique (CNRS), National Taras Shevchenko University of Kiev, Centre de Recherche Public de la Santé, Università degli Studi di Siena = University of Siena (UNISI), Institute of Organic Chemistry of NASU [Kyiv], and National Academy of Sciences of Ukraine (NASU)

Subjects
0301 basic medicine, calixarenes, Anti-HIV Agents, 030106 microbiology, Organophosphonates, Aucun, Mice, Transgenic, Molecular Dynamics Simulation, 03 medical and health sciences, chemistry.chemical_compound, Inhibitory Concentration 50, Mice, Calixarene, Animals, [CHIM]Chemical Sciences, Zinc finger, biology, Chemistry, Isothermal titration calorimetry, Nucleocapsid Proteins, NC inhibitors, Phosphonate, Reverse transcriptase, 3. Good health, 030104 developmental biology, Infectious Diseases, Biochemistry, Chaperone (protein), biology.protein, Nucleic acid, HIV-1, fluorescence, Fluorescence anisotropy, nucleocapsid protein, Molecular Chaperones, Protein Binding
Abstract

International audience; The nucleocapsid protein (NC) is a highly conserved protein that plays key roles in HIV-1 replication through its nucleic acid chaperone properties mediated by its two zinc fingers and basic residues. NC is a promising target for antiviral therapy, particularly to control viral strains resistant to currently available drugs. Since calixarenes with antiviral properties have been described, we explored the ability of calixarene hydroxymethylphosphonic or sulfonic acids to inhibit NC chaperone properties and exhibit antiviral activity. By using fluorescence-based assays, we selected four calixarenes inhibiting NC chaperone activity with submicromolar IC50 values. These compounds were further shown by mass spectrometry, isothermal titration calorimetry, and fluorescence anisotropy to bind NC with no zinc ejection and to compete with nucleic acids for the binding to NC. Molecular dynamic simulations further indicated that these compounds interact via their phosphonate or sulfonate groups with the basic surface of NC but not with the hydrophobic plateau at the top of the folded fingers. Cellular studies showed that the most soluble compound CIP201 inhibited the infectivity of wild-type and drug-resistant HIV-1 strains at low micromolar concentrations, primarily targeting the early steps of HIV-1 replication. Moreover, CIP201 was also found to inhibit the flipping and polymerization activity of reverse transcriptase. Calixarenes thus form a class of noncovalent NC inhibitors, endowed with a new binding mode and multitarget antiviral activity.

Published
2020
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3. Synthesis of an enantiomerically pure inherently chiral calix[4]arene phosphonic acid and its evaluation as an organocatalyst

Author

Eric Manoury, V. I. Boiko, Jean-Claude Daran, Oleksandr A. Yesypenko, Andrii Karpus, Vitaly I. Kalchenko, Zoia Voitenko, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), National Taras Shevchenko University of Kiev, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, National Academy of Sciences of Ukraine (NASU), and Institute of Organic Chemistry of NASU [Kyiv]

Subjects
Organophosphorus compounds, Aromatic compounds, 010405 organic chemistry, Organic Chemistry, Epoxide, Reaction products, Molecules, 010402 general chemistry, Inherent chirality, 01 natural sciences, Hydrocarbons, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Organocatalysis, Calixarene, Organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Enantiomer, Brønsted–Lowry acid–base theory, Benzoic acid
Abstract

International audience; A facile method for the preparation of enantiomerically pure inherently chiral calix[4]arene phosphonic acid (cR,pR)-7 in four steps starting from the readily available and previously synthesized (cS)-enantiomer of calix[4]arene acetic acid 1 or its methyl ester 2 was developed. The first tests of this unique calixarene Brönsted acid with inherent chirality in organocatalysis of the aza-Diels–Alder reaction of imines with Danishefsky’s diene and epoxide ring opening by benzoic acid were performed. The calixarene phosphonic acid (cR,pR)-7 shows good catalytic activities but with low enantioselectivities in these reactions.

Published
2018
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4. Exploring the effects of trifluoromethyl group in the design of organocatalysts, enzyme inhibitors and in the conformational control of saturated nitrogen-containing heterocycles

Author

Sukach, Volodymyr, Melnykov, Sergii, Bertho, Sylvain, Retailleau, Pascal, Vovk, Mykhailo, Gillaizeau, Isabelle, Studium, Le, Le Studium Loire Valley Institute for Advanced Studies, 45000 Orléans, France, Institut de Chimie Organique et Analytique (ICOA), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institute of Organic Chemistry of NASU [Kyiv], National Academy of Sciences of Ukraine (NASU), Enamine Ltd, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), and This project has been supported by LE STUDIUM Loire Valley Institute for Advanced Studies, Orléans & Tours, France with funding from the European Union's Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No. 665790

Subjects
[SDV] Life Sciences [q-bio], b-amino acids, [SDV]Life Sciences [q-bio], Organofluorine compounds, trifluoromethyl group, decarboxylative addition, ketimines
Abstract

This is the final version of the article, which has been published in final form at : http://www.lestudium-ias.com/content/exploring-effects-trifluoromethyl-group-design-organocatalysts-enzyme-inhibitors-and-0; The fluoroalkyl group plays an important role in the design of novel pharmacologically active agents since its introduction into organic compounds often leads to improved potency, stability and activity. Herein we wish to report an application of fluoroalkyl ketimines in decarboxylative Mannich reaction with a focus on the chemistry of unprotected NH-ketimines and heterocyclic ketimines. This study addresses the influence of the N-unprotected form of the ketimine function on the efficiency and selectivity of decarboxylative addition of malonic acid and its derivatives. The methods developed provide straightforward access to a range of valuable fluoroalkyl -amino acids and their derivatives promising as novel organofluorine building blocks.

Published
2018
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5. Dramatic Changes in the Solubilities of Ions Induced by Ligand Addition in Biphasic System D2O/DNO3//[C1C4im][Tf2N]: A Phenomenological Study

Author

Laure Cointeaux, Maria Petrova, Dariia Ternova, Ali Ouadi, Vitaly I. Kalchenko, Nicolas Papaiconomou, Isabelle Billard, Valérie Mazan, S. I. Miroshnichenko, Maria Boltoeva, Clotilde Gaillard, Prasanta K. Mohapatra, Département Recherches Subatomiques (DRS-IPHC), Institut Pluridisciplinaire Hubert Curien (IPHC), Université de Strasbourg (UNISTRA)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'Electrochimie et de Physico-chimie des Matériaux et des Interfaces (LEPMI ), Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Institut de Physique Nucléaire de Lyon (IPNL), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'Electrochimie et de Physico-chimie des Matériaux et des Interfaces (LEPMI), Université Grenoble Alpes (UGA)-Université Joseph Fourier - Grenoble 1 (UJF)-Institut National Polytechnique de Grenoble (INPG)-Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP)-Centre National de la Recherche Scientifique (CNRS), Institute of Organic Chemistry of NASU [Kyiv], National Academy of Sciences of Ukraine (NASU), Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Institut de Chimie du CNRS (INC)-Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3), Bhabha Atomic Research Centre (BARC), and Government of India, Department of Atomic Energy

Subjects
Aqueous solution, Tributylphosphine oxide, 010405 organic chemistry, Chemistry, Ligand, Significant difference, Inorganic chemistry, Protonation, [CHIM.MATE]Chemical Sciences/Material chemistry, [CHIM.INOR]Chemical Sciences/Inorganic chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Surfaces, Coatings and Films, Ion, chemistry.chemical_compound, Ionic liquid, Materials Chemistry, Physical and Theoretical Chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience; The solubilities of C 1 C 4 im + and Tf 2 N − in nitric aqueous phases have been measured for several ligand types and concentrations (0.04 M tributylphosphine oxide, 0.05 M N,N′-dimethyl-N,N′-dibutylmalonamide, 0.10 M 1-methyl-3-[4-(dibutylphosphinoyl)butyl]-3H-imidazol-1-ium bis(trifluoromethylsulphonyl)imidate, and 1.1 M N,N-dihexyloctanamide). The data evidence a significant difference between the solubilities of the cations and anions of the ionic liquid as a consequence of several ion-exchange and/or ion-pairing mechanisms involving all ions present in the system as well as the protonation/nitric-extraction ability of the ligand.

Published
2016
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6. Synthesis of polyfluoroalkyl containing thiopyran derivatives and their applications in fluoroorganic chemistry

Author

Sergiy A. Siry, Jean-Philippe Bouillon, Vadim M. Timoshenko, Institute of Organic Chemistry of NASU [Kyiv], National Academy of Sciences of Ukraine (NASU), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Thiopyran, Double bond, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Organic Chemistry, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, Sulfur, Cycloaddition, 0104 chemical sciences, Inorganic Chemistry, Elimination reaction, chemistry.chemical_compound, chemistry, Nucleophile, Fluorine, Environmental Chemistry, Organic chemistry, Physical and Theoretical Chemistry, ComputingMilieux_MISCELLANEOUS, Biological evaluation
Abstract

An overview of syntheses and chemical properties of polyfluoroalkyl 2 H - and 4 H -thiopyrans, their hydrogenated (3,4- and 3,6-dihydrothiopyrans, and tetrahydrothiopyrans) and S-oxidized derivatives is presented. The first part is devoted to the synthetic methods starting from acyclic or cyclic precursors, and on multicomponent reactions. The second one deals with the chemical properties of thiopyran derivatives such as elimination reactions, [4+2] cycloadditions, sulfur or C C double bond oxidations, and reactions with nucleophiles. The last part is focused on the biological evaluation of polyfluoroalkyl 2 H -thiopyrans, especially as potential cardiotonic agents.

Published
2012
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7. Evidence for the formation of UO2(NO3)42− in an ionic liquid by EXAFS

Author

Olga Klimchuk, Christoph Hennig, Ali Ouadi, Clotilde Gaillard, Isabelle Billard, Institut de Physique Nucléaire de Lyon (IPNL), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3), Institut Pluridisciplinaire Hubert Curien (IPHC), Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Institute of Organic Chemistry of NASU [Kyiv], National Academy of Sciences of Ukraine (NASU), Laboratoire d'Electrochimie et de Physico-chimie des Matériaux et des Interfaces (LEPMI ), Institut de Chimie du CNRS (INC)-Institut National Polytechnique de Grenoble (INPG)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Université Joseph Fourier - Grenoble 1 (UJF)-Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])-Centre National de la Recherche Scientifique (CNRS), Institute of Resource Ecology [Dresden] (IRE), and Helmholtz-Zentrum Dresden-Rossendorf (HZDR)

Subjects
Extended X-ray absorption fine structure, 010405 organic chemistry, Inorganic chemistry, chemistry.chemical_element, Ionic Liquids, Uranium, 010402 general chemistry, UO2(NO3)42, 01 natural sciences, 0104 chemical sciences, Ion, Inorganic Chemistry, chemistry.chemical_compound, EXAFS, chemistry, Uranyl nitrate, Nitrate, Ionic liquid, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Imide, Dissolution, [CHIM.RADIO]Chemical Sciences/Radiochemistry
Abstract

The complexation between uranium(vi) and nitrate ions in a hydrophobic ionic liquid (IL), namely [BMI][NO(3)] (BMI = 1-butyl-3-methylimidazolium(+)), is investigated by EXAFS spectroscopy. It was performed by dissolution of uranyl nitrate UO(2)(NO(3))(2)·6H(2)O or UO(2)(Tf(2)N)(2) (Tf(2)N = bis(trifluoromethylsulfonyl)imide (CF(3)SO(2))(2)N(-)). The formation of the complex UO(2)(NO(3))(4)(2-) is evidenced.

Published
2012
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8. Interfacial Interactions of Cations with Amphiphilic Dihydroxyphosphonyl-calix-[4]-arene Mesosystems

Author

Emeline Houel, Vitaly I. Kalchenko, Sergey Cherenok, Eric Da Silva, Adina N. Lazar, Anthony W. Coleman, Andrew Solovyov, Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Laboratoire de Neuropathologie Raymond Escourolle [CHU Pitié-Salpétriêre], CHU Pitié-Salpêtrière [AP-HP], Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP), Catalyse Synthèse et Environnement (CASYEN), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École Supérieure de Chimie Physique Électronique de Lyon (CPE)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire des Multimatériaux et Interfaces (LMI), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institute of Organic Chemistry of NASU [Kyiv], National Academy of Sciences of Ukraine (NASU), Institut de biologie et chimie des protéines [Lyon] (IBCP), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Neuropathologie Raymond Escourolle, Sorbonne Université (SU)-Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Sorbonne Université (SU)-Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), Université des Antilles (UA)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-AgroParisTech-Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA), Assistance publique - Hôpitaux de Paris (AP-HP) (APHP)-CHU Pitié-Salpêtrière [APHP]-Sorbonne Université (SU), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)

Subjects
Langmuir, Nanostructure, Analytical chemistry, Aqueous dispersion, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Chloride, Colloid, Monolayer, Amphiphile, Electrochemistry, medicine, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, General Materials Science, Spectroscopy, ComputingMilieux_MISCELLANEOUS, Chemistry, Atomic force microscopy, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Surfaces and Interfaces, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 0104 chemical sciences, Physical chemistry, 0210 nano-technology, medicine.drug
Abstract

Two novel amphiphilic phosphorylated-calix-[4]-arenes, 5,11,17,23-tetrakis(dihydroxyphosphonyl)-25,26,27,28-tetradecyloxy-calix-[4]-arene and 5,11,17,23-tetrakis(dihydroxyphosphonyl)-25,26,27,28-tetradodecyloxy-calix-[4]-arene, have been synthesized, and their interactions with the cations Na+, K+, Mg2+, and Ca2+ have been measured at varying concentrations of the chloride salts. The systems were studied both at the air−water interface and in aqueous suspension as colloidal nanostructures. In the Langmuir experiments, monolayer expansion and increase in collapse pressure were observed for Na+ at a concentration of 145 mM. For Mg2+, there was monolayer expansion accompanied by the formation of a second phase at a subphase concentration of 30 mM. In contrast, in the case of Ca2+ there is an apparent contraction of the monolayer. The nanostructures were imaged by means of atomic force microscopy in the noncontact mode. As aqueous dispersions, no change in size or stability of the colloidal systems was observ...

Published
2002
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