Author: "Arnaud Rives" - Searchworks@Jio Institute Digital Library Search Results

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32 results on '"Arnaud Rives"'

1. Dendrogenin A drives LXR to trigger lethal autophagy in cancers

Author: Gregory Segala, Marion David, Philippe de Medina, Mathias C. Poirot, Nizar Serhan, François Vergez, Aurelie Mougel, Estelle Saland, Kevin Carayon, Julie Leignadier, Nicolas Caron, Maud Voisin, Julia Cherier, Laetitia Ligat, Frederic Lopez, Emmanuel Noguer, Arnaud Rives, Bruno Payré, Talal al Saati, Antonin Lamaziere, Gaëtan Despres, Jean-Marc Lobaccaro, Silvere Baron, Cecile Demur, Fabienne de Toni, Clément Larrue, Helena Boutzen, Fabienne Thomas, Jean-Emmanuel Sarry, Marie Tosolini, Didier Picard, Michel Record, Christian Récher, Marc Poirot, and Sandrine Silvente-Poirot
Subjects: Science
Abstract: Dendrogenin A, cholesterol metabolite, has tumor suppressive properties but the mechanisms are unknown. Here the authors show that Dendrogenin A can induce autophagy-mediated cell death in both melanoma and acute myeloid leukaemia.
Published: 2017
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2. Selective Targeting of the Interconversion between Glucosylceramide and Ceramide by Scaffold Tailoring of Iminosugar Inhibitors

Author: Cécile Baudoin-Dehoux, Tessa Castellan, Frédéric Rodriguez, Arnaud Rives, Fabien Stauffert, Virginie Garcia, Thierry Levade, Philippe Compain, and Yves Génisson
Subjects: iminosugars, glucocerebrosidase, pharmacological chaperones, glycosidase inhibitors, glucosylceramide synthase inhibitors, Gaucher disease, ligand docking, Organic chemistry, QD241-441
Abstract: A series of simple C-alkyl pyrrolidines already known as cytotoxic inhibitors of ceramide glucosylation in melanoma cells can be converted into their corresponding 6-membered analogues by means of a simple ring expansion. This study illustrated how an isomerisation from iminosugar pyrrolidine toward piperidine could invert their targeting from glucosylceramide (GlcCer) formation toward GlcCer hydrolysis. Thus, we found that the 5-membered ring derivatives did not inhibit the hydrolysis reaction of GlcCer catalysed by lysosomal β-glucocerebrosidase (GBA). On the other hand, the ring-expanded C-alkyl piperidine isomers, non-cytotoxic and inactive regarding ceramide glucosylation, revealed to be potent inhibitors of GBA. A molecular docking study showed that the positions of the piperidine ring of the compound 6b and its analogous 2-O-heptyl DIX 8 were similar to that of isofagomine. Furthermore, compound 6b promoted mutant GBA enhancements over 3-fold equivalent to that of the related O-Hept DIX 8 belonging to one of the most potent iminosugar-based pharmacological chaperone series reported to date.
Published: 2019
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3. HPLC Analysis and Skin Whitening Effects of Umbelliprenin-containing Extracts of Anethum Graveolens, Pimpinella Anisum, and Ferulago Campestris

Author: Vito Alessandro Taddeo, Francesco Epifano, Francesca Preziuso, Serena Fiorito, Nicolas Caron, Arnaud Rives, Philippe de Medina, Marc Poirot, Sandrine Silvente-Poirot, and Salvatore Genovese
Subjects: anise, apiaceae, dill, field ferula, melanin, melanogenesis, oxyprenylated coumarins, skin whitening effect, umbelliprenin, Organic chemistry, QD241-441
Abstract: Umbelliprenin has recently been shown to have great potential as a skin whitening agent. Wishing to investigate the same effect in plant species known to biosynthesize this coumarin, three plants belonging to the Apiaceae family, namely Anethum graveolens L. (dill), Pimpinella anisum L. (anise), and Ferulago campestris (Besser) Grecescu (field ferula) were screened by HPLC analysis for their respective content of umbelliprenin in extracts obtained with different solvent mixtures and by maceration and ultrasound-assisted processes. EtOH was shown to be the best solvent, providing umbelliprenin yields ranging from 1.7% to 14.4% (with respect to the total amount of extract obtained). Extracts with the highest content of this farnesyloxycoumarin were then assayed as modulators of melanogenesis in cultured murine Melan A cells employing the same umbelliprenin obtained by chemical synthesis as the reference. A parallelism between the content of the coumarin and the recorded depigmenting effect (60% for the EtOH extract of F. campestris as the best value) was revealed for all plants extracts when applied at a dose of 100 μg/mL. Our results demonstrate that the same potential of umbelliprenin can be ascribed also to umbelliprenin-enriched plant extracts which reinforces enforce the widespread use of phyto-preparations for cosmetic purposes (e.g., A. graveolens).
Published: 2019
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4. Carbo‐mer of barrelene: a rigid 3D‐carbon‐expanded molecular barrel

Author: Brice Kauffmann, Valérie Maraval, Alix Saquet, Arnaud Rives, Albert Poater, Chongwei Zhu, Remi Chauvin, Carine Duhayon, 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), Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona (IQCC), Universitat de Girona (UdG), Institut Européen de Chimie et Biologie (IECB), Centre National de la Recherche Scientifique (CNRS)-Université de Bordeaux (UB)-Institut National de la Santé et de la Recherche Médicale (INSERM), Centre National de la Recherche Scientifique (CNRS), CNRS ЯÉCIPROCS network, and Spanish MINECO for project PGC2018-097722-B-I00
Subjects: Supramolecular chemistry, Carbo-mer, Ionic bonding, Ether, 010402 general chemistry, Electrochemistry, 01 natural sciences, Catalysis, chemistry.chemical_compound, Barrelene, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Butatriene, Alkyne, 010405 organic chemistry, Chemistry, Organic Chemistry, Covalent cage, General Chemistry, Carbon, 0104 chemical sciences, Crystallography, Charcoal, Density functional theory
Abstract: International audience; After extensive studies of 1D and 2D skeletal carbo‐mers based on C8π‐conjugatingdialkynylbutatriene units(DABs: ~C≡C–(R)C=C=C=C(R)–C≡C~) bridging spor sp2centers in carbo‐butene, ‐xylylene or ‐benzene derivatives, 3D versions are envisaged through carbo‐barrelenes and partially reduced derivatives thereofwhere two or three DAB blades span a bridge between sp3carbinol vertices or ether thereof. For R = Ph, stable representatives were synthesized through a pivotal [6]pericyclynedione, and extensively characterized by spectroscopic, electrochemical and crystallographic methods. Density functional theory calculations allow detailed analysis of structural and electronic features of the 7 Å high barrel‐shaped molecules, and show that they can behave as cages for ionic species. Beyond aesthetical concerns, the results could open prospects of applications in host‐guest supramolecular chemistry and single molecule charge transport.
Published: 2021
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5. Dendrogenin A Synergizes with Cytarabine to Kill Acute Myeloid Leukemia Cells In Vitro and In Vivo

Author: Nizar, Serhan, Pierre-Luc, Mouchel, Philippe de, Medina, Gregory, Segala, Aurélie, Mougel, Estelle, Saland, Arnaud, Rives, Antonin, Lamaziere, Gaëtan, Despres, Jean-Emmanuel, Sarry, Clément, Larrue, François, Vergez, Laetitia, Largeaud, Michel, Record, Christian, Récher, Sandrine, Silvente-Poirot, Marc, Poirot, Institut Universitaire du Cancer de Toulouse - Oncopole (IUCT Oncopole - UMR 1037), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-CHU Toulouse [Toulouse]-Institut National de la Santé et de la Recherche Médicale (INSERM), Centre de Recherches en Cancérologie de Toulouse (CRCT), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Service d'Hématologie [IUCT Toulouse], Université Fédérale Toulouse Midi-Pyrénées-Institut Universitaire du Cancer de Toulouse - Oncopole (IUCT Oncopole - UMR 1037), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-CHU Toulouse [Toulouse]-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-CHU Toulouse [Toulouse]-Institut National de la Santé et de la Recherche Médicale (INSERM), Affichem, Dendrogenix [Liège, Belgium], Microorganismes et physiopathologie intestinale (ERL INSERM U1157 - CNRS UMR 7203), Laboratoire des biomolécules (LBM UMR 7203), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Département de Chimie - ENS Paris, École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Département de Chimie - ENS Paris, Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC), Poirot, Marc, Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre Hospitalier Universitaire de Toulouse (CHU Toulouse)-Institut National de la Santé et de la Recherche Médicale (INSERM), Service Hématologie - IUCT-Oncopole [CHU Toulouse], Pôle Biologie [CHU Toulouse], Centre Hospitalier Universitaire de Toulouse (CHU Toulouse)-Centre Hospitalier Universitaire de Toulouse (CHU Toulouse)-Pôle IUCT [CHU Toulouse], Centre Hospitalier Universitaire de Toulouse (CHU Toulouse), Université Pierre et Marie Curie - Paris 6 (UPMC)-Département de Chimie - ENS Paris, École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Département de Chimie - ENS Paris, Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and This work was supported by an internal grant from the 'Institut National de la Recherche Médicale',the university of Toulouse III, Onco San Tech (projet DEMODA RMN13001BBA).
Subjects: Acute myeloid leukemia, tumor suppressor, primary cancer cells, [SDV]Life Sciences [q-bio], synergy, lcsh:Neoplasms. Tumors. Oncology. Including cancer and carcinogens, lcsh:RC254-282, Article, [SDV] Life Sciences [q-bio], hemic and lymphatic diseases, Dendrogenin A, cholesterol metabolism, lipids (amino acids, peptides, and proteins)
Abstract: International audience; Dendrogenin A (DDA) is a mammalian cholesterol metabolite that displays potent antitumor properties on acute myeloid leukemia (AML). DDA triggers lethal autophagy in cancer cells through a biased activation of the oxysterol receptor LXRβ, and the inhibition of a sterol isomerase. We hypothesize that DDA could potentiate the activity of an anticancer drug acting through a different molecular mechanism, and conducted in vitro and in vivo combination tests on AML cell lines and patient primary tumors. We report here results from tests combining DDA with antimetabolite cytarabine (Ara-C), one of the main drugs used for AML treatment worldwide. We demonstrated that DDA potentiated and sensitized AML cells, including primary patient samples, to Ara-C in vitro and in vivo. Mechanistic studies revealed that this sensitization was LXRβ-dependent and was due to the activation of lethal autophagy. This study demonstrates a positive in vitro and in vivo interaction between DDA and Ara-C, and supports the clinical evaluation of DDA in combination with Ara-C for the treatment of AML.
Published: 2020
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6. A fast UPLC–HILIC method for an accurate quantiﬁcation of dendrogenin A in human tissues

Author: Regis Soules, Etienne Chatelut, Fabien Audouard-Combe, Marc Poirot, Ben Allal, Arnaud Rives, Sandrine Silvente-Poirot, Camille Franchet, Philippe de Medina, Emilie Huc-Claustre, Florence Dalenc, Centre de Recherches en Cancérologie de Toulouse (CRCT), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Equipe Labellisée par la Ligue Nationale contre le Cancer, LNCC, Waters S.A.S. [Saint-Quentin En Yvelines, France], 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), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut Claudius-Regaud (IUCO Toulouse), Institut Universitaire du Cancer Toulouse - Oncopôle (IUCT), Institut Universitaire du Cancer de Toulouse - Oncopole (IUCT Oncopole - UMR 1037), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-CHU Toulouse [Toulouse]-Institut National de la Santé et de la Recherche Médicale (INSERM), M. Poirot and S. Silvente-Poirot's team was funded by the Institut National de la Santé et de la Recherche Médicale (INSERM), the Université de Toulouse III, the Institut National du Cancer (INCA, PRTKK15-118, PLBIO18-130), the Fondation Toulouse Cancer Santé (2017CS065), and the associations 'Céline' and 'Flo'., Equipe labellisée Ligue contre le Cancer, Affichem [Toulouse, France], Dendrogenix [Liège, Belgium], Institut Claudius Regaud, Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre Hospitalier Universitaire de Toulouse (CHU Toulouse)-Institut National de la Santé et de la Recherche Médicale (INSERM), Service Anatomie et cytologie pathologiques [CHU Toulouse], Pôle Biologie [CHU Toulouse], Centre Hospitalier Universitaire de Toulouse (CHU Toulouse)-Centre Hospitalier Universitaire de Toulouse (CHU Toulouse), Poirot, Marc, CRLCC Institut Claudius Regaud, Pôle Institut Universitaire du Cancer - Oncopole [CHU Toulouse] (Pôle IUC - Oncopole), CHU Toulouse [Toulouse]-Oncopole de Toulouse, Service d'Anatomo-Pathologie [CHU Toulouse], Centre Hospitalier Régional Universitaire de Toulouse (CHRU Toulouse), CHU Toulouse [Toulouse]-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, Endocrinology, Diabetes and Metabolism, Metabolite, [SDV]Life Sciences [q-bio], Clinical Biochemistry, Breast Neoplasms, UPLC-MS, Mass spectrometry, Biochemistry, High-performance liquid chromatography, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, Endocrinology, Oxysterol, In vivo, Quantification, [SDV.BBM] Life Sciences [q-bio]/Biochemistry, Molecular Biology, Protein precipitation, Humans, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, Breast, [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM], Molecular Biology, [SDV.BBM.BC] Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM], Chromatography, Hydrophilic interaction chromatography, Method development, Imidazoles, Cell Biology, In vitro, 3. Good health, [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biomolecules [q-bio.BM], [SDV] Life Sciences [q-bio], 030104 developmental biology, Cholesterol, chemistry, Steroidal alkaloid, Dendrogenin B, 030220 oncology & carcinogenesis, Cancer cell, Dendrogenin A, Molecular Medicine, Female, Cholestanols, Chromatography, Liquid
Abstract: International audience; Dendrogenin A (DDA) is a newly-discovered steroidal alkaloid, which remains to date the first ever found in mammals. DDA is a cholesterol metabolites that induces cancer cell differentiation and death in vitro and in vivo, and thus behave like a tumor suppressor metabolite. Preliminary studies performed on 10 patients with estrogen receptor positive breast cancers (ER(+)BC) showed a strong decrease in DDA levels between normal matched tissue and tumors. This suggests that a deregulation on DDA metabolism is associated with breast carcinogenesis. To further investigate DDA metabolism on large cohorts of patients we have developed an ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS) procedure for the quantification of DDA in liquid and in solid tissues. This method enabled the identification of DDA analogues such as its geometric isomer C17 and dendrogenin B (C26) in human samples showing that other 5,6α-epoxycholesterol conjugation products with biogenic amines exist as endogenous metabolites . We report here the first complete method of quantification of DDA in liquid and solid tissues using hydrophilic interaction liquid chromatography (HILIC). Two different methods of extraction using either a Bligh and Dyer organic extraction or protein precipitation were successfully applied to quantify DDA in solid and liquid tissues. The protein precipitation method was the fastest. The fact that this method is automatable opens up possibilities to study DDA metabolism in large cohorts of patients.
Published: 2019
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7. The cholesterol-derived metabolite dendrogenin A functionally reprograms breast adenocarcinoma and undifferentiated thyroid cancer cells

Author: Lavinia Vija-Racaru, Arnaud Mallinger, Marc Poirot, Sandrine Silvente-Poirot, Frédéric Courbon, Arnaud Rives, Bruno Payré, Philippe de Medina, Mathilde Bauriaud-Mallet, Severine Brillouet, Centre de Recherches en Cancérologie de Toulouse (CRCT), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Service de Médecine Nucléaire [Toulouse], CHU Toulouse [Toulouse], 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), Centre de Microscopie Électronique Appliquée à la Biologie (CMEAB), Hôpital de Rangueil, CHU Toulouse [Toulouse]-CHU Toulouse [Toulouse]-Toulouse Réseau Imagerie-Genotoul ( TRI-Genotoul), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), This work was supported by the Institut National de la Santé et de la Recherche Médicale (INSERM), France and the Université de Toulouse, France., Affichem, Plateforme GénotoulCMEAB, Université Fédérale Toulouse Midi-Pyrénées, Departement /u563 : Oncogenèse, Signalisation et Innovation thérapeutique, Centre de Physiopathologie Toulouse Purpan (CPTP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut Claudius Regaud, Sterol metabolism and therapeutic innovations in oncology, Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut Claudius Regaud, Centre de Physiopathologie Toulouse Purpan ex IFR 30 et IFR 150 (CPTP), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut Claudius Regaud, Institut Claudius Regaud, CRLCC Institut Claudius Regaud-CRLCC Institut Claudius Regaud-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Service de Médecine Nucléaire - Pierre-Paul Riquet [CHU Toulouse], Pôle imagerie médicale [CHU Toulouse], Centre Hospitalier Universitaire de Toulouse (CHU Toulouse)-Centre Hospitalier Universitaire de Toulouse (CHU Toulouse), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Toulouse Réseau Imagerie-Genotoul ( TRI-Genotoul), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Département de Médecine Nucléaire [CHU Toulouse], Centre Hospitalier Universitaire de Toulouse (CHU Toulouse), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), and Poirot, Marc
Subjects: 0301 basic medicine, Endocrinology, Diabetes and Metabolism, medicine.medical_treatment, Cellular differentiation, [SDV]Life Sciences [q-bio], Clinical Biochemistry, Apoptosis, [SDV.BC.BC]Life Sciences [q-bio]/Cellular Biology/Subcellular Processes [q-bio.SC], Autoantigens, Biochemistry, Iodine Radioisotopes, Mice, 0302 clinical medicine, Endocrinology, Breast cancer, Iron-Binding Proteins, Tumor Cells, Cultured, Receptor, Thyroid cancer, ComputingMilieux_MISCELLANEOUS, Symporters, biology, Chemistry, Cell Cycle, Thyroid, Imidazoles, Receptors, Thyrotropin, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, 3. Good health, [SDV] Life Sciences [q-bio], [SDV.SP] Life Sciences [q-bio]/Pharmaceutical sciences, medicine.anatomical_structure, [SDV.SP.PHARMA] Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, 030220 oncology & carcinogenesis, Differentiation, Molecular Medicine, Female, Tumor-suppressor, Mice, Nude, Antineoplastic Agents, Breast Neoplasms, [SDV.CAN]Life Sciences [q-bio]/Cancer, [SDV.BC]Life Sciences [q-bio]/Cellular Biology, Adenocarcinoma, Iodide Peroxidase, Thyroglobulin, 03 medical and health sciences, [SDV.CAN] Life Sciences [q-bio]/Cancer, Thyroid peroxidase, [SDV.BC.BC] Life Sciences [q-bio]/Cellular Biology/Subcellular Processes [q-bio.SC], medicine, Animals, Humans, Cholesterol metabolism, Thyroid Neoplasms, Iodide transport, [SDV.BC] Life Sciences [q-bio]/Cellular Biology, Molecular Biology, Cell Proliferation, Cell Biology, medicine.disease, Xenograft Model Antitumor Assays, 030104 developmental biology, Cancer research, biology.protein, Dendrogenin A, [SDV.SP.PHARMA]Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, Cholestanols, Hormone
Abstract: International audience; Dendrogenin A (DDA) is a tumor suppressor mammalian cholesterol-derived metabolite and a new class of ligand of the Liver X receptor (LXR), which displays tumor cell differentiation. In human MCF7 breast adenocarcinoma cells, DDA-induced cell differentiation was associated with an increased accumulation of neutral lipids and proteins found in milk indicating that DDA re-activates some functions of lactating cells. Active iodide transport occurs in the normal lactating mammary cells through the sodium/iodide symporter (NIS) and iodide (I) is secreted into milk to be used by the nursing newborn for thyroid hormones biosynthesis. In the present study, we assessed whether DDA may induce other characteristic of lactating cells such as NIS expression and iodine uptake in MCF7 breast cancer cells and extended this study to the papillary B-CPAP and undifferentiated anaplastic 8505c thyroid cancer cells. Moreover, we evaluated DDA impact on the expression of thyroid specific proteins involved in thyroid hormone biogenesis. We report here that DDA induces NIS expression in MCF7 cells and significantly increases the uptake of 131-I by acting through the LXR. In addition, DDA induces phenotypic, molecular and functional characteristics of redifferentiation in the two human thyroid carcinoma cell lines and the uptake of 131-I in the undifferentiated 8505c cells was associated with a strong expression of all the specific proteins involved in thyroid hormone biosynthesis, TSH receptor, thyroperoxidase and thyroglobulin. 131-I incorporation in the 8505c cells was stimulated by DDA as well as by the synthetic LXR ligand, GW3965. Together these data show that the re-differentiation of breast and thyroid cancer cells by DDA, is associated with the recovery of functional NIS expression and involves an LXR-dependent mechanism. These results open new avenues of research for the diagnosis of thyroid cancers as well as the development of new therapeutic approaches for radioiodine refractory thyroid cancers.
Published: 2019
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8. Natural and semisynthetic oxyprenylated aromatic compounds as stimulators or inhibitors of melanogenesis

Author: Philippe de Medina, Nicolas Caron, Francesco Epifano, Sandrine Silvente-Poirot, Serena Fiorito, Arnaud Rives, Salvatore Genovese, Marc Poirot, Dipartimento di Scienze del Farmaco, Università degli studi 'G. d'Annunzio' Chieti-Pescara [Chieti-Pescara] (Ud'A), Centre de Recherches en Cancérologie de Toulouse (CRCT), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Affichem S.A. [Toulouse, France], and Poirot, Marc
Subjects: Melanogenesis, Cell Survival, [SDV]Life Sciences [q-bio], Anthraquinones, [SDV.BC]Life Sciences [q-bio]/Cellular Biology, Benzoates, 01 natural sciences, Biochemistry, Benzaldehyde, Mice, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, Coumarins, Drug Discovery, Melanin biosynthesis, Animals, Organic chemistry, Skin tanning effect, Molecular Biology, [SDV.BC] Life Sciences [q-bio]/Cellular Biology, Cells, Cultured, 030304 developmental biology, Whitening Agents, Benzoic acid, Melanins, Oxyprenylated natural products, Aldehydes, Biological Products, 0303 health sciences, Molecular Structure, 010405 organic chemistry, Chemistry, Organic Chemistry, Skin whitening effect, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, Coumarin, 0104 chemical sciences, 3. Good health, [SDV] Life Sciences [q-bio], [SDV.SP] Life Sciences [q-bio]/Pharmaceutical sciences, Cinnamates, [SDV.SP.PHARMA] Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, Polar effect, [SDV.SP.PHARMA]Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, Anthraquinone Derivatives
Abstract: International audience; It has been very recently shown how naturally occurring oxyprenylated coumarins are effective modulators of melanogenesis. In this short communication we wish to generalize the potentialities as skin tanning or whitening agents of a wider panel of natural and semisynthetic aromatic compounds, including coumarins, cinnamic and benzoic acids, cinnamaldehydes, benzaldehyde, and anthraquinone derivatives. A total number of 43 compounds have been tested assaying their capacity to inhibit or stimulate melanin biosynthesis in cultured murine Melan A cells. The wider number of chemicals herein under investigation allowed to depict a detailed structure-activity relationship, as the following: (a) benzoic acid derivatives are slightly pigmenting agent, for which the effect is more pronounced in compounds with longer O-side chains; (b) independently from the type of substitution, cinnamic acids are able to increase melanin biosynthesis, while benzaldehydes are able to decrease it; (c) coumarins with a 3,3-dimethylallyl or shorter skeletons as substituents in position 7 are tanning agents, while coumarins with farnesyloxy groups are whitening ones; (d) double oxyprenylation in position 6 and 7 and 3,3-dimethylallyl or geranyl skeletons have slight depigmenting capacities, while farnesyl skeletons tend to marginally increase the tanning effect; (e) the presence of electron withdrawing groups (acetyl, COOH, and -Cl) and geranyl or farnesyl oxyprenylated chains respectively in positions 3 and 7 of the coumarin nucleus lead to a whitening effect, and finally (f) oxyprenylated anthraquinones have only a weak depigmenting capacity.
Published: 2019
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9. Lipidic Carbo-benzenes: Molecular Probes of Magnetic Anisotropy and Stacking Properties of α-Graphyne

Author: Valérie Maraval, Remi Chauvin, Chongwei Zhu, Arnaud Rives, Carine Duhayon, 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), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées
Subjects: 010405 organic chemistry, Chemistry, Organic Chemistry, Stacking, Aromaticity, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, 3. Good health, Crystal, Graphyne, Crystallography, Magnetic anisotropy, chemistry.chemical_compound, Organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Absorption (chemistry), Methylene, Solubility
Abstract: International audience; Solubilization of the C-18 fundamental circuit of alpha-graphyne has been envisaged by decoration with aliphatic chains R =n-CnH2n+1. The synthesis and characterization of p-dialkyl-tetraphenyl-carbo-bentenes (n = 2, 8, 14, 20) are thus presented and compared to the monoalkyl series produced concomitantly. In both series, a dramatic enhancement of solubility in organic solvents (CH2Cl2, CHCl3) is observed for n >= 8, and in the dialkyl series, the melting-decomposition temperature of the solid products is shown to decrease linearly from 208 degrees C for n = 2 to 149 degrees C for n = 20. Fluoroalkyl analogues with R = n-C8H4F13 are also described. The products display classical UV-vis electronic spectra of carbo-benzenes in solution (lambda(max) = 445.5 +/- 1 nm, epsilon approximate to 200 000 L.mol(-1).cm(-1)). They are also characterized by UV-vis absorption in the solid state, which is found to be correlated with the color and crystal packing. The methylene groups of R provide an experimental probe of the magnetic anisotropy and aromaticity of the C-18 ring through the NMR shielding of the H-1 nuclei from ca. 4.70 to 1.25 ppm going away from the border of the ring (as far as 8 angstrom away). All alkyl-carbobenzenes were also found to be highly crystalline. Seven of them have been characterized by X-ray diffraction analysis and the C-18 columnar packing compared in a systematic manner. Crystals of the diethyl and bistetradecyl derivatives, containing no solvent molecule, provided the first examples of direct pi-stacking of carbo-benzene rings, with inter-ring distances very close to calculated interlayer distances in AB and ABC alpha-graphityne (3.255 and 3.206 angstrom vs 3.266 and 3.201 angstrom, respectively).
Published: 2017
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10. Synthesis of Functional Carbo-benzenes with Functional Properties: The C2 Tether Key

Author: Kévin Cocq, Valérie Maraval, Arnaud Rives, Cécile Barthes, Remi Chauvin, 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), and 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)
Subjects: chemistry.chemical_classification, 010405 organic chemistry, Charge separation, Aryl, Organic Chemistry, Alkyne, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Computational chemistry, Carbo-mer, Molecule, Chemical stability, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Molecular materials, Alkyl
Abstract: Beyond demonstration of conceptual relevance and synthetic feasibility of aryl/alkyl-substituted representatives, carbo-benzene molecules started to gain prospects of broader impact through the emergence of alkynyl derivatives. This is first illustrated by examples of di- and hexaalkynyl-carbo-benzenes, a carbo-naphthalene, a carbo-biphenyl, and two carbo-terphenyls. A focus is then given to dialkynyl derivatives by reference to the peripherally C2-extruded parents. In the centrosymmetric quadrupolar series, the C2 expansion or ethynylogation effect is more particularly considered for 9H-fluoren-2-yl, tris(O-n-alkyl)pyrogallyl, indol-3-yl, 4-anilinyl, and tetraphenyl-carbo-phenyl substituents on the following respective properties: two-photon absorption, chemical stability, columnar mesogenicity, on-surface photoinduced charge separation vs single-molecule conductance, and reduction potential. Topical results and prospects of application are discussed on the basis of crystallographic, spectroscopic, and electrochemical analyses vs DFT-calculated nuclear and electronic structures. For the sake of the discussion consistency, complementary experimental and computational results are disclosed in the dianilinyl series. Overall, it is shown that combined advances in strategy, protocols, and substrate scope of acetylenic synthesis remain crucial for the development of yet poorly explored but promising types of molecular materials.1 Introduction2 Hexaalkynyl-carbo-benzene3 ortho-Dialkynyl-carbo-benzene4 para-Dialkynyl-carbo-benzenes4.1 Bistrimethylsilylethynyl-carbo-benzene4.2 Bisfluorenylethynyl-carbo-benzene4.3 Bistrialkoxyarylethynyl-carbo-benzenes4.4 Bisindolylethynyl-carbo-benzene4.5 Bisanilinylethynyl-carbo-benzene5 Carbo-oligo(phenyleneethynylene)s6 Conclusions
Published: 2019
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11. En route to a dianilinyl-substituted carbo-cyclohexadiene with promising electrical properties

Author: Valérie Maraval, Arnaud Rives, Zoia Voitenko, Oleg Lozynskyi, Cécile Barthes, Remi Chauvin, National Taras Shevchenko University of Kiev, 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), and 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)
Subjects: Carbo-cyclohexadiene, Stereochemistry, Macrocyclization, Conductance, Carbo-mers, chemistry.chemical_compound, Crystallography, Single molecule conductance, chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Butatrienes, Benzene, Derivative (chemistry), Quantum tunnelling
Abstract: International audience; The macro-aromatic carbo-benzene core para-disubstituted by 4-anilinyl groups is known to be an efficient single-molecule conductor, exhibiting a conductance of 106 nS measured by the scanning tunneling microscopy-break junction technique. The linear carbo-butadiene analogue bearing the same anilinyl substituents was found to be less efficient, with a conductance of 2.7 nS. The reason of this difference could be elucidated through the study of the charge transport properties of a cyclically locked carbo-butadiene core in a carbo-cyclohexadiene derivative. In this paper, advances in the synthesis of this challenging dianilinyl-substituted carbo-cyclohexadiene are presented.
Published: 2015
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12. Improvement of 5,6α-epoxycholesterol, 5,6β-epoxycholesterol, cholestane-3β,5α,6β-triol and 6-oxo-cholestan-3β,5α-diol recovery for quantification by GC/MS

Author: Julie Leignadier, Marc Poirot, Sandrine Silvente-Poirot, Luigi Iuliano, Chiara Zerbinati, Arnaud Rives, Regis Soules, Emmanuel Noguer, Philippe de Medina, Centre de Recherches en Cancérologie de Toulouse (CRCT), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Affichem S.A. [Toulouse, France] (Société de Biotechnologie médicale), Department of Medico-Surgical Sciences and Biotechnologies [Latina, Italy], Vascular Biology & Mass Spectrometry Laboratory [Latina, Italy], Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome]-Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome], This work was funded by the Institut National de la Santé et de la Recherche Médicale, the université Toulouse III, the Fondation de France (R11166BB), the Association pour la Recherche sur le Cancer (PJA 2013 12 00 342), the INCA (PRTK-K15-118), the European Union (FP7-309400: AFHELO and FP7-612261: TARGEAR)., European Project: 304900,EC:FP7:HEALTH,FP7-HEALTH-2012-INNOVATION-2,AFHELO(2012), European Project: 612261,EC:FP7:PEOPLE,FP7-PEOPLE-2013-IAPP,TARGEAR(2014), Sapienza - Università di Roma [Italy]-Sapienza - Università di Roma [Italy], Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome] (UNIROMA)-Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome] (UNIROMA), Poirot, Marc, Preclinical proof of concept of AF243 potency to prevent and/or treat sensorineural hearing loss - AFHELO - - EC:FP7:HEALTH2012-09-01 - 2016-05-31 - 304900 - VALID, and Targeting challenges of active ageing: innovative integrated strategies for the healing of age-related hearing loss - TARGEAR - - EC:FP7:PEOPLE2014-01-01 - 2017-12-31 - 612261 - VALID
Subjects: 0301 basic medicine, Oxysterol, trimethylsilylation, [SDV]Life Sciences [q-bio], Diol, Molecular Conformation, [SDV.CAN]Life Sciences [q-bio]/Cancer, Isotope dilution, Mass spectrometry, Ring B oxysterols, Biochemistry, Gas Chromatography-Mass Spectrometry, 03 medical and health sciences, chemistry.chemical_compound, [SDV.CAN] Life Sciences [q-bio]/Cancer, Hydrolase, [SDV.BBM] Life Sciences [q-bio]/Biochemistry, Molecular Biology, Humans, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, Solid phase extraction, Gas chromatrography, [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM], [SDV.BBM.BC] Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM], Molecular Biology, [SDV.MHEP.EM] Life Sciences [q-bio]/Human health and pathology/Endocrinology and metabolism, chemistry.chemical_classification, [SDV.MHEP] Life Sciences [q-bio]/Human health and pathology, Chromatography, Organic Chemistry, Cell Biology, [SDV.MHEP.EM]Life Sciences [q-bio]/Human health and pathology/Endocrinology and metabolism, 3. Good health, [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biomolecules [q-bio.BM], [SDV] Life Sciences [q-bio], Cholesterol, 030104 developmental biology, Enzyme, Metabolism, chemistry, Trimethylsilylation, ring B oxysterols, epoxycholesterol, gas chromatrography, metabolism, Gas chromatography–mass spectrometry, Epoxycholesterol, Cholestanols, [SDV.MHEP]Life Sciences [q-bio]/Human health and pathology
Abstract: International audience; 5,6α-epoxycholesterol (5,6α-EC) and 5,6β-epoxycholesterol (5,6β-EC) are oxysterols involved in the anticancer pharmacology of the widely used antitumor drug tamoxifen. They are both metabolized into cholestane-3β,5α,6β-triol (CT) by the cholesterol-5,6-epoxide hydrolase (ChEH) enzyme, and CT is metabolized by an as-yet uncharacterized enzyme into 6-oxo-cholestan-3β,5α-diol (OCDO). A recent feasibility study showed that the 5,6-ECs may represent surrogate markers of tamoxifen activity in breast cancer patients undergoing endocrine therapy, thus there is a growing interest in their accurate quantification. These oxysterols are usually quantified by gas-liquid chromatography coupled to mass spectrometry (GC/MS), using an isotope dilution methodology with the corresponding deuterated oxysterol. This method is considered to be relative quantitative since all of the standards used are deuterated oxysterols, however it is not known whether the preparation of each oxysterol is affected in the same way by the extraction, pre-purification by solid phase extraction (SPE) and trimethylsilylation steps, particularly when using biological samples that contain many other reactive compounds. Thus, in this study we investigated the yield of the 5,6-ECs, CT and OCDO recovery from patient serum samples at different stages of their work-up and trimethylsilylation prior to GC/MS analysis, using [14C]-labeled analogs to follow these oxysterols at each step. We measured a 40 to 60% loss of material for the 5,6-ECs and OCDO, however we also describe the conditions that improved their recovery. Our data also show that the use of deuterated 5,6α-EC, 5,6β-EC, CT and OCDO is an absolute requirement for their accurate quantification.
Published: 2017
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13. Quantitative analysis of the tumor suppressor dendrogenin A using liquid chromatography tandem mass spectrometry

Author: Arnaud Rives, Philippe de Medina, Claude Netter, Julie Leignadier, Emmanuel Noguer, Emilie Huc-Claustre, Citra Nagarathinam, Nizar Serhan, Regis Soules, Marc Poirot, Sandrine Silvente-Poirot, Affichem S.A. [Toulouse, France] (Société de Biotechnologie médicale), Centre de Recherches en Cancérologie de Toulouse (CRCT), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées, Thermo Fisher Scientific [Villebon sur Yvette, France], This work was funded by the Institut National de la Santé et de la Recherche Médicale, the université Toulouse III, the Fondation de France (R11166BB), the Association pour la Recherche sur le Cancer (PJA 2013 12 00 342), the INCA (PRTK-K15-118), and the European Union (FP7-309400: AFHELO and FP7-612261: TARGEAR)., European Project: 304900,EC:FP7:HEALTH,FP7-HEALTH-2012-INNOVATION-2,AFHELO(2012), European Project: 612261,EC:FP7:PEOPLE,FP7-PEOPLE-2013-IAPP,TARGEAR(2014), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT), Poirot, Marc, Preclinical proof of concept of AF243 potency to prevent and/or treat sensorineural hearing loss - AFHELO - - EC:FP7:HEALTH2012-09-01 - 2016-05-31 - 304900 - VALID, and Targeting challenges of active ageing: innovative integrated strategies for the healing of age-related hearing loss - TARGEAR - - EC:FP7:PEOPLE2014-01-01 - 2017-12-31 - 612261 - VALID
Subjects: 0301 basic medicine, Polyamine, Metabolite, [SDV]Life Sciences [q-bio], Normal tissue, Molecular Conformation, Tandem mass spectrometry, 01 natural sciences, Biochemistry, High-performance liquid chromatography, law.invention, chemistry.chemical_compound, law, Liquid chromatography–mass spectrometry, Tandem Mass Spectrometry, Phytosterol, [SDV.BBM.BC] Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM], Chromatography, High Pressure Liquid, [SDV.MHEP.EM] Life Sciences [q-bio]/Human health and pathology/Endocrinology and metabolism, [SDV.MHEP] Life Sciences [q-bio]/Human health and pathology, Imidazoles, Steroidal alkaloid, Hydrogen-Ion Concentration, [SDV.MHEP.EM]Life Sciences [q-bio]/Human health and pathology/Endocrinology and metabolism, 3. Good health, [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biomolecules [q-bio.BM], [SDV] Life Sciences [q-bio], Cholesterol, Female, Histamine, Breast Neoplasms, [SDV.CAN]Life Sciences [q-bio]/Cancer, 03 medical and health sciences, [SDV.CAN] Life Sciences [q-bio]/Cancer, [SDV.BBM] Life Sciences [q-bio]/Biochemistry, Molecular Biology, Humans, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, Fragmentation (cell biology), [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM], Molecular Biology, Chromatography, 010401 analytical chemistry, Organic Chemistry, Cell Biology, 0104 chemical sciences, Dendrogenin, 030104 developmental biology, chemistry, Suppressor, Quantitative analysis (chemistry), Cholestanols, [SDV.MHEP]Life Sciences [q-bio]/Human health and pathology
Abstract: International audience; Dendrogenin A (DDA) was recently identified as a mammalian cholesterol metabolite that displays tumor suppressor and neurostimulating properties at low doses. In breast tumors, DDA levels were found to be decreased compared to normal tissues, evidencing a metabolic deregulation of DDA production in cancers. DDA is an amino-oxysterol that contains three protonatable nitrogen atoms. This makes it physico-chemically different from other oxysterols and it therefore requires specific analytical methods We have previously used a two-step method for the quantification of DDA in biological samples: 1) DDA purification from a Bligh and Dyer extract by RP-HPLC using a 250×4.6mm column, followed by 2) nano-electrospray ionization mass spectrometry (MS) fragmentation to analyze the HPLC fraction of interest. We report here the development a liquid chromatography tandem mass spectrometry method for the analysis of DDA and its analogues. This new method is fast (10min), resolving (peak width
Published: 2017
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14. Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species

Author: Salvatore Genovese, Serena Fiorito, Vito Alessandro Taddeo, Philippe de Medina, Francesco Epifano, Cécile Bize, and Arnaud Rives
Subjects: Human welfare, Metabolite, Anti-Inflammatory Agents, Pharmaceutical Science, 01 natural sciences, Antioxidants, Analytical Chemistry, chemistry.chemical_compound, Prenylation, Coumarins, Drug Discovery, Organic chemistry, Humans, Umbelliferones, Pharmacology, Molecular Structure, 010405 organic chemistry, Drug candidate, Hydrolysis, Organic Chemistry, Coumarin, 0104 chemical sciences, Umbelliprenin, 010404 medicinal & biomolecular chemistry, Complementary and alternative medicine, chemistry, Molecular Medicine, Degradation (geology), Stress conditions, Oxidation-Reduction, Apiaceae
Abstract: Umbelliprenin is a secondary plant metabolite that displays promising chemopreventive, anti-inflammatory, and antigenotoxic properties. It possesses potential for applications to human welfare notably to prevent the emergence of cancer. For this purpose, stability studies are needed to define proper storage conditions and adapted formulations for this drug candidate. The identification of degradative products is a major concern for the preclinical development of umbelliprenin, providing also interesting information related to potential original phytochemicals formed in plants exposed to stressors. The stability profile of umbelliprenin under various stress conditions including exposure to heat, light, oxidation, and hydrolytic medium was assessed via HPLC/UV data. The data support that umbelliprenin undergoes inter- and intramolecular [2+2] cycloaddition under light exposure, leading respectively to a cyclobutane-umbelliprenin dimer and a 16-membered macrocycle. Their structures were characterized via MS and NMR data. It was shown that UV-A filters prevent this process, whereas UV-B filters and antioxidants are not or weakly effective. The study provides useful information for the preclinical development of umbelliprenin as an original chemopreventive agent.
Published: 2017

15. 3D and 2D supramolecular assemblies and thermotropic behaviour of a carbo-benzenic mesogen

Author: Brice Kauffmann, Hsiu-Fu Hsu, Chien-Jhang Su, Carine Duhayon, Valérie Maraval, Arnaud Rives, Tsai-Hui Wang, Chongwei Zhu, Chun-hsien Chen, Remi Chauvin, Shern-Long Lee, 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), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées, Department of Chemistry, Tamkang University, Tamkang University [New Taipei] (TKU), Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University (CEMAD), National Taiwan Normal University (NTNU), Institut Européen de Chimie et Biologie (IECB), and Université de Bordeaux (UB)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Materials science, 010405 organic chemistry, Mesogen, Metals and Alloys, Supramolecular chemistry, Mesophase, General Chemistry, 010402 general chemistry, 01 natural sciences, Thermotropic crystal, Catalysis, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Crystallography, Lattice constant, Liquid crystal, Materials Chemistry, Ceramics and Composites, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Single crystal, Powder diffraction
Abstract: International audience; Hexaalkoxy-di( phenylethynyl)-tetraphenyl-carbo-benzenes bearing six CnH2n+1 aliphatic chains (n = 12, 18) have been synthesized and characterized, including by single crystal XRD analysis. For n = 12, a liquid crystal behaviour was observed in the range of 109-130 degrees C. DSC, POM and PXRD analyses evidenced a rectangular columnar mesophase at 115 degrees C. The determined 3D lattice constants are consistent with 2D STM images of the so-called "carbo-mesogen'' deposited on an HOPG surface.
Published: 2017
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16. Indoleamine 2,3-dioxygenase inhibitory activity of derivatives of marine alkaloid tsitsikammamine A

Author: Eduard Dolusic, Céline Meinguet, Johan Wouters, Raphaël Frédérick, Bernard Masereel, Evelyne Delfourne, Benoît Van den Eynde, Pierre Larrieu, Arnaud Rives, Sébastien Blanc, Vincent Stroobant, Thierry Ferain, Luc Pilotte, and Delphine Colette
Subjects: Cell Survival, Clinical Biochemistry, Molecular modeling, Pharmaceutical Science, Biochemistry, Cell Line, Structure-Activity Relationship, Alkaloids, Drug Discovery, Humans, Indoleamine-Pyrrole 2,3,-Dioxygenase, Structure–activity relationship, Pyrroles, Indoleamine 2,3-dioxygenase, Cytotoxicity, Molecular Biology, Pyrroloiminoquinones, Cancer immunology, chemistry.chemical_classification, Binding Sites, biology, Topoisomerase, Cellular Assay, Alkaloid, Organic Chemistry, Tsitsikammamines, Antimicrobial, Protein Structure, Tertiary, Molecular Docking Simulation, 3-dioxygenase, Enzyme, chemistry, Quinolines, biology.protein, Molecular Medicine, Indoleamine 2
Abstract: Tsitsikammamines are marine alkaloids whose structure is based on the pyrroloiminoquinone scaffold. These and related compounds have attracted attention due to various interesting biological properties, including cytotoxicity, topoisomerase inhibition, antimicrobial, antifungal and antimalarial activity. Indoleamine 2,3-dioxygenase (IDO1) is a well-established therapeutic target as an important factor in the tumor immune evasion mechanism. In this preliminary communication, we report the inhibitory activity of tsitsikammamine derivatives against IDO1. Tsitsikammamine A analogue 11b displays submicromolar potency in an enzymatic assay. A number of derivatives are also active in a cellular assay while showing little or no activity towards tryptophan 2,3-dioxygenase (TDO), a functionally related enzyme. This IDO1 inhibitory activity is rationalized by molecular modeling studies. An interest is thus established in this class of compounds as a potential source of lead compounds for the development of new pharmaceutically useful IDO1 inhibitors.
Published: 2013
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17. First Perphenylatedcarbo-Oligoacetylenes: An Extension of the Polytriacetylene Family

Author: Arnaud Rives, Valérie Maraval, Remi Chauvin, and Nathalie Saffon-Merceron
Subjects: chemistry.chemical_classification, Absorption spectroscopy, Stereochemistry, Organic Chemistry, General Chemistry, Polymer, Carbon-13 NMR, Chromophore, Catalysis, Crystal, Crystallography, Polyacetylene, chemistry.chemical_compound, chemistry, Proton NMR, Reactivity (chemistry)
Abstract: The first examples of a novel family of sp-carbon-rich n-π-conjugated oligomers/polymers, namely carbo-mers of polyacetylene, also referred to as "1,4-PTA" isomers of the classical polytriacetylenes (1,2-PTAs), are described in the perphenylated series. The two first representatives proved to be stable in solution, and exhibit a zig-zag arrangement in the crystal state. The third member of the family, isolated in SnCl(2) matrix, proved to be stable in the solid state and was characterized by MALDI-TOF MS, (1)H NMR, CPMAS (13)C NMR, and absorption spectroscopy. An explanation for its reactivity in solution is proposed. The chromophoric properties in the visible region are shown to vary significantly and consistently along the series.
Published: 2012
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18. Abstract 5238: Characterization of the enzyme generating the cholesterol metabolite and tumor suppressor dendrogenin A in the breast and its deregulations in breast cancer

Author: Ned A. Porter, Emmanuel Noguer, Emanuala Gadaleta, Thierry Dubois, Magali Lacroix-Triki, Florence Dalenc, Claude Chalala, Marc Poirot, Hye-Young H. Kim, Regis Soules, Sandrine Silvente-Poirot, Louise J. Jones, Arnaud Rives, Lisa Barrett, Leonor Chaltiel, Bengt Mannervik, Pilippe Rochaix, Brigitta Sjödin, Thomas Filleron, Raphaëlle Duprez-Paumier, Michel Record, Sergio Roman-Roman, and Camille Franchet
Subjects: chemistry.chemical_classification, Cancer Research, Messenger RNA, Metabolite, medicine.medical_treatment, Cancer, medicine.disease, Molecular biology, law.invention, Steroid, chemistry.chemical_compound, Breast cancer, Enzyme, Oncology, chemistry, Biosynthesis, law, medicine, Recombinant DNA
Abstract: Dendrogenin A (DDA) is a tumor suppressor metabolite identified in human tissues that arises from the conjugation of 5,6α-epoxycholesterol (5,6α-EC) with histamine (HA) by a yet unidentified enzyme. DDA is present in the normal breast but its levels were found drastically decreased in breast tumors, showing that a deregulation of DDA metabolism occurred during breast carcinogenesis. It was shown that DDA displayed chemopreventive and anticancer properties (de Medina et al, Nat Commun, 2013; Voisin et al, PNAS, 2017; Segala et al, Nat Commun, in press). In addition, DDA blocks the biosynthesis of a newly identified cholesterol tumor promoter named 6-oxo-cholestan-3β,5α-diol (OCDO) (Voisin et al, PNAS, 2017). DDA and OCDO arise from 5,6-EC. We showed the existence of a metabolic balance between these two 5,6-EC derivatives in normal breast and BC that controls or stimulates BC progression (Silvente-Poirot & Poirot, Science, 2014, Voisin et al, PNAS, 2017). We addressed here the question of the identification and characterization of the DDA synthase (DDAS) and we determined whether its expression could reflect DDA levels in patient breast tumor and normal tissue. We report that the recombinant human glutathione transferase A1-1 (GST A1-1) produced DDA from 5,6α-EC and histamine (HA). The chemical characterization of the DDA product was performed by chromatography and mass spectrometry fragmentation. DDAS activity was found to be a new and important activity of GST A1-1 in addition to known glutathione transferase and steroid isomerase activities. The measured Michaelis constants of GST A1-1 for its new substrates were: Km5,6α-EC=0.27±0.05 µM and KmHA=0.35±0.3 µM, and the maximum velocity for the transformation of each substrates Vm5,6α-EC=0.81±0.2 µmol.min-1.mg and VmHA=0.66±0.2 µmol.min-1.mg. Interestingly, we showed that OCDO and other ring-B oxysterols, as well as several natural substrates and product of the GST A1-1, were potent inhibitors of DDAS activity while xenobiotics substrates of GST, and side chain oxysterols were not. Patient BC samples (n=50) showed significant decreased DDA levels and lower GST A1-1 protein expression compared to normal matched tissues, indicating that the decreased production of DDA in tumors is due to decreased expression of its enzyme. The analyses of two human BC mRNA databases from the Barts Cancer Institute (London, UK) and the Curie Institute (Paris, France) showed that the expression of GST A1-1 was lost in ER(+) BC tumors compared to normal breast tissue. Interestingly, DDAS was selectively expressed in the cytoplasm of epithelial cells from lactating ducts and lobular terminal units. Since these cells are the origin of most BC, the loss of DDAS expression and DDA biosynthesis combine to OCDO production, which controls DDAS activity, may constitute a major oncogenic process leading to BC development in human. Citation Format: Marc Poirot, Emmanuel Noguer, Florence Dalenc, Regis Soules, Lisa Barrett, Arnaud Rives, Hye-Young Kim, Brigitta Sjödin, Camille Franchet, Pilippe Rochaix, Raphaelle Duprez-Paumier, Magali Lacroix-Triki, Thomas Filleron, Leonor Chaltiel, Louise Jones, Emanuala Gadaleta, Claude Chalala, Sergio Roman-Roman, Thierry Dubois, Ned A. Porter, Bengt Mannervik, Michel Record, Sandrine Silvente-Poirot. Characterization of the enzyme generating the cholesterol metabolite and tumor suppressor dendrogenin A in the breast and its deregulations in breast cancer [abstract]. In: Proceedings of the American Association for Cancer Research Annual Meeting 2018; 2018 Apr 14-18; Chicago, IL. Philadelphia (PA): AACR; Cancer Res 2018;78(13 Suppl):Abstract nr 5238.
Published: 2018
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19. Enantioselective Access to All-trans 5-Alkylpiperidine-3,4-diols: Application to the Asymmetric Synthesis of the 1-N-Iminosugar (+)-Isofagomine

Author: Yves Genisson, Michel Baltas, Vanessa Faugeroux, Nathalie Saffon, and Arnaud Rives
Subjects: Reaction conditions, chemistry.chemical_compound, Chemistry, Stereochemistry, Organic Chemistry, Enantioselective synthesis, All trans, Iminosugar, Stereoselectivity, Piperidine, Cyanide anion, Catalysis
Abstract: Access to 3,4-disubstituted N-benzylprolinol derivatives is described that, after optimization of the ring-enlargement reaction conditions, could be efficiently transformed into the corresponding 3-hydroxypiperidines. This approach was applied to the asymmetric synthesis of (+)-isofagomine relying on regio- and stereoselective oxirane opening with the cyanide anion of a pivotal epoxypyrrolidine.
Published: 2009
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20. Towards graphyne molecular electronics

Author: Zhihai Li, Arnaud Rives, Mark A. Ratner, Manuel Smeu, Valérie Maraval, Remi Chauvin, Eric Borguet, Temple University [Philadelphia], Pennsylvania Commonwealth System of Higher Education (PCSHE), Northwestern University [Evanston], 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), and 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)
Subjects: Multidisciplinary, Materials science, Graphene, business.industry, General Physics and Astronomy, Conductance, Molecular electronics, Nanotechnology, General Chemistry, General Biochemistry, Genetics and Molecular Biology, law.invention, Graphyne, chemistry.chemical_compound, Semiconductor, Hexabenzocoronene, chemistry, law, Chemical physics, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Break junction, business, Quantum tunnelling
Abstract: α-Graphyne, a carbon-expanded version of graphene (‘carbo-graphene’) that was recently evidenced as an alternative zero-gap semiconductor, remains a theoretical material. Nevertheless, using specific synthesis methods, molecular units of α-graphyne (‘carbo-benzene’ macrocycles) can be inserted between two anilinyl (4-NH2-C6H4)-anchoring groups that allow these fragments to form molecular junctions between gold electrodes. Here, electrical measurements by the scanning tunnelling microscopy (STM) break junction technique and electron transport calculations are carried out on such a carbo-benzene, providing unprecedented single molecule conductance values: 106 nS through a 1.94-nm N–N distance, essentially 10 times the conductance of a shorter nanographenic hexabenzocoronene analogue. Deleting a C4 edge of the rigid C18 carbo-benzene circuit results in a flexible ‘carbo-butadiene’ molecule that has a conductance 40 times lower. Furthermore, carbo-benzene junctions exhibit field-effect transistor behaviour when an electrochemical gate potential is applied, opening the way for device applications. All the results are interpreted on the basis of theoretical calculations. α-Graphyne, a carbon-expanded version of graphene, is predicted to exhibit high conductivity due to its Dirac cone electronic structure. Here, Li et al.design and synthesize a series of molecular fragments of α-graphyne, on the basis of which single molecular junctions are realized.
Published: 2015
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21. First example of ring carbo-mer of 1,4-cyclohexadiene

Author: Valérie Maraval, Evelyne Chelain, Arnaud Rives, Thierry Brigaud, Cécile Barthes, Remi Chauvin, 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), Laboratoire de Chimie Biologique (LCB), Université de Cergy Pontoise (UCP), and Université Paris-Seine-Université Paris-Seine
Subjects: chemistry.chemical_compound, Nucleophilic trifluoromethylation, Computational chemistry, Chemistry, Organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Butatrienes, 1,4-Cyclohexadiene, Ring (chemistry), Carbo-mers, Carbo-cyclohexadienes
Abstract: International audience; While a series of carbo-mers of 1,3-cyclohexadienes was reported through the use of a specifically developed synthetic strategy, no example of their 1,4-regioisomers was known. Inspired by the methodology elaborated for the preparation of the 1,3-isomers, the synthesis of the first example of carbo-mer of 1,4-cyclohexadiene is presented. Comparison of physico-chemical properties of this first representative with those of the recently described 1,3-regioisomer, especially UV-vis absorption properties, is also addressed.
Published: 2015
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22. Carbo-cyclohexadienes vs. carbo-benzenes: Structure and conjugative properties

Author: Yulian M. Volovenko, Zoia Voitenko, Arnaud Rives, Iaroslav Baglai, Valérie Maraval, Cécile Barthes, Remi Chauvin, Nathalie Saffon-Merceron, Alix Saquet, 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), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), and National Taras Shevchenko University of Kiev
Subjects: Crystal, Crystallography, Stereochemistry, Chemistry, Cyclohexadienes, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Chemistry, Conjugated system, Chromophore, Electrochemistry, Spectral line
Abstract: International audience; Ideally Cs-/C2v-symmetric chromophores, constituted by two electro-active groups conjugated through the carbo-mer of the cyclohexa-1,3-diene core, are selectively prepared by the SnCl2-mediated reduction of tailored hexaoxy-[6]pericyclynes: in the latter substrates, one of the 1,4-dioxybut-2-yne edges is "chemically locked" by two CF3 substituents preventing complete reduction to the corresponding aromatic carbo-benzenic core, which is expected to be more "[small pi]-insulating" between the electro-active ends. The bis-trifluoromethylated carbo-cyclohexadiene products are also shown to be significantly stabilized with respect to their bis-phenylated analogues. Their structural (crystal X-ray diffraction analyses), spectroscopical (NMR and UV-vis spectra), physio-optical (dichromism in solution) and electrochemical (cyclic voltammograms) properties are compared on the basis of the electron-donating/electron-withdrawing nature of the substituents. These properties are also compared with those of their aromatic carbo-benzene and flexible carbo-n-butadiene counterparts.
Published: 2015
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23. Total synthesis of the marine pyrroloiminoquinone alkaloid tsitsikammamine A

Author: Laurent Legentil, Arnaud Rives, Evelyne Delfourne, and Tamara Delaine
Subjects: Indole test, chemistry.chemical_compound, Ethanol, chemistry, Alkaloid, Organic Chemistry, Drug Discovery, Structural isomer, Michael reaction, Organic chemistry, Total synthesis, Biochemistry
Abstract: A concise route to the marine pyrroloiminoquinone alkaloid tsitsikammamine A and a regioisomer was developed. The synthesis was based on a Michael reaction between the indole dione 6 and 2′-amino-1-(4-methoxyphenyl)ethanol.
Published: 2009
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24. Functional carbo-butadienes: Nonaromatic conjugation effects through a 14-carbon, 24-pi-electron backbone

Author: Arnaud Rives, Valérie Maraval, Remi Chauvin, Nathalie Saffon-Merceron, 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), Institut de Chimie de Toulouse (ICT-FR 2599), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)
Subjects: molecular wires, Stereochemistry, chemistry.chemical_element, Electron, 010402 general chemistry, Ring (chemistry), alkynes, 01 natural sciences, Catalysis, chemistry.chemical_compound, chromophores, Voltammetry, carbo-mers, cumulenes, 010405 organic chemistry, Chemistry, Aryl, Organic Chemistry, ring carbomers, mers, General Chemistry, aromaticity, Chromophore, 0104 chemical sciences, switches, derivatives, fluorescence, benzenes, Absorption (chemistry), homoaromaticity, Carbon, conjugation
Abstract: 0947-6539; A systematic study of carbo-butadiene motifs not embedded in an aromatic carbo-benzene ring is described. Dibutatrienylacetylene (DBA) targets R-1 C(R)=C=C=C(Ph) C equivalent to C-C(Ph)=C=C=C(R)-R-2 are devised, in which R is C equivalent to CSiiPr(3) and R-1 and R-2 are R, H, or 4-X-C6H4, with the latter including three known representatives (X: H, NMe2, or NH2). The synthesis method is based on the SnCl2-mediated reduction of pentaynediols prepared by early or late divergent strategies; the latter allows access to a OMe-NO2 push-pull diaryl-DBA. If R-1 and R-2 are H, an over-reduced dialkynylbutatriene (DAB) with two allenyl caps was isolated instead of the unsubstituted DBA. If R-1 = R-2 = R, the tetraalkynyl-DBA target was obtained, along with an over-reduced DBA product with a 12-membered 1,2-alkylidene-1H(2),2H(2)-carbo-cyclobutadiene ring. X-ray crystallography shows that all of the acyclic DBAs adopt a planar trans-transoid-trans configuration. The maximum UV/Vis absorption wavelength is found to vary consistently with the overall pi-conjugation extent and, more intriguingly, with the p-donor character of the aryl X substituents, which varies consistently with the first (reversible) reduction potential and first (irreversible) oxidation peak, as determined by voltammetry.
Published: 2014
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25. ChemInform Abstract: Highly π Electron-Rich Macro-Aromatics: Bis(p-aminophenyl)-carbo-benzenes and Their DBA Acyclic References

Author: Iaroslav Baglai, Valérie Maraval, Remi Chauvin, Nathalie Saffon-Merceron, Volodymyr Malytskyi, Zoia V. Voitenko, and Arnaud Rives
Subjects: Series (mathematics), Chemistry, General Medicine, Electron, Electrochemistry, Medicinal chemistry
Abstract: The spectroscopic (in CHCl3) and electrochemical properties (in CH2Cl2) of the series of stable quadrupolar title compounds (I) are investigated and compared to the acyclic reference series (II).
Published: 2012
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26. Highly π electron-rich macro-aromatics: bis(p-aminophenyl)-carbo-benzenes and their DBA acyclic references

Author: Zoia V. Voitenko, Nathalie Saffon-Merceron, Volodymyr Malytskyi, Arnaud Rives, Valérie Maraval, Iaroslav Baglai, Remi Chauvin, 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), Taras Shevchenko National University of Kyiv, Institut de Chimie de Toulouse (ICT-FR 2599), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)
Subjects: Series (mathematics), 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Metals and Alloys, General Chemistry, Electron, [CHIM.MATE]Chemical Sciences/Material chemistry, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, 3. Good health, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Materials Chemistry, Ceramics and Composites, Macro, health care economics and organizations
Abstract: International audience; A series of stable quadrupolar bis(p-aminophenyl)-carbo-benzenes, featuring both donor–donor–donor p-frustration and central macro-aromaticity, is described and compared to the acyclic dibutatrienylacetylene (DBA) reference series.
Published: 2012
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27. From Hexaoxy-[6]Pericyclynes to Carbo -Cyclohexadienes, Carbo -Benzenes, and Dihydro- Carbo -Benzenes: Synthesis, Structure, and Chromophoric and Redox Properties

Author: David Kieffer, Remi Chauvin, Christine Lepetit, Dmytro Kandaskalov, Léo Leroyer, Valérie Maraval, Nathalie Saffon-Merceron, Arnaud Rives, 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), Institut de Chimie de Toulouse (ICT-FR 2599), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)
Subjects: Double bond, Stereochemistry, reduction, 010402 general chemistry, alkynes, 01 natural sciences, Catalysis, chemistry.chemical_compound, Electron affinity, dichromism, Molecular orbital, [CHIM.COOR]Chemical Sciences/Coordination chemistry, carbo-mers, chemistry.chemical_classification, 010405 organic chemistry, Chemistry, Aryl, Organic Chemistry, Aromaticity, General Chemistry, aromaticity, Chromophore, 0104 chemical sciences, NMR spectra database, Crystallography, Cyclic voltammetry
Abstract: International audience; When targeting the quadrupolar p-dianisyltetraphenyl-carbo-benzene by reductive treatment of a hexaoxy-[ 6]pericyclyne precursor 3 with SnCl2/HCl, a strict control of the conditions allowed for the isolation of three C18-macrocyclic products: the targeted aromatic carbo-benzene 1, a sub-reduced non-aromatic carbo-cyclohexadiene 4A, and an over-reduced aromatic dihydro-carbo-benzene 5A. Each of them was fully characterized by its absorption and NMR spectra, which were interpreted by comparison with calculated spectra from static structures optimized at the DFT level. According to the nucleus-independent chemical shift (NICS) value (NICS ≈ -13 ppm), the macrocyclic aromaticity of 5A is indicated to be equivalent to that of 1. This is confirmed by the strong NMR spectroscopic deshielding of the ortho- CH protons of the aryl substituents, but also by the strong shielding of the internal proton of the endocyclic trans- CH=CH double bond that results from the hydrogenation of one of the C≡C bonds of 3. Both the aromatics 1 and 5A exhibit a high crystallinity, revealed by SEM and TEM images, which allowed for a structural determination by using an X-ray microsource. A good agreement with calculated molecular structures was found, and columnar assemblies of the C18 macrocycles were evidenced in the crystal packing. The non-aromatic carbo-cyclohexadiene 4A is shown to be an intermediate in the formation of 1 from 3. It exhibits a remarkable dichromism in solution, which is related to the occurrence of two intense bands in the visible region of its UV/Vis spectrum. These properties could be attributed to the dibutatrienylacetylene(DBA) unit that occurs in the three chromophores, but which is not involved in a macrocyclic p-delocalization in 4A only. A versatile redox behavior of the carbo chromophores is evidenced by cyclic voltammetry and was analyzed by calculation of the ionization potential, electron affinity, and frontier molecular orbitals.
Published: 2012
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28. Asymmetric synthesis and cytotoxic activity of isomeric phytosphingosine derivatives

Author: Yves Génisson, Nathalie Andrieu-Abadie, Nathalie Saffon, Cécile Baudoin-Dehoux, and Arnaud Rives
Subjects: Models, Molecular, Molecular Structure, Stereochemistry, Chemistry, Cell Survival, Hydrolysis, Organic Chemistry, Enantioselective synthesis, Stereoisomerism, Biochemistry, Mice, Sphingosine, Cell Line, Tumor, Cytotoxic T cell, Animals, Physical and Theoretical Chemistry, Cytotoxicity, Long chain, B16 melanoma
Abstract: New phytosphingosine analogues have been conceived, synthesised and their cytotoxicity in B16 murine melanoma cells tested. These compounds embed an isomeric substitution pattern resulting from a formal permutation of the C-2 and C-4 substituents along the aliphatic skeleton of the original sphingoid base. Five different stereoisomers have been accessed through regio- and stereocontrolled opening of the oxirane of long chain epoxyamine precursors. The corresponding N-hexyl and N-octanoyl derivatives have also been prepared. In cell viability experiments all the primary amines were found to be more active than the natural phytosphingosine with IC(50) in the low μM range for the most potent compounds.
Published: 2011

29. Synthesis of cytotoxic aza analogues of jaspine B

Author: Thierry Levade, Nathalie Andrieu-Abadie, Arnaud Rives, Sonia Ladeira, Yves Génisson, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), 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)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Structure Fédérative Toulousaine en Chimie Moléculaire (SFTCM), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Institut de médecine moléculaire de Rangueil (I2MR), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-IFR150-Institut National de la Santé et de la Recherche Médicale (INSERM), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées, Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées- Institut Fédératif de Recherche Bio-médicale Institution (IFR150)-Institut National de la Santé et de la Recherche Médicale (INSERM), and Simon, Marie Francoise
Subjects: Pyrrolidines, 010405 organic chemistry, Stereochemistry, Organic Chemistry, Melanoma, Experimental, Tumor cells, Stereoisomerism, Metabolism, 010402 general chemistry, 01 natural sciences, Sphingolipid, Chemical synthesis, Pyrrolidine, 0104 chemical sciences, chemistry.chemical_compound, Mice, chemistry, Sphingosine, Cell Line, Tumor, Cytotoxic T cell, Animals, Humans, Staudinger reaction, Cytotoxicity
Abstract: International audience; A straightforward access to pyrrolidine-based analogues of jaspine B was developed. Five stereoisomers were prepared including the all-cis derivatives presenting the configuration of the natural anhydrophytosphingosine. The synthesis of the latter relied on an original Staudinger-type cyclization process. The compounds were evaluated regarding their ability to alter tumor cells' viability and to interfere with the metabolism of sphingolipids.
Published: 2010
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30. ChemInform Abstract: Synthesis and Antitumor Evaluation of Analogues of the Marine Pyrroloiminoquinone Tsitsikammamines

Author: Tamara Delaine, Benjamin Le Calvé, Laurent Legentil, Evelyne Delfourne, Arnaud Rives, and Robert Kiss
Subjects: Chemistry, Stereochemistry, Michael reaction, General Medicine, Cancer cell lines, In vitro
Abstract: Two series of analogues of the marine pyrroloiminoquinone alkaloids tsitsikammamine have been synthesized on the basis of a Michael addition between 2'-amino-1-(4-methoxyphenyl)-ethanol and two indolediones. All the compounds were evaluated in vitro for antiproliferative activity against distinct cancer cell lines.
Published: 2010
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31. Synthesis and antitumor evaluation of analogues of the marine pyrroloiminoquinone tsitsikammamines

Author: Tamara Delaine, Benjamin Le Calvé, Robert Kiss, Laurent Legentil, Evelyne Delfourne, and Arnaud Rives
Subjects: Pharmacology, Chemistry, Stereochemistry, Cell growth, Oceans and Seas, Alkaloid, Organic Chemistry, Antineoplastic Agents, Biological activity, General Medicine, Chemical synthesis, In vitro, Quinone, Inhibitory Concentration 50, Cell Line, Tumor, Drug Discovery, Quinolines, Michael reaction, Humans, Cancer cell lines, Cell Proliferation
Abstract: Two series of analogues of the marine pyrroloiminoquinone alkaloids tsitsikammamine have been synthesized on the basis of a Michael addition between 2'-amino-1-(4-methoxyphenyl)-ethanol and two indolediones. All the compounds were evaluated in vitro for anti proliferative activity against distinct cancer cell lines.
Published: 2010

32. ChemInform Abstract: Total Synthesis of the Marine Pyrroloiminoquinone Alkaloid Tsitsikammamine A

Author: Tamara Delaine, Evelyne Delfourne, Laurent Legentil, and Arnaud Rives
Subjects: Indole test, Chemistry, Stereochemistry, Alkaloid, Structural isomer, Michael reaction, Total synthesis, General Medicine
Abstract: A concise route to the marine pyrroloiminoquinone alkaloid tsitsikammamine A and a regioisomer was developed. The synthesis was based on a Michael reaction between the indole dione 6 and 2′-amino-1-(4-methoxyphenyl)ethanol.
Published: 2009
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32 results on '"Arnaud Rives"'

1. Dendrogenin A drives LXR to trigger lethal autophagy in cancers

2. Selective Targeting of the Interconversion between Glucosylceramide and Ceramide by Scaffold Tailoring of Iminosugar Inhibitors

3. HPLC Analysis and Skin Whitening Effects of Umbelliprenin-containing Extracts of Anethum Graveolens, Pimpinella Anisum, and Ferulago Campestris

4. Carbo‐mer of barrelene: a rigid 3D‐carbon‐expanded molecular barrel

5. Dendrogenin A Synergizes with Cytarabine to Kill Acute Myeloid Leukemia Cells In Vitro and In Vivo

6. A fast UPLC–HILIC method for an accurate quantiﬁcation of dendrogenin A in human tissues

7. The cholesterol-derived metabolite dendrogenin A functionally reprograms breast adenocarcinoma and undifferentiated thyroid cancer cells

8. Natural and semisynthetic oxyprenylated aromatic compounds as stimulators or inhibitors of melanogenesis

9. Lipidic Carbo-benzenes: Molecular Probes of Magnetic Anisotropy and Stacking Properties of α-Graphyne

10. Synthesis of Functional Carbo-benzenes with Functional Properties: The C2 Tether Key

11. En route to a dianilinyl-substituted carbo-cyclohexadiene with promising electrical properties

12. Improvement of 5,6α-epoxycholesterol, 5,6β-epoxycholesterol, cholestane-3β,5α,6β-triol and 6-oxo-cholestan-3β,5α-diol recovery for quantification by GC/MS

13. Quantitative analysis of the tumor suppressor dendrogenin A using liquid chromatography tandem mass spectrometry

14. Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species

15. 3D and 2D supramolecular assemblies and thermotropic behaviour of a carbo-benzenic mesogen

16. Indoleamine 2,3-dioxygenase inhibitory activity of derivatives of marine alkaloid tsitsikammamine A

17. First Perphenylatedcarbo-Oligoacetylenes: An Extension of the Polytriacetylene Family

18. Abstract 5238: Characterization of the enzyme generating the cholesterol metabolite and tumor suppressor dendrogenin A in the breast and its deregulations in breast cancer

19. Enantioselective Access to All-trans 5-Alkylpiperidine-3,4-diols: Application to the Asymmetric Synthesis of the 1-N-Iminosugar (+)-Isofagomine

20. Towards graphyne molecular electronics

21. First example of ring carbo-mer of 1,4-cyclohexadiene

22. Carbo-cyclohexadienes vs. carbo-benzenes: Structure and conjugative properties

23. Total synthesis of the marine pyrroloiminoquinone alkaloid tsitsikammamine A

24. Functional carbo-butadienes: Nonaromatic conjugation effects through a 14-carbon, 24-pi-electron backbone

25. ChemInform Abstract: Highly π Electron-Rich Macro-Aromatics: Bis(p-aminophenyl)-carbo-benzenes and Their DBA Acyclic References

26. Highly π electron-rich macro-aromatics: bis(p-aminophenyl)-carbo-benzenes and their DBA acyclic references

27. From Hexaoxy-[6]Pericyclynes to Carbo -Cyclohexadienes, Carbo -Benzenes, and Dihydro- Carbo -Benzenes: Synthesis, Structure, and Chromophoric and Redox Properties

28. Asymmetric synthesis and cytotoxic activity of isomeric phytosphingosine derivatives

29. Synthesis of cytotoxic aza analogues of jaspine B

30. ChemInform Abstract: Synthesis and Antitumor Evaluation of Analogues of the Marine Pyrroloiminoquinone Tsitsikammamines

31. Synthesis and antitumor evaluation of analogues of the marine pyrroloiminoquinone tsitsikammamines

32. ChemInform Abstract: Total Synthesis of the Marine Pyrroloiminoquinone Alkaloid Tsitsikammamine A

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