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Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties.
Zaghouani, Mehdi; Gayraud, Oscar; Jactel, Vincent; Prévost, Sébastien; Dezaire, Ambre; Sabbah, Michèle; Escargueil, Alexandre; Lai, Thanh-Lan; Le Clainche, Christophe; Rocques, Nathalie; Romero, Stéphane; Gautreau, Alexis; Blanchard, Florent; Frison, Gilles; Nay, Bastien.
Affiliation
  • Zaghouani M; Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, CNRS, 57 rue Cuvier, 75005, Paris, France.
  • Gayraud O; Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau, France.
  • Jactel V; Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau, France.
  • Prévost S; Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, CNRS, 57 rue Cuvier, 75005, Paris, France.
  • Dezaire A; Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau, France.
  • Sabbah M; Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, CNRS, 57 rue Cuvier, 75005, Paris, France.
  • Escargueil A; Sorbonne Université, INSERM, Laboratoire de Biologie du Cancer et Thérapeutique, Centre de Recherche Saint-Antoine, 75012, Paris, France.
  • Lai TL; Sorbonne Université, INSERM, Laboratoire de Biologie du Cancer et Thérapeutique, Centre de Recherche Saint-Antoine, 75012, Paris, France.
  • Le Clainche C; Sorbonne Université, INSERM, Laboratoire de Biologie du Cancer et Thérapeutique, Centre de Recherche Saint-Antoine, 75012, Paris, France.
  • Rocques N; Institute for Integrative Biology of the Cell (I2BC), CEA, CNRS, Université Paris-Sud, Université Paris-Saclay, 91198, Gif-sur-Yvette Cedex, France.
  • Romero S; Institute for Integrative Biology of the Cell (I2BC), CEA, CNRS, Université Paris-Sud, Université Paris-Saclay, 91198, Gif-sur-Yvette Cedex, France.
  • Gautreau A; Laboratoire de Biochimie, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau, France.
  • Blanchard F; Laboratoire de Biochimie, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau, France.
  • Frison G; Laboratoire de Biochimie, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau, France.
  • Nay B; Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France.
Chemistry ; 24(62): 16686-16691, 2018 Nov 07.
Article in En | MEDLINE | ID: mdl-30168631
ABSTRACT
An intramolecular Diels-Alder (IMDA) reaction efficiently accelerated by Schreiner's thiourea is reported, to build a functionalized cytochalasin scaffold (periconiasin series) for biological purposes. DFT calculation highlighted a unique multidentate cooperative hydrogen bonding in this catalysis. The deprotection end game afforded a collection of diverse structures and showed the peculiar reactivity of the Diels-Alder cycloadducts upon functionalization. Biological studies revealed strong cytotoxicity of a few compounds on breast cancer cell lines while actin polymerization is preserved.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Cytochalasins / Antineoplastic Agents Limits: Humans Language: En Journal: Chemistry Journal subject: QUIMICA Year: 2018 Document type: Article Affiliation country: France
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Cytochalasins / Antineoplastic Agents Limits: Humans Language: En Journal: Chemistry Journal subject: QUIMICA Year: 2018 Document type: Article Affiliation country: France