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Chempluschem. 2012 Nov 01;77(11):1001-1016. doi: 10.1002/cplu.201200141.

Synthesis, Physicochemical Studies, Molecular Dynamics Simulations, and Metal-Ion-Dependent Antiproliferative and Antiangiogenic Properties of Cone ICL670-Substituted Calix[4]arenes.

ChemPlusChem

Pascal Rouge, Alexandra Dassonville-Klimpt, Christine Cézard, Stéphanie Boudesocque, Roger Ourouda, Carole Amant, François Gaboriau, Isabelle Forfar, Jean Guillon, Emmanuel Guillon, Enguerran Vanquelef, Piotr Cieplak, François-Yves Dupradeau, Laurent Dupont, Pascal Sonnet

Affiliations

  1. Laboratoire des Glucides, CNRS FRE 3517, UFR de Pharmacie, Université de Picardie Jules Verne, 1, rue des Louvels, 80037 Amiens cedex 1 (France).
  2. Institut de Chimie Moléculaire de Reims (ICMR), UMR CNRS 7312, UFR des Sciences Exactes et Naturelles, Université de Reims Champagne-Ardenne, Reims (France).
  3. Hémostase et remodelage vasculaire post-ischémique, EA3801, Université de Picardie Jules Verne, 1, rue des Louvels, 80037 Amiens cedex 1 (France).
  4. Hémostase et remodelage vasculaire post-ischémique, EA3801, Université de Picardie Jules Verne, 1, rue des Louvels, 80037 Amiens cedex 1 (France) ; Laboratoire d'Oncobiologie Moléculaire, CHU d'Amiens, Amiens (France).
  5. Inserm U991 (EA/MDC), Université de Rennes I, Hôpital Pontchaillou, Rennes (France).
  6. CNRS FRE 3396 (Pharmacochimie), UFR de Pharmacie, Université de Bordeaux Segalen, Bordeaux (France).
  7. Sandford-Burnham Medical Research Institute, 10901 North Torrey Pines Road, La Jolla, CA 92037 (USA).

PMID: 25599014 PMCID: PMC4293705 DOI: 10.1002/cplu.201200141

Abstract

Iron chelators, through their capacity to modulate the iron concentration in cells, are promising molecules for cancer chemotherapy. Chelators with high lipophilicity easily enter into cells and deplete the iron intracellular pool. Consequently, iron-dependent enzymes, such as ribonucleotide reductase, which is over-expressed in cancer cells, become nonfunctional. A series of calix[4]arene derivatives substituted at the lower rim by ICL670, a strong Fe

Keywords: calixarenes; chelates; iron; lipophilicity; molecular dynamics

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