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576 THE FERROCIFEN FAMILY AS POTENT AND SELECTIVE ANTITUMOR COMPOUNDS: MECHANISMS OF ACTION of ROS, the halting of the S/G2/M cell cycle, a modest apoptosis, the evidence of senescence, and the vacuolization of cells. In addition, the observed effect is ER α independent, ERβ is inoperative as is GPR30 [85]. QM metabolites have been identified and characterized [109–111]. At first sight, the ansa series 40 appears similar to the open series except for a stronger antiproliferative effect and a different mechanism. The two series have been tested by the National Cancer Institute (NCI) on 60 cancer cell lines. The mechanisms are different from any found in the National Institutes of Health (NIH) database, and also different from each other [130]. In particular, the generation of QM has not been observed in the ansa series with three-carbon bridges. Despite the similarities in the antiproliferative effects, it is possible that the target proteins or intermediaries are different between the two series, which both start with oxidation of the ferrocene to a ferricinium ion. Steric hindrance of the phenol function of 15 and 40 by –O-(CH 2 )
N(CH 3 ) 2 chains leads to different antiproliferative compounds that presumably operate via a pincer complexation of the basic substituents. These entities also reveal antibacterial and antifungal properties [131, 133, 134]. They thus open other horizons. Finally, organometallic pinacols of the ansa series show powerful antiproliferative effects [129] probably via a free-radical mechanism. The formulation of ferrocifens by LNC allows certain active species to be delivered in vivo. This is an essential step toward future development. The success of this step augurs well as the obstacles are gradually lifted [115, 123, 155–157]. The stakes, both scientific and social, are considerable. At present, these species, with their very rich potential, are an illustration of what we can look forward to in medical organometallic chemistry. ACKNOWLEDGEMENTS We wish to thank all those who contributed to this research, and whose names appear in the references. We thank B. McGlinchey for linguistic assistance. The ANRs Mecaferrol and FerVect have allowed fruitful collaborations between our group and those of C. Amatore, D. Mansuy, C. Passirani, A. Vessi`eres, R. A. Toillon, M. J. M. McGlinchey. REFERENCES 1. Schreiber, S. L.; Kapoor, T. M.; Wess, G. Chemical Biology From Small Molecules to Systems Biology and Drug Design; Wiley-VCH Verlag GmBH: Weinheim, 2007, Vol. 1. 2. Waldmann, H.; Janning, P. Chemical Biology: Learning through Case Studies; Wiley-VCH Verlag GmBH: Weinheim, 2009. 3. Lippard, S. J. Nat. Chem. Biol. 2006, 2 , 504. 4. Top, S.; Jaouen, G.; Vessi`eres, A.; Abjean, J. P.; Davoust, D.; Rodger, C. A.; Sayer, B. G.; McGlinchey, M. J. Organometallics 1985, 4 , 2143. 5. Jaouen, G.; Vessi`eres, A.; Top, S.; Ismail, A. A.; Butler, I. S. J. Am. Chem. Soc. 1985, 107 , 4778. 6. Jaouen, G.; Vessi`eres, A. Pure Appl. Chem. 1985, 57 , 1865. 7. Hodgkin, D. C.; Kamper, J.; Mackay, M.; Pickworth, J.; Trueblood, K. N.; White, J. G. Nature 1956, 178 , 64. 8. Volbeda, A.; Charon, M. H.; Piras, C.; Hatchikian, E. C.; Frey, M.; Fontecilla Camps, J. C. Nature 1995, 373 , 580. 9. Peters, J. W.; Lanzilotta, W. N.; Lemon, B. J.; Seefeldt, L. C. Science 1998, 282 , 1853. 10. Bioorganometallics; Jaouen, G., Ed.; Wiley-VCH Verlag GmBH: Weinheim, 2006. 11. Jaouen, G.; Beck, W.; McGlinchey, M. J. In Bioorganometallics: Biomolecules, Labeling, Medicine; Jaouen, G., Ed.; Wiley-VCH Verlag GmBH: Weinheim, 2006; p 1. 12. Hartinger, C. G.; Dyson, P. J. Chem. Soc. Rev. 2009, 38 , 391. 13. Hillard, E. A.; Jaouen, G. Organometallics 2011, 30 , 20. 14. Jaouen, G.; Dyson, P. J. In Comprehensive Organometallic Chemistry III ; Crabtree, R. H.; Mingos, D. M. P., Eds.; Elsevier: Oxford, 2007; Vol. 12, p 445. 15. Jaouen, G.; Metzler-Nolte, N. In Medicinal Organometallic Chemistry, 1st ed.; Topics in Organometallic Chemistry, Vol. 32; Springer-Verlag: Heidelberg, 2010. 16. Bioinorganic Medicinal Chemistry; Alessio E., Ed.; Wiley-VCH Verlag GmBH: Weinheim, 2011. 17. Patra, M.; Gasser, G. Chembiochem 2012, 13 , 1232. 18. David, S. S.; Meggers, E. Curr. Opin. Chem. Biol. 2008, 12 , 194. 19. Haas, K. L.; Franz, K. J. Chem. Rev. 2009, 109 , 4921. 20. Coogan, M. P.; Dyson, P. J.; Bochmann, M. Organometallics 2012, 31 , 5671. REFERENCES 577 21. Crabtree, R. H. Organometallics 2011, 30 , 17. 22. Artero, V.; Chavarot-Kerlidou, M.; Fontecave, M. Angew. Chem. Int. Ed. 2011, 50 , 7238. 23. Piers, W. E. Organometallics 2011, 30 , 13. 24. Le Goff, A.; Artero, V.; Jousselme, B.; Tran, P. D.; Guillet, N.; Metaye, R.; Fihri, A.; Palacin, S.; Fontecave, M. Science 2009,
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