Modification of the estrogenic properties of diphenols by the incorporation of ferrocene. Generation of antiproliferative effects in vitro

A Vessieres (1) , Siden Top (1) , Pascal Pigeon (1) , E Hillard , L Boubeker , D Spera , G Jaouen (1)

1 CBCM - Chimie et biochimie des complexes moléculaires

We report here the synthesis and the strong and unexpected antiproliferative effect of the organometallic diphenolic compound 1,1-bis(4'-hydroxyphenyl)-2-ferrocenyl-but-1-ene (4) on both hormone-dependent (MCF7) and -independent (MDA-MB231) breast cancer cells (IC50 = 0.7 and 0.6 mu M). Surprisingly, 6 [1,2-bis(4'-hydroxyphenyl)-2-ferrocenyl-but-1-ene], the regioisomer of 4, shows only a modest effect on these cell lines. This pertinent organometallic modification seems to trigger an intracellular oxidation of the structurally favorable compound 4, leading to the generation of a potent cytotoxic compound.

Domaines: Chimie

A Vessieres, Siden Top, Pascal Pigeon, E Hillard, L Boubeker, et al.. Modification of the estrogenic properties of diphenols by the incorporation of ferrocene. Generation of antiproliferative effects in vitro. Journal of Medicinal Chemistry, 2005, 48 (12), pp.3937-3940. ⟨10.1021/jm050251o⟩. ⟨hal-01230403⟩