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Modification of the Estrogenic Properties of Diphenols by the Incorporation of Ferrocene. Generation of Antiproliferative Effects in Vitro

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Vessières, Anne, Top, Siden, Pigeon, Pascal, Hillard, Elizabeth, Boubeker, Leila, Spera, Daniela, Jaouen, Gérard·2005·Journal of Medicinal Chemistry

Abstract

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 (IC(50) = 0.7 and 0.6 microM). 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.

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Metadata

Authors
Vessières, A., Top, S., Pigeon, P., Hillard, E., Boubeker, L., Spera, D., & Jaouen, G.
Venue
Journal of Medicinal Chemistry
Published
2005-05-14
Volume
48
Issue
12
Pages
3937-3940
ISSN
  • 0022-2623 (ISSN-L)
  • 1520-4804
OpenAlex
W2018234652
Cited by
206
References
0
FWCI
6.55
Type
journal article
Language
en
Open access
green

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CoChat. (2026). Citation check: Modification of the Estrogenic Properties of Diphenols by the Incorporation of Ferrocene. Generation of Antiproliferative Effects in Vitro. https://app.cochat.ai/papers/10.1021/jm050251o
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Vessières, A., Top, S., Pigeon, P., Hillard, E., Boubeker, L., Spera, D., & Jaouen, G. (2005). Modification of the Estrogenic Properties of Diphenols by the Incorporation of Ferrocene. Generation of Antiproliferative Effects in Vitro. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm050251o

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