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Modification of the Estrogenic Properties of Diphenols by the Incorporation of Ferrocene. Generation of Antiproliferative Effects in Vitro
Open accessAbstract
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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Cited by
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van Rijt, S. H., & Sadler, P. J. (2009) · Drug Discovery Today · doi:10.1016/j.drudis.2009.09.003 · Cited by 592
The potential of organometallic complexes in medicinal chemistry
Gasser, G., & Metzler-Nolte, N. (2012) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2012.01.013 · Cited by 516
A New Age for Iron: Antitumoral Ferrocenes
Braga, S. S., & Silva, A. M. S. (2013) · Organometallics · doi:10.1021/om400446y · Cited by 309
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Dougan, S. J., Habtemariam, A., McHale, S. E., Parsons, S., & Sadler, P. J. (2008) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0800076105 · Cited by 303
Metadata
- Authors
- Vessières, A., Top, S., Pigeon, P., Hillard, E., Boubeker, L., Spera, D., & Jaouen, G.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- 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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