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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Breast Neoplasms
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Cell Line, Tumor
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Estrogen Receptor alpha / chemistry
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Estrogen Receptor alpha / metabolism
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Estrogen Receptor beta / chemistry
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Estrogen Receptor beta / metabolism
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Estrogens / chemical synthesis*
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Estrogens / chemistry
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Estrogens / pharmacology
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Female
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Ferrous Compounds / chemical synthesis*
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Ferrous Compounds / chemistry
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Ferrous Compounds / pharmacology
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Humans
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In Vitro Techniques
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Metallocenes
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Neoplasms, Hormone-Dependent
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Organometallic Compounds / chemical synthesis*
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Organometallic Compounds / chemistry
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Organometallic Compounds / pharmacology
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Phenols / chemical synthesis*
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Phenols / chemistry*
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Phenols / pharmacology
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Structure-Activity Relationship
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Uterus / metabolism
Substances
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1,1-bis(4'-hydroxyphenyl)-2-ferrocenylbut-1-ene
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Antineoplastic Agents
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Estrogen Receptor alpha
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Estrogen Receptor beta
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Estrogens
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Ferrous Compounds
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Metallocenes
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Organometallic Compounds
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Phenols
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ferrocene