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Vectorized ferrocenes with estrogens and vitamin D2: synthesis, cytotoxic activity and docking studiesElectronic supplementary information (ESI) available. See DOI: 10.1039/c1dt10995b.

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Title: Vectorized ferrocenes with estrogens and vitamin D2: synthesis, cytotoxic activity and docking studiesElectronic supplementary information (ESI) available. See DOI: 10.1039/c1dt10995b.
Authors: Vera, José1, Gao, Li Ming1, Santana, Alberto1, Matta, Jaime2, Meléndez, Enrique1
Source: Dalton Transactions: An International Journal of Inorganic Chemistry. Sep2011, Vol. 40 Issue 37, p9557-9565. 9p.
Subjects: Ferrocene, Estrogen, Ergocalciferol, Biosynthesis, Cell-mediated cytotoxicity, Electrochemical analysis, Hydroxyl group, Hydrophobic surfaces
Abstract: Three ferrocene complexes vectorized with estrogens and vitamin D2were synthesized and fully characterized by spectroscopic, electrochemical and computational methods. The synthesis of these esters was accomplished by reacting ferrocenoyl chloride with the corresponding ROH groups (R = ergocalciferol, estradiol, estrone). The cytotoxicity of these complexes in HT-29 colon cancer and MCF-7 breast cancer cell lines was investigated in vitro. Only ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate showed good cytotoxic activity in both cell lines, exceeding those of ferrocenium and ferrocene. In MCF-7, ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate exhibited remarkable IC50, in the low micromolar range. This may be attributed to the presence of the estradiol vector. Docking studies between alpha-estrogen receptor ligand binding site and ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate revealed some key hydrophobic interactions that might explain the cytotoxic activity of this ester. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
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Abstract:Three ferrocene complexes vectorized with estrogens and vitamin D2were synthesized and fully characterized by spectroscopic, electrochemical and computational methods. The synthesis of these esters was accomplished by reacting ferrocenoyl chloride with the corresponding ROH groups (R = ergocalciferol, estradiol, estrone). The cytotoxicity of these complexes in HT-29 colon cancer and MCF-7 breast cancer cell lines was investigated in vitro. Only ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate showed good cytotoxic activity in both cell lines, exceeding those of ferrocenium and ferrocene. In MCF-7, ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate exhibited remarkable IC50, in the low micromolar range. This may be attributed to the presence of the estradiol vector. Docking studies between alpha-estrogen receptor ligand binding site and ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate revealed some key hydrophobic interactions that might explain the cytotoxic activity of this ester. [ABSTRACT FROM AUTHOR]
ISSN:14779226
DOI:10.1039/c1dt10995b