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Dalton Trans. 2011 Oct 7;40(37):9557-65. doi: 10.1039/c1dt10995b. Epub 2011 Aug 18.

Vectorized ferrocenes with estrogens and vitamin D2: synthesis, cytotoxic activity and docking studies.

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  • 1University of Puerto Rico, Department of Chemistry, PO Box 9019, Mayaguez, PR 00681.

Abstract

Three ferrocene complexes vectorized with estrogens and vitamin D(2) were 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 IC(50), 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.

PMID:
21850331
[PubMed - indexed for MEDLINE]
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