Journal
JOURNAL OF INORGANIC BIOCHEMISTRY
Volume 105, Issue 11, Pages 1373-1382Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.jinorgbio.2011.07.015
Keywords
Ferrocene bioconjugates; Gold; Antitumor properties; Amino acid esters; Biological ligands
Funding
- Direccion General de Investigacion Cientifica y Tecnica [CTQ2010-20500-C02-01]
- Gobierno de Aragon [PM067/2007]
- FCT [2009PT0068]
- CSIC [2009PT0068]
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Several bioconjugates of ferrocene with biological compounds such as aminoacid esters and related species have been prepared by reaction of chlorocarbonyl ferrocene with the corresponding amino acid ester (histidine methyl ester, tryptophan methyl ester, methionine methyl ester and lysine ethyl ester) or histamine or prolinamide in the presence of NEt3. The reaction of the tryptophan or prolinamide ferrocene conjugates with [Au(acac)(PR3)] (acac= acetylacetonate) results in the substitution of the proton of the cyclic NH groups by the fragment AuPR3+ affording the complexes [Au(FcCO-tryptophan-OMe)(PR3)] or [Au(FcCO-prolinamide)(PR3)] (Fc= ferrocenyl group). The reaction of FcCO-Met-OMe with [Au(OTf(PR3)] (OTF= trifluoromethysulfonate) or [Au(C6F5)(3)(OEt2)] yields the gold(l) or gold(III) derivatives [Au(FcCO-Met-OMe) (PR3)]OTf or [Au(C6F5)(3)(FcCO-Met-OMe)]. respectively. Cytotoxicity studies towards several cancer lines such as MCF-7, HeLa or NIE-115 have been performed. The ferrocene bioconjugates show no activity whereas the gold complexes exhibit antiproliferative effect. Preliminary studies of interaction of compounds with cells were carried out with the goal of increasing our knowledge on the mechanism of action of these potential drugs. (C) 2011 Elsevier Inc. All rights reserved.
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