Vera, José L.

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    Synthesis, characterization, cytotoxic studies, and biosensor development of ferrocenecarboxylate complexes
    (2013) Vera, José L.; Meléndez, Enrique; College of Arts and Sciences - Sciences; Cádiz, Mayra E.; Morell, Luis A.; Román Velázquez, Félix R.; Santana, Alberto; Department of Chemistry; Cáceres Valencia, Pablo G.
    The application of ferrocene chemistry in biosensing and as potential anti-cancer drug is presented in this research work. A series of modified ferrocenes with a variety of groups were synthesized and their structures characterized by 1H and 13C NMR, IR, elemental analysis, electrochemical methods and molecular modeling methods. Three ferrocenes modified with hormones and Vitamin D2 (estrone-3-(ferrocenecarboxylate), estradiol-3-(ferrocenecarboxylate), and ergocalciferol-3-(ferrocenecarboxylate)) were designed to lead the drugs for the hormone dependent cancers. The cytotoxic activity of these complexes in colon cancer (HT29) and hormone dependent breast cancer (MCF-7) cell lines was investigated in vitro. Only estradiol-3-(ferrocenecarboxylate) showed good cytotoxic activity in both cell lines, exceeding those of ferrocenium and ferrocene. In MCF-7, estradiol-3-(ferrocenecarboxylate) exhibited remarkable IC50, in the low micromolar range. This may be attributed to the presence of the estradiol vector. Computational studies between alpha-estrogen receptor ligand binding domain site and estradiol-3-(ferrocenecarboxylate) revealed various hydrophobic interactions that might explain the cytotoxic activity of this ester. In order to investigate the role of the phenyl group and redox active pendant groups on ferrocene, we synthesized 4-fluorophenyl ferrocencarboxylate, 4-chlorophenyl ferrocencarboxylate, 4-bromophenyl ferrocencarboxylate, 4-iodophenyl ferrocencarboxylate and its analog replacing the halide with the redox active species pyrrol (4(1H-pyrrol-yl)phenyl ferrocenecarboxylate). Cytotoxic properties tested in MCF-7 breast cancer and MCF-10A healthy breast cell lines. Only 4-chlorophenyl ferrocencarboxylate and 4-bromophenyl ferrocencarboxylate displayed high cytotoxic activity on MCF-7 and low cytotoxic activity on healthy breast cells MCF-10A, providing a potential to be developed as drugs. The pyrrol substituent showed high cytotoxic activity on both cell lines and low potential as anti-cancer drug. However, 4(1H-pyrrol-yl)phenyl ferrocenecarboxylate has other applications, in particular as amperometric biosensor. A mixture of pyrrol, 4(1H-pyrrolyl)phenyl ferrocenecarboxylate and glucose oxidase were submitted to a steady potential forming a matrix of polymers. This matrix contains ferrocene as a mediator and enhances the electrochemical signal upon glucose detection rendering in a more sensitive biosensor.