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Ferrocenyl-l-amino acid copper(ii) complexes showing remarkable photo-induced anticancer activity in visible light
Tridib Goswami K., Sudarshan Gadadhar, Babu Balaji, , Anjali Karande A., Akhil Chakravarty R.
Published in
Volume: 43
Issue: 31
Pages: 11988 - 11999
Ferrocene-conjugated copper(ii) complexes [Cu(Fc-aa)(aip)](ClO4) (1-3) and [Cu(Fc-aa)(pyip)](ClO4) (4-6) of l-amino acid reduced Schiff bases (Fc-aa), 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline (aip) and 2-(1-pyrenyl)-1H-imidazo[4,5-f][1,10]phenanthroline (pyip), where Fc-aa is ferrocenylmethyl-l-tyrosine (Fc-Tyr in 1, 4), ferrocenylmethyl-l-tryptophan (Fc-Trp in 2, 5) and ferrocenylmethyl-l-methionine (Fc-Met in 3, 6), were prepared and characterized and their photocytotoxicity was studied (Fc = ferrocenyl moiety). Phenyl analogues, viz. [Cu(Ph-Met)(aip)](ClO4) (7) and [Cu(Ph-Met)(pyip)](ClO4) (8), were prepared and used as control compounds. The bis-imidazophenanthroline copper(ii) complexes, viz. [Cu(aip)2(NO3)](NO3) (9) and [Cu(pyip) 2(NO3)](NO3) (10), were also prepared and used as controls. Complexes 1-6 having a redox inactive cooper(ii) center showed the Fc+-Fc redox couple at ∼0.5 V vs. SCE in DMF-0.1 mol [Bu n4N](ClO4). The copper(ii)-based d-d band was observed near 600 nm in DMF-Tris-HCl buffer (1:1 v/v). The ferrocenyl complexes showed low dark toxicity, but remarkably high photocytotoxicity in human cervical HeLa and human breast adenocarcinoma MCF-7 cancer cells giving an excellent photo-dynamic effect while their phenyl analogues were inactive. The photo-exposure caused significant morphological changes in the cancer cells when compared to the non-irradiated ones. The photophysical processes were rationalized from the theoretical studies. Fluorescence microscopic images showed 3 and 6 localizing predominantly in the endoplasmic reticulum (ER) of the cancer cells, thus minimizing any undesirable effects involving nuclear DNA. This journal is {\textcopyright} the Partner Organisations 2014.
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