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Spectroscopy, electrochemistry and antiproliferative properties of Au(III), Pt(II) and Cu(II) complexes bearing modified 2,2':6',2"-terpyridine ligands. Impact of metal center and substituent incorporated into terpy framework.

Abstract

Structural, spectroscopic and electrochemical properties of six complexes [AuCl(L1)](PF6)2‧CH3CN (1), [AuCl(L2)](PF6)2 (2), [PtCl(L1)](BPh4).CH3CN (3), [PtCl(L2)](SO3CF3) (4), [CuCl2(L1)] (5) and [CuCl2(L2)]‧CH3CN (6) with modified 2,2′:6′,2′′-terpyridine ligands, 4-(4-methoxyphenyl)-2,2:6,2-terpyridine (L1) and 4-(4-methoxynaphthalen-1-yl)-2,2:6,2-terpyridine (L2), were thoroughly investigated and significant role of the substituent (4-methoxyphenyl or 4-methoxynaphthalen-1-yl) and metal center was demonstrated. The naphthyl-based substituent was found to increase the emission quantum yield of luminescent Au(III) and Pt(II) complexes. Furthermore, the antiproliferative potential of the reported complexes was examined towards human colorectal (HCT116) and ovarian (A2780) carcinoma cell lines as well as towards normal human fibroblasts. Au(III) complex 2 and Cu(II) complex 5 were found to have a higher antiproliferative effect in HCT116 colorectal and A2780 ovarian carcinoma cells when compared with the Pt(II) complex with the same ligand (4). The order of cytotoxicity in both cell lines is 2 > 6 > 1 > 3 > 4. Complex 2 seems to be the more cytotoxic towards HCT116 and A2780 cancer cell lines with IC50 values 300x and 130x higher in normal human fibroblasts compared to the respective cancer cells. The viability loss induced by the complexes agrees with Hoechst 33258 staining and the typical morphological apoptotic characteristics like chromatin condensation and nuclear fragmentation and flow cytometry assay. The induction of apoptosis correlate with the induction of reactive oxygen species (ROS). Fluorescence microscopy analysis indicate that after a 3 h incubation, complexes 1–4 are localized inside HCT116 cells and the high levels of internalization correlate with their cytotoxicity.

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Publication details

The article was received on 09 Feb 2018, accepted on 03 Apr 2018 and first published on 04 Apr 2018


Article type: Paper
DOI: 10.1039/C8DT00558C
Citation: Dalton Trans., 2018, Accepted Manuscript
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    Spectroscopy, electrochemistry and antiproliferative properties of Au(III), Pt(II) and Cu(II) complexes bearing modified 2,2':6',2"-terpyridine ligands. Impact of metal center and substituent incorporated into terpy framework.

    A. Maroń, K. A. Czerwińska, B. Machura, L. R. Raposo, C. Rodrigues, A. Fernandes, J. Malecki, A. Szłapa-Kula, S. Kula and S. Krompiec, Dalton Trans., 2018, Accepted Manuscript , DOI: 10.1039/C8DT00558C

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