Journal
JOURNAL OF COORDINATION CHEMISTRY
Volume 69, Issue 18, Pages 2707-2722Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/00958972.2016.1214949
Keywords
Pyrrolyl-imine; gold(III); DFT; cytotoxic activity; DNA
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Funding
- FAPESP (Fundacao de Amparo a Pesquisa do Estado de Sao Paulo) [2012/08230-2]
- CNPq (Conselho Nacional de Desenvolvimento Cientifico e Tecnologico) [130697/2012-5, 402627/2012-1, 442123/2014-0]
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A gold(III) complex with N,N-ethylenebis(pyrrol-2-yl-methyleneamine) (H(2)pyren) was synthesized and characterized by physicochemical and spectroscopic measurements. Density functional theory (DFT) studies and cytotoxic assays were performed. Infrared, mass spectrometry, and H-1, C-13, and {N-15,H-1} nuclear magnetic resonance analyses indicate that pyren is deprotonated and gold(III) is four coordinate in a square planar environment, with the pyrrole and imine nitrogens as donors. The structure was confirmed by powder X-ray diffraction and confirmed as a minimum of the potential energy surface by DFT. Cytotoxic activity of [Au(pyren)](+) was active against three tumorigenic cell lines with IC50 values of 35M. Interaction studies with CT-DNA by fluorescence and competition with ethidium bromide (EB) showed a quenching of the emission band of DNA with a Stern-Volmer quenching constant value of (3.0 +/- 0.1)x10(4)M(-1) and a decrease in fluorescence quenching of EB-DNA system, respectively, confirming that DNA is a possible target for the complex via an intercalative binding, which was confirmed by DNA conformational changes observed with circular dichroism spectroscopy. [GRAPHICS]
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