Crystal structure and cytotoxic activities of a bis(pyrrolyl-imine) gold(III) complex

Author(s)

Profirio, Daniel De Moraes ; Ferraz De Paiva, Raphael Enoque ; Abbehausen, Camilla ; Cuin, Alexandre ; Masciocchi, Norberto ; Machado, Daisy ; Lancellotti, Marcelo ; Corbi, Pedro Paulo ; Barboza Formiga, Andre Luiz

• Document type: Journal article
• Source: Journal of Coordination Chemistry; v. 69, n. 18, p. 2707-2722, 2016.
• Web of Science Citations: 1

Abstract

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] (AU)

• FAPESP's process: 12/08230-2 - Synthesis, characterization and pharmacological studies of Ag(I), Au(I), Pt(II) and Pd(II) complexes with bioactive ligands
• Grantee: Pedro Paulo Corbi
• Support Opportunities: Regular Research Grants