Synthesis, spectroscopic characterization, DFT studies and biological assays of a novel gold(I) complex with 2-mercaptothiazoline


Autoria(s): ABBEHAUSEN, Camilla; CASTRO, Juliana F.; SPERA, Marcelle B. M.; HEINRICH, Tassiele A.; COSTA-NETO, Claudio M.; LUSTRI, Wilton R.; FORMIGA, Andre L. B.; CORBI, Pedro P.
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

19/10/2012

19/10/2012

2011

Resumo

A new gold(I) complex with 2-mercaptothiazoline (MTZ) with the coordination formula [AuCN(C(3)H(5)NS(2))] was synthesized and characterized by chemical and spectroscopic measurements, OFT studies and biological assays. Infrared (IR) and (1)H, (13)C and (15)N nuclear magnetic resonance (NMR) spectroscopic measurements indicate coordination of the ligand to gold(I) through the nitrogen atom. Studies based on OFT confirmed nitrogen coordination to gold(I) as a minimum of the potential energy surface with calculations of the hessians showing no imaginary frequencies. Thermal decomposition starts at temperatures near 160 degrees C, leading to the formation of Au as the final residue at 1000 degrees C. The gold(I) complex with 2-mercaptothiazoline (Au-MTZ) is soluble in dimethyl sulfoxide (DMSO), and is insoluble in water, methanol, ethanol, acetonitrile and hexane. The antibacterial activities of the Au-MTZ complex were evaluated by an antibiogram assay using the disc diffusion method. The compound showed an effective antibacterial activity against Staphylococcus aureus (Gram-positive) and Escherichia coli and Pseudomonas aeruginosa (Gram-negative) bacterial cells. Biological analysis for evaluation of the cytotoxic effect of the Au-MTZ complex was performed using HeLa cells derived from human cervical adenocarcinoma. The complex presented a potent cytotoxic activity, inducing 85% of cell death at a concentration of 2.0 mu mol L(-1). (C) 2011 Elsevier Ltd. All rights reserved.

FAPESP (Fundacao de Amparo a Pesquisa do Estado de Sao Paulo, Brazil)[Proc. 2006/55367-2]

CNPq (Conselho Nacional de Desenvolvimento Cientifico e Tecnologico, Brazil)[Proc. 141617/2010-1]

Identificador

POLYHEDRON, v.30, n.13, p.2354-2359, 2011

0277-5387

http://producao.usp.br/handle/BDPI/23768

10.1016/j.poly.2011.06.021

http://dx.doi.org/10.1016/j.poly.2011.06.021

Idioma(s)

eng

Publicador

PERGAMON-ELSEVIER SCIENCE LTD

Relação

Polyhedron

Direitos

restrictedAccess

Copyright PERGAMON-ELSEVIER SCIENCE LTD

Palavras-Chave #Gold(I) #2-Mercaptothiazoline #Infrared spectroscopy #NMR spectroscopy #Antibacterial activity #Cytotoxic assays #MOLECULAR-ORBITAL METHODS #GAUSSIAN-TYPE BASIS #ORGANIC-MOLECULES #CRYSTAL-STRUCTURE #CELL LINES #LIGANDS #DENSITY #Chemistry, Inorganic & Nuclear #Crystallography
Tipo

article

original article

publishedVersion