Synthesis, spectroscopic characterization, DFT studies and biological assays of a novel gold(I) complex with 2-mercaptothiazoline |
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Authors: | Camilla Abbehausen,Juliana F. CastroMarcelle B.M. Spera,Tassiele A. HeinrichClaudio M. Costa-Neto,Wilton R. LustriAndré L.B. Formiga,Pedro P. Corbi |
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Affiliation: | a Institute of Chemistry, University of Campinas - UNICAMP, P.O. Box 6154, 13083-970 Campinas, SP, Brazil b Department of Biochemistry and Immunology, School of Medicine of Ribeirão Preto, University of São Paulo - USP, 14049-900 Ribeirão Preto, SP, Brazil c Department of Biological and Health Sciences - UNIARA, 14801-320 Araraquara, SP, Brazil |
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Abstract: | A new gold(I) complex with 2-mercaptothiazoline (MTZ) with the coordination formula [AuCN(C3H5NS2)] was synthesized and characterized by chemical and spectroscopic measurements, DFT studies and biological assays. Infrared (IR) and 1H, 13C and 15N nuclear magnetic resonance (NMR) spectroscopic measurements indicate coordination of the ligand to gold(I) through the nitrogen atom. Studies based on DFT 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 °C, leading to the formation of Au0 as the final residue at 1000 °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 μmol L−1. |
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Keywords: | MTZ, mercaptothiazoline NMR, nuclear magnetic resonance IR, infrared Au-MTZ, gold(I) complex with mercaptothiazoline MIC, minimal inhibitory concentration TMS, tetramethylsilane DMSO, dimethyl sulfoxide LANL2DZ, Los Alamos National Laboratory, 2nd version on double zeta function B3LYP, Becke 3-Lee Young Parr functional ATCC, American type collection cell MH, Mueller-Hinton agar BHI, brain-heart infusion medium CFU, colony forming unit DMEM, Dulbecco&rsquo s Modified Eagle&rsquo s Medium FCS, Fetal Calf Serum MTT, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium salt PBS, phosphate buffered saline |
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