A silver complex with tryptophan: Synthesis, structural characterization, DFT studies and antibacterial and antitumor assays in vitro

被引:35
作者
Carvalho, Marcos A. [1 ]
de Paiva, Raphael E. F. [1 ]
Bergamini, Fernando R. G. [1 ]
Gomes, Alexandre F. [1 ]
Gozzo, Fabio C. [1 ]
Lustri, Wilton R. [2 ]
Formiga, Andre L. B. [1 ]
Shishido, Silvia M. [3 ]
Ferreira, Carmen V. [3 ]
Corbi, Pedro P. [1 ]
机构
[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazil
[2] Centro Univ Araraquara, Biol & Hlth Sci Dept, BR-14801320 Araraquara, SP, Brazil
[3] Univ Estadual Campinas, Lab Bioassays & Signal Transduct, Dept Biochem, Inst Biol, BR-13083970 Campinas, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
L-tryptophan; Silver; Solid-state NMR; ESI-QTOF mass spectrometry; Antibacterial agent; Antitumoral assays; MOLECULAR-ORBITAL METHODS; GAUSSIAN-TYPE BASIS; ANTIMICROBIAL ACTIVITIES; CRYSTAL-STRUCTURES; TRIPHENYLPHOSPHINE LIGANDS; PALLADIUM(II) COMPLEX; POTENTIALS; POLYMER;
D O I
10.1016/j.molstruc.2012.07.044
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The synthesis, spectroscopic characterization and biological assays of a new silver(I) complex with L-tryptophan (TRP) are presented. Elemental and thermal analyses and ESI-QTOF mass spectrometric measurements of the solid compound suggest the composition AgC11H11N2O2. Infrared and solid-state NMR analyses indicate coordination of TRP to Ag(I) ion through the nitrogen of the NH2 group and also through the oxygen of carboxylate group. Theoretical (DFT) calculations permit proposing an optimized geometry for the complex. Antibacterial assays indicated that the Ag-TRP complex is effective against Staphylococcus aureus and Enterococcus faecalis (Gram-positive), and Pseudomonas aeruginosa and Escherichia coli (Gram-negative) bacterial strains. The complex was also cytotoxic against Panc-1 (human pancreatic carcinoma) and SK-Mel 103 (human melanoma) cells. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:125 / 131
页数:7
相关论文
共 45 条
[1]   Chemical, spectroscopic characterization, DFT studies and initial pharmacological assays of a silver(I) complex with N-acetyl-L-cysteine [J].
Abbehausen, Camilla ;
Heinrich, Tassiele A. ;
Abrao, Emiliana P. ;
Costa-Neto, Claudio M. ;
Lustri, Wilton R. ;
Formiga, Andre L. B. ;
Corbi, Pedro P. .
POLYHEDRON, 2011, 30 (04) :579-583
[2]  
[Anonymous], 1994, 040783 JCPDSICDD
[3]  
Atilio I.A., 2006, INORG CHEM, V45, P1638
[4]   Prolonged antimicrobial activity of a catheter containing chlorhexidine-silver sulfadiazine extends protection against catheter infections in vivo [J].
Bassetti, S ;
Hu, J ;
D'Agostino, RB ;
Sherertz, RJ .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2001, 45 (05) :1535-1538
[5]  
BAUER AW, 1966, AM J CLIN PATHOL, V45, P493
[6]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[7]  
Bobiev G.M., 2008, PHARM CHEM J, V42, P614
[8]  
Bobiev G.M., 2008, PHARM CHEM J, V42, P708
[9]   COORDINATION PROPERTIES OF SILVER DIPHOSPHINE COMPLEXES - CRYSTAL-STRUCTURES AND MOLECULAR-STRUCTURES OF AG(2)X(2)(M-PP)(2) (X=I, CL, NO3 M-PP=1,3-BIS[(DIPHENYLPHOSPHINO)METHYL]BENZENE) AND AG(2)X(2)(O-PP)(2) (X=I CL O-PP=1,2-BIS[(DIPHENYLPHOSPHINO)METHYL]BENZENE) - SYNTHESIS AND H-1-NMR AND P-31-NMR SPECTROSCOPY OF SILVER DIPHOSPHINE COMPLEXES [J].
CARUSO, F ;
CAMALLI, M ;
RIMML, H ;
VENANZI, LM .
INORGANIC CHEMISTRY, 1995, 34 (03) :673-679
[10]   Synthesis, spectroscopic characterization, DFT studies, and initial antibacterial assays in vitro of a new palladium(II) complex with tryptophan [J].
Carvalho, M. A. ;
Souza, B. C. ;
Paiva, R. E. F. ;
Bergamini, F. R. G. ;
Gomes, A. F. ;
Gozzo, F. C. ;
Lustri, W. R. ;
Formiga, A. L. B. ;
Rigatto, G. ;
Corbi, P. P. .
JOURNAL OF COORDINATION CHEMISTRY, 2012, 65 (10) :1700-1711