Synthesis, structures, and ESI-mass studies of silver(I) derivatives of imidazolidine-2-thiones: Antimicrobial potential and biosafety evaluation

被引:27
作者
Aulakh, Jaspreet K. [1 ]
Lobana, Tarlok S. [1 ]
Sood, Henna [2 ]
Arora, Daljit S. [2 ]
Smolinski, Victoria A. [3 ]
Duff, Courney E. [3 ]
Jasinski, Jerry P. [3 ]
机构
[1] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India
[2] Guru Nanak Dev Univ, Dept Microbiol, Amritsar 143005, Punjab, India
[3] Keene State Coll, Dept Chem, Keene, NH 03435 USA
关键词
Silver(I) halides; Imidazolidine-2-thiones; Cellular toxicity; Antimicrobial activity; Molecular structure; N-SUBSTITUTED IMIDAZOLIDINE-2-THIONES; COPPER(II) MOLECULAR-SPECTROSCOPY; X-RAY STRUCTURES; SOLUTION NMR; SOLID-STATE; HETEROCYCLIC THIONES; IN-VITRO; CRYSTAL-STRUCTURES; SPECTRAL CHARACTERIZATION; PALLADIUM(II) COMPLEXES;
D O I
10.1016/j.jinorgbio.2017.10.002
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The basic objective of this investigation is to explore potential metallo-organic antimicrobial agents based on silver heterocyclic-2-thiones. In this respect, a series of silver(I) halide complexes with imidazolidine-2-thiones (L-NR, R = H, Me, Et, Pr-n, Be, Ph), namely, mononuclear [AgX(L-NR)(PPh3)(2)] (X, R: Cl, Bu, I; Br, Ph, 7); [AgX (L-NR)(3)] (Br, Bu, 5; Br, Pr-n, 8) and halogen bridged dinuclear [Ag-2([1-X)(2)(L-NR)(2)(PPll(3))(2)] (Cl, Bu", 2; Cl, Ph, 3; CI, Pr-n, 4; Br, Ph, 6) have been synthesized and characterized using modern techniques. The thio-ligands are terminally S-bonded in all the complexes. The in vitro antimicrobial potential and biosafety evaluation of the above complexes as well as that of previously reported analogous silver complexes has been studied against Gram positive bacteria, namely, Staphylococcus aureus (MTCC 740) and Methicillin resistant Staphylococcus aureus (MRSA), Gram negative bacteria Klebsiella pnewnoniae (MTCC 109), Salmonella typhimurium (MTCC 98) and a yeast Candida albicans (MTCC 227). Most of the complexes tested have shown significant antimicrobial activity with low values of minimum inhibitory concentration (MIC). Significantly, the activity against MRSA is an important outcome of this investigation. Among complexes tested for their cytotoxicity using MTT [3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide] assay, some complexes showed low cellular toxicity with high percent cell viability. A dinuclear complex [Ag-2(p-Cl)(2)(L-NPh)(2)(PPh3)(2)] 3 with 93.3% cell viability emerges the most important candidate for further investigations.
引用
收藏
页码:18 / 31
页数:14
相关论文
共 63 条
[1]   Antibacterial properties of a silver chloride-coated nylon wound dressing [J].
Adams, AP ;
Santschi, EM ;
Mellencamp, MA .
VETERINARY SURGERY, 1999, 28 (04) :219-225
[2]   Recent studies in the coordination chemistry of heterocyclic thiones and thionates [J].
Akrivos, PD .
COORDINATION CHEMISTRY REVIEWS, 2001, 213 :181-210
[3]   Complexation of Cd(SeCN)2 with imidazolidine-2-thione and its derivatives: Solid state, solution NMR and anti-bacterial studies [J].
Al-Maythalony, Bassem A. ;
Wazeer, Mohammed I. M. ;
Isab, Anvarhusein A. ;
Nael, M. T. ;
Ahmad, Saeed .
SPECTROSCOPY-AN INTERNATIONAL JOURNAL, 2008, 22 (05) :361-370
[4]   Silver(I) complexes of imidazolidine-2-thione and triphenylphosphines: Solid-state, solution NMR and antimicrobial activity studies [J].
Al-Zamil, Norah O. ;
Al-Sadhan, Khulood A. ;
Isab, Anvarhusein A. ;
Wazeer, Mohamed I. M. ;
Al-Arfaj, Abdul Rehman A. .
SPECTROSCOPY-AN INTERNATIONAL JOURNAL, 2007, 21 (01) :61-67
[5]  
[Anonymous], 1960, The Nature of the Chemical Bond, 3rd ed
[6]   Variable coordination and C-S bond cleavage activity of N-substituted imidazolidine-2-thiones towards copper: synthesis, spectroscopy, structures, ESI-mass and antimicrobial studies [J].
Aulakh, Jaspreet K. ;
Lobana, Tarlok S. ;
Sood, Henna ;
Arora, Daljit S. ;
Garcia-Santos, Isabel ;
Hundal, Geeta ;
Kaur, Manpreet ;
Smolenski, Victoria A. ;
Jasinski, Jerry P. .
DALTON TRANSACTIONS, 2017, 46 (04) :1324-1339
[7]   Synthesis and characterization of the bimetallic polymers [MS4Ag2(Hmimt)2]n (where M = Mo or W, Hmimt=1-methylimidazoline-2(3H)-thione):: crystal structures of [WS4Ag2(Hmimt)2]n and [Ag2I2(Hmimt)]n [J].
Beheshti, A ;
Clegg, W ;
Brooks, NR ;
Sharafi, F .
POLYHEDRON, 2005, 24 (03) :435-441
[8]   Solvent-assisted mechanochemical synthesis of metal complexes [J].
Bowmaker, Graham A. ;
Chaichit, Narongsak ;
Pakawatchai, Chaveng ;
Skelton, Brian W. ;
White, Allan H. .
DALTON TRANSACTIONS, 2008, (22) :2926-2928
[9]   Structural and spectroscopic studies of some adducts of silver(I) salts with ethylenethiourea [J].
Bowmaker, Graham A. ;
Chaichit, Narongsak ;
Pakawatchai, Chaveng ;
Skelton, Brian W. ;
White, Allan H. .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2009, 87 (01) :161-170
[10]   Silver(I) complexes with heterocyclic thiones and tertiary phosphines as ligands. Part 4. Dinuclear complexes of silver(I) bromide: the crystal structure of bis[bromo-(pyrimidine-2-thione)(triphenylphosphine)silver(I)] [J].
Cox, PJ ;
Aslanidis, P ;
Karagiannidis, P ;
Hadjikakou, S .
INORGANICA CHIMICA ACTA, 2000, 310 (02) :268-272