Synthesis, Characterization and Antimicrobial properties of Methylbenzyl and Nitrobenzyl containing Imidazolium-based Silver N-Heterocyclic Carbenes

被引:16
作者
Aher, Sainath [1 ]
Das, Anamika [2 ]
Muskawar, Prashant [3 ]
Osborne, Jabez [2 ]
Bhagat, Pundlik [1 ]
机构
[1] VIT Univ, Sch Adv Sci, Dept Chem, Vellore 632014, Tamil Nadu, India
[2] VIT Univ, Sch Biosci & Biotechnol, Dept Biosci, Vellore 632014, Tamil Nadu, India
[3] St Gadge Baba Amravati Univ, Amlokchand Mahavidyalaya, Dept Chem, Amravati 444602, India
关键词
Antimicrobial; Cell wall distortion; Minimum inhibitory concentration; N-heterocyclic carbenes; Silver; ANTIBACTERIAL ACTIVITY; COMPLEXES; SULFADIAZINE;
D O I
10.1016/j.molliq.2017.03.021
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
series of imidazolium-based novel ionic liquids (ILs) containing methylbenzyl and nitrobenzyl substituents were prepared and further converted to neutral as well as ionic silver complexes. The ILs and their Ag-NHCs (N-Heterocyclic Carbenes) were successfully characterized by NMR, FT-IR, and EI-MS studies. The Ms and Ag-NHCs were screened for antimicrobial activity based on the zone of inhibition, Minimum Inhibitory Concentration (MIC) determination, and stability studies against Salmonella enterica and Staphylococcus aureus. The neutral complex NS-32 ((1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-3-(4-nitrobenzyl)-2,3-dihydroimidazol-2-yl)silver bromide) was the most active with MIC of 25 mu M and showed efficient growth inhibition of bacterial pathogens even up to 21 d. The complex NS-32 was further monitored for cell wall disruption by scanning electron microscopy (SEM). The photomicrographs of bacterial cells obtained by SEM after treatment of NS-32 with S. enterica and S. aureus showed rupture of a cell wall, thus proving it to be the site of action and ultimately having inhibitory effects on the microbial cell growth. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:270 / 277
页数:8
相关论文
共 31 条
[1]  
Aher S., 2017, J MOL
[2]   History of the Medical Use of Silver [J].
Alexander, J. Wesley .
SURGICAL INFECTIONS, 2009, 10 (03) :289-292
[3]   ELECTRON-DISTRIBUTION IN A STABLE CARBENE [J].
ARDUENGO, AJ ;
DIAS, HVR ;
DIXON, DA ;
HARLOW, RL ;
KLOOSTER, WT ;
KOETZLE, TF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6812-6822
[4]   SILVER SULFADIAZINE - IN-VITRO ANTIBACTERIAL ACTIVITY [J].
CARR, HS ;
WLODKOWSKI, TJ ;
ROSENKRANZ, HS .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1973, 4 (05) :585-587
[5]   Synthesis of well-defined N-heterocyclic carbene silver(I) complexes [J].
de Frémont, P ;
Scott, NM ;
Stevens, ED ;
Ramnial, T ;
Lightbody, OC ;
Macdonald, CLB ;
Clyburne, JAC ;
Abernethy, CD ;
Nolan, SP .
ORGANOMETALLICS, 2005, 24 (26) :6301-6309
[6]   Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts [J].
Demberelnyamba, D ;
Kim, KS ;
Choi, SJ ;
Park, SY ;
Lee, H ;
Kim, CJ ;
Yoo, ID .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (05) :853-857
[7]   MECHANISM OF SILVER SULFADIAZINE ACTION ON BURN WOUND INFECTIONS [J].
FOX, CL ;
MODAK, SM .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1974, 5 (06) :582-588
[8]  
Gupta A., 1998, APPL ENVIRON MICROB, V64, P1
[9]   Synthesis and biological evaluation of N-heterocyclic carbene-silver(I) acetate complexes derived from 4,5-ditolyl-imidazole [J].
Hackenberg, Frauke ;
Lally, Grainne ;
Mueller-Bunz, Helge ;
Paradisi, Francesca ;
Quaglia, Daniela ;
Streciwilk, Wojciech ;
Tacke, Matthias .
INORGANICA CHIMICA ACTA, 2013, 395 :135-144
[10]   Silver(I)-N-heterocyclic carbene complexes of nitrile-functionalized imidazol-2-ylidene ligands as anticancer agents [J].
Hague, Rosenani A. ;
Budagumpi, Srinivasa ;
Zulikha, H. Zetty ;
Hasanudin, Noorhafizah ;
Ahamed, Mohamed B. Khadeer ;
Majid, Amin M. S. Abdul .
INORGANIC CHEMISTRY COMMUNICATIONS, 2014, 44 :128-133