Tetracationic compounds based on 1,4-diazabicyclo[2.2.2]octane: antibacterial activity and reactions with N-containing nucleophiles

被引:3
作者
Burakova, E. A. [1 ]
Saranina, I. V. [1 ]
Tikunova, N. V. [1 ]
Sil'nikov, V. N. [1 ]
机构
[1] Russian Acad Sci, Novosibirsk Inst Chem Biol & Fundamental Med, Siberian Branch, 8 Prosp Akad Lavrenteva, Novosibirsk 630090, Russia
关键词
tetracationic compounds; quaternary ammonium compounds (QAC); 1,4-di-azabicyclo[2.2.2]octane (DABCO); antibacterial activities; ANTIMICROBIAL ACTIVITIES; QUATERNARY; SALTS;
D O I
10.1007/s11172-015-1023-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Antibacterial activity of tetracationic compounds based on 1,4-diazabicyclo[2.2.2]octane (DABCO) bis-quaternary salts with dodecyl substituents bound by linker groups containing four carbon atoms was studied. All the compounds exhibited activity against the test-strains under study. The gram-positive culture S. aureus was found to be the most sensitive to the influence of compounds in question. The highest activity against S. aureus was exhibited by the compounds containing a but-2-yne or a butane linker; their efficiency exceeded that of the reference compound, antibiotic Ciprofloxacin. For the gram-negative culture P. aeruginosa, the highest activity was exhibited by the compound containing a but-2-yne linker. The compounds with a but-2-yne or a butane linker are stable in the presence of nitrogen-containing nucleophiles, which makes them promising for further studies.
引用
收藏
页码:1400 / 1405
页数:6
相关论文
共 27 条
[1]   Preparation and investigation of antibacterial carbohydrate-based surfaces [J].
Abel, T ;
Cohen, JI ;
Engel, R ;
Filshtinskaya, M ;
Melkonian, A ;
Melkonian, K .
CARBOHYDRATE RESEARCH, 2002, 337 (24) :2495-2499
[2]  
BABAIAN AT, 1960, DOKL AKAD NAUK SSSR+, V133, P1334
[3]   Structure-activity relationships in new polycationic molecules based on two 1,4-diazabicyclo[2.2.2]octanes as artificial ribonucleases [J].
Burakova, E. ;
Kovalev, N. ;
Zenkova, M. ;
Vlassov, V. ;
Silnikov, V. .
BIOORGANIC CHEMISTRY, 2014, 57 :127-131
[4]   Ready for a world without antibiotics? The Pensieres Antibiotic Resistance Call to Action [J].
Carlet, Jean ;
Jarlier, Vincent ;
Harbarth, Stephan ;
Voss, Andreas ;
Goossens, Herman ;
Pittet, Didier .
ANTIMICROBIAL RESISTANCE AND INFECTION CONTROL, 2012, 1
[5]   STRUCTURAL AND MECHANISTIC EFFECTS ON THE RATES OF RING-OPENING REACTIONS IN THE 5-16-MEMBERED-RING REGION [J].
CERICHELLI, G ;
ILLUMINATI, G ;
LILLOCCI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (20) :3952-3957
[6]   Basic ionic liquids based on monoquaternized 1,4-diazobicyclo[2.2.2]octane (dabco) and dicyanamide anion: Physicochemical and solvent properties [J].
Chiappe, Cinzia ;
Melai, Bernardo ;
Sanzone, Angelo ;
Valentini, Giulia .
PURE AND APPLIED CHEMISTRY, 2009, 81 (11) :2035-2043
[7]  
COPE A, 1960, ORGANIC REACTIONS, V11
[8]  
David M., 2012, INT J ANTIMICROB AG, V39, P283
[9]   Polycationic Glycosides [J].
Engel, Robert ;
Ghani, Ishrat ;
Montenegro, Diego ;
Thomas, Marie ;
Klaritch-Vrana, Barbara ;
Castano, Alejandra ;
Friedman, Laura ;
Leb, Jay ;
Rothman, Leah ;
Lee, Heidi ;
Capodiferro, Craig ;
Ambinder, Daniel ;
Cere, Eva ;
Awad, Christopher ;
Sheikh, Faiza ;
Rizzo, JaimeLee ;
Nisbett, Lisa-Marie ;
Testani, Erika ;
Melkonian, Karin .
MOLECULES, 2011, 16 (02) :1508-1518
[10]  
Fedorova A. A., 2012, THESIS NOVOSIBIRSK I