Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori

被引:61
作者
Andrews, Philip C. [1 ]
Ferrero, Richard L. [2 ]
Junk, Peter C. [1 ]
Kumar, Ish [1 ]
Luu, Quynh [1 ]
Nguyen, Kim [1 ]
Taylor, James W. [1 ]
机构
[1] Monash Univ, Sch Chem, Melbourne, Vic 3800, Australia
[2] Monash Inst Med Res, Ctr Innate Immun & Infect Dis, Melbourne, Vic 3168, Australia
关键词
SOLVENT-FREE; INFECTION; CHEMISTRY; ULCER; SUSCEPTIBILITY; CARBOXYLATES; CRYSTAL; AGENTS;
D O I
10.1039/c000164c
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The formation of bismuth(III) complexes of carboxylates and benzoates derived from the 1 : 3 reaction of BiPh(3) with the common non-steroidal anti-inflammatory drugs ( NSAIDs) ketoprofen, naproxen, ibuprofen, mefenamic acid, diflunisal, 5-chlorosalicylic acid, fenbufen, sulindac, tolfenamic acid and flufenamic acid, has been achieved using both solvent-free and solvent-mediated methods. The thermochemical profiles of the solvent-free reactions were studied using DSC-TGA. All reactions produced the tris-substituted complexes of general formula [BiL(3)](n), with the complexes derived from ketoprofen and sulindac having an additional single bismuth bound H(2)O molecule in the inner coordination sphere. The complexes are stable in air over a period of six months, do not undergo significant decomposition when suspended overnight in water, but decompose in 1 M HCl solution to release the free acid form of the NSAID. All ten complexes show excellent in vitro activity against Helicobacter pylori with MIC values of >= 6.25 mu g mL(-1).
引用
收藏
页码:2861 / 2868
页数:8
相关论文
共 37 条
[31]   Treatment and dosing of Helicobacter pylori infection:: when pharmacology meets clinic [J].
Treiber, Gerhard ;
Malfertheiner, Peter ;
Klotz, Ulrich .
EXPERT OPINION ON PHARMACOTHERAPY, 2007, 8 (03) :329-350
[32]   CRYSTAL AND MOLECULAR-STRUCTURE OF BISMUTH(III) 2,2-DIMETHYLPROPANOATE [J].
TROYANOV, SI ;
PISAREVSKY, AP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (03) :335-336
[33]   Antibacterial tests of bismuth(III)-quinolone (ciprofloxacin, cf) compounds against Helicobacter pylori and some other bacteria.: Crystal structure of (cfH2)2[Bi2Cl10]•4H2O [J].
Turel, I ;
Golic, L ;
Bukovec, P ;
Gubina, M .
JOURNAL OF INORGANIC BIOCHEMISTRY, 1998, 71 (1-2) :53-60
[34]   Nod1 responds to peptidoglycan delivered by the Helicobacter pylori cag pathogenicity island [J].
Viala, J ;
Chaput, C ;
Boneca, IG ;
Cardona, A ;
Girardin, SE ;
Moran, AP ;
Athman, R ;
Mémet, S ;
Huerre, MR ;
Coyle, AJ ;
DiStefano, PS ;
Sansonetti, PJ ;
Labigne, A ;
Bertin, J ;
Philpott, DJ ;
Ferrero, RL .
NATURE IMMUNOLOGY, 2004, 5 (11) :1166-1174
[35]   Determination of the enantiomeric purity of naproxen - An organic chemistry laboratory experiment [J].
Walsh, TD ;
Koontz, CS .
JOURNAL OF CHEMICAL EDUCATION, 1997, 74 (05) :585-586
[36]   Gastrointestinal toxicity of nonsteroidal antiinflammatory drugs [J].
Wolfe, MM ;
Lichtenstein, DR ;
Singh, G .
NEW ENGLAND JOURNAL OF MEDICINE, 1999, 340 (24) :1888-1899
[37]   Biocoordination chemistry of bismuth: Recent advances [J].
Yang, Nan ;
Sun, Hongzhe .
COORDINATION CHEMISTRY REVIEWS, 2007, 251 (17-20) :2354-2366