Document Detail

Anti-Clostridium difficile potential of tetramic acid derivatives from Pseudomonas aeruginosa quorum-sensing autoinducers.
MedLine Citation:
PMID:  19917748     Owner:  NLM     Status:  MEDLINE    
We have examined the potential bactericidal activities of several tetramic acids derived from Pseudomonas autoinducers against Clostridium difficile, a cause of antibiotic-associated pseudomembranous colitis. Clinical isolates of C. difficile (n=4) were incubated in broth with a chemically synthesized Pseudomonas autoinducer and its tetramic acid derivatives. The structure-activity relationship and the mechanisms of action were examined by a time-killing assay and by determination of the morphological/staining characteristics. The use of some tetramic acids derived from N-3-oxododecanoyl L-homoserine lactone resulted in more than 3-log reductions in the viability of C. difficile within 30 min at 30 microM. The outer membrane was suggested to be one of the targets for the bactericidal activity of tetramic acid, because disturbance of the bacterial outer surface was demonstrated by alteration of the Gram-staining characteristic and electron microscopy. The data for the tetramic acid derivatives demonstrate that the keto-enol structure and the length of the acyl side chain of tetramic acid may be essential for the antibacterial activity of this molecule. These results suggest the potential for tetramic acid derivatives to be novel agents with activity against C. difficile.
Chihiro Ueda; Kazuhiro Tateda; Manabu Horikawa; Soichiro Kimura; Yoshikazu Ishii; Kaoru Nomura; Kanako Yamada; Takashi Suematsu; Yasuhisa Inoue; Masaji Ishiguro; Shinichi Miyairi; Keizo Yamaguchi
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Publication Detail:
Type:  Journal Article     Date:  2009-11-16
Journal Detail:
Title:  Antimicrobial agents and chemotherapy     Volume:  54     ISSN:  1098-6596     ISO Abbreviation:  Antimicrob. Agents Chemother.     Publication Date:  2010 Feb 
Date Detail:
Created Date:  2010-01-25     Completed Date:  2010-03-04     Revised Date:  2010-09-28    
Medline Journal Info:
Nlm Unique ID:  0315061     Medline TA:  Antimicrob Agents Chemother     Country:  United States    
Other Details:
Languages:  eng     Pagination:  683-8     Citation Subset:  IM    
Department of Microbiology and Infectious Diseases, Toho University School of Medicine, 5-21-16 Ohmorinishi, Ohtaku, Tokyo 143-8540, Japan.
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MeSH Terms
Anti-Bacterial Agents / chemical synthesis,  chemistry,  pharmacology*
Clostridium difficile / drug effects*,  ultrastructure
Homoserine / analogs & derivatives*,  chemistry
Lactones / chemistry*
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Microscopy, Electron, Transmission
Pyrrolidinones / chemical synthesis,  chemistry,  pharmacology*
Quorum Sensing / physiology
Reg. No./Substance:
0/Anti-Bacterial Agents; 0/Lactones; 0/Pyrrolidinones; 152833-54-0/Pseudomonas aeruginosa autoinducer; 498-19-1/Homoserine; 503-83-3/tetramic acid

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