Document Detail

Biscatecholate-monohydroxamate mixed ligand siderophore-carbacephalosporin conjugates are selective sideromycin antibiotics that target Acinetobacter baumannii.
MedLine Citation:
PMID:  23614627     Owner:  NLM     Status:  MEDLINE    
Chemical syntheses and biological evaluation of biscatecholate-monohydroxamate mixed ligand sideromycins utilizing the carbacephalosporin β-lactam antibiotic loracarbef and the fluoroquinolone antibiotic ciprofloxacin are described. The mixed ligand β-lactam sideromycin (1b) had remarkably selective and extremely potent antibacterial activity against the Gram-negative pathogen Acinetobacter baumannii ATCC 17961 (MIC = 0.0078 μM). The antibacterial activity of the β-lactam sideromycin was inversely related to the iron(III) concentration in the testing media and was antagonized by the presence of the competing parent siderophore. These data suggested that active transport of the mixed ligand β-lactam sideromycin across the outer cell membrane of A. baumannii via siderophore-uptake pathways was responsible for the selective and potent antibacterial activity.
Timothy A Wencewicz; Marvin J Miller
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Publication Detail:
Type:  Journal Article     Date:  2013-05-08
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  56     ISSN:  1520-4804     ISO Abbreviation:  J. Med. Chem.     Publication Date:  2013 May 
Date Detail:
Created Date:  2013-05-23     Completed Date:  2013-07-23     Revised Date:  2014-05-27    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4044-52     Citation Subset:  IM    
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MeSH Terms
Acinetobacter Infections / microbiology
Acinetobacter baumannii / drug effects*
Anti-Bacterial Agents / chemical synthesis*,  pharmacology*
Cephalosporins / chemistry*,  pharmacology*
Culture Media
Ferrous Compounds / chemical synthesis*,  pharmacology*
Indicators and Reagents
Iron / chemistry
Microbial Sensitivity Tests
Peptides / chemical synthesis*,  pharmacology*
Topoisomerase II Inhibitors
Grant Support
Reg. No./Substance:
0/Anti-Bacterial Agents; 0/Cephalosporins; 0/Culture Media; 0/Ferrous Compounds; 0/Indicators and Reagents; 0/Peptides; 0/Topoisomerase II Inhibitors; 0/carbacephems; 56509-18-3/sideromycins; 9002-18-0/Agar; E1UOL152H7/Iron

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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