Document Detail

Synthesis and biological evaluation of new acinetoferrin homologues for use as iron transport probes in mycobacteria.
MedLine Citation:
PMID:  15369397     Owner:  NLM     Status:  MEDLINE    
Four new acinetoferrin homologues were synthesized using a modular synthetic approach. Two linear and two cyclic imide derivatives were generated and evaluated for growth stimulating behavior in Mycobacterium avium subsp paratuberculosis. The yield for the tandem coupling of a functionalized aminohydroxamic acid motif (2 equiv) to a tert-butyl citrate derivative was significantly improved using DCC and N-hydroxysuccinimide. (1)H NMR spectroscopy (CD(3)OD) provided a convenient method for monitoring the final imidization step in TFA using the doublet patterns between 2.5 and 3.06 ppm. New protocols demonstrated that only a 20% growth enhancement was observed with M. avium subsp. paratuberculosis using the imide of acinetoferrin. Last, a siderophore from Streptomyces pilosus, deferrioxamine B, was shown to cross-feed M. avium subsp. paratuberculosis with the same efficiency as the more costly, native chelator, mycobactin J.
Richard A Gardner; George Ghobrial; Saleh A Naser; Otto Phanstiel
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  47     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  2004 Sep 
Date Detail:
Created Date:  2004-09-16     Completed Date:  2004-11-01     Revised Date:  2007-11-15    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4933-40     Citation Subset:  IM    
Department of Chemistry and Department of Molecular Biology and Microbiology, University of Central Florida, Orlando, Florida 32816-2366, USA.
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MeSH Terms
Biochemistry / methods*
Biological Transport / drug effects
Cell Division / drug effects
Citrates / chemistry*,  metabolism,  pharmacology
Deferoxamine / metabolism,  pharmacology
Drug Evaluation, Preclinical / methods
Hydroxamic Acids / chemistry*,  metabolism,  pharmacology
Iron / metabolism*
Iron Chelating Agents / chemistry,  pharmacology
Magnetic Resonance Spectroscopy / methods
Mycobacterium / drug effects,  metabolism*
Mycobacterium avium / drug effects,  metabolism
Mycobacterium avium subsp. paratuberculosis / drug effects,  growth & development,  metabolism
Oxazoles / metabolism,  pharmacology
Reg. No./Substance:
0/Citrates; 0/Hydroxamic Acids; 0/Iron Chelating Agents; 0/Oxazoles; 0/acinetoferrin; 0/mycobactins; 70-51-9/Deferoxamine; 7439-89-6/Iron

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