| Synthesis and biological evaluation of new acinetoferrin homologues for use as iron transport probes in mycobacteria. | |
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MedLine Citation:
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PMID: 15369397 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Richard A Gardner; George Ghobrial; Saleh A Naser; Otto Phanstiel |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 47 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 2004 Sep |
Date Detail:
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Created Date: 2004-09-16 Completed Date: 2004-11-01 Revised Date: 2007-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: United States |
Other Details:
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Languages: eng Pagination: 4933-40 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Department of Molecular Biology and Microbiology, University of Central Florida, Orlando, Florida 32816-2366, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Biochemistry
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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 |
| Chemical | |
Reg. No./Substance:
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0/Citrates; 0/Hydroxamic Acids; 0/Iron Chelating Agents; 0/Oxazoles; 0/acinetoferrin; 0/mycobactins; 70-51-9/Deferoxamine; 7439-89-6/Iron |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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