| Piperazimycins: cytotoxic hexadepsipeptides from a marine-derived bacterium of the genus Streptomyces. | |
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MedLine Citation:
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PMID: 17221946 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Three potent cancer cell cytotoxins, piperazimycins A-C (1-3), have been isolated from the fermentation broth of a Streptomyces sp., cultivated from marine sediments near the island of Guam. The structures of these cyclic hexadepsipeptides were assigned by a combination of spectral, chemical, and crystallographic methods. The piperazimycins are composed of rare amino acids, including hydroxyacetic acid, alpha-methylserine, gamma-hydroxypiperazic acid, and gamma-chloropiperazic acid. The novel amino acid residues 2-amino-8-methyl-4,6-nonadienoic acid and 2-amino-8-methyl-4,6-decadienoic acid were found as components of piperazimycins A and C, respectively. When screened in the National Cancer Institute's 60 cancer cell line panel, piperazimycin A exhibited potent in vitro cytotoxicity toward multiple tumor cell lines with a mean GI50 of 100 nM. |
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Authors:
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Eric D Miller; Christopher A Kauffman; Paul R Jensen; William Fenical |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Jan |
Date Detail:
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Created Date: 2007-01-15 Completed Date: 2007-03-20 Revised Date: 2007-12-03 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 323-30 Citation Subset: IM |
Affiliation:
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Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California-San Diego, La Jolla, California 92093-0204, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Cell Line, Tumor Cell Proliferation / drug effects Crystallography, X-Ray Depsipeptides / chemistry, isolation & purification, pharmacology* Drug Screening Assays, Antitumor Humans Magnetic Resonance Spectroscopy / methods, standards Models, Molecular Molecular Conformation Reference Standards Sensitivity and Specificity Stereoisomerism Streptomyces / chemistry* Structure-Activity Relationship |
| Grant Support | |
ID/Acronym/Agency:
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CA44848/CA/NCI NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Depsipeptides; 0/piperazimycin A; 0/piperazimycin B; 0/piperazimycin C |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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