Document Detail


Minutissamides A-D, antiproliferative cyclic decapeptides from the cultured cyanobacterium Anabaena minutissima.
MedLine Citation:
PMID:  21699148     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Four cyclic decapeptides, minutissamides A-D (1-4), were isolated from the cultured cyanobacterium Anabaena minutissima (UTEX 1613). The planar structures were determined using various spectroscopic techniques including HRESIMS and 1D and 2D NMR experiments. The absolute configurations of the α-amino acid residues were assigned using Marfey's method after acid hydrolysis. The absolute configuration of a β-amino acid residue was assigned by a combination of the advanced Marfey's method, J-based configurational analysis, and ROE spectroscopic analysis. The structures of minutissamides A-D (1-4) were characterized by the presence of three nonstandard α-amino acid residues (two α,β-dehydro-α-aminobutyric acids and one N-methylated Asn) and one β-amino acid residue (2-hydroxy-3-amino-4-methyldodecanoic acid or 2-hydroxy-3-amino-4-methylhexadecanoic acid). Minutissamides A-D (1-4) exhibited antiproliferative activity against the HT-29 human colon cancer cell line with IC₅₀ values of 2.0, 20.0, 11.8, and 22.7 μM, respectively.
Authors:
Hahk-Soo Kang; Aleksej Krunic; Qi Shen; Steven M Swanson; Jimmy Orjala
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2011-06-23
Journal Detail:
Title:  Journal of natural products     Volume:  74     ISSN:  1520-6025     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2011 Jul 
Date Detail:
Created Date:  2011-07-22     Completed Date:  2011-10-07     Revised Date:  2013-06-28    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1597-605     Citation Subset:  IM    
Affiliation:
Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago , 833 S. Wood Street, Chicago, Illinois 60612, USA.
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MeSH Terms
Descriptor/Qualifier:
Anabaena / chemistry*
Antineoplastic Agents / chemistry,  isolation & purification*,  pharmacology*
Drug Screening Assays, Antitumor
HT29 Cells
Humans
Inhibitory Concentration 50
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Peptides, Cyclic / chemistry,  isolation & purification*,  pharmacology*
Grant Support
ID/Acronym/Agency:
P01 CA125066/CA/NCI NIH HHS; P01 CA125066-04/CA/NCI NIH HHS
Chemical
Reg. No./Substance:
0/Antineoplastic Agents; 0/Peptides, Cyclic
Comments/Corrections

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