Document Detail


Saquayamycins G-K, cytotoxic angucyclines from Streptomyces sp. Including two analogues bearing the aminosugar rednose.
MedLine Citation:
PMID:  22758660     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Streptomyces sp. KY40-1, a strain isolated from the Kentucky Appalachian foothills, is the producer of moromycins A (18) and B (19). Further investigations of this strain led to the isolation and structure elucidation of the five new saquayamycins G-K (1-5), along with known compounds. Two of the new compounds bear the unusual aminosugar rednose, which was found here for the first time in angucyclines. The different attachment positions of this aminosugar in these two compounds indicate a high acceptor substrate flexibility of the responsible glycosyl transferase or alternatively the involvement of multiple glycosyl transferases. The cytotoxic activity of the isolated compounds was determined using human prostate cancer (PC-3) and non-small-cell lung cancer (H460) cell lines. Cell viability assays showed that saquayamycins J (4), K (5), A (7), and B (8) were most active in PC3 cells, with saquayamycin B (8) showing the highest activity (GI(50) = 0.0075 μM). The aminosugar-containing saquayamycins H (2) and saquayamycin B (8) showed the highest activity against H460 cells, with a GI(50) of 3.3 and 3.9 μM, respectively. The results presented here provide more insights into the structure-activity relationship of saquayamycins with respect to the nature, number, and linkage of sugar residues.
Authors:
Khaled A Shaaban; Tamer A Ahmed; Markos Leggas; Jürgen Rohr
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-07-03
Journal Detail:
Title:  Journal of natural products     Volume:  75     ISSN:  1520-6025     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2012 Jul 
Date Detail:
Created Date:  2012-07-27     Completed Date:  2012-11-06     Revised Date:  2013-07-31    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1383-92     Citation Subset:  IM    
Affiliation:
Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky , 789 South Limestone Street, Lexington, Kentucky 40536-0596, USA.
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MeSH Terms
Descriptor/Qualifier:
Amino Sugars / chemistry,  isolation & purification*,  pharmacology*
Anthraquinones / chemistry,  isolation & purification,  pharmacology
Antineoplastic Agents / chemistry,  isolation & purification*,  pharmacology*
Drug Screening Assays, Antitumor
Humans
Kentucky
Male
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Streptomyces / chemistry*
Structure-Activity Relationship
Grant Support
ID/Acronym/Agency:
CA 091901/CA/NCI NIH HHS; CA 102102/CA/NCI NIH HHS; R01 CA091901/CA/NCI NIH HHS; R01 CA102102/CA/NCI NIH HHS
Chemical
Reg. No./Substance:
0/Amino Sugars; 0/Anthraquinones; 0/Antineoplastic Agents; 99260-65-8/saquayamycin
Comments/Corrections

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