Document Detail

Latrunculin with a highly oxidized thiazolidinone ring: structure assignment and actin docking.
MedLine Citation:
PMID:  17929935     Owner:  NLM     Status:  MEDLINE    
A new latrunculin, oxalatrunculin B (3), was isolated from Red Sea sponge Negombata corticata. Extensive spectroscopic analysis revealed an unprecedented heterocycle in which the rare thiazolidinone ring found in latrunculins was oxidized with three additional oxygens. An actin polymerization inhibition assay agreed with MM-PBSA free energy calculations that 3 binds more weakly than latrunculin B to actin. Significant antifungal and anticancer activity of 3 was found, suggesting an alternate target in addition to actin for latrunculin bioactivity.
Safwat A Ahmed; Srinivas Odde; Pankaj R Daga; John J Bowling; Mostafa K Mesbah; Diaa T Youssef; Sherief I Khalifa; Robert J Doerksen; Mark T Hamann
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2007-10-12
Journal Detail:
Title:  Organic letters     Volume:  9     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2007 Nov 
Date Detail:
Created Date:  2007-11-01     Completed Date:  2007-12-11     Revised Date:  2013-06-12    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4773-6     Citation Subset:  IM    
Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt.
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MeSH Terms
Actins / chemistry*,  metabolism*
Bicyclo Compounds, Heterocyclic / chemistry*,  metabolism*,  pharmacology
Binding Sites
Cell Line, Tumor
Cell Survival / drug effects
Computer Simulation
Magnetic Resonance Spectroscopy
Models, Molecular
Oxygen / chemistry*
Protein Structure, Tertiary
Thiazolidines / chemistry*,  metabolism*,  pharmacology
Grant Support
1R01 AI 36596/AI/NIAID NIH HHS; C06 RR 14503-01/RR/NCRR NIH HHS; R01 AI036596/AI/NIAID NIH HHS; R01 AI036596-08/AI/NIAID NIH HHS
Reg. No./Substance:
0/Actins; 0/Bicyclo Compounds, Heterocyclic; 0/Thiazolidines; 76343-93-6/latrunculin A; 76343-94-7/latrunculin B; 7782-44-7/Oxygen

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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