Document Detail

Effects of thymoquinone-fatty acid conjugates on cancer cells.
MedLine Citation:
PMID:  19322799     Owner:  NLM     Status:  MEDLINE    
4-Acylhydrazones and 6-alkyl derivatives of thymoquinone (TQ) were tested for growth inhibition of human HL-60 leukemia, 518A2 melanoma, KB-V1/Vbl cervix, and MCF-7/Topo breast carcinoma cells. Unsaturated side chains conferred greater activities than equally long saturated chains. The number of C==C bonds was less decisive than chain length. The 6-hencosahexaenyl conjugate 3 e was most active in all resistant tumor cells, with IC(50) (72 h) values as low as 30 nM in MCF-7/Topo cells. The conjugates are likely to operate by mechanisms different from that of TQ. For instance, 3 e induced distinct caspase-independent apoptosis in HL-60 and 518A2 cells concomitant with a loss of mitochondrial membrane potential and a subsequent rise in the levels of reactive oxygen species.
Sandra Breyer; Katharina Effenberger; Rainer Schobert
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  ChemMedChem     Volume:  4     ISSN:  1860-7187     ISO Abbreviation:  -     Publication Date:  2009 May 
Date Detail:
Created Date:  2009-05-11     Completed Date:  2009-07-27     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101259013     Medline TA:  ChemMedChem     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  761-8     Citation Subset:  IM    
Organic Chemistry Laboratory, University of Bayreuth, Universitätsstr. 30, 95440 Bayreuth, Germany.
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MeSH Terms
Antineoplastic Agents / chemical synthesis,  chemistry,  pharmacology*
Benzoquinones / chemical synthesis,  chemistry*
Caspases / chemistry,  metabolism
Cell Line, Tumor
Docosahexaenoic Acids / chemical synthesis,  chemistry
Drug Screening Assays, Antitumor
Fatty Acids / chemical synthesis,  chemistry*
Nigella sativa / chemistry
Reactive Oxygen Species / metabolism
Seeds / chemistry
Reg. No./Substance:
0/Antineoplastic Agents; 0/Benzoquinones; 0/Fatty Acids; 0/Reactive Oxygen Species; 25167-62-8/Docosahexaenoic Acids; 490-91-5/thymoquinone; EC 3.4.22.-/Caspases

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

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