Document Detail

Synthesis and in vitro and in vivo evaluation of a series of dihydroisocoumarin derivatives conjugated with fatty acids, alcohols, and amines as potential anticancer agents.
MedLine Citation:
PMID:  19708666     Owner:  NLM     Status:  MEDLINE    
In this paper, we report the synthesis and biological activity of a series of dihydroisocoumarin analogues conjugated with fatty acids, alcohols, or amines, of varying hydrocarbon chain length and degree of unsaturation, to the dihydroisocoumarins, kigelin and mellein, at the C-7 and C-8 positions on the core dihydroisocoumarin structure. These compounds were evaluated for their antiproliferative activity against human breast cancer (MCF-7 and MDA-MB-468) and melanoma cells (SK-MEL-28 and Malme-3M) using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. Two compounds conjugated with gamma-linolenyl alcohol (18:3 n-6) demonstrated potent antiproliferative activity in vitro with one of these 4-hydroxy-3-oxo-1,3-dihydro-isobenzofuran-5-carboxylic acid octadeca-6,9,12-trienyl ester, demonstrating significant antitumor activity in vivo in a number of human tumor xenograft models.
Catherine A Higgins; Zoica Delbederi; Kelly McGarel; Timothy Mills; Owen McGrath; Stephanie Feutren-Burton; William Watters; Paul Armstrong; Patrick G Johnston; David Waugh; Hendrik van den Berg
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Bioconjugate chemistry     Volume:  20     ISSN:  1520-4812     ISO Abbreviation:  Bioconjug. Chem.     Publication Date:  2009 Sep 
Date Detail:
Created Date:  2009-09-16     Completed Date:  2009-12-30     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9010319     Medline TA:  Bioconjug Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1737-51     Citation Subset:  IM    
Centre for Cancer Research and Cell Biology (CCRCB), Queens University Belfast, Belfast, Northern Ireland, BT9 7BL, United Kingdom.
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MeSH Terms
Alcohols / chemistry
Amines / chemistry
Antineoplastic Agents / chemical synthesis*,  pharmacology
Breast Neoplasms / drug therapy
Cell Line, Tumor
Drug Screening Assays, Antitumor
Fatty Acids / chemistry
Isocoumarins / chemical synthesis*,  pharmacology
Melanoma / drug therapy
Structure-Activity Relationship
Xenograft Model Antitumor Assays
Reg. No./Substance:
0/Alcohols; 0/Amines; 0/Antineoplastic Agents; 0/Fatty Acids; 0/Isocoumarins

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

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