Document Detail


Conjugates of the fungal cytotoxin illudin M with improved tumour specificity.
MedLine Citation:
PMID:  18715789     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A simplified procedure for the isolation of gram quantities of illudin M from culture broths of basidiomycete Omphalotus olearius is described. Esters of illudin M with docosahexaenoic acid, chlorambucil, demethylcantharidinic acid (endothall) and 2,2'-bipyridyl-5,5'-dicarboxylic acid were synthesised and tested for cytotoxicity and induction of apoptosis in two clinically relevant tumour cell lines (Panc-1 pancreas carcinoma and HT-29 colon carcinoma) and in non-malignant human foreskin fibroblasts. The demethylcantharidin and the bipyridine conjugates retained the cytotoxicity of the parent illudin M while displaying an improved specificity for the tumour cells over the fibroblasts.
Authors:
Rainer Schobert; Bernhard Biersack; Sebastian Knauer; Matthias Ocker
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-08-07
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  16     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2008 Sep 
Date Detail:
Created Date:  2008-09-17     Completed Date:  2008-12-05     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  8592-7     Citation Subset:  IM    
Affiliation:
Organic Chemistry Laboratory, University of Bayreuth, Universitätsstrasse 30, 95440 Bayreuth, Germany. Rainer.Schobert@uni-bayreuth.de
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MeSH Terms
Descriptor/Qualifier:
Agaricales / growth & development,  metabolism*
Cell Line, Tumor / drug effects
Chlorambucil / chemistry,  pharmacology
Colonic Neoplasms / metabolism,  pathology
Cytotoxins / chemistry,  isolation & purification,  pharmacology*
Dicarboxylic Acids / chemistry,  pharmacology
Docosahexaenoic Acids / chemistry,  pharmacology
Esters / chemistry,  pharmacology*
Fibroblasts / cytology,  drug effects*
Humans
Pancreatic Neoplasms / metabolism,  pathology
Sesquiterpenes / chemistry,  isolation & purification,  pharmacology
Structure-Activity Relationship
Toxicity Tests
Chemical
Reg. No./Substance:
0/Cytotoxins; 0/Dicarboxylic Acids; 0/Esters; 0/Sesquiterpenes; 1146-04-9/illudin M; 145-73-3/endothall; 25167-62-8/Docosahexaenoic Acids; 305-03-3/Chlorambucil

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


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