Document Detail


Synthesis and cytotoxicity of some d-mannose click conjugates with aminobenzoic acid derivatives.
MedLine Citation:
PMID:  22960207     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Two sets of new conjugates obtained from d-mannose derivatives and o-, m-, and p-substituted benzoic acid esters interconnected through a triazole ring were synthesized by Cu(I) catalyzed azide-alkyne cycloaddition. All synthesized compounds were tested for their in vitro cytotoxic activity against seven cancer cell lines with/without multidrug resistance phenotype as well as non-tumor MRC-5 and BJ fibroblasts. Butyl ester of 4-aminobenzoic acid 6c showed the highest activity among all tested compounds, however, it was active only against K562 myeloid leukemia cells. N-Glycosyltriazole conjugates, both acetylated and nonacetylated at mannose moiety, were almost completely inactive. In contrast, some of the acetylated O-glycosyl conjugates showed cytotoxic activity which was cell line dependent and strongly affected by position of benzoic acid substitution as well as a length of its ester alkyl chain; the most potent compound was acetylated mannoside conjugated with octyl ester of m-substituted benzoic acid. However, deacetylation resulting in hydrophilicity increase of the glycosides almost completely abolished their cytotoxic potency.
Authors:
Ludmila Hradilová; Monika Poláková; Barbora Dvořáková; Marián Hajdúch; Ladislav Petruš
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-8-10
Journal Detail:
Title:  Carbohydrate research     Volume:  361C     ISSN:  1873-426X     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2012 Aug 
Date Detail:
Created Date:  2012-9-10     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  -    
Other Details:
Languages:  ENG     Pagination:  1-6     Citation Subset:  -    
Copyright Information:
Copyright © 2012 Elsevier Ltd. All rights reserved.
Affiliation:
Department of Organic Chemistry, Palacky University, Tr. 17. listopadu 12, 771 46 Olomouc, Czech Republic; Farmak a.s., Na Vlčinci 3, 77117 Olomouc, Czech Republic.
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