Influence of esterification and modification of A-ring in a group of lupane acids on their cytotoxicity.
The aim of this work was to find an optimal ester group for preparation of lupane derivatives connecting high cytotoxicity with good chemical and pharmacological properties. Activities of methyl-, pivaloyloxymethyl- (Pom-), and acetoxymethyl- (Acm-) esters were compared with the activity of free acids. Although the methyl- and Pom-esters were generally less active than free acids, some Acm-esters had cytotoxicity similar to or even better than the starting compounds. Cytotoxic activity was measured in five cancer cell lines.
Urban
Milan
M
Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Prague 2, Czech Republic.
Sarek
Jan
J
Tislerova
Iva
I
Dzubak
Petr
P
Hajduch
Marian
M
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D004951:Esterification; D006801:Humans; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D053978:Pentacyclic Triterpenes
D002264:Carboxylic Acids; D014315:Triterpenes; C480546:lupane; D053978:Pentacyclic Triterpenes