Enhancing the divergent activities of betulinic acid via neoglycosylation.
Using neoglycosylation, the impact of differential glycosylation upon the divergent anticancer and anti-HIV properties of the triterpenoid betulinic acid (BA) was examined. Each member from a library of 37 differentially glycosylated BA variants was tested for anticancer and anti-HIV activities. Enhanced analogs for both desired activities were discovered with the corresponding antitumor or antiviral enhancements diverging, on the basis of the appended sugar, into two distinct compound subsets.
Goff
Randal D
RD
University of Wisconsin National Cooperative Drug Discovery Group, Pharmaceutical Sciences Division, School of Pharmacy, University of Wisconsin-Madison, 777 Highland Ave., Madison, Wisconsin 53705, USA.
Thorson
Jon S
JS
D019380:Anti-HIV Agents / Q000737:chemistry* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D006801:Humans; D053978:Pentacyclic Triterpenes; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology*; D000094062:Betulinic Acid
D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D006027:Glycosides; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; D000094062:Betulinic Acid