Synthesis and anti-HIV activity of bi-functional betulinic acid derivatives.

Journal Article (Journal Article)

Betulinic acid (BA) derivatives with a side chain at C-3 can inhibit HIV-1 maturation. On the other hand, BA derivatives with a side chain at C-28 can block HIV-1 entry. In order to combine the anti-maturation and anti-entry activities in a single molecule, new bi-functional BA derivatives containing side chains at C-3 and C-28 have been synthesized. The most potent compound ([[N-[3beta-O-(3',3'-dimethylsuccinyl)-lup-20(29)-en-28-oyl]-7-aminoheptyl]-carbamoyl]methane) inhibited HIV-1 at an EC50 of 0.0026 microM and was at least 20 times more potent than either the anti-maturation lead compound DSB or the anti-entry lead compound IC9564. This bi-functional BA derivative was active against both HIV entry and maturation. These results suggest that bi-functional BA derivatives with dual mechanisms of action have the potential to become clinically useful for AIDS therapy.

Full Text

Duke Authors

Cited Authors

  • Huang, L; Ho, P; Lee, K-H; Chen, C-H

Published Date

  • April 1, 2006

Published In

Volume / Issue

  • 14 / 7

Start / End Page

  • 2279 - 2289

PubMed ID

  • 16314103

International Standard Serial Number (ISSN)

  • 0968-0896

Digital Object Identifier (DOI)

  • 10.1016/j.bmc.2005.11.016


  • eng

Conference Location

  • England