1. Synthesis of glycolipid analogues that disrupt binding of HIV-1 gp120 to galactosylceramide.
- Author
-
Weber KT, Hammache D, Fantini J, and Ganem B
- Subjects
- 1-Deoxynojirimycin chemical synthesis, 1-Deoxynojirimycin metabolism, 1-Deoxynojirimycin pharmacology, Anti-HIV Agents chemical synthesis, Anti-HIV Agents metabolism, Anti-HIV Agents pharmacology, Glycolipids pharmacology, Lipid Bilayers, Structure-Activity Relationship, 1-Deoxynojirimycin analogs & derivatives, Galactosylceramides metabolism, Glycolipids chemical synthesis, Glycolipids metabolism, HIV Envelope Protein gp120 metabolism
- Abstract
HIV-1 has been shown to infect CD4 negative cells by the binding of HIV gp120 to the glycolipid galactosylceramide (1) (GalCer). Several analogues of 1 were prepared to investigate the specific orientation of 1 in the membrane bilayer that is involved in gp120 binding. Interestingly, N-stearyl-1-deoxynojirimycin (8) displayed potent and specific affinity for gp120 equal to that of 1, a finding that may shed light on the antiviral activity of N-butyl-1-deoxynojirimycin.
- Published
- 2000
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