New Catanionic Glycolipids. 1. Synthesis, Characterization, and Biological Activity of Double-Chain and Gemini Catanionic Analogues of Galactosylceramide (galβ₁cer)

Abstract

New double-chain and gemini catanionic analogues of the glycolipid galβ1ceridentified as a cell receptor of the HIV-1 viruswere easily prepared in two steps from unprotected lactose. Due to their sugar moiety, these new catanionic surfactants were able to be cationized by sodium ions and therefore to be characterized in their monomeric forms by electrospray mass spectrometry. To our knowledge, this is the first time that catanionic surfactants have been directly observed, proving undoubtedly their existence as monomeric species. These new catanionic glycolipids showed interesting anti-HIV-1 activities, acting as monomeric analogues of galβ1cer. Finally, these new catanionic glycolipids were characterized by their surface active properties, by lamellar mesophases, and by their aptitude to spontaneously form vesicles.