Glycolipids as potential immunologic adjuvants.
A group of 1-thio-beta-L-fucopyranosides containing hexadecane, 9-octadecene, adamantane, 1,2-diphenyltetrafluoroethane, and 3-hexynyl- and 3,6-dioxaoctylcholesterols were synthesized as potential immunologic adjuvants. Many of these fucosyl lipids and 6-(5-cholesten-3 beta-yloxy)hexyl 1 thioglycosides were found to give good response to subunit A/Victoria influenza virus. Carbohydrates with L-fucose and D-galactose backbones appeared essential for adjuvant activity. Lactose which has a terminal D-galactose moiety was found to be active, whereas L-arabinose which lacks a 5-(hydroxymethyl) group was inactive.
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis*; D000818:Animals; D000956:Antigens, Viral; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D006017:Glycolipids / Q000138:chemical synthesis* / Q000494:pharmacology; D009980:Influenza A virus / Q000276:immunology; D051379:Mice; D008934:Mitogens; D013997:Time Factors
D000276:Adjuvants, Immunologic; D000956:Antigens, Viral; D006017:Glycolipids; D008934:Mitogens