Open AccessFurther study of biological activities of chemically synthesized analogues of lipid A in artificial membrane vesicles
Author(s) -
YASUDA Tatsuji,
KANEGASAKI Shiro,
TSUMITA Toru,
TADAKUMA Takushi,
IKEWAKI Nobunao,
HOMMA J. Yuzuru,
INAGE Masaru,
KUSUMOTO Shoichi,
SHIBA Tetsuo
Publication year - 1984
Publication title -
european journal of biochemistry
Language(s) - English
Resource type - Journals
eISSN - 1432-1033
pISSN - 0014-2956
DOI - 10.1111/j.1432-1033.1984.tb08094.x
Subject(s) - liposome , chemistry , lipid a , immunogenicity , amide , vesicle , glucosamine , membrane , biochemistry , phosphate , adjuvant , amino acid , stereochemistry , amphiphile , organic chemistry , antigen , lipopolysaccharide , biology , copolymer , immunology , endocrinology , genetics , polymer
In the previous paper [ Eur. J. Biochem. 124 , 405 (1982)], we demonstrated that chemically synthesized lipid‐A analogues such as the 1‐monophosphate or 1,4′‐diphosphate of 6‐ O ‐(2‐deoxy‐2‐tetradecanoylamino‐6‐ O ‐tetradecanoyl‐ d ‐glucopyranosyl)‐2‐deoxy‐2‐tetradecanolyamino‐3,4‐di‐ O ‐tetradecanoyl‐2‐glucopyranose enhanced immunogenicity of liposomal model membranes sensitized with amphipathic antigen when they were incorporated in the same liposomes. Here we extend the observation by testing the recently synthesized analogues including diglucosamine analogues carrying hydroxy and acyloxy fatty acids. Among the analogues tested, those which showed higher adjuvant and mitogenic activities in the liposomal system were N ‐acylated and O ‐acylated β‐1,6‐linked d ‐glucosamine disaccharides carrying either amide‐bound 3‐hydroxytetradecanoic acids in addition to phosphate in position 1 of the reducing sugar or amide‐bound 3‐tetradecanoyloxytetradecanoic acids. The analogue carrying both amide‐bound 3‐hydroxytetradecanoic acids and phosphate in position 4 of the non‐reducing sugar showed weak adjuvant activity and marginal mitogenic activity.