Immunostimulatory activities of monoglycosylated α- d-pyranosylceramides

• Published in: Bioorganic & medicinal chemistry Vol. 5; no. 12; pp. 2245 - 2249
• Main Authors: Uchimura, Akira, Shimizu, Toshiyuki, Morita, Masahiro, Ueno, Hitomi, Motoki, Kazuhiro, Fukushima, Hideaki, Natori, Takenori, Koezuka, Yasuhiko
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-12-1997
• Subjects: Adjuvants, Immunologic - chemical synthesis; Adjuvants, Immunologic - chemistry; Adjuvants, Immunologic - pharmacology; Animals; Female; Galactosylceramides - chemical synthesis; Galactosylceramides - chemistry; Galactosylceramides - pharmacology; Glucosylceramides - chemical synthesis; Glucosylceramides - pharmacology; immunostimulatory activity; Mice; Mice, Inbred BALB C; Mice, Inbred C57BL; monoglycosylated α-galactosylceramide; monoglycosylated α-glucosylceramide; α-galactosylceramide; α-gluctosylceramide; monoglycosylated α-glucosylceramide; immunostimulatory activity; monoglycosylated α-galactosylceramide; α-gluctosylceramide; α-galactosylceramide
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/S0968-0896(97)00169-7

We compared the immunostimulatory effects of chemically synthesized α-galactosylceramides (α-GalCers), α-glucosylceramides (α-GluCers), 6″-monoglycosylated α-GalCer and 6″- or 4″-monoglycosylated α-GluCer and made the following observations: (1) the length of the fatty acid side chain in the ceramide portions greatly affects the immunostimulatory effects of α-GalCers and α-GluCers; (2) the configuration of the 4″-hydroxyl group of the inner pyranose moiety plays an important role in the immunostimulatory effects of monoglycosylated α-
d-pyranosylceramides; (3) the free 4″-hydroxyl group of the inner pyranose of monoglycosylated α-
d-pyranosylceramides plays a more important role in their immunostimulatory effects than the free 6″-hydroxyl group.
We compared the immunostimulatory effects of α-galactosylceramides (α-GalCers), α-glucosylceramides (α-GluCers), 6-monoglycosylated α-GalCer and 6- or 4-monoglycosylated α-GluCer which were chemically synthesized, and found; 1) the lengths of the fatty acid side chain in the ceramide portion greatly affect the immunostimulatory effects of α-GalCers and α-GluCers; 2) the configuration of 4-hydroxyl group of the inner pyranose moiety plays an important role in the immunostimulatory effects of monoglycosylated α-
d-pyranosylceramides.