Effects of α- and β-Galactosylated C2-Ceramides on the Immune System

• Published in: Journal of medicinal chemistry Vol. 41; no. 4; pp. 650 - 652
• Main Authors: Sakai, Teruyuki, Ueno, Hitomi, Natori, Takenori, Uchimura, Akira, Motoki, Kazuhiro, Koezuka, Yasuhiko
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 12.02.1998; Amer Chemical Soc
• Subjects: Adjuvants, Immunologic - chemical synthesis; Adjuvants, Immunologic - chemistry; Adjuvants, Immunologic - pharmacology; Animals; Biological and medical sciences; Chemistry, Medicinal; Female; Galactosides - chemical synthesis; Galactosides - chemistry; Galactosides - pharmacology; Immunomodulators; Immunosuppressive Agents - chemical synthesis; Immunosuppressive Agents - chemistry; Immunosuppressive Agents - pharmacology; Life Sciences & Biomedicine; Lymphocyte Culture Test, Mixed; Lymphocytes - cytology; Lymphocytes - drug effects; Lymphocytes - immunology; Medical sciences; Mice; Mice, Inbred BALB C; Mice, Inbred C57BL; Models, Molecular; Molecular Conformation; Molecular Structure; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; Sphingosine - analogs & derivatives; Sphingosine - chemical synthesis; Sphingosine - chemistry; Sphingosine - pharmacology; Spleen - immunology; Structure-Activity Relationship; PROGRAMMED CELL-DEATH; CERAMIDE; ANTITUMOR ACTIVITIES; Mixed lymphocyte reaction; Aldose; Rodentia; Splenocyte; In vitro; Biological activity; Allogeneic system; Immunomodulator; Vertebrata; Immunostimulant agent; Mammalia; Mouse; Anomer; Animal; Ceramide; Glycoside; Chemical synthesis
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm970613v

In contrast to the immunosuppressive effects of C2-ceramide (C2-Cer), α-galactosylceramides with ceramides having more than 10 carbons in fatty acid chains have immunostimulatory activities. We therefore synthesized α- and β-galactosylated C2-Cers in order to examine their effects on the immune system. β-Galactosylated C2-Cer and C2-Cer suppressed the allogeneic mixed leukocyte reaction (MLR) responses, but α-galactosylated C2-Cer stimulated the MLR response.