title: RCAI-61 and related 6'-modified analogs of KRN7000: their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo.
abstract: We synthesized ten new analogs of 6'-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by α-selective galactosylation of ceramide 9 with the 6-modified D-galactopyranosyl fluorides (8a-8f) or L-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6'-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-γ even at a low concentration in mice in vivo.
authors.affiliation: Glycosphingolipid Synthesis Group, Laboratory for Immune Regulation, Research Center for Allergy and Immunology, RIKEN, Hirosawa 2-1, Wako, Saitama 351-0198, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Tashiro
authors.forename: Ryusuke
authors.initials: R
authors.lastname: Nakagawa
authors.forename: Tomokuni
authors.initials: T
authors.lastname: Shigeura
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Watarai
authors.forename: Masaru
authors.initials: M
authors.lastname: Taniguchi
authors.forename: Kenji
authors.initials: K
authors.lastname: Mori
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001681:Biological Assay; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000494:pharmacology; D007371:Interferon-gamma / Q000819:agonists* / Q000096:biosynthesis / Q000276:immunology; D018664:Interleukin-12 / Q000819:agonists / Q000096:biosynthesis / Q000276:immunology; D015847:Interleukin-4 / Q000037:antagonists & inhibitors / Q000096:biosynthesis / Q000276:immunology; D007694:Killer Cells, Natural / Q000166:cytology / Q000187:drug effects* / Q000276:immunology; D051379:Mice
chemical_list: D000276:Adjuvants, Immunologic; D000970:Antineoplastic Agents; D005699:Galactosylceramides; D018664:Interleukin-12; D015847:Interleukin-4; D007371:Interferon-gamma; C103873:KRN 7000