title: RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines.
abstract: Conformationally restricted analogues of KRN7000, an alpha-d-galactosyl ceramide, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells to produce cytokines. RCAI-8, 9, 51, and 52 are the analogues with a pyrrolidine ring, and RCAI-18, 19, 49, and 50 are those with an azetidine ring. RCAI-18 was shown to be a potent inducer of cytokine production by mouse NKT cells, while RCAI-51 was a moderately active inducer.
authors.affiliation: Glycosphingolipid Synthesis Group, Laboratory for Immune Regulation, Research Center for Allergy and Immunology, RIKEN, Hirosawa 2-1, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Fuhshuku
authors.forename: Naomi
authors.initials: N
authors.lastname: Hongo
authors.forename: Takuya
authors.initials: T
authors.lastname: Tashiro
authors.forename: Yui
authors.initials: Y
authors.lastname: Masuda
authors.forename: Ryusuke
authors.initials: R
authors.lastname: Nakagawa
authors.forename: Ken-ichiro
authors.initials: K
authors.lastname: Seino
authors.forename: Masaru
authors.initials: M
authors.lastname: Taniguchi
authors.forename: Kenji
authors.initials: K
authors.lastname: Mori
mesh_terms: D000818:Animals; D001384:Azetidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016207:Cytokines / Q000032:analysis / Q000096:biosynthesis*; D005699:Galactosylceramides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007694:Killer Cells, Natural / Q000187:drug effects* / Q000276:immunology; D051379:Mice; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D001384:Azetidines; D016207:Cytokines; D005699:Galactosylceramides; D011759:Pyrrolidines; C103873:KRN 7000