title: RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines.
abstract: RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage instead of an amide bond, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells. RCAI-17, 22, 24-26, 29, 31, 34-36, and 88 are the aromatic sulfonamide analogs, while RCAI-39 and 40 are the aliphatic ones. RCAI-38 is a C-galactoside analog of RCAI-26, which is the p-toluenesulfonamide analog of KRN7000. According to their bioassay, these sulfonamide analogs were shown to be the stimulants of mouse NKT cells to induce the production of Th2-biased cytokines in vitro, while RCAI-38 did not induce any cytokine production.
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: Takuya
authors.initials: T
authors.lastname: Tashiro
authors.forename: Naomi
authors.initials: N
authors.lastname: Hongo
authors.forename: Ryusuke
authors.initials: R
authors.lastname: Nakagawa
authors.forename: Ken-Ichiro
authors.initials: K
authors.lastname: Seino
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Watarai
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Ishii
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; D016207:Cytokines / Q000096:biosynthesis*; D005260:Female; D005699:Galactosylceramides / Q000138:chemical synthesis / Q000494:pharmacology*; D007371:Interferon-gamma / Q000096:biosynthesis; D018793:Interleukin-13 / Q000096:biosynthesis; D015847:Interleukin-4 / Q000096:biosynthesis; D007694:Killer Cells, Natural / Q000187:drug effects* / Q000276:immunology / Q000378:metabolism; D051379:Mice; D008810:Mice, Inbred C57BL; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis / Q000494:pharmacology*; D018418:Th2 Cells / Q000187:drug effects / Q000276:immunology / Q000378:metabolism
chemical_list: D000276:Adjuvants, Immunologic; D000970:Antineoplastic Agents; D016207:Cytokines; D005699:Galactosylceramides; D018793:Interleukin-13; D013449:Sulfonamides; D015847:Interleukin-4; D007371:Interferon-gamma; C103873:KRN 7000