title: Synthesis and biological activity of ester and ether analogues of alpha-galactosylceramide (KRN7000).
abstract: Alpha-Galactosylceramide (alphaGalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in alphaGalCer is replaced with ester or ether groups were synthesized from d-arabinitol or l-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFNgamma and IL-4 production of iNKT cells, while ether (31b) and 4-methoxy ester (76) analogues of alpha-galactosylceramide were not active for iNKT cells.
authors.affiliation: Laboratory for Immune Regulation, Research Center for Allergy and Immunology, RIKEN, Hirosawa 2-1, Wako-shi, Saitama 351-0198, Japan. shiozaki@rcai.riken.jp
authors.forename: Masao
authors.initials: M
authors.lastname: Shiozaki
authors.forename: Takuya
authors.initials: T
authors.lastname: Tashiro
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Koshino
authors.forename: Ryusuke
authors.initials: R
authors.lastname: Nakagawa
authors.forename: Sayo
authors.initials: S
authors.lastname: Inoue
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: D000818:Animals; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005699:Galactosylceramides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007371:Interferon-gamma / Q000096:biosynthesis / Q000097:blood; D015847:Interleukin-4 / Q000096:biosynthesis / Q000097:blood; D051379:Mice; D008968:Molecular Conformation; D055611:Natural Killer T-Cells / Q000187:drug effects* / Q000276:immunology; D013237:Stereoisomerism
chemical_list: D004952:Esters; D004987:Ethers; D005699:Galactosylceramides; D015847:Interleukin-4; D007371:Interferon-gamma; C103873:KRN 7000