title: 4,5-cis unsaturated α-GalCer analogues distinctly lead to CD1d-mediated Th1-biased NKT cell responses.
abstract: The total synthesis of 4,5-cis unsaturated α-GalCer analogues was achieved, and their immune-response altering activity was assessed in vitro as well as in vivo in mice. Using glycosyl iodide as a glycosyl donor, construction of the sphingosine unit was shortened by four steps and single α-stereoselectivity was achieved in good yield (67%). With regard to the therapeutic use of α-GalCer, the novel analogues (1b and 1c) distinctly induced a Th1-biased cytokine response, avoiding induction of a contradictory response and overstimulation.
authors.affiliation: †Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China.
authors.forename: Yanli
authors.initials: Y
authors.lastname: Cui
authors.affiliation: ‡State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.
authors.forename: Zhiyuan
authors.initials: Z
authors.lastname: Li
authors.affiliation: †Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China.
authors.forename: Zhaodong
authors.initials: Z
authors.lastname: Cheng
authors.affiliation: ‡State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.
authors.forename: Chengfeng
authors.initials: C
authors.lastname: Xia
authors.affiliation: §Institut Parisien de Chimie Moleculaire, UMR CNRS 8232, Universite Pierre et Marie Curie-Paris 6, 75005 Paris, France.|∥Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. China.
authors.forename: Yongmin
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000818:Animals; D055610:Antigens, CD1d / Q000378:metabolism*; D016207:Cytokines / Q000378:metabolism; D004797:Enzyme-Linked Immunosorbent Assay; D005699:Galactosylceramides / Q000737:chemistry* / Q000494:pharmacology*; D051379:Mice; D008810:Mice, Inbred C57BL; D015394:Molecular Structure; D055611:Natural Killer T-Cells / Q000187:drug effects* / Q000276:immunology / Q000378:metabolism; D013237:Stereoisomerism; D018417:Th1 Cells / Q000187:drug effects* / Q000276:immunology / Q000378:metabolism; D014407:Tumor Cells, Cultured
chemical_list: D055610:Antigens, CD1d; C584692:CD1d antigen, mouse; D016207:Cytokines; D005699:Galactosylceramides; C493154:alpha-galactosylceramide