Synthesis and Th1-immunostimulatory activity of α-galactosylceramide analogues bearing a halogen-containing or selenium-containing acyl chain

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• 作者：Md. Imran Hossain^a ; ^b ; Shinya Hanashima^a ; ^{hanashimas13@chem.sci.osaka-u.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Takuto Nomura^a ; Sé ; bastien Lethu^b ; Hiroshi Tsuchikawa^a ; Michio Murata^a ; ^b ; ^{murata@chem.sci.osaka-u.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Hiroki Kusaka^c ; Shunsuke Kita^c ; Katsumi Maenaka^c
• 关键词：α-GalCer ; Cytokines ; CD1d ; Natural product synthesis ; Glycosylation
• 刊名：Bioorganic & Medicinal Chemistry
• 出版年：2016
• 出版时间：15 August 2016
• 年：2016
• 卷：24
• 期：16
• 页码：3687-3695
• 全文大小：1305 K

文摘

A novel series of CD1d ligand α-galactosylceramides (α-GalCers) were synthesized by incorporation of the heavy atoms Br and Se in the acyl chain backbone of α-galactosyl-N-cerotoylphytosphingosine. The synthetic analogues are potent CD1d ligands and stimulate mouse invariant natural killer T (iNKT) cells to selectively enhance Th1 cytokine production. These synthetic analogues would be efficient X-ray crystallographic probes to disclose precise atomic positions of alkyl carbons and lipid–protein interactions in KRN7000/CD1d complexes.