Issue 7, 2011
From the journal:

MedChemComm

RCAI-39, 41, 53, 100, 127 and 128, the analogues of KRN7000, activate mouse natural killer T cells to produce Th2-biased cytokines by their administration as liposomal particles†‡

Takuya Tashiro,a   Yasuyuki Ishii,b   Tomokuni Shigeura,c   Ryusuke Nakagawa,cd   Hiroshi Watarai,c   Masaru Taniguchic  and  Kenji Mori*a  

* Corresponding authors

a Glycosphingolipid Synthesis Group, Laboratory for Immune Regulation, Research Center for Allergy and Immunology, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama, Japan
E-mail: kjk-mori@arion.ocn.ne.jp
Fax: +81 48 467 9381
Tel: +81 48 462 1339

b Laboratory for Vaccine Design, Research Center for Allergy and Immunology, RIKEN Yokohama Institute, 1-7-22 Suehiro-cho, Tsurumi-ku, Yokohama-shi, Kanagawa, Japan

c Laboratory for Immune Regulation, Research Center for Allergy and Immunology, RIKEN Yokohama Institute, 1-7-22 Suehiro-cho, Tsurumi-ku, Yokohama-shi, Kanagawa, Japan

d Department of Immunology, Faculty of Medicine, University of Yamanashi, Yamanashi, Japan

Abstract

α-Galactosphingolipid analogues of KRN7000 with a sulfonamide (RCAI-39), a carbamate (RCAI-41), an α,α-difluorocarboxamide (RCAI-100) or an N-methylcarboxamide linkage (RCAI-127) instead of a carboxamide bond of KRN7000 were synthesized. Their bioactivities for mouse natural killer T cells were examined. Bioactivities of truncated analogues, OCH and RCAI-53, and β-galactosphingolipid (RCAI-128) were also examined. All of these glycosphingolipids induced Th2-biased cytokine production by their administration as liposomal particles. Among them, liposomes containing RCAI-127 induced the most potent Th2-biased response.

Graphical abstract: RCAI-39, 41, 53, 100, 127 and 128, the analogues of KRN7000, activate mouse natural killer T cells to produce Th2-biased cytokines by their administration as liposomal particles

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Article information

DOI
https://doi.org/10.1039/C1MD00067E
Article type
Concise Article
Submitted
03 Mar 2011
Accepted
30 Mar 2011
First published
12 May 2011

Med. Chem. Commun., 2011,2, 620-625

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RCAI-39, 41, 53, 100, 127 and 128, the analogues of KRN7000, activate mouse natural killer T cells to produce Th2-biased cytokines by their administration as liposomal particles

T. Tashiro, Y. Ishii, T. Shigeura, R. Nakagawa, H. Watarai, M. Taniguchi and K. Mori, Med. Chem. Commun., 2011, 2, 620 DOI: 10.1039/C1MD00067E

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