RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines

Ken ichi Fuhshuku; Naomi Hongo; Takuya Tashiro; Yui Masuda; Ryusuke Nakagawa; Ken ichiro Seino; Masaru Taniguchi; Kenji Mori

doi:10.1016/j.bmc.2007.10.008

RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines

Ken ichi Fuhshuku, Naomi Hongo, Takuya Tashiro, Yui Masuda, Ryusuke Nakagawa, Ken ichiro Seino, Masaru Taniguchi, Kenji Mori

Department of Microbiology and Immunology

Research output: Contribution to journal › Article › peer-review

45 Citations (Scopus)

Abstract

Conformationally restricted analogues of KRN7000, an α-d-galactosyl ceramide, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells to produce cytokines. RCAI-8, 9, 51, and 52 are the analogues with a pyrrolidine ring, and RCAI-18, 19, 49, and 50 are those with an azetidine ring. RCAI-18 was shown to be a potent inducer of cytokine production by mouse NKT cells, while RCAI-51 was a moderately active inducer.

Original language	English
Pages (from-to)	950-964
Number of pages	15
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	2
DOIs	https://doi.org/10.1016/j.bmc.2007.10.008
Publication status	Published - 2008 Jan 15

Keywords

Azetidines
Glycosphingolipids
KRN7000
NKT cell
Pyrrolidines
α-Galactosyl ceramides

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Fuhshuku, K. I., Hongo, N., Tashiro, T., Masuda, Y., Nakagawa, R., Seino, K. I., Taniguchi, M., & Mori, K. (2008). RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines. Bioorganic and Medicinal Chemistry, 16(2), 950-964. https://doi.org/10.1016/j.bmc.2007.10.008

RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring : Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines. / Fuhshuku, Ken ichi; Hongo, Naomi; Tashiro, Takuya; Masuda, Yui; Nakagawa, Ryusuke; Seino, Ken ichiro; Taniguchi, Masaru; Mori, Kenji.

In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 2, 15.01.2008, p. 950-964.

Research output: Contribution to journal › Article › peer-review

Fuhshuku, KI, Hongo, N, Tashiro, T, Masuda, Y, Nakagawa, R, Seino, KI, Taniguchi, M & Mori, K 2008, 'RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines', Bioorganic and Medicinal Chemistry, vol. 16, no. 2, pp. 950-964. https://doi.org/10.1016/j.bmc.2007.10.008

Fuhshuku KI, Hongo N, Tashiro T, Masuda Y, Nakagawa R, Seino KI et al. RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines. Bioorganic and Medicinal Chemistry. 2008 Jan 15;16(2):950-964. https://doi.org/10.1016/j.bmc.2007.10.008

Fuhshuku, Ken ichi ; Hongo, Naomi ; Tashiro, Takuya ; Masuda, Yui ; Nakagawa, Ryusuke ; Seino, Ken ichiro ; Taniguchi, Masaru ; Mori, Kenji. / RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring : Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines. In: Bioorganic and Medicinal Chemistry. 2008 ; Vol. 16, No. 2. pp. 950-964.

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abstract = "Conformationally restricted analogues of KRN7000, an α-d-galactosyl ceramide, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells to produce cytokines. RCAI-8, 9, 51, and 52 are the analogues with a pyrrolidine ring, and RCAI-18, 19, 49, and 50 are those with an azetidine ring. RCAI-18 was shown to be a potent inducer of cytokine production by mouse NKT cells, while RCAI-51 was a moderately active inducer.",

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author = "Fuhshuku, {Ken ichi} and Naomi Hongo and Takuya Tashiro and Yui Masuda and Ryusuke Nakagawa and Seino, {Ken ichiro} and Masaru Taniguchi and Kenji Mori",

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AU - Fuhshuku, Ken ichi

AU - Hongo, Naomi

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AU - Masuda, Yui

AU - Nakagawa, Ryusuke

AU - Seino, Ken ichiro

AU - Taniguchi, Masaru

AU - Mori, Kenji

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RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines

Abstract

Keywords

ASJC Scopus subject areas

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