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

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

46 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
Externally published	Yes

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 et al.

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. doi: 10.1016/j.bmc.2007.10.008

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title = "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 = "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",

note = "Funding Information: We thank Dr. H. Nomi, Ms. A. Wakamatsu, Ms. N. Hirai, Ms. K. Utsunomiya, Ms. Y. Nagata, and Mr. H. Kamijuku for their technical support. Our thanks are due to Mr. K. Sakai and Dr. M. Iida (both at Seikagaku Kogyo Co.) for their helpful comments. ",

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AU - Fuhshuku, Ken ichi

AU - Hongo, Naomi

AU - Tashiro, Takuya

AU - Masuda, Yui

AU - Nakagawa, Ryusuke

AU - Seino, Ken ichiro

AU - Taniguchi, Masaru

AU - Mori, Kenji

N1 - Funding Information: We thank Dr. H. Nomi, Ms. A. Wakamatsu, Ms. N. Hirai, Ms. K. Utsunomiya, Ms. Y. Nagata, and Mr. H. Kamijuku for their technical support. Our thanks are due to Mr. K. Sakai and Dr. M. Iida (both at Seikagaku Kogyo Co.) for their helpful comments.

PY - 2008/1/15

Y1 - 2008/1/15

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AB - 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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KW - Glycosphingolipids

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KW - NKT cell

KW - Pyrrolidines

KW - α-Galactosyl ceramides

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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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