RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo

Takuya Tashiro; Ryusuke Nakagawa; Sayo Inoue; Masao Shiozaki; Hiroshi Watarai; Masaru Taniguchi; Kenji Mori

doi:10.1016/j.tetlet.2008.09.074

RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo

Takuya Tashiro, Ryusuke Nakagawa, Sayo Inoue, Masao Shiozaki, Hiroshi Watarai, Masaru Taniguchi, Kenji Mori

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

37 Citations (Scopus)

Abstract

RCAI-61, the 6′-O-methylated analog of KRN7000, and six other analogs with modified 6′-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl α-d-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl β-l-arabinopyranoside. Bioassay showed RCAI-61 to be a much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-γ in vivo.

Original language	English
Pages (from-to)	6827-6830
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2008.09.074
Publication status	Published - 2008 Nov 24
Externally published	Yes

Keywords

CD1d
IFN-γ
KRN7000
α-Galactosylceramides

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.09.074

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title = "RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo",

abstract = "RCAI-61, the 6′-O-methylated analog of KRN7000, and six other analogs with modified 6′-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl α-d-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl β-l-arabinopyranoside. Bioassay showed RCAI-61 to be a much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-γ in vivo.",

keywords = "CD1d, IFN-γ, KRN7000, α-Galactosylceramides",

author = "Takuya Tashiro and Ryusuke Nakagawa and Sayo Inoue and Masao Shiozaki and Hiroshi Watarai and Masaru Taniguchi and Kenji Mori",

note = "Funding Information: We thank Professor H. Watanabe and Dr. K. Ishigami (the Unversity of Tokyo) for their helpful comments. T.T. is grateful to Professor T. Nakata (Science University of Tokyo) for his encouragement. This work was supported partly by Grant-in-Aid for Young Scientists (B) (No. 20790108) from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan.",

year = "2008",

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day = "24",

doi = "10.1016/j.tetlet.2008.09.074",

language = "English",

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T1 - RCAI-61, the 6′-O-methylated analog of KRN7000

T2 - its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo

AU - Tashiro, Takuya

AU - Nakagawa, Ryusuke

AU - Inoue, Sayo

AU - Shiozaki, Masao

AU - Watarai, Hiroshi

AU - Taniguchi, Masaru

AU - Mori, Kenji

N1 - Funding Information: We thank Professor H. Watanabe and Dr. K. Ishigami (the Unversity of Tokyo) for their helpful comments. T.T. is grateful to Professor T. Nakata (Science University of Tokyo) for his encouragement. This work was supported partly by Grant-in-Aid for Young Scientists (B) (No. 20790108) from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan.

PY - 2008/11/24

Y1 - 2008/11/24

N2 - RCAI-61, the 6′-O-methylated analog of KRN7000, and six other analogs with modified 6′-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl α-d-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl β-l-arabinopyranoside. Bioassay showed RCAI-61 to be a much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-γ in vivo.

AB - RCAI-61, the 6′-O-methylated analog of KRN7000, and six other analogs with modified 6′-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl α-d-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl β-l-arabinopyranoside. Bioassay showed RCAI-61 to be a much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-γ in vivo.

KW - CD1d

KW - IFN-γ

KW - KRN7000

KW - α-Galactosylceramides

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JO - Tetrahedron Letters

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ER -

RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo

Abstract

Keywords

ASJC Scopus subject areas

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