Synthesis and innate immunosuppressive effect of 1,2-cyclopentanediol derivatives

Haruhisa Kikuchi; Kaori Okazaki; Mizuki Sekiya; Yasuyuki Uryu; Kazunori Ueda; Yasuhiro Katou; Shoichiro Kurata; Yoshiteru Oshima

doi:10.1016/j.ejmech.2011.01.049

Synthesis and innate immunosuppressive effect of 1,2-cyclopentanediol derivatives

Haruhisa Kikuchi, Kaori Okazaki, Mizuki Sekiya, Yasuyuki Uryu, Kazunori Ueda, Yasuhiro Katou, Shoichiro Kurata, Yoshiteru Oshima

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

10 Citations (Scopus)

Abstract

Innate immunity is the front line of self-defense against infectious microorganisms. In mammals, innate immunity interacts with adaptive immunity and plays a key role in regulating the immune response. Therefore, innate immunity is a good pharmaceutical target for the development of immune regulators. After searching for natural substances that regulate innate immunity using an ex vivo Drosophila culture system, we identified a cyclopentanediol-type compound 1 as an immunosuppressor. In this study, we synthesized and evaluated 1 and its derivatives. Several methylamide- or phenylamide-containing derivatives showed effects that were 20-25 times more potent than those of 1.

Original language	English
Pages (from-to)	1263-1273
Number of pages	11
Journal	European Journal of Medicinal Chemistry
Volume	46
Issue number	4
DOIs	https://doi.org/10.1016/j.ejmech.2011.01.049
Publication status	Published - 2011 Apr
Externally published	Yes

Keywords

Cyclopentanediol
Drosophila
Immunosuppressor
Innate immunity
TNF-α

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2011.01.049

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abstract = "Innate immunity is the front line of self-defense against infectious microorganisms. In mammals, innate immunity interacts with adaptive immunity and plays a key role in regulating the immune response. Therefore, innate immunity is a good pharmaceutical target for the development of immune regulators. After searching for natural substances that regulate innate immunity using an ex vivo Drosophila culture system, we identified a cyclopentanediol-type compound 1 as an immunosuppressor. In this study, we synthesized and evaluated 1 and its derivatives. Several methylamide- or phenylamide-containing derivatives showed effects that were 20-25 times more potent than those of 1.",

keywords = "Cyclopentanediol, Drosophila, Immunosuppressor, Innate immunity, TNF-α",

author = "Haruhisa Kikuchi and Kaori Okazaki and Mizuki Sekiya and Yasuyuki Uryu and Kazunori Ueda and Yasuhiro Katou and Shoichiro Kurata and Yoshiteru Oshima",

note = "Funding Information: We are grateful to the Bloomington Stock Center, Drosophila Genetic Resource Center at the Kyoto Institute of Technology, and the Genetic Strain Research Center of the National Institute of Genetics for the fly stocks. This work was supported in part by a Grant-in-Aid for Scientific Research (No. 21249004 , 21117005 , 21310134 , 21117005 and 21710215 ) from the Ministry of Education, Science, Sports and Culture of Japan ; the Uehara Memorial Foundation ; the Takeda Science Foundation ; the Mitsubishi Foundation ; and Program for Promotion of Basic Research Activities for Innovative BioSciences. ",

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AU - Kikuchi, Haruhisa

AU - Okazaki, Kaori

AU - Sekiya, Mizuki

AU - Uryu, Yasuyuki

AU - Ueda, Kazunori

AU - Katou, Yasuhiro

AU - Kurata, Shoichiro

AU - Oshima, Yoshiteru

N1 - Funding Information: We are grateful to the Bloomington Stock Center, Drosophila Genetic Resource Center at the Kyoto Institute of Technology, and the Genetic Strain Research Center of the National Institute of Genetics for the fly stocks. This work was supported in part by a Grant-in-Aid for Scientific Research (No. 21249004 , 21117005 , 21310134 , 21117005 and 21710215 ) from the Ministry of Education, Science, Sports and Culture of Japan ; the Uehara Memorial Foundation ; the Takeda Science Foundation ; the Mitsubishi Foundation ; and Program for Promotion of Basic Research Activities for Innovative BioSciences.

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KW - Cyclopentanediol

KW - Drosophila

KW - Immunosuppressor

KW - Innate immunity

KW - TNF-α

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Synthesis and innate immunosuppressive effect of 1,2-cyclopentanediol derivatives

Abstract

Keywords

ASJC Scopus subject areas

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