Design, synthesis, and biological evaluation of biotin-labeled (-)-ternatin, a potent fat-accumulation inhibitor against 3T3-L1 adipocytes

Kenichiro Shimokawa; Kaoru Yamada; Osamu Ohno; Yuichi Oba; Daisuke Uemura

doi:10.1016/j.bmcl.2008.11.003

Design, synthesis, and biological evaluation of biotin-labeled (-)-ternatin, a potent fat-accumulation inhibitor against 3T3-L1 adipocytes

Kenichiro Shimokawa, Kaoru Yamada, Osamu Ohno, Yuichi Oba, Daisuke Uemura

Department of Chemistry

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

4 Citations (Scopus)

Abstract

The design, synthesis, and biological activity of biotin-labeled (-)-ternatin are reported. Chemical modification, that is, biotinylation, was conducted using Click chemistry at the 6-position (NMe-d-ProGly moiety), which was a plausible location selected on the basis of our SAR studies. The compound displayed sufficient fat-accumulation inhibitory effect against 3T3-L1 adipocytes for further bio-organic studies.

Original language	English
Pages (from-to)	92-95
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	1
DOIs	https://doi.org/10.1016/j.bmcl.2008.11.003
Publication status	Published - 2009 Jan 1

Keywords

Biotinylation
Click chemistry
Cyclic peptide
Fat-accumulation inhibitory effect
Ternatin

ASJC Scopus subject areas

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

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10.1016/j.bmcl.2008.11.003

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Design, synthesis, and biological evaluation of biotin-labeled (-)-ternatin, a potent fat-accumulation inhibitor against 3T3-L1 adipocytes. / Shimokawa, Kenichiro; Yamada, Kaoru; Ohno, Osamu; Oba, Yuichi; Uemura, Daisuke.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 1, 01.01.2009, p. 92-95.

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

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abstract = "The design, synthesis, and biological activity of biotin-labeled (-)-ternatin are reported. Chemical modification, that is, biotinylation, was conducted using Click chemistry at the 6-position (NMe-d-ProGly moiety), which was a plausible location selected on the basis of our SAR studies. The compound displayed sufficient fat-accumulation inhibitory effect against 3T3-L1 adipocytes for further bio-organic studies.",

keywords = "Biotinylation, Click chemistry, Cyclic peptide, Fat-accumulation inhibitory effect, Ternatin",

author = "Kenichiro Shimokawa and Kaoru Yamada and Osamu Ohno and Yuichi Oba and Daisuke Uemura",

note = "Funding Information: This study was supported in part by Grants-in-Aid for Scientific Research for Creative Scientific Research (Grant No. 16GS0206) and the Global COE program in Chemistry at Nagoya University (Grant No. B-021) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We are indebted to Ono Pharmaceutical Co., Ltd. and Banyu Pharmaceutical Co., Ltd. for their financial support. ",

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AU - Ohno, Osamu

AU - Oba, Yuichi

AU - Uemura, Daisuke

N1 - Funding Information: This study was supported in part by Grants-in-Aid for Scientific Research for Creative Scientific Research (Grant No. 16GS0206) and the Global COE program in Chemistry at Nagoya University (Grant No. B-021) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We are indebted to Ono Pharmaceutical Co., Ltd. and Banyu Pharmaceutical Co., Ltd. for their financial support.

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Design, synthesis, and biological evaluation of biotin-labeled (-)-ternatin, a potent fat-accumulation inhibitor against 3T3-L1 adipocytes

Abstract

Keywords

ASJC Scopus subject areas

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