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

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

6 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
Externally published	Yes

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

Access to Document

10.1016/j.bmcl.2008.11.003

Cite this

@article{d183672898724fbf8c075e68726e0ed3,

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

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.",

year = "2009",

month = jan,

day = "1",

doi = "10.1016/j.bmcl.2008.11.003",

language = "English",

volume = "19",

pages = "92--95",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "1",

}

TY - JOUR

T1 - Design, synthesis, and biological evaluation of biotin-labeled (-)-ternatin, a potent fat-accumulation inhibitor against 3T3-L1 adipocytes

AU - Shimokawa, Kenichiro

AU - Yamada, Kaoru

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.

PY - 2009/1/1

Y1 - 2009/1/1

N2 - 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.

AB - 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.

KW - Biotinylation

KW - Click chemistry

KW - Cyclic peptide

KW - Fat-accumulation inhibitory effect

KW - Ternatin

UR - http://www.scopus.com/inward/record.url?scp=57749114510&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=57749114510&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2008.11.003

DO - 10.1016/j.bmcl.2008.11.003

M3 - Article

C2 - 19022665

AN - SCOPUS:57749114510

VL - 19

SP - 92

EP - 95

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 1

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this