Structure-based hybridization of the bioactive natural products rhizonin A and ternatin leading to a selective fat-accumulation inhibitor against 3T3-L1 adipocytes

Kenichiro Shimokawa; Kaoru Yamada; Daisuke Uemura

doi:10.1016/j.bmcl.2008.11.109

Structure-based hybridization of the bioactive natural products rhizonin A and ternatin leading to a selective fat-accumulation inhibitor against 3T3-L1 adipocytes

Bioorg Med Chem Lett. 2009 Feb 1;19(3):867-9. doi: 10.1016/j.bmcl.2008.11.109. Epub 2008 Dec 6.

Authors

Kenichiro Shimokawa¹, Kaoru Yamada, Daisuke Uemura

Affiliation

¹ Department of Chemistry, Graduate School of Science, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8602, Japan.

PMID: 19097891
DOI: 10.1016/j.bmcl.2008.11.109

Abstract

Based on the structural similarity between the naturally occurring cyclic heptapeptides rhizonin A and ternatin, two novel analogues were designed. The synthetic analogues were assessed with regard to their fat-accumulation inhibitory effect against 3T3-L1 adipocytes, and this led to the discovery of a potent and selective fat-accumulation inhibitor compared to the parent compound rhizonin A.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

3T3-L1 Cells
Adipocytes / cytology*
Adipocytes / metabolism
Animals
Chemistry, Pharmaceutical / methods*
Drug Design
Flavonoids / chemistry*
Inhibitory Concentration 50
Mice
Models, Biological
Models, Chemical
Molecular Conformation
Nucleic Acid Hybridization
Peptides / chemistry
Peptides, Cyclic / chemistry*

Substances

Flavonoids
Peptides
Peptides, Cyclic
ternatin (flavonoid)
rhizonin A