Design, synthesis, and evaluation of a water soluble C5-monoketone type curcumin analogue as a potent amyloid β aggregation inhibitor

Mayumi Hotsumi; Misato Tajiri; Yuri Nikaido; Taki Sato; Koki Makabe; Hiroyuki Konno

doi:10.1016/j.bmcl.2019.06.052

Design, synthesis, and evaluation of a water soluble C5-monoketone type curcumin analogue as a potent amyloid β aggregation inhibitor

Bioorg Med Chem Lett. 2019 Aug 15;29(16):2157-2161. doi: 10.1016/j.bmcl.2019.06.052. Epub 2019 Jun 27.

Authors

Mayumi Hotsumi¹, Misato Tajiri¹, Yuri Nikaido¹, Taki Sato¹, Koki Makabe¹, Hiroyuki Konno²

Affiliations

¹ Department of Biochemical Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan.
² Department of Biochemical Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan. Electronic address: konno@yz.yamagata-u.ac.jp.

PMID: 31262559
DOI: 10.1016/j.bmcl.2019.06.052

Abstract

A structure activity relationship study of curcumin analogues for the inhibition of amyloid β aggregation is described. Optimization of the o-phenol and olefin spacer resulted in the identification of the C5-monoketone type curcumin analogue AY1319, which exhibited potent anti-amyloid β aggregation activity (leading to nanorod-like fragments), sufficient water solubility, and low cytotoxicity.

Keywords: Aggregation; Amyloid β; Curcumin; Water soluble.

Publication types

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

MeSH terms

Amyloid beta-Peptides / antagonists & inhibitors*
Curcumin / chemical synthesis*
Curcumin / chemistry
Humans
Structure-Activity Relationship

Substances

Amyloid beta-Peptides
Curcumin