フルタ　トシアキ   Furuta Toshiaki   古田　寿昭    所属   東邦大学  理学部 生物分子科学科    職種   教授
論文種別	原著
言語種別	英語
査読の有無	査読あり
招待の有無	招待あり
表題	Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds.
掲載誌名	正式名：Jove-Journal of Visualized Experiments 略　 称：J. Vis. Exp.
掲載区分	国外
巻・号・頁	(152),pp.e60021
総ページ数	10
著者・共著者	A. Z. Suzuki, Y. Shiraishi, H. Aoki, H. Sasaki, R. Watahiki and T. Furuta
担当区分	最終著者,責任著者
発行年月	2019/10/01
概要	Caged compounds enable the photo-mediated manipulation of the cell physiology with high spatiotemporal resolution. However, the limited structural diversity of currently available caging groups and the difficulties in synthetic modification without sacrificing their photolysis efficiencies are obstacles to expanding the repertoire of caged compounds for live cell applications. As the chemical modification of coumarin-type photo-caging groups is a promising approach for the preparation of caged compounds with diverse physical and chemical properties, we report a method for the synthesis of clickable caged compounds that can be modified easily with various functional units via the copper(I)-catalyzed Huisgen cyclization. The modular platform molecule contains a (6-bromo-7-hydroxycoumarin-4-yl)methyl (Bhc) group as a photo-caging group, which exhibits a high photolysis efficiency compared to those of the conventional 2-nitrobenzyls. General procedures for the preparation of clickable caged compounds containing amines, alcohols, and carboxylates are presented. Additional properties such as the water solubility and cell targeting ability can be readily incorporated into clickable caged compounds. Furthermore, the physical and photochemical properties, including the photolysis quantum yield, were measured and were found to be superior to those of the corresponding Bhc caged compounds. The described protocol could therefore be considered a potential solution for the lack of structural diversity in the available caged compounds.