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
表題	Synthesis of hydrophilic caged DAG-lactones for chemical biology applications
掲載誌名	正式名：Organic & Biomolecular Chemistry
掲載区分	国外
巻・号・頁	18(22),pp.4217-4223
総ページ数	3.876
著者・共著者	T. Kobayakawa, H. Takano, T. Ishii, K. Tsuji, N. Ohashi, W. Nomura, T. Furuta, H. Tamamura
発行年月	2020/06/14
概要	The 6-bromo-7-hydroxy-coumarin-4-ylmethyl (Bhc) group has been used widely in cage chemistry because of its high molar absorptivity and photolytic efficiency. One of the drawbacks of coumarins however is their low aqueous solubility. Aqueous solubility is important in the behavior of caged compounds because hydrophobic caged compounds might be aggregated in physiological conditions and consequently the photocleavage would be impaired. The 8-azacoumarin-4-ylmethyl derivatives with bromine (8-aza-Bhc) or iodine (8-aza-Ihc), which were previously developed in this laboratory, have aqueous solubilities that are higher than those of related coumarins. Here, to improve the hydrophilicity and management of caged diacylglycerol lactones (DAG-lactones), 8-aza-Bhc and 8-aza-Ihc were introduced into the DAG-lactone structure. The synthesized caged compounds showed high hydrophilicity compared with the parent Bhc-caged DAG-lactone, and the 8-aza-Ihc-caged DAG-lactone (2) showed excellent photolytic efficiency, which allows rapid release of the DAG-lactone (1) by brief photoirradiation. The 8-aza-7-hydroxy-6-iodo-coumarin-4-ylmethyl group might be useful for caging of bioactive compounds, especially hydrophobic compounds.