Coumarin-Quinazolinone conjugate with large two photon action cross-section assisted by intramolecular hydrogen bond for bioimaging
Coumarin-Quinazolinone conjugate with large two photon action cross-section assisted by intramolecular hydrogen bond for bioimaging
复制标题
具有大双光子作用截面的香豆素-喹唑啉酮缀合物，分子内氢键辅助，用于生物成像
DOI：
10.1016/j.snb.2019.126720
复制
发表时间：
2019-10-15
影响因子：
8.4
通讯作者：
Huang, Jing
中科院分区：
文献类型：
--
作者：
Yang, Jihuan;Zhang, Yaya;Huang, Jing
Two photon (TP) fluorescence bioimaging proves to be a powerful tool for biomarker detection and disease diagnosis. However, the probes possessing both good optical properties and biocompatibility are limited. Herein a novel scaffold based on the conjugate of coumarin and quinazolinone (CQ) exhibited brilliant TP fluorescence properties (action cross-section value Phi delta(max) = 299 GM and TP action cross section per molecular weight Phi delta(max)/MW = 0.83) in water. The fluorescence properties are mainly attributed to the enlarged conjugate structure by intramolecular hydrogen bond. The TP fluorescence can be easily switched via amide group modification-deprotection strategy to regulate the formation of hydrogen bond. As a proof of concept, CQ was further engineered with p-nitrobenzyl moiety to afford 2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-(4-nitrobenzyl) quinazolin-4(3H)-one (NBCQ) for mitochondria nitroreductase (NTR) imaging in normoxia and hypoxia, which proved to be a sensitive and selective "off-on" NTR fluorescent probe.
