喹啉酮
结合
分子内力
香豆素
氢键
动作(物理)
化学
组合化学
光化学
分子
有机化学
物理
数学
数学分析
量子力学
作者
Jihuan Yang,Yaya Zhang,Xue-Jiao Bai,Guorui Li,Zhiming Xing,Cheng Zhong,Jia Zhou,Song Liu,Zhibin Song,Jing Huang
标识
DOI:10.1016/j.snb.2019.126720
摘要
Abstract 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 Φδmax = 299 GM and TP action cross section per molecular weight Φδmax/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.
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