Theoretical study on oxidation mechanism of fluorescent probe, coumarin‐7‐pinacolboronate by various reactive oxygen species

化学 过氧化氢 过氧亚硝酸盐 活性氧 香豆素 次氯酸 荧光 光化学 反应机理 氧气 反应中间体 氧化还原 组合化学 有机化学 超氧化物 生物化学 催化作用 物理 量子力学
作者
Yujie Guo,Yan Leng,Hongbo Liu,Chungang Min,Ai‐Min Ren,Qinhong Yin
出处
期刊:Journal of Physical Organic Chemistry [Wiley]
卷期号:37 (2) 被引量:1
标识
DOI:10.1002/poc.4585
摘要

Abstract Hydrogen peroxide (H 2 O 2 ) as relatively stable reactive oxygen species gains considerable attention because it can regulate physiological and pathological processes. In order to better detect H 2 O 2 , fluorescent probes were widely applied. Over the past 20 years, a great deal of boronate‐based fluorescent molecular probes appeared due to relatively simple oxidation reaction. However, the reaction mechanisms that boronate derivatives were converted into fluorescent product by H 2 O 2 are poorly studied. In this paper, taking coumarin‐7‐pinacolboronate (CBU) as an example, the oxidation mechanism of boronate‐based probes by various reactive oxygen species was studied by theoretical calculations. The results found that (1) the chemical reaction mechanisms are nearly identical for the reactions of CBU with hydrogen peroxide, hypochlorous acid, peroxynitrite, and tyrosine hydroperoxide, respectively. (2) There is not radical intermediate during the reaction. (3) The different reactive oxygen species has a strong influence on rate limiting step and reaction rate.
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