Hydrogen peroxide (H₂O₂) as relatively stable reactive oxygen species gains considerable attention because it can regulate physiological and pathological processes. In order to better detect H₂O₂, 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 H₂O₂ 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.

中文翻译：

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不同活性氧对荧光探针香豆素-7-频那醇硼酸酯氧化机理的理论研究

过氧化氢（H ₂ O ₂）作为相对稳定的活性氧，因其可以调节生理和病理过程而受到广泛关注。为了更好地检测H ₂ O ₂，​​荧光探针被广泛应用。近20年来，由于氧化反应相对简单，出现了大量基于硼酸盐的荧光分子探针。然而，硼酸酯衍生物被H ₂ O ₂转化为荧光产物的反应机理却鲜有研究。本文以香豆素-7-频哪醇硼酸酯（CBU）为例，通过理论计算研究了各种活性氧对硼酸酯基探针的氧化机理。结果发现：（1）CBU分别与过氧化氢、次氯酸、过氧亚硝酸盐和酪氨酸过氧化氢反应的化学反应机理几乎相同。(2)反应过程中不存在自由基中间体。(3)不同的活性氧对限速步骤和反应速率有很大影响。