Zhang Quanjuan, Zhang Na, Long Yi-Tao, Qian Xuhong, Yang Youjun
State Key Laboratory of Bioreactor Engineering, ‡Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, and §Department of Chemistry, East China University of Science and Technology , Meilong Road 130, Shanghai 200237, China.
Bioconjug Chem. 2016 Feb 17;27(2):341-53. doi: 10.1021/acs.bioconjchem.5b00396. Epub 2015 Aug 3.
Peroxynitrite is a prominent biological reactive nitrogen species from radical combination of nitric oxide and superoxide and fundamentally involved in broad spectrum physiological and pathological processes. Though redox-inert itself, peroxynitrite anion (OONO(-)) attacks various biological electrophiles to generate an array of potent 2-e(-) or 1-e(-) oxidants, which result in cell injuries. Development of fluorescent probes for peroxynitrite, free from interference from hypochlorite, has been an active endeavor of the chemical community. We previously reported a peroxynitrite probe (PN600), which could differentiate hypochlorite from peroxynitrite through a multichannel signaling mechanism. Herein, this intriguing selectivity was accounted for through a structure-reactivity relationship study. Also, this work, together with rich literature contributions, has allowed a qualitative guideline in the use of electron-rich aromatic moieties to design probes against peroxynitrite and/or hypochlorite. The viability of this guideline was further testified by development of another list of peroxynitrite selective probes.
过氧亚硝酸盐是由一氧化氮和超氧化物自由基结合产生的一种重要的生物活性氮物质，从根本上参与了广泛的生理和病理过程。尽管过氧亚硝酸盐阴离子（OONO(-)）本身是氧化还原惰性的，但它会攻击各种生物亲电试剂，产生一系列强效的2电子或1电子氧化剂，从而导致细胞损伤。开发不受次氯酸盐干扰的过氧亚硝酸盐荧光探针一直是化学界积极努力的方向。我们之前报道了一种过氧亚硝酸盐探针（PN600），它可以通过多通道信号机制区分次氯酸盐和过氧亚硝酸盐。在此，通过结构-反应性关系研究解释了这种有趣的选择性。此外，这项工作与丰富的文献贡献一起，为使用富电子芳香基团设计针对过氧亚硝酸盐和/或次氯酸盐的探针提供了定性指导。另一系列过氧亚硝酸盐选择性探针的开发进一步证明了该指导方针的可行性。
