基于 3-Benzothiazol-2-yl-7-hydroxy-chromen-2-one 的新型硼酸盐探针用于检测过氧亚硝酸盐和次氯酸盐,Molecules

当前位置： X-MOL 学术 › Molecules › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

基于 3-Benzothiazol-2-yl-7-hydroxy-chromen-2-one 的新型硼酸盐探针用于检测过氧亚硝酸盐和次氯酸盐
Molecules ( IF 4.2 ) Pub Date : 2021-09-30 , DOI: 10.3390/molecules26195940
Julia Modrzejewska ₁ , Marcin Szala ₁ , Aleksandra Grzelakowska ₁ , Małgorzata Zakłos-Szyda ₂ , Jacek Zielonka ₃ , Radosław Podsiadły ₁

Affiliation

香豆素的衍生物，含有氧化剂敏感的硼酸酯基团，最近被开发用于炎症氧化剂的荧光检测。在这里，我们报告了 3-(2-苯并噻唑基)-7-香豆素硼酸频哪醇酯 ( BC-BE ) 作为检测过氧亚硝酸盐 (ONOO ^– )的荧光探针的合成和表征，具有高稳定性和快速响应时间。在BC-BE探针水解的磷酸盐缓冲液，以3-（2-苯并噻唑基）-7-香豆素硼酸（BC-BA），其即使在延长的孵育时间（24小时）后是在溶液中是稳定的。BC-BA被 H ₂ O ₂缓慢氧化形成酚类产物 3-benzothiazol-2-yl-7-hydroxy-chromen-2-one ( BC-OH )。另一方面，BC-BA探针与 ONOO ^-反应迅速。的能力BC-BA探针检测ONOO ^-同时使用正品ONOO测定^-和系统的O-共产生稳态通量₂^•^-和^• NO。BC-BA由ONOO氧化^-到BC-OH。然而，在该反应中，3-benzothiazol-2-yl-chromen-2-one ( BC-H ) 在次要途径中形成，作为过氧亚硝酸盐特异性产物。BC-OH在BC-BA与 HOCl的反应中也会形成BC-OH，随后BC-OH与 HOCl 的反应导致形成氯化酚类产物，该产物可用作 HOCl 的特定产物。我们得出结论，BC-BA显示出作为一种改进的荧光探针的潜力，用于在生物环境中检测过亚硝酸盐和次氯酸盐。通过基于 HPLC 的氧化剂特异性产物鉴定来补充荧光测量将有助于鉴定检测到的氧化剂。

"点击查看英文标题和摘要"

Novel Boronate Probe Based on 3-Benzothiazol-2-yl-7-hydroxy-chromen-2-one for the Detection of Peroxynitrite and Hypochlorite

Derivatives of coumarin, containing oxidant-sensitive boronate group, were recently developed for fluorescent detection of inflammatory oxidants. Here, we report the synthesis and the characterization of 3-(2-benzothiazolyl)-7-coumarin boronic acid pinacol ester (BC-BE) as a fluorescent probe for the detection of peroxynitrite (ONOO^–), with high stability and a fast response time. The BC-BE probe hydrolyzes in phosphate buffer to 3-(2-benzothiazolyl)-7-coumarin boronic acid (BC-BA) which is stable in the solution even after a prolonged incubation time (24 h). BC-BA is slowly oxidized by H₂O₂ to form the phenolic product, 3-benzothiazol-2-yl-7-hydroxy-chromen-2-one (BC-OH). On the other hand, the BC-BA probe reacts rapidly with ONOO⁻. The ability of the BC-BA probe to detect ONOO^– was measured using both authentic ONOO^– and the system co-generating steady-state fluxes of O₂^•^– and ^•NO. BC-BA is oxidized by ONOO^– to BC-OH. However, in this reaction 3-benzothiazol-2-yl-chromen-2-one (BC-H) is formed in the minor pathway, as a peroxynitrite-specific product. BC-OH is also formed in the reaction of BC-BA with HOCl, and subsequent reaction of BC-OH with HOCl leads to the formation of a chlorinated phenolic product, which could be used as a specific product for HOCl. We conclude that BC-BA shows potential as an improved fluorescent probe for the detection of peroxynitrite and hypochlorite in biological settings. Complementation of the fluorescence measurements by HPLC-based identification of oxidant-specific products will help to identify the oxidants detected.

更新日期：2021-09-30

点击分享查看原文

点击收藏

公开下载

阅读更多本刊最新论文本刊介绍/投稿指南

全部期刊列表>>