<br>基于3-苯并噻唑-2-基-7-羟基-苯并吡喃-2-酮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-苯并噻唑-2-基-7-羟基-苯并吡喃-2-酮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

最近开发了含有对氧化剂敏感的硼酸酯基团的香豆素衍生物，用于荧光检测炎症氧化剂。在此，我们报道了 3-(2-苯并噻唑基)-7-香豆素硼酸频哪醇酯 ( BC-BE ) 的合成和表征，作为检测过氧亚硝酸盐 (ONOO ^– ) 的荧光探针，具有高稳定性和快速检测能力。响应时间。 BC-BE探针在磷酸盐缓冲液中水解为 3-(2-苯并噻唑基)-7-香豆素硼酸 ( BC-BA )，即使在延长的孵育时间（24 小时）后，该物质在溶液中仍保持稳定。 BC-BA被 H ₂ O ₂缓慢氧化，形成酚类产物 3-苯并噻唑-2-基-7-羟基-苯并吡喃-2-酮 ( BC-OH )。另一方面， BC-BA探针与ONOO ^-快速反应。 BC-BA探头检测^ONOO的能力是使用真实的^ONOO和共同生成 O ₂ ^• ^-和^• NO 稳态通量的系统来测量的。 BC-BA被 ONOO ^–氧化为BC-OH 。然而，在此反应中，3-苯并噻唑-2-基-苯并吡喃-2-酮 ( BC-H ) 在次要途径中形成，作为过氧亚硝酸盐特异性产物。 BC-BA与 HOCl 反应时也会形成BC-OH ，随后BC-OH与 HOCl 反应生成氯化酚产物，该产物可用作 HOCl 的特定产物。我们得出的结论是， BC-BA显示出作为改进的荧光探针在生物环境中检测过氧亚硝酸盐和次氯酸盐的潜力。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

阅读更多本刊新发论文本刊介绍/投稿指南