基于共价组装的荧光探针用于通过洛森重排检测神经毒剂类似物（DCP）。

"Covalent-Assembly"-Based Fluorescent Probe for Detection of a Nerve-Agent Mimic (DCP) via Lossen Rearrangement.

机构信息

Department of Chemistry and Chemical Engineering, School of Chemistry and Biological Engineering , University of Science and Technology Beijing , Beijing 100083 , China.

出版信息

Anal Chem. 2019 Sep 3;91(17):10979-10983. doi: 10.1021/acs.analchem.9b01006. Epub 2019 Aug 15.

DOI:10.1021/acs.analchem.9b01006

PMID:31373196

Abstract

The highly selective and sensitive fluorescence "light-up" probe, 5'-(dimethylamino)-2'-formyl--hydroxy-[1,1'-biphenyl]-2-carboxamide(), has been fabricated for the nerve-agent mimic diethyl chlorophosphate (DCP). The probe is designed by combining two novel strategies of "covalent assembly" and Lossen rearrangement. Formation of a phosphoryl intermediate from DCP and a hydroxamic acid group in yields an isocyanate that quickly undergoes Lossen rearrangement to produce an aniline that condenses intramolecularly to a fluorescent phenanthridine system. shows superior properties to probe DCP, such as rapid response (within 100 s), low detection limit (10.4 nM), specificity, and excellent linearity ( = 0.9993) in the range from 2 to 16 μM. More importantly, its application of detecting DCP vapor has also been achieved with satisfying results.

摘要

已制备出高选择性和高灵敏度的荧光“点亮”探针 5'-(二甲基氨基)-2'-甲酰基--羟基-[1,1'-联苯]-2-甲酰胺()，用于模拟神经毒剂二乙基膦酸酯 (DCP)。该探针是通过结合两种新的“共价组装”和Lossen 重排策略设计而成。DCP 和羟胺基团形成的磷酰基中间体生成异氰酸酯，该异氰酸酯迅速经历 Lossen 重排，生成苯胺，苯胺分子内缩合形成荧光菲啶体系。探针在检测 DCP 方面表现出优于探针 DCP 的优越性能，例如快速响应（在 100 秒内）、低检测限（10.4 nM）、特异性和在 2 至 16 μM 范围内的优异线性（= 0.9993）。更重要的是，它在检测 DCP 蒸气方面的应用也取得了令人满意的结果。