A Fluorogenic and Chromogenic Probe Distinguishes Fluoride Anions and Thiols: Implications for Discrimination of Fluorid
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ORIGINAL ARTICLE
A Fluorogenic and Chromogenic Probe Distinguishes Fluoride Anions and Thiols: Implications for Discrimination of Fluoride-Containing G Series and Sulfur-Containing V Series Nerve Agents Wei-hui Wu 1 & Xin Wang 1 & Liang Zong 1 & Dan Li 1 & Yan-hua Xiao 1 & Shao-hui Sui 1 & Jian Li 1 & Meng Liu 1 & Gao-yun Chen 1 & Teng Luo 1 & Min Liu 1 & Xin-ming Wang 1 & Zhi-gang Jiang 1 Received: 18 August 2020 / Accepted: 30 October 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract A coumarin-based probe, FP2, was designed for the differential detection of fluoride anions and thiols, i.e., the corresponding nucleophilic substitution products from fluorine-containing G agents and sulfur-containing V agents, thus having the potential to discriminate between these two nerve agents. FP2 with two functional reaction groups, α, β-unsaturated ketone and silyl groups, can react selectively with fluoride anions and thiols at the μM level respectively. Intriguingly, in the THF solution, FP2 reacts with the fluoride anion but not with the thiol, whereas in the EtOH/HEPES solution, FP2 reacts with the thiol but not with the fluoride anion. As a result, FP2 can produce different fluorophores in the two detection solutions, thus displaying significant fluorescence changes. In addition, the FP2 detection system can show a significant color change from colorless to yellow within seconds when detecting fluoride anions in THF detection solutions, and from yellow to light blue when detecting thiols in EtOH/ HEPES solutions, which will facilitate visual detection by emergency responders at the scene of an incident involving a nerve agent. Keywords Probe . Fluorescence . Nerve agents . Detection . Discrimination
Introduction Nerve agents are a group of organophosphorus compounds that can inhibit the enzyme acetylcholinesterases, causing human beings’ incapacitation and death within minutes of exposure [1–3]. These organophosphates comprise two major series (Scheme 1a): fluoride-containing G-series, such as sarin (GB) and soman (GD), and sulphur-containing V-series, such as Oethyl-S-[2-(diisopropylamino)ethyl]methylphosphorothioate (VX) [5–7]. While the military use of such nerve agents is strictly restricted by international laws, their recurring use in conflict zones and in terrorist attacks makes them increasing threats to humanity. Therefore, rapid, sensitive and selective detection of
* Wei-hui Wu [email protected] * Zhi-gang Jiang [email protected] 1
Institute of Chemical Defence, Beijing 102205, People’s Republic of China
these organophosphates is essential to minimize exposure and reduce casualties. To this end, a series of methods have been developed for the detection of nerve agents, such as mass spectrometry, ion mobility spectrometry, biosensing, and electrical sensors [8–11]. Among these detection methods, optical sensors, especially fluorescent probes, have become the simplest and most convenient ones due to their simplicity, low cost, and high sensitivity [1, 4, 7, 12–20], and the
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