Dataset Information

A Selective Fluorescence Turn-On Probe for the Detection of DCNP (Nerve Agent Tabun Simulant).

ABSTRACT: Diethylcyanophosphonate (DCNP) is a simulant of Tabun (GA) which is an extremely toxic chemical substance and is used as a chemical warfare (CW) nerve agent. Due to its toxic properties, monitoring methods have been constantly come under the spotlight. What we are proposing within this report is a next-generation fluorescent probe, DMHN1, which allows DCNP to become fully traceable in a sensitive, selective, and responsive manner. This is the first fluorescent turn-on probe within the dipolar naphthalene platform induced by ESIPT (excited state intramolecular proton transfer) suppression that allows us to sense DCNP without any disturbance by other similar G-series chemical weapons. The successful demonstrations of practical applications, such as in vitro analysis, soil analysis, and the development of an on-site real-time prototype sensing kit, encourage further applications in a variety of fields.

SUBMITTER: Jung Y

PROVIDER: S-EPMC6766206 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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A Selective Fluorescence Turn-On Probe for the Detection of DCNP (Nerve Agent Tabun Simulant).

Jung Yuna Y Kim Dokyoung D

Materials (Basel, Switzerland) 20190911 18

Diethylcyanophosphonate (DCNP) is a simulant of Tabun (GA) which is an extremely toxic chemical substance and is used as a chemical warfare (CW) nerve agent. Due to its toxic properties, monitoring methods have been constantly come under the spotlight. What we are proposing within this report is a next-generation fluorescent probe, <b>DMHN1</b>, which allows DCNP to become fully traceable in a sensitive, selective, and responsive manner. This is the first fluorescent turn-on probe within the dip ...[more]

PMID: 31514369

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Project description:The goal was to test 14 nerve agent model compounds of soman, sarin, tabun, and cyclohexyl methylphosphonofluoridate (GF) for their suitability as substitutes for true nerve agents. We wanted to know whether the model compounds would form the identical covalent adduct with human butyrylcholinesterase that is produced by reaction with true nerve agents. Nerve agent model compounds containing thiocholine or thiomethyl in place of fluorine or cyanide were synthesized as Sp and Rp stereoisomers. Purified human butyrylcholinesterase was treated with a 45-fold molar excess of nerve agent analogue at pH 7.4 for 17 h at 21 degrees C. The protein was denatured by boiling and was digested with trypsin. Aged and nonaged active site peptide adducts were quantified by matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry of the tryptic digest mixture. The active site peptides were isolated by HPLC and analyzed by MALDI-TOF-TOF mass spectrometry. Serine 198 of butyrylcholinesterase was covalently modified by all 14 compounds. Thiocholine was the leaving group in all compounds that had thiocholine in place of fluorine or cyanide. Thiomethyl was the leaving group in the GF thiomethyl compounds. However, sarin thiomethyl compounds released either thiomethyl or isopropyl, while soman thiomethyl compounds released either thiomethyl or pinacolyl. Thiocholine compounds reacted more rapidly with butyrylcholinesterase than thiomethyl compounds. Labeling with the model compounds resulted in aged adducts that had lost the O-alkyl group (O-ethyl for tabun, O-cyclohexyl for GF, isopropyl for sarin, and pinacolyl for soman) in addition to the thiocholine or thiomethyl group. The nerve agent model compounds containing thiocholine and the GF thiomethyl analogue were found to be suitable substitutes for true soman, sarin, tabun, and GF in terms of the adduct that they produced with human butyrylcholinesterase. However, the soman and sarin thiomethyl compounds yielded two types of adducts, one of which was thiomethyl phosphonate, a modification not found after treatment with authentic soman and sarin.

Dataset Information

A Selective Fluorescence Turn-On Probe for the Detection of DCNP (Nerve Agent Tabun Simulant).

Publications

A Selective Fluorescence Turn-On Probe for the Detection of DCNP (Nerve Agent Tabun Simulant).

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