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A Chromogenic Probe for the Selective Recognition of Sarin and Soman Mimic DFP.

El Sayed S, Pascual L, Agostini A, Martínez-Máñez R, Sancenón F, Costero AM, Parra M, Gil S - ChemistryOpen (2014)

Bottom Line: Colour modulation is based on the combined reaction of phosphorylation of 1 and fluoride-induced hydrolysis of a silyl ether moiety.Other nerve agent simulants, certain anions, oxidant species and other organophosphorous compounds were unable to induce colour changes in 1.This is one of the very few examples of a selective detection, in solution and in the gas phase, of a sarin and soman simulant versus other reactive derivatives such as the tabun mimic diethylcyanophosphate (DCNP).

View Article: PubMed Central - PubMed

Affiliation: Centro de Reconocimiento Molecular y Desarrollo Tecnológico (IDM), Unidad Mixta Universidad Politécnica de Valencia, Universidad de Valencia (Spain) ; Departamento de Química, Universidad Politécnica de Valencia, Camino de Vera s/n 46022 Valencia (Spain) E-mail: rmaez@qim.upv.es ; CIBER de Bioingeniería Biomateriales y Nanomedicina (CIBER-BBN).

ABSTRACT
The synthesis, characterization and sensing features of a novel probe 1 for the selective chromogenic recognition of diisopropylfluorophosphate (DFP), a sarin and soman mimic, in 99:1 (v/v) water/acetonitrile and in the gas phase is reported. Colour modulation is based on the combined reaction of phosphorylation of 1 and fluoride-induced hydrolysis of a silyl ether moiety. As fluoride is a specific reaction product of the reaction between DFP and the -OH group, the probe shows a selective colour modulation in the presence of this chemical. Other nerve agent simulants, certain anions, oxidant species and other organophosphorous compounds were unable to induce colour changes in 1. This is one of the very few examples of a selective detection, in solution and in the gas phase, of a sarin and soman simulant versus other reactive derivatives such as the tabun mimic diethylcyanophosphate (DCNP).

No MeSH data available.


Chemical structures of nerve agents sarin, soman, tabun, their simulants (DFP, DCP and DCNP), selected organophosphates (OP1–OP8) and compounds 1 and 2.
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fig01: Chemical structures of nerve agents sarin, soman, tabun, their simulants (DFP, DCP and DCNP), selected organophosphates (OP1–OP8) and compounds 1 and 2.

Mentions: The easy fabrication of nerve gases and their indiscriminate use by certain nations and by terrorist groups have increased the efforts of the scientific community toward the detection and remediation of these deadly chemicals.3 Currently, the most used methods for monitoring the presence of nerve agents are based on the use of biosensors,4 ion mobility spectroscopy,5 electrochemical methods,6 micro-cantilevers,7 photonic crystals8 and optical fiber arrays.9 Recently, as an alternative to these instrumental methods, the development of fluorogenic and chromogenic probes has gained increasing interest. 3b, 10 Chromogenic systems are especially appealing because there are few techniques as simple as visual detection and they allow rapid and sensitive detection to the naked eye in situ or at site without any sample pre-treatment. However, in this field there are relatively few examples of selective probes for the detection of nerve gases.11 Usually in these studies, nerve gas simulants such as diethylcyanophosphate (DCNP), diisopropylfluorophosphate (DFP) and diethylchlorophosphate (DCP) are used (see Figure 1). These compounds show similar reactivity to real nerve agents, that is, sarin, soman and tabun, but lack their severe toxicity (see Figure 1).


A Chromogenic Probe for the Selective Recognition of Sarin and Soman Mimic DFP.

El Sayed S, Pascual L, Agostini A, Martínez-Máñez R, Sancenón F, Costero AM, Parra M, Gil S - ChemistryOpen (2014)

Chemical structures of nerve agents sarin, soman, tabun, their simulants (DFP, DCP and DCNP), selected organophosphates (OP1–OP8) and compounds 1 and 2.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4232269&req=5

fig01: Chemical structures of nerve agents sarin, soman, tabun, their simulants (DFP, DCP and DCNP), selected organophosphates (OP1–OP8) and compounds 1 and 2.
Mentions: The easy fabrication of nerve gases and their indiscriminate use by certain nations and by terrorist groups have increased the efforts of the scientific community toward the detection and remediation of these deadly chemicals.3 Currently, the most used methods for monitoring the presence of nerve agents are based on the use of biosensors,4 ion mobility spectroscopy,5 electrochemical methods,6 micro-cantilevers,7 photonic crystals8 and optical fiber arrays.9 Recently, as an alternative to these instrumental methods, the development of fluorogenic and chromogenic probes has gained increasing interest. 3b, 10 Chromogenic systems are especially appealing because there are few techniques as simple as visual detection and they allow rapid and sensitive detection to the naked eye in situ or at site without any sample pre-treatment. However, in this field there are relatively few examples of selective probes for the detection of nerve gases.11 Usually in these studies, nerve gas simulants such as diethylcyanophosphate (DCNP), diisopropylfluorophosphate (DFP) and diethylchlorophosphate (DCP) are used (see Figure 1). These compounds show similar reactivity to real nerve agents, that is, sarin, soman and tabun, but lack their severe toxicity (see Figure 1).

Bottom Line: Colour modulation is based on the combined reaction of phosphorylation of 1 and fluoride-induced hydrolysis of a silyl ether moiety.Other nerve agent simulants, certain anions, oxidant species and other organophosphorous compounds were unable to induce colour changes in 1.This is one of the very few examples of a selective detection, in solution and in the gas phase, of a sarin and soman simulant versus other reactive derivatives such as the tabun mimic diethylcyanophosphate (DCNP).

View Article: PubMed Central - PubMed

Affiliation: Centro de Reconocimiento Molecular y Desarrollo Tecnológico (IDM), Unidad Mixta Universidad Politécnica de Valencia, Universidad de Valencia (Spain) ; Departamento de Química, Universidad Politécnica de Valencia, Camino de Vera s/n 46022 Valencia (Spain) E-mail: rmaez@qim.upv.es ; CIBER de Bioingeniería Biomateriales y Nanomedicina (CIBER-BBN).

ABSTRACT
The synthesis, characterization and sensing features of a novel probe 1 for the selective chromogenic recognition of diisopropylfluorophosphate (DFP), a sarin and soman mimic, in 99:1 (v/v) water/acetonitrile and in the gas phase is reported. Colour modulation is based on the combined reaction of phosphorylation of 1 and fluoride-induced hydrolysis of a silyl ether moiety. As fluoride is a specific reaction product of the reaction between DFP and the -OH group, the probe shows a selective colour modulation in the presence of this chemical. Other nerve agent simulants, certain anions, oxidant species and other organophosphorous compounds were unable to induce colour changes in 1. This is one of the very few examples of a selective detection, in solution and in the gas phase, of a sarin and soman simulant versus other reactive derivatives such as the tabun mimic diethylcyanophosphate (DCNP).

No MeSH data available.