Organic-Molecule-Based Fluorescent Chemosensor for Nerve Agents and Organophosphorus Pesticides

Marrs TC (1993) Organophosphate poisoning. Pharmacol Therap 58(1):51–66 Thakur A, Patil P, Sharma A, Flora SJS (2020) Advances in the development of reactivators for the treatment of organophosphorus inhibited cholinesterase. Curr Org Chem 24(24):2845–2864. https://doi.org/10.2174/1385272824999201020203544 Sidell F, Borak J (1992) Chapter chemical warfare agents introduction decontamination. Ann Emerg Med 21:611–625 Wadia RS, Sadagopan C, Amin RB (1974) Neurological manifestations of organophosphorous insecticide poisoning. J Neurol Neurosurg Psychiatry 37:841–847 Czajka M, Matysiak-Kucharek M, Jodłowska-Jędrych B, Sawicki K, Fal B, Drop B, Kruszewski M, Kapka-Skrzypczak L (2019) Organophosphorus pesticides can influence the development of obesity and type 2 diabetes with concomitant metabolic changes. Environ Res 178:108685. https://doi.org/10.1016/j.envres.2019.108685 Jokanovi M (2009) Medical treatment of acute poisoning with organophosphorus and carbamate pesticides. Toxicol Lett 190:107–115. https://doi.org/10.1016/j.toxlet.2009.07.025 Tougu V (2005) Acetylcholinesterase: mechanism of catalysis and inhibition. Curr Med Chem Nerv Syst Agents 1:155–170. https://doi.org/10.2174/1568015013358536 Silman I, Sussman JL (2005) Acetylcholinesterase: “classical” and “non-classical” functions and pharmacology. Curr Opin Pharmacol 5:293–302. https://doi.org/10.1016/j.coph.2005.01.014 Chauhan S, Chauhan S, D’Cruz R, Faruqi S, Singh KK, Varma S, Singh M, Karthik V (2008) Chemical warfare agents. Environ Toxicol Pharmacol 26:113–122. https://doi.org/10.1016/j.etap.2008.03.003 Soltaninejad K, Shadnia S (2014) History of the use and epidemiology of organophosphorus poisoning. Springer, pp 25–43. https://doi.org/10.1007/978-1-4471-5625-3 Costanzi S, Machado JH, Mitchell M (2018) Nerve agents: what they are, how they work, how to counter them. ACS Chem Neurosci 9:873–885. https://doi.org/10.1021/acschemneuro.8b00148 Koblentz GD (2019) Chemical-weapon use in Syria: atrocities, attribution, and accountability. Nonprolif Rev 26:575–598. https://doi.org/10.1080/10736700.2019.1718336 Shih TM, Kan RK, McDonough JH (2005) In vivo cholinesterase inhibitory specificity of organophosphorus nerve agents. Chem Biol Interact 157–158:293–303. https://doi.org/10.1016/j.cbi.2005.10.042 Kenyon IR, Gutschmidt K, Cosivi O (2005) Legal aspects and international assistance related to the deliberate use of chemicals to cause harm. Toxicology 214:249–255. https://doi.org/10.1016/j.tox.2005.06.017 Haines DD, Fox SC (2014) Acute and long-term impact of chemical weapons: lessons from the Iran-Iraq War. Forensic Sci Rev 26(2):97–114 Profile C (1997) Definitive evidence for the acute sarin poisoning diagnosis in the Tokyo subway. Toxicol Appl Pharmacol 203:198–203 Rosman Y, Eisenkraft A, Milk N, Shiyovich A, Ophir N, Shrot S, Kreiss Y, Kassirer M (2014) Lessons learned from the Syrian sarin attack: evaluation of a clinical syndrome through social media. Ann Intern Med 160(9):644–648 Kim K, Tsay OG, Atwood DA, Churchill DG (2011) Destruction and detection of chemical warfare agents. Chem Rev 111:5345–5403. https://doi.org/10.1021/cr100193y Li X, Cui H, Zeng Z (2018) A simple colorimetric and fluorescent sensor to detect organophosphate pesticides based on adenosine triphosphate-modified gold nanoparticles. Sensors 18(12), 4302 (Switzerland). https://doi.org/10.3390/s18124302 Déjous C, Rebière D, Pistré J, Tiret C, Planade R (1995) A surface acoustic wave gas sensor: detection of organophosphorus compounds. Sens Actuators B Chem 24:58–61. https://doi.org/10.1016/0925-4005(95)85012-0 Orbulescu J, Constantine CA, Rastogi VK, Shah SS, Defrank JJ, Leblanc RM (2006) Detection of organophosphorus compounds by covalently immobilized organophosphorus hydrolase. Anal Chem 78:7016–7021 Marx S, Zaltsman A (2003) Molecular imprinting of sol gel polymers for the detection of paraoxon in water. Int J Environ Anal Chem 83:671–680. https://doi.org/10.1080/0306731021000015029 Hou X, Zheng X, Zhang C, Ma X (2014) Ultrasound-assisted dispersive liquid–liquid microextraction based on the solidification of a floating organic droplet followed by gas chromatography for the determination of eight pyrethroid pesticides in tea samples. J Chromatogr B 969:123–127. https://doi.org/10.1016/j.jchromb.2014.08.010 Jafari MT, Saraji M, Sherafatmand H (2014) Polypyrrole/montmorillonite nanocomposite as a new solid phase microextraction fiber combined with gas chromatography—corona discharge ion mobility spectrometry for the simultaneous determination of diazinon and fenthion organophosphorus pesticide. Anal Chim Acta 814:69–78. https://doi.org/10.1016/j.aca.2014.01.037 Zhao X, Kong W, Wei J, Yang M (2014) Gas chromatography with flame photometric detection of 31 organophosphorus pesticide residues in Alpinia oxyphylla dried fruits. Food Chem 162:270–276. https://doi.org/10.1016/j.foodchem.2014.04.060 Black RM, Clarke RJ, Read RW, Reid MTJ (1994) Application of gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry to the analysis of chemical warfare samples, found to contain residues of the nerve agent sarin, sulphur mustard and their degradation products. J Chromatogr A 662:301–321. https://doi.org/10.1016/0021-9673(94)80518-0 Rodrigues ET, Pardal MÂ, Salgueiro-González N, Muniategui-Lorenzo S, Alpendurada MF (2016) A single-step pesticide extraction and clean-up multi-residue analytical method by selective pressurized liquid extraction followed by on-line solid phase extraction and ultra-high-performance liquid chromatography-tandem mass spectrometry for complex matrices. J Chromatogr A. https://doi.org/10.1016/j.chroma.2016.05.036 Synaridou MS, Sakkas VA, Stalikas CD, Albanis TA (2014) Evaluation of magnetic nanoparticles to serve as solid-phase extraction sorbents for the determination of endocrine disruptors in milk samples by gas chromatography mass spectrometry. J Chromatogr A. https://doi.org/10.1016/j.chroma.2014.04.092 Zhong Q, Shen L, Liu J, Yu D, Li S, Yao J, Zhan S, Huang T, Hashi Y, Kawano S, Liu Z, Zhou T (2016) Pre-column dilution large volume injection performance liquid chromatography-tandem mass spectrometry for the analysis of multi-class pesticides in cabbages. J Chromatogr A 1442:53–61. https://doi.org/10.1016/j.chroma.2016.03.010 Giordano B, Collins G (2007) Synthetic methods applied to the detection of chemical warfare nerve agents. Curr Org Chem 11:255–265. https://doi.org/10.2174/138527207779940883 Liu T, Cao P, Geng J, Li J, Wang M (2013) Determination of triazine herbicides in milk by cloud point extraction and high-performance liquid chromatography. Food Chem. https://doi.org/10.1016/j.foodchem.2013.07.062 Watanabe E, Baba K (2015) Highly sensitive quantification of pyrethroid insecticide etofenprox in vegetables with high-performance liquid chromatography and fluorescence detection. J Chromatogr A 1385:35–41. https://doi.org/10.1016/j.chroma.2015.01.056 Yang M, Xi X, Wu X, Lu R, Zhou W, Zhang S, Gao H (2015) Vortex-assisted magnetic β-cyclodextrin/attapulgite-linked ionic liquid dispersive liquid–liquid microextraction coupled with high-performance liquid chromatography for the fast determination of four fungicides in water samples. J Chromatogr A. https://doi.org/10.1016/j.chroma.2015.01.016 Wu D, Sedgwick AC, Gunnlaugsson T, Akkaya EU, Yoon J, James TD (2017) Fluorescent chemosensors: the past, present and future. Chem Soc Rev 46:7105–7123. https://doi.org/10.1039/c7cs00240h Coto PB, Serrano-Andrés L, Gustavsson T, Fujiwara T, Lim EC (2011) Intramolecular charge transfer and dual fluorescence of 4-(dimethylamino) benzonitrile: ultrafast branching followed by a two-fold decay mechanism. Phys Chem Chem Phys 13(33):15182–15188. https://doi.org/10.1039/C1CP21089K Kavarnos GJ (1990) Fundamental concepts of photoinduced electron transfer. In: Mattay J (ed) Photoinduced electron transfer I. Springer, Berlin, Heidelberg, pp 21–58 Valeur B, Berberan-Santos MN (2012) Molecular fluorescence. Mol Fluoresc. https://doi.org/10.1002/9783527650002 De Silva AP, Moody TS, Wright GD (2009) Fluorescent PET (Photoinduced Electron Transfer) sensors as potent analytical tools. Analyst 134:2385–2393. https://doi.org/10.1039/b912527m Qin T, Huang Y, Zhu K, Wang J, Pan C, Liu B, Wang L (2019) A flavonoid-based fluorescent test strip for sensitive and selective detection of a gaseous nerve agent simulant. Anal Chim Acta 1076:125–130. https://doi.org/10.1016/j.aca.2019.05.025 Chen Y, Lam JW, Kwok RT, Liu B, Tang BZ (2019) Aggregation-induced emission: fundamental understanding and future developments. Mater Horiz 6(3):428–433 Van Houten KA, Heath DC, Pilato RS (1998) Rapid luminescent detection of phosphate esters in solution and the gas phase using (dppe)Pt{S2C2(2-pyridyl)(CH2CH2OH)}. J Am Chem Soc 120:12359–12360. https://doi.org/10.1021/ja982365d Zhang SW, Swager TM (2003) Fluorescent detection of chemical warfare agents: functional group specific ratiometric chemosensors. J Am Chem Soc 125:3420–3421. https://doi.org/10.1021/ja029265z Dale TJ, Rebek J (2006) Fluorescent sensors for organophosphorus nerve agent mimics. J Am Chem Soc 128:4500–4501. https://doi.org/10.1021/ja057449i Walton I, Davis M, Munro L, Catalano VJ, Cragg PJ, Huggins MT, Wallace KJ (2012) A fluorescent dipyrrinone oxime for the detection of pesticides and other organophosphates. Org Lett 14:2686–2689. https://doi.org/10.1021/ol300799f Wallace KJ, Fagbemi RI, Folmer-Andersen FJ, Morey J, Lynth VM, Anslyn EV (2006) Detection of chemical warfare simulants by phosphorylation of a coumarin oximate. Chem Commun 37:3886–3888 Lee JY, Lee YH, Byun YG (2012) Detection of chemical warfare nerve agents via a Beckmann fragmentation of aldoxime. Phosphorus Sulfur Silicon Relat Elem 187:641–649. https://doi.org/10.1080/10426507.2011.636110 Cai YC, Li C, Song QH (2017) Selective and visual detection of a nerve agent mimic by phosphorylation and protonation of quinolin oximes. J Mater Chem C 5:7337–7343. https://doi.org/10.1039/c7tc02617j Dale TJ, Rebek J (2009) Hydroxy oximes as organophosphorus nerve agent sensors. Angew Chem 121(42):7990–7992. https://doi.org/10.1002/anie.200902820 Han S, Xue Z, Wang Z, Wen TB (2010) Visual and fluorogenic detection of a nerve agent simulant via a Lossen rearrangement of rhodamine-hydroxamate. Chem Commun 46:8413–8415. https://doi.org/10.1039/c0cc02881a Wu X, Wu Z, Han S (2011) Chromogenic and fluorogenic detection of a nerve agent simulant with a rhodamine-deoxylactam based sensor. Chem Commun 47:11468–11470. https://doi.org/10.1039/c1cc15250e Wu Z, Wu X, Yang Y, Wen T, Han S (2012)A rhodamine-deoxylactam based sensor for chromo-fluorogenic detection of nerve agent simulant. Bioorg Med Chem Lett 22:6358–6361. https://doi.org/10.1016/j.bmcl.2012.08.077 Hu XX, Su YT, Ma YW, Zhan XQ, Zheng H, Jiang YB (2015) A near infrared colorimetric and fluorometric probe for organophosphorus nerve agent mimics by intramolecular amidation. Chem Commun 51:15118–15121. https://doi.org/10.1039/c5cc04630k Ali SS, Gangopadhyay A, Maiti K, Mondal S, Pramanik AK, Guria UN, Uddin MR, Mandal S, Mandal D, Mahapatra AK (2017) A chromogenic and ratiometric fluorogenic probe for rapid detection of a nerve agent simulant DCP based on a hybrid hydroxynaphthalene-hemicyanine dye. Org Biomol Chem 15:5959–5967. https://doi.org/10.1039/c7ob01252g Zhou X, Zeng Y, Liyan C, Wu X, Yoon J (2016) A fluorescent sensor for dual-channel discrimination between phosgene and a nerve-gas mimic. Angew Chem Int Ed 55:4729–4733. https://doi.org/10.1002/anie.201601346 Zeng L, Zeng H, Jiang L, Wang S, Hou J, Yoon J (2019) A single fluorescent chemosensor for simultaneous discriminative detection of gaseous phosgene and a nerve agent mimic. Anal Chem 91:12070–12076. https://doi.org/10.1021/acs.analchem.9b03230 Kumar V, Rana H (2015) Chromogenic and fluorogenic detection and discrimination of nerve agents Tabun and Vx. Chem Commun 51:16490–16493. https://doi.org/10.1039/c5cc06580a Jang YJ, Tsay OG, Murale DP, Jeong JA, Segev A, Churchill DG (2014) Novel and selective detection of Tabun mimics. Chem Commun 50:7531–7534. https://doi.org/10.1039/c4cc02689f Kim T, Maity SB, Bouffard J, Kim Y, Kim T, Maity SB, Bouffard J, Kim Y (2016) Molecular rotors for the detection of chemical warfare agent simulants. Anal Chem. https://doi.org/10.1021/acs.analchem.6b02516 Lu Z, Fan W, Shi X, Black CA, Fan C, Wang F (2018) A highly specific BODIPY-based fluorescent probe for the detection of nerve-agent simulants. Sens Actuators B Chem 255:176–182. https://doi.org/10.1016/j.snb.2017.08.019 Barba-Bon A, Costero AM, Gil S, Harriman A, Sancenõn F (2014) Highly selective detection of nerve-agent simulants with BODIPY dyes. Chem A Eur J 20:6339–6347. https://doi.org/10.1002/chem.201304475 Royo S, Costero AM, Parra M, Gil S, Martínez-Máñez R, Sancenõn F (2011) Chromogenic, specific detection of the nerve-agent mimic DCNP (a tabun mimic). Chem A Eur J 17:6931–6934. https://doi.org/10.1002/chem.201100602 Yao J, Fu Y, Xu W, Fan T, Gao Y (2016) Concise and efficient fluorescent probe via an intromolecular charge transfer for the chemical warfare agent mimic diethylchlorophosphate vapor detection. Anal Chem. https://doi.org/10.1021/acs.analchem.5b04777 Cai YC, Li C, Song QH (2017) Fluorescent chemosensors with varying degrees of intramolecular charge transfer for detection of a nerve agent mimic in solutions and in vapor. ACS Sens 2(6):834–841 Kundu S, Saha S, Sahoo P (2019) Rapid and selective visual detection of DCNP (nerve gas mimic) in sea water and soil with a simple paper strip. Results Chem 1:100014. https://doi.org/10.1016/j.rechem.2019.100014 Jung Y, Kim D (2019) A selective fluorescence turn-on probe for the detection of DCNP (nerve agent tabun simulant). Materials (Basel). https://doi.org/10.3390/ma12182943 Qu F, Zhou X, Xu J, Li H, Xie G (2009) Luminescence switching of CdTe quantum dots in presence of p-sulfonatocalix[4]arene to detect pesticides in aqueous solution. Talanta 78:1359–1363. https://doi.org/10.1016/j.talanta.2009.02.013 Jenkins AL, Uy OM, Murray GM (1997) Polymer based lanthanide luminescent sensors for the detection of nerve agents. Anal Commun 34(8):221–224. https://doi.org/10.1039/A704220E Jenkins AL, Uy OM, Murray GM (1999) Polymer-based lanthanide luminescent sensor for detection of the hydrolysis product of the nerve agent Soman in water. Anal Chem 71:373–378 Knapton D, Burnworth M, Rowan SJ, Weder C (2006) fluorescent organometallic sensors for the detection of chemical-warfare-agent mimics. Angew Chem 118:5825–5829. https://doi.org/10.1002/anie.200601634 Fu Y, Yu J, Wang K, Liu H, Yu Y, Liu A, Cheng J (2018) Simple and efficient chromophoric-fluorogenic probes for diethylchlorophosphate vapor. ACS Sens 3(8):1445–1450. https://doi.org/10.1021/acssensors.8b00313 Jiang H, Wu P, Zhang Y, Jiao Z, Xu W, Zhang X, Cheng J (2017) Hyperbranched polymer based fluorescent probes for ppt level nerve agent simulant vapor detection. Anal Methods 9(11):1748–1754. https://doi.org/10.1039/C6AY03427F Hu X, Wang F, Peng Q, Hu J, Peng H, Li L, Zheng B, Du J, Xiao D (2019) Construction of a luminescent sensor based on a lanthanide complex for the highly efficient detection of methyl parathion. RSC Adv 9:13048–13053. https://doi.org/10.1039/c9ra01748h Wang M, Su K, Cao J, She Y, Abd El-Aty AM, Hacımüftüoğlu A, Wang J, Yan M, Hong S, Lao S, Wang Y (2019) “Off-On” non-enzymatic sensor for malathion detection based on fluorescence resonance energy transfer between β-cyclodextrin@Ag and fluorescent probe. Talanta 192:295–300. https://doi.org/10.1016/j.talanta.2018.09.060 Cui Z, Han C, Li H (2011) Dual-signal fenamithion probe by combining fluorescence with colorimetry based on Rhodamine B modified silver nanoparticles. Analyst 136:1351–1356. https://doi.org/10.1039/c0an00617c Ibrahim IA, Abbas AM, Darwish HM (2017) Fluorescence sensing of dichlorvos pesticide by the luminescent Tb(III)-3-ally-salicylohydrazide probe. Luminescence 32:1541–1546. https://doi.org/10.1002/bio.3357 Singh J, Parkash J, Kaur V, Singh R (2019) Zn2+ conjugated Schiff base organic nanoparticles for selective quantification and degradation of diethyl chlorophosphate in aqueous media: application to green vegetables. Sens Actuators B Chem. https://doi.org/10.1016/j.snb.2019.126923 Azab HA, Khairy GM, Kamel RM (2015) Time-resolved fluorescence sensing of pesticides chlorpyrifos, crotoxyphos and endosulfan by the luminescent Eu(III)-8-allyl-3-carboxycoumarin probe. Spectrochim Acta Part A Mol Biomol Spectrosc 15:10. https://doi.org/10.1016/j.saa.2015.03.098 Luo Q, Lai J, Qiu P, Wang X (2018) An ultrasensitive fluorescent sensor for organophosphorus pesticides detection based on RB-Ag/Au bimetallic nanoparticles. Sens Actuators B Chem 263:517–523. https://doi.org/10.1016/j.snb.2018.02.101 Xu X, Guo Y, Wang X, Li W, Qi P, Wang Z, Wang X, Gunasekaran S, Wang Q (2018) Sensitive detection of pesticides by a highly luminescent metal-organic framework. Sens Actuators B Chem 260:339–345. https://doi.org/10.1016/j.snb.2018.01.075 Raj P, Singh A, Kaur K, Aree T, Singh A, Singh N (2016) Fluorescent chemosensors for selective and sensitive detection of phosmet/chlorpyrifos with octahedral Ni2+ complexes. Inorg Chem 55:4874–4883. https://doi.org/10.1021/acs.inorgchem.6b00332 Delattre F, Cazier F, Cazier F, Tine A (2009) Use a fluorescent molecular sensor for the detection of pesticides and herbicides in water. Curr Anal Chem 5(1):48–52 Hou J, Dong G, Tian Z, Lu J, Wang Q, Ai S, Wang M (2016) A sensitive fluorescent sensor for selective determination of dichlorvos based on the recovered fluorescence of carbon dots-Cu(II) system. Food Chem 202:81–87. https://doi.org/10.1016/j.foodchem.2015.11.134 Tao CL, Chen B, Liu XG, Zhou LJ, Zhu XL, Cao J, Tang BZ (2017) A highly luminescent entangled metal–organic framework based on pyridine-substituted tetraphenylethene for efficient pesticide detection. Chem Comm 53(72):9975–9978. https://doi.org/10.1039/C7CC05031C Zhang B, Yan J, Shang Y, Wang Z (2018) Synthesis of fluorescent micro-and mesoporous polyaminals for detection of toxic pesticides. Macromolecules 51(5):1769–1776. https://doi.org/10.1021/acs.macromol.7b02669 Han T, Wang G (2019) Peroxidase-like activity of acetylcholine-based colorimetric detection of acetylcholinesterase activity and an organophosphorus inhibitor. J Mater Chem B 7(16):2613–2618. https://doi.org/10.1039/C8TB02616E Sharma P, Kumar M, Bhalla V (2020) “Metal-free” fluorescent supramolecular assemblies for distinct detection of organophosphate/organochlorine pesticides. ACS Omega. https://doi.org/10.1021/acsomega.0c02315