Fluorescent chemosensors for toxic organophosphorus pesticides: A review

Sensors

Volumn 10, Issue 7, 2010, Pages 7018-7043

  Obare, Sherine O ^a   De, Chandrima ^a   Guo, Wen ^a   Haywood, Tajay L ^a   Samuels, Tova A ^a   Adams, Clara P ^a   Masika, Noah O ^a   Murray, Desmond H ^b,c   Anderson, Ginger A ^a,c   Campbell, Keith ^b,c   Fletcher, Kenneth ^b,c  

^a WESTERN MICHIGAN UNIVERSITY   (United States)

^b ANDREWS UNIVERSITY   (United States)

^c Building Excellence in Science and Technology ^*  (United States)

Author keywords

Dual modes of signal transduction; Fluorescent chemosensors; Organophosphorus compounds; Pollutants

Indexed keywords

CHEMICAL WARFARE AGENTS; DUAL MODES; FLUORESCENT CHEMOSENSORS; HUMAN HEALTH CONCERNS; ORGANOPHOS-PHORUS PESTICIDES; ORGANOPHOSPHORUS COMPOUNDS; POLLUTANTS; SELECTIVITY AND SENSITIVITY;

AGRICULTURE; AQUIFERS; CHEMICAL WARFARE; FLUORESCENCE; FUNCTIONAL GROUPS; HYDROGEOLOGY; PESTICIDES; PHOSPHORUS COMPOUNDS; SIGNAL TRANSDUCTION;

PHYSIOLOGY;

FLUORESCENT DYE; ORGANOPHOSPHORUS COMPOUND; PESTICIDE;

REVIEW;

FLUORESCENT DYES; ORGANOPHOSPHORUS COMPOUNDS; PESTICIDES;

EID: 77957105186     PISSN: 14248220     EISSN: None     Source Type: Journal    
DOI: 10.3390/s100707018     Document Type: Review

References (62)

1. Ariese, F.; Ernst, W.H.O.; Sijm, D.T.H.M. Natural and synthetic organic compounds in the environment-A symposium report. Environ. Toxicol. Pharmacol. 2001, 10, 65-80.
2. Karr, J.R.; Dudley, D.R. Ecological perspective on water quality goals. Environ. Manage. 1981, 5, 55-68.
3. U.S. EPA. Pesticides and food: Why children may be especially sensitive to pesticides. Available online: http://www.epa.gov/pesticides/food/pest.htm (accessed on February 26, 2010).
4. Survey, U.S.G. Organophosphorus pesticides occurrence and distribution in surface and ground water of the United States. Available online: http://ga.water.usgs.gov/publications/ofr00-187.pdf. (accessed on 26 February 2010).
5. The Pesticide Action Network (PAN). Pesticide Action Network (PAN) pesticide database. Available online: http://www.pesticideinfo.org. (accessed on 26 February 2010).
6. International Programme on Chemical Safety (INCHEM). International Programme on Chemical Safety INCHEM Database. Available online: http://www.inchem.org (accessed on 26 February 2010).
7. Ullmann's Agrochemicals. Wiley-VCH: Weinheim, Germany, 26 March 2007; Volume 1.
8. Celik, S.; Kunc, S.; Asan, T. Degradation of some pesticides in the field and effect of processing. Analyst 1995, 120, 1739-1743.
9. Bouchard, M.F.; Bellinger, D.C.; Wright, R.O.; Weisskopf, M.G. Attention-deficit/hyperactivity disorder and urinary metabolites of organophosphate pesticides. Pediatrics 2010, 125, 1216-1226.
10. Liu, G.L.; Lin, Y. Electrochemical sensor for organophosphate pesticides and nerve agents using Zirconia nanoparticles as selective Sorbents. Anal. Chem. 1995, 77, 5894-5901.
11. Gilliom, R.J.B.; Barbash, J.E.; Kolpin, D.W.; Larson, S.J. Testing water quality for pesticide pollution. Environ. Sci. Technol. 1999, 33, 164A-169A.
12. Vermeire, T.; MacPhail, R.; Waters, M. Integrated human and ecological risk assessment: A case study of organophosphorous pesticides in the environment. Hum. Ecol. Risk. Assessment 2003, 9, 343-357.
13. Walker, B.J. Organophosphorus Chemistry. Penguin: London, UK, 1972.
14. Jenkins, A.L.; Uy, O.M.; Murray, G.M. Polymer based lanthanide luminescent sensors for the detection of nerve agents. Anal. Commun. 1997, 34, 221-224.
15. Jenkins, A.L.; Uy, O.M.; Murray, G.M. Polymer-based lanthanide luminescent sensor for detection of the hydrolysis product of the nerve agent Soman in water. Anal. Chem. 1999, 71, 373-378.
16. Jenkins, A.L.; Yin, R.; Jensen, J.L. Molecularly imprinted polymer sensors for pesticide and insecticide detection in water. Analyst 2001, 126, 798-802.
17. Rudzinski, C.M.; Young, A.M.; Nocera, D.G. A supramolecular microfluidic optical chemosensor. J. Am. Chem. Soc. 2002, 124, 1723-1727.
18. Russell, A.J.; Berberich, J.A.; Drevon, G.E.; Koepsel, R.R. Biomaterials for mediation of chemical and biological warfare agents. Annu. Rev. Biomed. Eng. 2003, 5, 1-27.
19. Sohn, H.; Letant, S.; Sailor, M.J.; Trogler, W.C. Detection of fluorophosphonate chemical warfare agents by catalytic hydrolysis with a porous silicon interferometer. J. Am. Chem. Soc. 2000, 122, 5399-5400.
20. Steiner, W.E.; Klopsch, S.J.; English, W.A.; Clowers, B.H.; Hill, H.H. Detection of a chemical warfare agent simulant in various aerosol matrixes by ion mobility time-of-flight mass spectrometry. Anal. Chem. 2005, 77, 4792-4799.
21. 31P NMR chemical shifts and structures of some organophosphorus pesticides. Anal. Chim. Acta. 1970, 52, 139-141.
22. Michel, H.O.; Gordon, E.C.; Epstein, J. Detection and estimation of isopropyl methylphosphonofluoridate and O-ethyl S-diisopropylaminoethyl methylphosphonothioate in seawater in parts-per-trillion level. Environ. Sci. Technol. 1973, 7, 1045-1049.
23. Novak, T.J.; Daasch, L.W.; Epstein, J. Decomposition at 90 degrees celcius of the cholinesterase substrate indoxyl acetate impregnated on paper supports. Anal. Chem. 1979, 51, 1271-1275.
24. Wallace, K.J.; Morey, J.; Lynch, V.M.; Anslyn, E.V. Colorimetric detection of chemical warfare simulants. New J. Chem. 2005, 29, 1469-1474.
25. Ngehngwainbi, J.; Foley, P.H.; Kuan, S.S.; Guilbault, G.G. Parathion antibodies on piezoelectric crystals. J. Am. Chem. Soc. 1986, 108, 5444-5447.
26. Nieuwenhuizen, M.S.; Harteveld, J.L.N. Studies on a surface acoustic wave (SAW) dosimeter sensor for organophosphorous nerve agents. Sens. Actuat. B 1997, 40, 167-173.
27. Yamaguchi, S.; Yoshimura, L.; Kohira, T.; Tamaru, S.; Hamachi, I. Cooperation between artificial receptors and supramolecular hydrogels for sensing and discriminating phosphate derivatives. J. Am. Chem. Soc. 2005, 127, 11835-11841.
28. Zhang, S.W.; Swager, T.M. Fluorescent detection of chemical warfare agents: Functional group specific ratiometric chemosensors. J. Am. Chem. Soc. 2003, 125, 3420-3421.
29. 2OH)}. J. Am. Chem. Soc. 1998, 120, 12359-12360.
30. Evtugyn, G.A.; Budnikov, H.C.; Nikolskaya, E.B. Influence of surface-active compounds on the response and sensitivity of cholinesterase biosensors for inhibitor determination. Analyst 1996, 121, 1911-1915.
31. Sherma, J. Pesticides. Anal. Chem. 1995, 67, R1-R20.
32. Trojanowicz, M. Determination of pesticides using electrochemical enzymatic biosensors. Electroanalysis 2002, 14, 1311-1328.
33. Martínez-Máñez, R.; Sancenón, F. Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev. 2003, 103, 4419-4476.
34. Brufani, M.; Marta, M.; Pomponi, M. Anticholinesterase activity of a new carbamate, heptylphysostigmine, in view of its use in patients with Alzheimer-type dementia. Eur. J. Biochem. 1986, 157, 115-120.
35. Lei, Y.; Mulchandani, P.; Wang, J.; Chen, W.; Mulchandani, A. Highly sensitive and selective amperometric microbial biosensor for direct determination of p-nitrophenyl-substituted organophosphate nerve agents. Environ. Sci. Technol. 2005, 39, 8853-8857.
36. Mionetto, N.; Marty, J.L.; Karube, I. Acetylcholinesterase in organic-solvents for the detection of pesticides-Biosensor application. Biosens. Bioelectr. 1994, 9, 463-470.
37. Palleschi, G.; Bernabei, M.; Cremisini, C.; Mascini, N. Determination of organophosphorus insecticides with a choline electrochemical biosensor. Sens. Actuat. B 1992, 7, 513-517.
38. Cao, X.; Mello, S.V.; Leblanc, R.M.; Rastogi, V.K.; Cheng, T.C.; DeFrank, J.J. Detection of paraoxon by immobilized organophosphorus hydrolase in a langmuir-blodgett film. Colloids Surf. A 2004, 250, 349-356.
39. Rudzinski, C.M.Y.; Young, A.M.; Nocera, D.G. Supramolecular Microfluidic Optical Chemosensor. J. Am. Chem. Soc. 2002, 124, 1723-1727.
40. Burnworth, M.; Rowan, S.J.; Weder, C. Fluorescent Sensors for the detection of chemical warfare agents. Chem. Eur. J. 2007, 13, 7828-7836.
41. Rogers, K.R.; Cao, C.J.; Valdes, J.J.; Elderfrawi, A.T.; Eldefrai, M.E. Acetylcholinesterase fiber-optic biosensor for detection of anticholinesterases. Appl. Toxicol. 1991, 16, 810-820.
42. Cao, H.; Nam, J.; Harmon, H.J.; Branson, D.H. Spectrophotometric detection of organophosphate diazinon by porphyrin solution and porphyrin-dyed cotton fabric. Dyes Pigments 2007, 74, 176-180.
43. Dave, K.I.; Miller, C.E.; Wild, J.R. Characterization of organophosphorus hydrolases and the genetic manipulation of the phosphotriesterase from Pseudomonas diminuta. Chem-Biol. Interact. 1993, 87, 55-68.
44. Ma, L.Y.; Wang, H.Y.; Xie, H.; Xu, L.X. A long lifetime chemical sensor: study on fluorescence property of fluorescein isothiocyanate and preparation of pH chemical sensor. Spectrochim. Acta A 2004, 60, 1865-1872.
45. Kolosova, A.Y.; Park, J.H; Eremin, S.A.; Kang, S.J.; Chung, D. Fluorescence polarization immunoassay based on a monoclonal antibody for the detection of the organophosphorus pesticide parathion-methyl. J. Agric. Food Chem. 2003, 51, 1107-1114.
46. Kolosova, A.Y.; Park, J.H; Eremin, S.A.; Park, S.J.; Kang, S.J.; Lee, H.S.; Chung, D.H. Comparative study of three mmunoassays based on monoclonal antibodies for detection of the pesticide parathion-methyl in real samples. Anal. Chim. Acta 2004, 511, 323-331.
47. Lee, E.K.; Kim, Y.J.; Park, W.C.; Chung, T.W.; Lee, Y.T. Monoclonal antibody-based enzyme-linked immunosorbent assays for the detection of the organophosphorus insecticide diazinon. Anal. Chim. Acta. 2005, 530, 143-153.
48. Tang, S.J.; Zhang, M.; Cheng, C.G.; Lu, Y.T. Development of fluorescence polarization immunoassay for the detection of the organophosphorus pesticides parathion and azinophos-methyl. J. Immuno. Immunochem. 2008, 29, 356-369.
49. Zhang, S.W.; Swager, T.M. Fluorescent detection of chemical warfare agents: Functional group specific ratiometric chemosensors. J. Am. Chem. Soc. 2003, 125, 3420-3421.
50. Dale, T.J.; Rebek, J. Fluorescent sensors for organophosphorus nerve agent mimics. J. Am. Chem. Soc. 2006, 128, 4500-4501.
51. Paliwal, S.; Wales, M.; Good, T.; Grimsley, J.; Wild, J.; Simonian, A. Fluorescence-based sensing of p-nitrophenol and p-nitrophenyl substituent organophosphates. Anal. Chim. Acta. 2007, 596, 9-15.
52. Delattre, F.; Cazier, F.; Cazier, F.; Tine, A. Use a fluorescent molecular sensor for the detection of pesticides and herbicides in water. Curr. Anal. Chem. 2009, 5, 48-52.
53. Sun, X.Y.; Xia, K.H.; Liu, B. Design of fluorescent self-assembled multilayers and interfacial sensing for organophosphorus pesticides. Talanta 2008, 76, 747-751.
54. Beaudoin, D.S.; Obare, S.O. Dual optical and electrochemical saccharide detection based on a dipyrido[3,2-a:2'3'-c]phenazine (DPPZ) ligand. Tetrahedron Lett. 2008, 49, 6054-6057.
55. De, C.; Samuels, T.A.; Haywood, T.L.; Anderson, G.A.; Campbell, K.; Fletcher, K.; Murray, D.H.; Obare, S.O. Dual colorimetric and electrochemical sensing of organothiophosphorus pesticides by an azastilbene derivative Tetrahedron Lett. 2010, 51, 1754-1757.
56. Wheeler, O.H.; Batlle de Pabon, H.N. Synthesis of stilbenes. A comparative study. J. Org. Chem. 1965, 30, 1473-1477.
57. Becker, K.B. Synthesis of stilbenes. Synthesis 1983, 5, 341-368.
58. Takahashi, K.; Okamoto, T.; Yamada, K.; Iida, H. A Convenient synthesis of substituted stilbenes by condensation of o- or p-Tolunitrile with p-Substituted benzaldehydes. Synthesis 1977, 1, 58.
59. Wang, S.L.; Ho, T.I. Protonation dependent electron transfer in 2-styrylquinolines Chem. Phys. Lett. 1997, 268, 434-438.
60. Ko, H.J.; Park, T.H. Dual signal transduction mediated by a single type of olfactory receptor expressed in a heterologous system. Biol. Chem. 2006, 387, 59-68.
61. Allen, K.N.; Dunaway-Mariano, D. Phosphoryl group transfer: Evolution of a catalytic scaffold Trends Biochem. Sci. 2004, 29, 495-503.
62. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A., Jr.; Vreven, T.V.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H.P.; Cross, J.B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez, C.; Pople, J.A. Gaussian 03, Gaussian, Inc.: Wallingford CT, USA, 2004.