Oxidation of diazinon and malathion by myeloperoxidase

Pesticide Biochemistry and Physiology

Volumn 100, Issue 2, 2011, Pages 140-144

  Lazarević Pašti, Tamara ^a   Čolović, Mirjana ^a   Savić, Jasmina ^a   Momić, Tatjana ^a   Vasić, Vesna ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Aceylcholinesterase; Kinetic constants; Myeloperoxidase; Organophosphates; Oxidation

Indexed keywords

EID: 79955875646     PISSN: 00483575     EISSN: 10959939     Source Type: Journal    
DOI: 10.1016/j.pestbp.2011.03.001     Document Type: Article

References (50)

1. Casida J. Pest toxicology: the primary mechanisms of pesticide action. Chem. Res. Toxicol. 2009, 22:609-619.
2. Kulkarni A.P., Hodgson E. Metabolism of insecticides by mixed function oxidase systems. Pharmacol. Therapeut. 1980, 8:379-475.
3. Sultatos L.G. Mammalian toxicology of organophosphorous pesticides. J. Toxicol. Environ. Health 1994, 43:271-289.
4. Colovic M., Krstic D., Petrovic S., Leskovac A., Joksic G., Savic J., Franko M., Trebse P., Vasic V. Toxic effects of diazinon and its photodegradation products. Toxicol. Lett. 2010, 193:9-18.
5. Fallscheer H., Cook J. Report on enzymatic methods for insecticides. J. Assoc. Offic. Agric. Chem. 1956, 39:691-697.
6. Krstic D., Colovic M., Bavcon Kralj M., Franko M., Krinulovic K., Trebse P., Vasic V. Inhibition of AChE by malathion and some structurally similar compounds. J. Enz. Inh. Med. Chem. 2008, 23:562-573.
7. Shemer H., Linden K.G. Degradation and by-product formation of diazinon in water during UV and UV/H2O2 treatment. J. Hazard. Mater. 2006, 136:553-559.
8. Jauregui J., Valderrama B., Albores A., Vazquez-Duhalt R. Microsomal transformation of organophosphorus pesticides by white rot fungi. Biodegradation 2003, 14:397-406.
9. Kouloumbos V., Tsipi D., Hiskia A., Nikolic D., van Breemen R. Identification of photocatalytic degradation products of diazinon in TiO2 aqueous suspensions using GC/MS/MS and LC/MS with quadrupole time-of-flight mass spectrometry. J. Am. Soc. Mass Spectrom. 2003, 14:803-817.
10. Pérez-Ruiz T., Martínez-Lozano C., Tomás V., Martín J. High-performance liquid chromatographic assay of phosphate and organophosphorus pesticides using a post-column photochemical reaction and fluorimetric detection. Anal. Chim. Acta 2005, 540:383-391.
11. Lee H.S., Kim Y.A., Cho Y.A., Lee Y.T. Oxidation of organophosphorus pesticides for the sensitive detection by a cholinesterase-based biosensor. Chemosphere 2002, 46:571-576.
12. Hernandez J., Robledo N.R., Velasco L., Quintero R., Pickard M.A., Vazquez-Duhalt R. Chloroperoxidase-mediated oxidation of organophosphorus pesticides. Pestic. Biochem. Phys. 1998, 61:87-94.
13. Marty J.L., Mionetto N., Lacorte S., Barceló D. Validation of an enzymatic biosensor with various liquid chromatographic techniques for determining organophosphorus pesticides and carbaryl in freeze-dried waters. Anal. Chim. Acta 1995, 311:265-271.
14. Barceló D., Lacorte S., Marty J.L. Validation of an enzymatic biosensor with liquid chromatography for pesticide monitoring. Trends Anal. Chem. 1995, 14:334-340.
15. Schulze H., Schmid R., Bachmann T. Rapid detection of neurotoxic insecticides in food using disposable acetylcholinesterase-biosensors and simple solvent extraction. Anal. Bioanal. Chem. 2002, 372:268-272.
16. Schulze H., Vorlová S., Villatte F., Bachmann T.T., Schmid R.D. Design of acetylcholinesterases for biosensor applications. Biosens. Bioelectron. 2003, 18:201-209.
17. Bavcon Kralj M., Trebše P., Franko M. Oxidation as a pre-step in determination of organophosphorus compounds by the AChE-TLS bioassay. Acta Chim. Slov. 2006, 53:43-51.
18. Kumaran S., Tran-Minh C. Determination of organophosphorous and carbamate insecticides by flow injection analysis. Anal. Biochem. 1992, 200:187-194.
19. Kumaran S., Morita M. Application of a cholinesterase biosensor to screen for organophosphorus pesticides extracted from soil. Talanta 1995, 42:649-655.
20. Kim Y.A., Lee H.S., Park Y.C., Lee Y.T. A convenient method for oxidation of organophosphorus pesticides in organic solvents. Environ. Res. 2000, 84:303-309.
21. Skowronska A., Krawczyk E. A general method for the conversion of thiophosphoryl and selenophosphoryl groups into phosphoryl groups by ozone oxidation. Synthesis 1983, 6:509-510.
22. Michalski J., Okruszek A., Stec W. Stereochemistry of oxidation of organophosphorus thiono-compounds and PIII compounds by nitric acid and dinitrogen tetroxide. Chem. Commun. D 1970, 1495-1497.
23. Stec W.J., Okruszek A., Michalski J. Organophosphorus compounds of sulfur and selenium Stereochemistry of oxidation of thiono- and selenophosphoryl compounds with hydrogen peroxide. J. Org. Chem. 1976, 41:233-238.
24. Luckenbach R., Kern M. Stereospezifische Überfuhrüng chiraler acyclischer tertiärer phosphinsulphide in die entsprechenden tertiären phosphioxide mit dymethilsulphoxid (DMSO). Chem. Berichte 1975, 108:3533-3537.
25. Herriott A.W. Peroxy acid oxidation of phosphinothioates, a reversal of stereochemistry. J. Am. Chem. Soc. 1971, 93:3304-3305.
26. Bellet E.M., Casida J.E. Products of peracid oxidation of organothiophosphorus compounds. J. Agric. Food Chem. 1974, 22:207-211.
27. Segall Y., Casida J.E. Oxidative conversion of phosphorothiolates to phosphinyloxysulfonates probably via phosphorothiolate - oxides. Tetrahedron Lett. 1982, 23:139-142.
28. Jackson J.A., Berkman C.E., Thompson C.M. Stereoselective and chemoselective oxidation of phosphorothionates using MMPP. Tetrahedron Lett. 1992, 33:6061-6064.
29. Helinski J., Skrzypczynski Z., Wasiak J., Michalski J. Efficient oxygenation of thiophosphoryl and selenophosphoryl groups using trifluoroacetic anhydride. Tetrahedron Lett. 1990, 31:4081-4084.
30. Bruzik K.S., Stec W.J. Reversible oxidation of phosphylthionates and phosphylselenonates with trifluoroacetic anhydride. J. Org. Chem. 1990, 55:6131-6135.
31. Sánchez-Baeza F., Durand G., Barceló D., Messeguer A. Dimethyldioxirane conversion of phosphine sulfides and phosphorothioates into their corresponding oxygen analogues. Tetrahedron Lett. 1990, 31:3359-3362.
32. Wozniak L.A., Stec W.J. Oxidation in organophosphorus chemistry: potassium peroxymonosulphate. Tetrahedron Lett. 1999, 40:2637-2640.
33. Terreni M., Pregnolato M., Resnati G., Benfenati E. Selective sulfur oxygenation in phosphoroamidate, thionophosphate, and thiophosphate agrochemicals by perfluoro-cis-2,3-dialkyloxaziridine. Tetrahedron 1995, 51:7981-7992.
34. Arnone A., Pregnolato M., Resnati G., Terreni M. Conversion of thio- and selenophosphoryl into phosphoryl group by perfluoro cis-2,3-dialkyloxaziridines. J. Org. Chem. 1997, 62:6401-6403.
35. Knaak J.B., Stahmann M.A., Casida J.E. Insecticide metabolism in plants peroxidase and ethylenediaminetetraacetic acid-ferrous iron-catalyzed oxidation and hydrolysis of parathion. J. Agric. Food Chem. 1962, 10:154-158.
36. Vazquez-Duhalt R., Westlake D.W.S., Fedorak P.M. Cytochrome c as a biocatalyst for the oxidation of thiophenes and organosulfides. Enzyme Microb. Technol. 1993, 15:494-499.
37. Klebanoff S.J. Myeloperoxidase. P. Assoc. Am. Physician 1999, 111:383-389.
38. Shacter E., Lopez R.L., Pati S. Inhibition of the myeloperoxidase-H2O2-Cl- system of neutrophils by indomethacin and other non-steroidal anti-inflammatory drugs. Biochem. Pharmacol. 1991, 41:975-984.
39. Kettle A.J., Gedye C.A., Hampton M.B., Winterbourn C.C. Inhibition of myeloperoxidase by benzoic acid hydrazides. Biochem. J. 1995, 308:559-563.
40. T. Momic, J. Savic, V. Vasic, Oxidation of quercetin by myeloperoxidase, Ress. Lett. Phys. Chem. 2009 (2009).
41. Tischendorf F.W., Brattig N.W., Büttner D.W., Pieper A., Lintzel M. Serum levels of eosinophil cationic protein, eosinophil-derived neurotoxin and myeloperoxidase in infections with filariea and schistosomes. Acta Trop. 1996, 62:171-182.
42. Odajima T., Yamazaki I. Myeloperoxidase of the leukocyte of normal blood. I. reaction of myeloperoxidase with hydrogen peroxide. Biochim. Biophys. Acta 1970, 206:71-77.
43. Beers R.J., Sizer I.W. A spectrophotometric method for measuring the breakdown of hydrogen peroxide by catalase. J. Biol. Chem. 1952, 195:133-140.
44. Ellman G.L., Courtney K.D., Andres V., Featherstone R.M. A new, rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 1:88-90. IN1, 91-95.
45. Lazarević Pašti T., Momić T., Onjia A., Vujisić L., Vasić V. Myeloperoxidase-mediated oxidation of organophosphorus pesticides as a pre-step in their determination by AChE based bioanalytical methods. Microchim. Acta 2010, 170:289-297.
46. Boškin A., Tran C., Franko M. Oxidation of organophosphorus pesticides with chloroperoxidase enzyme in the presence of an ionic liquid as co-solvent. Environ. Chem. Lett. 2009, 7:267-270.
47. Bavcon Kralj M., Cernigoj U., Franko M., Trebse P. Comparison of photocatalysis and photolysis of malathion, isomalathion, malaoxon, and commercial malathion - products and toxicity studies. Water Res. 2007, 41:4504-4514.
48. Zhang Q., Pehkonen S.O. Oxidation of diazinon by aqueous chlorine: kinetics mechanisms, and product studies. J. Agric. Food Chem. 1999, 47:1760-1766.
49. Bergh C., Torgrip R., Östman C. Simultaneous selective detection of organophosphate and phthalate esters using gas chromatography with positive ion chemical ionization tandem mass spectrometry and its application to indoor air and dust. Rapid Commun. Mass Spectrom. 2010, 24:2859-2867.
50. Evtugyn G.A., Rizaeva E.P., Stoikova E.E., Latipova V.Z., Budnikov H.C. The application of cholinesterase potentiometric biosensor for preliminary screening of the toxicity of waste waters. Electroanalysis 1997, 9:1124-1128.