Hapten synthesis and monoclonal antibody-based immunoassay development for the detection of the fungicide kresoxim-methyl

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 5, 2008, Pages 1545-1552

  Mercader, Josep V ^a   Suárez Pantaleón, Celia ^a   Agulló, Consuelo ^b   Abad Somovilla, Antonio ^b   Abad Fuentes, Antonio ^a  

^a INSTITUTO DE AGROQUÍMICA Y TECNOLOGÍA DE ALIMENTOS CSIC   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Bridge; Dipeptide; ELISA; Hapten heterology; Linker; Pesticide; Qol fungicides; Spacer arm; Strobilurin

Indexed keywords

FUNGICIDE; HAPTEN; KRESOXIM METHYL; KRESOXIM-METHYL; METHACRYLIC ACID DERIVATIVE; MONOCLONAL ANTIBODY; PESTICIDE RESIDUE; PHENYLACETIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME LINKED IMMUNOSORBENT ASSAY; FOOD CONTAMINATION; HUMAN; IMMUNOLOGY; METHODOLOGY; SAFETY; SENSITIVITY AND SPECIFICITY;

ANTIBODIES, MONOCLONAL; CONSUMER PRODUCT SAFETY; ENZYME-LINKED IMMUNOSORBENT ASSAY; FOOD CONTAMINATION; FUNGICIDES, INDUSTRIAL; HAPTENS; HUMANS; METHACRYLATES; PESTICIDE RESIDUES; PHENYLACETATES; SENSITIVITY AND SPECIFICITY;

FUNGI;

EID: 41949121914     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf073039x     Document Type: Article

References (28)

1. Anke, T.; Oberwinkler, F.; Steglich, W.; Schramm, G. The strobilurins - new antifungal antibiotics from the basidiomycete Strobilurus tenacellus. J. Antibiot. 1977, 30, 806-810.
2. Sauter, H.; Steglich, W.; Anke, T. Strobilurins: evolution of a new class of active substances. Angew. Chem., Int. Ed. 1999, 38, 1328-1349.
3. Schirmer, U.; Karbach, S.; Pommer, E. H.; Ammermann, E.; Steghlich, W.; Schwalge, B. A. M.; Anke, T. (BASF); EP 203606 and EP 203608 (priority date, May 30, 1985).
4. EU Commission Directive 1999/1/EC (1999).
5. Bartlett, D. M.; Clough, J. M.; Godwin, J. R.; Hall, A. A.; Hamer, M.; Parr-Dobrzanski, B. The strobilurin fungicides. Pest Manag. Sci. 2002, 58, 649-662.
6. Pasquer, F.; Isidore, E.; Zarn, J.; Keller, B. Specific patterns of changes in wheat gene expression after treatment with three antifungal compounds. Plant Mol. Biol. 2005, 57, 693-707.
7. EC Health and Consumer Protection D.G. Plant Health. Technical review reports on new active substances - kresoxim-methyl, 1998.
8. Gisi, U.; Sierotzki, H.; Cook, A.; McCaffery, A. Mechanisms influencing the evolution of resistance to Qo inhibitor fungicides. Pest Manag. Sci. 2002, 58, 859-867.
9. EU Council Directives 76/895/EEC, 86/362/EEC, and 90/642/EEC, 2004.
10. Cabras, P.; Angioni, A.; Garau, V. L.; Pirisi, F. Gas chromatographic determination of azoxystrobin, fluazinam, kresoxim-methyl, mepanipyrim, and tetraconazole in grapes, must, and wine. J. AOAC Int. 1998, 81, 1185-1189.
11. Li, J. Z.; Wu, X.; Hu, J. Y. Determination of fungicide kresoxim-methyl residues in cucumber and soil by capillary gas chromatography with nitrogen - phosphorus detection. J. Environ. Sci. Health, B 2006, 41, 427-436.
12. De Melo Abreu, S.; Correia, M.; Herbert, P.; Santos, L.; Alves, A. Screening of grapes and wine for azoxystrobin, kresoxim-methyl and trifloxystrobin fungicides by HPLC with diode array detection. Food Addit. Contam. 2005, 22, 549-556.
13. Knopp, D. Immunoassay development for environmental analysis. Anal. Bioanal. Chem. 2006, 385, 425-427.
14. Furzer, G. S.; Veldhuis, L.; Hall, J. C. Development and comparison of three diagnostic immunoassay formats for the detection of azoxystrobin. J. Agric. Food Chem. 2006, 54, 688-693.
15. Wingert, H.; Sauter, H.; Brand, S.; Wenderoth, B.; Lorenz, G.; Ammermann, E. Preparation of methyl phenyl(di)thioglyoxylate O-methyloximes and analogs as agrochemical and industrial fungicides. Eur. Pat. Appl. EP 432503 A1, 1991; 149 pp.
16. Banerjee, K.; Ligon, A. P.; Schuermann, M.; Preut, H.; Spiteller, M. (E,E)-α-(Methoxyimino)-2-[({1-[3-trifluoromethyl)phenyl]ethylidene) amino)oxymethyl]benzeneacetic acid. Acta Crystallogr. 2005, E61 (6), o1528-o1529.
17. Nowinski, R. C.; Lostrom, M. E.; Tam, M. R.; Stone, M. R.; Burnette, W. N. The isolation of hybrid cell lines producing monoclonal antibodies against the p15(E) protein ecotropic murine leukemia viruses. Virology 1979, 93, 11-126.
18. Holthues, H.; Pfeifer-Fukumura, U.; Sound, I.; Bauman, W. Evaluation of the concept of heterology in a monoclonal antibody-based ELISA utilizing direct hapten linkage to polystyrene microtiter plates. J. Immunol. Methods 2005, 304, 68-77.
19. Estevez, M. C.; Kreuzer, M.; Sanchez-Baeza, F.; Marco, M. P. Analysis of nonylphenol: Advances and improvements in the immunochemical determination using antibodies raised against the technical mixture and hydrophilic immunoreagents. Environ. Sci. Technol. 2006, 40, 559-568.
20. Mercader, J. V.; Montoya, A. Development of monoclonal ELISAs for azinphos-methyl. 1. Hapten synthesis and antibody production. J. Agric. Food Chem. 1999, 47, 1276-1284.
21. Hatzidakis, G. I.; Tsatsakis, A. M.; Krambovitis, E. K.; Spyros, A.; Eremin, S. A. Use of L-lysine fluorescence derivatives as tracers to enhance the performance of polarization fluoroimmunoassays. A study using two herbicides as model antigens. Anal. Chem. 2002, 74, 2513-2521.
22. Matsushita, M.; Hoffman, T. Z.; Ashley, J. A.; Zhou, B.; Wirshing, P.; Janda, K. D. Cocaine catalytic antibodies: the primary importance of linker effects. Bioorg. Med. Chem. Lett. 2001, 11, 87-90.
23. 9-tetrahydrocannabinol. J. Med. Chem. 2005, 48, 7389-7399.
24. Gui, W. J.; Jin, R. Y.; Chen, Z. L.; Cheng, J. L.; Zhu, G. N. Hapten synthesis for enzyme-linked immunoassay of the insecticide triazophos. Anal. Biochem. 2006, 357, 9-14.
25. Kim, Y. J.; Kim, Y. A.; Lee, Y. T.; Lee, H. S. Enzyme-linked immonosorbent assays for the insecticide fenitrothion. Influence of hapten conformation and sample matrix on assay performance. Anal. Chim. Acta 2007, 591, 183-190.
26. Mercader, J. V.; Montoya, A. Development of monoclonal ELISAs for azinphos-methyl. 2. Assay optimization and water sample analysis. J. Agric. Food Chem. 1999, 47, 1285-1293.
27. Abad, A.; Montoya, A. Development of an enzyme-linked immunosorbent assay to carbaryl. 2. Assay optimization and application to the analysis of water samples. J. Agric. Food Chem. 1997, 45, 1495-1501.
28. Moreno, M. J.; Abad, A.; Montoya, A. Production of monoclonal antibodies to the N-methylcarbamate pesticide propoxur. J. Agric. Food Chem. 2001, 49, 72-78 .