Development of optically pure pyrethroid-like fluorescent substrates for carboxylesterases

Chemical Research in Toxicology

Volumn 18, Issue 3, 2005, Pages 516-527

  Huang, Huazhang ^a   Stok, Jeanette E ^a   Stoutamire, Donald W ^a   Gee, Shirley J ^a   Hammock, Bruce D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE DERIVATIVE; ALPHA 2 HYDROXY 2 (6 METHOXY 2 NAPHTHYL)ACETONITRILE; CARBOXYLESTERASE; CIPERMETHRIN; FENVALERATE; PYRETHROID; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENZYME ACTIVITY; ENZYME SUBSTRATE; FLUORESCENCE; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; NUCLEOTIDE SEQUENCE; OPTICS; PROTEIN HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

ANIMALS; CARBOXYLIC ESTER HYDROLASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORESCENCE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; INSECTICIDES; ISOMERISM; LIVER; MICE; MOLECULAR STRUCTURE; PYRETHRINS; SENSITIVITY AND SPECIFICITY; SUBSTRATE SPECIFICITY;

EID: 15344341737     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049773h     Document Type: Article

References (41)

1. Angerer, J., and Ritter, A. (1997) Determination of metabolites of pyrethroids in human urine using solid-phase extraction and gas chromatography-mass spectrometry. J. Chromatogr. B 695, 217-226.
2. Oppenoorth, F. J. (1985) Biochemistry and genetics of insecticide resistance. In Comprehensive Insect Physiology, Biochemistry and Pharmacology (Kerkut, G. A., and Gilbert, L. I., Eds.) Vol. 12, pp 731-773, Pergamon Press, Oxford.
3. Miyamoto, J., Kaneko, H., Tsuji, R., and Okuno, Y. (1995) Pyrethroids, nerve poisons: How their risks to human health should be assessed. Toxicol. Lett. 82/83, 933-940.
4. Rostron, C. (1989) The Toxicology of Cobalt and Pyrethroids: Reviews of Environmental Contamination and Toxicology (Ware, G. W., Ed.) Vol. 108, p 184, Springer-Verlag, New York.
5. WHO (1990) Environmental Health Criteria 94, pp 1-114, Permethrin, World Health Organization, Geneva.
6. Sogorb, M. A., and Vilanova, E. (2002) Enzymes involved in the detoxification of organophosphorus, carbamate and pyrethroid insecticides through hydrolysis. Toxicol. Lett. 128, 215-228.
7. Sakata, S., Mikami, N., and Yamada, H. (1992) Degradation of pyrethroid isomers by soil microorganisms. J. Pestic. Sci. 17 (3), 181-189.
8. Abernathy, C. O., Ueda, K., Engel, J. L., Gaughan, L. C., and Casida, J. E. (1973) Substrate-specificity and toxicological significance of pyrethroid-hydrolyzing esterases of mouse liver microsomes. Pestic. Biochem. Physiol. 3, 300-311.
9. Chiang, S. W., and Sun, C. N. (1996) Purification and characterization of carboxylesterases of a rice green leafhopper Nephotettix cincticeps Uhler. Pestic. Biochem. Physiol. 54, 181-189.
10. Riddles, P. W., Schnitzerling, H. J., and Davey, P. A. (1983) Application of trans and cis isomers of p-nitrophenyl-(1R,S)-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropane carboxylate to the assay of pyrethroid-hydrolyzing esterases. Anal. Biochem. 132, 105-109.
11. Soderlund, D. M., Abdel-Aal, Y. A. I., and Helmuth, D. W. (1982) Selective inhibition of separate esterases in rat and mouse liver microsomes hydrolyzing malathion, trans-permethrin and cis-permethrin. Pestic. Biochem. Physiol. 17, 162-169.
12. Shan, G., and Hammock, B. D. (2001) Development of sensitive esterase assays based on α-cyano-containing esters. Anal. Biochem. 299, 54-62.
13. Wheelock, C. E., Wheelock, A. M., Zhang, R., Stock, J. E., Morisseau, C., LeValley, S. E., Green, C. E., and Hammock, B. D. (2003) Evaluation of cyano-esters as fluorescent substrates for examining interindividual variation in general and pyrethroid-selective esterases in human liver microsomes. Anal. Biochem. 315, 208-222.
14. Stok, J. E., Huang, H., Jones, P. D., Wheelock, C. E., Morisseau, C., and Hammock, B. D. (2004) Identification, expression and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes. J. Biol. Chem. 279, 29863-29869.
15. Shan, G., Stoutamire, D. W., Wengatz, I., Gee, S. J., and Hammock, B. D. (1999) Development of an immunoassay for the pyrethroid insecticide esfenvalerate. J. Agric. Food Chem. 47, 2145-2155.
16. Fröhlick, R. F. G., Zabelinskaja-Mackova, A. A., Fechter, M. H., and Griengl, H. (2003) Novel access to chiral 1,1′-disubstituted ferrocene derivatives via double stereoselective cyanohydrin synthesis exploiting the hydroxynitrile lyases from Hevea brasiliensis. Tetrahedron: Asymmetry 14, 355-362.
17. Standard Operating Procedure for Potassium Cyanide, http:// www.dickinson.edu/departments/hazard/SOPs/SOP_KCN.html, Dickson College Health & Safety, Last significant modifications on Jan 10, 1999 (cited on June 15, 2003).
18. Shan, G., Hammer, R. P., and Ottea, J. A. (1997) Development of pyrethroid analogues for diagnosis of resistance mechanisms in the tobacco budworm, Heliothis virescens (F.). Proceedings of the Beltwide Cotton Conference, Vol. 2, pp 1018-1021, National Cotton Council of America Memphis, Tennessee.
19. Foggassy, E., Faigl, F., Soons, R., and Rakoczi, J. (1996) Process for the separation of isomeric cyclopropanecarboxylic acids. U.S. Patent 4,599,444.
20. Burt, P. E., Elliott, M., Farnham, A. W., Janes, N. F., Needham, P. H., and Pulman, D. A. (1974) The pyrethrins and related compounds. XIX Geometrical and optical isomers of 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylic acid and insecticidal esters with 5-benzyl-3-furylmethyl and 3-phenoxybenzyl alcohols. Pestic. Sci. 5, 791-799.
21. Tanaka, K., Mon, A., and Inoue, S. (1990) The cyclic dipeptide cyclo[(S)-phenylalanyl-(S)-histidyl] as a catalyst for asymmetric addition of hydrogen cyanide to aldehydes. J. Org. Chem. 55, 181-185.
22. Casas, J., Najera, C., Sansano, J. M., and Saa, J. M. (2002) BINOLAM, a recoverable chiral ligand for bifunctional enantioselective catalysis: The asymmetric synthesis of cyanohydrins. Org. Lett. 4, 2589-2592.
23. Roda, G., Riva, S., and Danieli, B. (1999) Almond oxynitrilase-catalyzed transformation of aldehydes is strongly influenced by naphthyl and alkoxy substituents. Tetrahedron: Asymmetry 10, 3939-3939.
24. Smith, P. K., Krohn, R. I., Hermanson, G. T., Mallia, A. K., Gartner, F. H., Provenzano, M. D., Fujimoto, E. K., Goeke, N. M., Olson, B. J., and Klenk, D. C. (1985) Measurement of protein using bicinchoninic acid. Anal. Biochem. 150, 76.
25. Griengl, H., Hickel, A., Johnson, D. V., Kratky, C., Schmidt, M., and Schwab, H. (1997). Enzymatic cleavage and formation of cyanohydrins: A relation of biological and synthetic relevance. Chem. Commun. 20, 1933-1940.
26. Gregory, R. J. H. (1999) Cyanohydrins in nature and laboratory: Biology, preparations and synthetic applications. Chem. Rev. 99, 3649-3682.
27. Gerrits, P. J., Zumbragel, F., and Marcus, J. (2001) Analyzing the hydrocyanation reaction: Chiral HPLC and the synthesis of racemic cyanohydrins. Tetrahedron 57, 8691-8698.
28. Trost, B. M., Belletire, J. L., Godleski, S., McDougal, P. G., Balkovec, J. M., Baldwin, J. J., Christy, M. E., Ponticello, G. S., Varga, S. L., and Springer, J. P. (1986) On the use of the O-methylmandelate ester for establishment of absolute configuration of secondary alcohols. J. Org. Chem. 51, 2370-2374.
29. Sous, A., Luna, H., Perez, H. I., Manjarrez, N., and Sanchez, R. (1998) (S)-Naproxen as a derivatizing agent to determine enantiomeric excess of cyanohydrins by HPLC. Tetrahedron Lett. 39, 8759-8762.
30. Liu, A. M. F., Somers, N. A., Kazlauskas, R. J., Brush, T. S., Zocher, F., Enzelberger, M. M., Bornscheuer, U. T., Horsman, G. P., Mezzetti, A., Schmidt-Dannert, C., and Schmid, R. D. (2001) Mapping the substrate selectivity of new hydrolases using colorimetric screening: Upases from Bacillus thermocatenulatus and Ophiostoma piliferum, esterases from Pseudomonas fluorescens and Streptomyces diastatochromogenes. Tetrahedron; Asymmetry 12, 545-556.
31. Wood, A. N. P., Fernandez-Lafuente, R., and Crowan, D. A. (1995) Purification and partial characterization of a novel thermophilic carboxylesterase with high mesophilic specific activity. Enzyme Microb. Technol. 17, 816-825.
32. Bornscheuer, U. T. (2002) Methods to increase enantioselectivity of lipases and esterases. Curr. Opin. Biotechnol. 13, 543-547.
33. Shinoi, S., Nobuyoshi, M., and Hirohiko, Y. (1992) Degradation of pyrethroid optical isomers by soil microorganisms. J. Pestic. Sci. 17, 181-189.
34. Ager, J. W. (1990) Conversion of pyrethroid isomers to more active species. U.S. Patent 5,128,497.
35. Elliott, M., Farnham, A. W., Janes, N. F., Needham, P. H., and Pullman, D. A. (1974) Synthetic insecticide with a new order activity. Nature 246, 169-170.
36. Takamatsu, Y., Kaneko, H., Abiko, J., Yoshitake, A., and Miyamoto, J. (1987) In vivo and in vitro stereoselective hydrolysis of four chiral isomers of fenvalerate. J. Pestic. Sci. 12, 397-404.
37. Butte, W., and Kemper, K. (1999) A spectrophotometric assay for pyrethroid-cleaving enzymes in human serum. Toxicol. Lett. 107, 49-53.
38. Huang, H., and Ottea, J. A. (2004) Development of pyrethroid substrates for esterases associated pyrethroid resistance in the tobacco budworm. Heliothis virescens. J. Agric. Food Chem. 52, 6539-6545.
39. Bilsback, M. M., Parker, C. M., and Wimberly, H. C. (1984) Comparative oral toxicity of technical MO 70616 and technical SD 42775 in rats. Shell Development Company Study No. WRC-RIR 357, Shell Development Company.
40. Steenkamp, L., and Brady, D. (2003) Screening of commercial enzymes for the enantioselective hydrolysis of R,S-naproxen ester. Enzyme Microb. Technol. 32, 472-477.
41. Kim, G., Choi, G., Kim, J., Lee, J., Jo, D., and Ryu, Y. (2002) Screening, production and properties of a stereospecific esterase from Pseudomonas sp. S34 with high selectivity to (S)-ketoprofen ethyl ester. J. Mol. Catal. B: Enzym. 17, 29-38.