Separation and toxicity of enantiomers of organophosphorus insecticide leptophos

Ecotoxicology and Environmental Safety

Volumn 55, Issue 2, 2003, Pages 236-242

  Yen, Jui Hung ^a   Tsai, Chia Chun ^a   Wang, Yei Shung ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Enantioseparation; HPLC; Leptophos; Whelk O1 column

Indexed keywords

ACETYLCHOLINESTERASE; CHOLINESTERASE; INSECTICIDE; LEPTOPHOS;

INSECTICIDE; ORGANOPHOSPHATE; SEPARATION; TOXICITY;

ANIMAL EXPERIMENT; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DAPHNIA; ENANTIOMER; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; NEUROTOXICITY; NONHUMAN; RACEMIC MIXTURE; SEPARATION TECHNIQUE; TOXICITY TESTING;

CLADOCERA; DAPHNIA; EQUUS CABALLUS; HEXAPODA; MAMMALIA;

EID: 0038368083     PISSN: 01476513     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0147-6513(02)00066-0     Document Type: Article

References (19)

1. Allahyari R., Hollingshaus J.G., Lapp R.L., Timm E., Jacobson R.A., Fukuto T.R. Resolution, absolute configuration, and acute and delayed neurotoxicity of the chiral isomers of O-aryl-O-methyl phenylphosphonothioate analogues related to leptophos. J. Agric. Food Chem. 28:1980;594-599.
2. Baker J.K., Clark A.M., Hufford C.D. High performance liquid chromatographic separation of the enantiomers and diastereomers of primaquine and its metabolites. J. Liq. Chromatogr. 9:1986;493-509.
3. Benschop H.P., Konings C.A.G., van Genderen J., de Jong L.P.A. Isolation, anticholinesterase properties, and acute toxicity in mice of the four stereoisomers of the nerve agent soman. Toxicol. Appl. Pharmacol. 72:1984;61-74.
4. Doyle T.D., Adams W.M., Fry F.S., Wainer I.W. The application of HPLC chiral stationary phases to stereochemical problems of pharmaceutical interest. a general method for the resolution of enantiomeric amine as β-naphthylcarbamate derivaties J. Liq. Chromatogr. 9:1986;455-471.
5. Duff K.J., Gray H.L., Gray R.J., Bahler C.C. Chiral stationary phases in concert with homologous chiral mobile phase additives. push/pull model Chirality. 5:1993;201-206.
6. Gal J. Determination of the enantiomeric composition of chiral aminoalcohols using chiral derivatization and reverse phase liquid chromoatography. J. Liq. Chromatogr. 9:1986;673-681.
7. Gao R.Y., Yang G.S., Yang H.Z., Chen Z.Y., Wang Q.S. Enantioseparation of fourteen O-ethyl O-phenyl N-isopropyl phosphoroamidothioates by high-performance liquid chromatography on a chiral stationary phase. J. Chromatogr. A. 763:1997;125-128.
8. Grieb S.J., Matlin S.A., Philips J.G., Belenguer A.M., Ritchie H.J. Chiral HPLC with carbohydrate carbamates. influence of support structure on enantioselectivity Chirality. 6:1994;129-134.
9. Hamilton M.A., Russo R.C., Thurston R.V. Trimmed Spearman-Karber method for estimating median lethal concentrations in toxicity bioassays. Environ. Sci. Technol. 11:1977;714-719.
10. Kientz C.E., Langenberg J.P., De Jong G.J., Brinkman U.A.T. Microcolumn liquid chromatography of the enantiomers of organophosphorus pesticides with thermionic and UV detection. J. High Resolut. Chromatogr. 14:1991;460-464.
11. Leader H., Casida J.E. Resolution and biological activity of the chiral isomers of O-(4-bromo-2-chlorophenyl) O-ethyl S-propyl phosphorothioate. J. Agric. Food Chem. 30:1982;546-551.
12. O'Brien, R.D., 1967. Insecticides Action and Metabolism. Academic Press, New York and London, pp. 282-287.
13. Okamoto Y., Hatada K. Resolution of enantiomers by HPLC on optically active poly(triphenylmethyl methacrylate). J. Liq. Chromatogr. 9:1986;369-384.
14. Okamoto Y., Kaida Y. Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary phase. J. Chromatogr. A. 666:1994;403-419.
15. Richardson R.J., Moore T.B., Kayyali U.S., Randall J.C. Chlorpyrifos. assessment of potential for delayed neurotoxicity by repeated dosing in adult hens with monitoring of brain acetylcholinesterase, brain and lymphocyte neurotoxic esterase, and plasma butyrylcholinesterase activities Fundam. Appl. Toxicol. 21:1993;89-96. (doi:10.1006/faat.1993.1076).
16. Welch C.J., Szczerba T., Perrin S.R. Some recent high-performance liquid chromatography separations of the enantiomers of pharmaceuticals and other compounds using the Whelk-O1 chiral stationary phase. J. Chromatogr. A. 758:1997;93-98.
17. Williams M.G., Zhong W.Z. Stereospecific determination of HIV aspartyl protease inhibitor, PNU-103017, in rat, dog and human plasma using a Pirkle-concept high-performance liquid chromatographic column. J. Chromatogr. B. 694:1997;169-177.
18. Yen J.-H., Hsei K.-C., Wang Y.-S. The separation and toxicity of enantiomers of the organophosphorus insecticide phenthoate. Taiwan J. Agric. Chem. Food Sci. 40(1):2002;62-69.
19. Zhang T., Francotte E. Chromatographic properties of composite chiral stationary phases based on cellulose derivatives. Chirality. 7:1995;425-433.