Inhibition of acetylcholinesterase by metabolites of copper pyrithione (CuPT) and its possible involvement in vertebral deformity of a CuPT-exposed marine teleostean fish

Comparative Biochemistry and Physiology - C Toxicology and Pharmacology

Volumn 149, Issue 4, 2009, Pages 624-630

  Mochida, Kazuhiko ^a   Ito, Katsutoshi ^a   Harino, Hiroya ^b   Tanaka, Hiroyuki ^a   Onduka, Toshimitsu ^a   Kakuno, Akira ^a   Fujii, Kazunori ^a  

^a FISHERIES RESEARCH AGENCY   (Japan)

^b OSAKA CITY INSTITUTE OF PUBLIC HEALTH AND ENVIRONMENTAL SCIENCES   (Japan)

Author keywords

2,2 dipyridyldisulfide; 2,2 dithiobispyridine N oxide; Antifouling biocide; Fundulus heteroclitus; In vitro metabolism; Liver microsomes; Thin layer chromatography

Indexed keywords

2,2' DIPYRIDYLDISULFIDE; 2,2' DITHIOBISPYRIDINE N OXIDE; ACETYLCHOLINESTERASE; ANTIFOULING AGENT; BIOCIDE; COPPER PYRITHIONE; PYRITHIONE; PYRITHIONE ZINC; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; ENZYME INHIBITION; FEMALE; LIVER MICROSOME; MALE; MUMMICHOG; NONHUMAN; PRIORITY JOURNAL; TELEOST; THIN LAYER CHROMATOGRAPHY; VERTEBRA MALFORMATION;

ANIMALIA; FUNDULUS HETEROCLITUS; TELEOST FISH;

EID: 63449142607     PISSN: 15320456     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpc.2009.01.003     Document Type: Article

References (38)

1. Adams M.D., Wedig J.H., Jordan R.L., Smith L.W., Henderson R., and Borzelleca J.F. Urinary excretion and metabolism of salts of 2-pyridinethiol-1-oxide following intravenous administration to female Yorkshire pigs. Toxicol. Appl. Pharmacol. 36 (1976) 523-531
2. Anderson C., Bartlett S.J., Gansner J.M., Wilson D., He L., Gitlin J.D., Kelsh R.N., and Dowden J. Chemical genetics suggests a critical role for lysyl oxidase in zebrafish notochord morphogenesis. Mol. Biosyst. 3 (2007) 51-59
3. Ansari B.A., and Kumar K. Malathion toxicity: embryotoxicity and survival of hatching of zebrafish (Brachydanio rerio). Acta Hydrochim. Hydrobiol. 14 (1986) 567-570
4. Bartolucci C., Perola E., Pilger C., Fels G., and Lamba D. Three-dimensional structure of a complex of galanthamine (Nivalin) with acetylcholinesterase from Torpedo californica: implications for the design of new anti-Alzheimer drugs. Proteins 42 (2001) 182-191
5. Bellas J., Granmo Å., and Beiras R. Embryotoxicity of the antifouling biocide zinc pyrithione to sea urchin (Paracentrotus lividus) and mussel (Mytilus edulis). Mar. Pollut. Bull. 50 (2005) 1382-1385
6. Cook L.W., Paradise C.J., and Lom B. The pesticide malathion reduces survival and growth in developing zebrafish. Environ. Toxicol. Chem. 24 (2005) 1745-1750
7. Couch J.A., Winstead J.T., and Goodman L.R. Kepone-induced scoliosis and its histological consequences in fish. Science 197 (1977) 585-587
8. Doose C.A., Szaleniec M., Behrend P., Müller A., and Jastorff B. Chromatographic behavior of pyrithiones. J. Chromatogr. 1052 (2004) 103-110
9. Ellmann G.L., Courtney K.D., Andres Jr. V., and Feather-stone R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7 (1961) 88-95
10. Eriksson Wiklund A.K., Börjesson T., and Wiklund S.J. Avoidance response of sediment living amphopods to zinc pyrithone as a measure of sediment toxicity. Mar. Pollut. Bull. 52 (2006) 96-99
11. Fent K. Ecotoxicology of organotin compounds. Crit. Rev. Toxicol. 26 (1996) 1-117
12. Fulton B., and Benfield P. Galanthamine. Drugs Aging 9 (1996) 60-65
13. Gibson W.B., Jeffcoat A.R., Turan T.S., Wendt R.H., Hughes P.F., and Twine M.E. Zinc pyridinethione: serum metabolites of zinc pyridinethione in rabbits, rats, monkeys, and dogs after oral dosing. Toxicol. Appl. Pharmacol. 62 (1982) 237-250
14. Goka K. Embryotoxicity of zinc pyrithione, an antidandruff chemical, in fish. Environ. Res. Sec. A 81 (1999) 81-83
15. Guo J.-X., Wu J.J.-Q., Wright J.B., and Lushington G.H. Mechanistic insight into acetylcholinesterase inhibition and acute toxicity of organophosphorus compounds: a molecular modeling study. Chem. Res. Toxicol. 19 (2006) 209-216
16. Harino H., Kitano M., Mori Y., Mochida K., Kakuno A., and Arima S. Degradation of antifouling booster biocides in water. J. Mar. Biol. Assoc. UK 85 (2005) 33-38
17. Hoffman D.J., and Sileo L. Neurotoxic and teratogenic effects of an organophosphorus insecticide (phenyl phosphonothioic acid-0-ethyl-0-[4-nitrophenyl] ester) on mallard development. Toxicol. Appl. Pharmacol. 73 (1984) 284-294
18. Jeffcoat A.R., Gibson W.B., Rodriguez P.A., Turan T.S., Hughes P.F., and Twine M.E. Zinc pyridinethione: urinary metabolites of zinc pyridinethione in rabbits, rats, monkeys, and dogs after oral dosing. Toxicol. Appl. Pharmacol. 56 (1980) 141-154
19. Karlsson J., and Eklund B. New biocide-free anti-fouling paints are toxic. Mar. Pollut. Bull. 49 (2004) 456-464
20. Knaak J.B., Dary C.C., Power F., Thompson C.B., and Blancato J.N. Physicochemical and biological data for the development of predictive organophosphorus pesticide QSARs and PBPK/PD models for human risk assessment. Crit. Rev. Toxicol. 34 (2004) 143-207
21. Kumar K., and Ansari B.A. Malathion toxicity: skeletal deformities in zebrafish (Brachydanio rerio, Cyprinidae). Pestic. Sci. 15 (1984) 107-111
22. Kobayashi N., and Okamura H. Effects of new antifouling compounds on the development of sea urchin. Mar. Pollut. Bull. 44 (2002) 748-751
23. Lien N.T.H., Adriaens D., and Janssen C.R. Morphological abnormalities in African cat fish (Clarias gariepinus) larvae exposed to malathion. Chemosphere 35 (1997) 1475-1486
24. Maraldo K., and Dahllöf I. Indirect estimation of degradation time for zinc pyrithione and copper pyrithione in seawater. Mar. Pollut. Bull. 48 (2004) 894-901
25. Meiniel R. Neuromuscular blocking agents and axial teratogenesis in the avian embryo. Can axial morphogenetic disorders be explained by pharmacological action upon muscle tissue?. Teratology 23 (1981) 259-271
26. Meneely G.A., and Wyttenbach C.R. Effects of the organophosphate insecticides diazinon and parathion on bobwhite quail embryos: skeletal defects and acetylcholineserase activity. J. Exp. Zool. 252 (1989) 60-70
27. Mochida K., Ito K., Harino H., Kakuno A., and Fujii K. Acute toxicity of pyrithione antifouling biocides and joint toxicity with copper to red sea bream (Pagrus major) and toy shrimp (Heptacarpus futilirostris). Environ. Toxicol. Chem. 25 (2006) 3058-3064
28. Mochida K., Ito K., Harino H., Onduka T., Kakuno A., and Fujii K. Early life-stage toxicity test for copper pyrithione and induction of skeletal anomaly in a teleost, the mummichog (Fundulus heteroclitus). Environ. Toxicol. Chem. 27 (2008) 367-374
29. Okamura H., and Mieno H. Present status of antifouling systems in Japan: tributyltin substitutes in Japan. In: Konstantinou I.K. (Ed). The Handbook of Environmental Chemistry, Vol. 5: Antifouling Paint Biocides (2006), Springer-Verlag, Germany 201-212
30. Petersen D.G., Dahllöf I., and Nielsen L.P. Effects of zinc pyrithione and copper pyrithione on microbial community function and structure in sediments. Environ. Toxicol. Chem. 23 (2004) 921-928
31. Pope C.N. Organophosphorus pesticides: do they all have the same mechanism of toxicity?. J. Toxicol. Environ. Health B 2 (1999) 161-181
32. Sakkas V.A., Shibata K., Yamaguchi Y., Sugaswa S., and Albanis T. Aqueous phototransformation of zinc pyrithione degradation kinetics and byproduct identification by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J. Chromatogr. A. 1144 (2007) 175-182
33. Sánchez-Bayo F., and Goka K. Unexpected effects of zinc pyrithione and imidacloprid on Japanese medaka fish (Oryzias latipes). Aquat. Toxicol. 74 (2005) 285-293
34. Seymour M.D., and Bailey D.L. Thin-layer chromatography of pyrithiones. J. Chromatogr. 206 (1981) 301-310
35. Shimizu A. Reproductive cycles in a reared strain of the mummichog, a daily spawner. J. Fish Biol. 51 (1997) 724-737
36. Turley P.A., Fenn R.J., and Ritter J.C. Pyrithiones as antifoulants: environmental chemistry and preliminary risk assessment. Biofouling 15 (2000) 175-182
37. Turley P.A., Fenn R.J., and Callow M.E. Exposure assessment for pyrithiones as antifoulants: environmental fate and loss of toxicity. Proc. Int. Symp. Antifoulant and Marine Environment (InSAFE) (2004), National Maritime Research Institute, Japan 204-212 January
38. Turley P.A., Fenn R.J., Ritter J.C., and Callow M.E. Pyrithiones as antifoulants: environmental fate and loss of toxicity. Biofouling 21 (2005) 31-40