Cartap Hydrolysis Relative to Its Action at the Insect Nicotinic Channel

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 1, 2004, Pages 95-98

  Lee, Seog Jong ^a   Caboni, Pierluigi ^a   Tomizawa, Motohiro ^a   Casida, John E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Bensultap; Cartap; Ion channel blocker; Nereistoxin; Nicotinic acetylcholine receptor

Indexed keywords

BENSULTAP; CARTAP; INSECTICIDE; MECAMYLAMINE; NEREISTOXIN; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR BLOCKING AGENT; PIPERIDINE DERIVATIVE; THIOCARBAMIC ACID DERIVATIVE; TRITIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; HONEYBEE; HYDROLYSIS; INSECT; INSECTICIDAL ACTIVITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PH;

ANIMALS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; INSECTS; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; THIOCARBAMATES; TOLUENE;

APIS MELLIFERA; INSECTA; TRITIUM;

EID: 0347355023     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0306340     Document Type: Article

References (22)

1. Kagabu, S. Chloronicotinyl insecticides - discovery, application and future perspective. Rev. Toxicol. 1997, 1, 75-129.
2. Tomizawa, M.; Casida, J. E. Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors. Annu. Rev. Entomol. 2003, 48, 339-364.
3. Casida, J. E.; Quistad, G. B. Golden age of insecticide research: past, present, or future? Annu. Rev. Entomol. 1998, 43, 1-16.
4. Konishi, K. New insecticidally active derivatives of nereistoxin. Agric. Biol. Chem. 1968, 32, 678-679.
5. Sakai, M. Nereistoxin and cartap; their mode of action as insecticides. Rev. Plant Prot. Res. 1969, 2, 17-28.
6. Konishi, K. Nereistoxin and its relatives. In Proceedings of the Second International IUPAC Congress of Pesticide Chemistry, Vol. I: Insecticides; Tahori, A. S., Ed.; Gordon and Breach Science Publishers: London, U.K., 1972; pp 179-189.
7. Richter, R.; Otto, D.; Mengs, H.-J. Insecticide compounds, acting on the acetylcholine receptor of the insect nervous system. In Chemistry of Plant Protection 2: Degradation of Pesticides, Desiccation, and Defoliation, ACh-Receptors as Targets; Haug, G., Hoffmann, H., Eds.; Springer-Verlag: Berlin, Germany, 1989; pp 157-195.
8. Tomlin, C. D. S., Ed. The Pesticide Manual, 12th ed.; British Crop Protection Council: Surrey, U.K., 2000; 1250 pp.
9. Okaichi, T.; Hashimoto, Y. The structure of nereistoxin. Agric. Biol. Chem. 1962, 26, 224-227.
10. Sakai, M. Studies on the insecticidal action of nereistoxin, 4-N,N-(dimethylamino)-1,3-dithiolane. V. Blocking action on the cockroach ganglion. Botyu-Kagaku 1967, 32, 21-33.
11. Deguchi, T.; Narahashi, T.; Haas, H. G. Mode of action of nereistoxin on the neuromuscular transmission in the frog. Pestic. Biochem. Physiol. 1971, 1, 196-204.
12. Nagata, K.; Iwanaga, Y.; Shono, T.; Narahashi, T. Modulation of the neuronal nicotinic acetylcholine receptor channel by imidacloprid and cartap. Pestic. Biochem. Physiol. 1997, 59, 119-128.
13. Sakai, M.; Sato, Y. Metabolic conversion of the nereistoxin-related compounds into nereistoxin as a factor of their insecticidal action. In Proceedings of the Second International IUPAC Congress of Pesticide Chemistry, Vol. I: Insecticides; Tahori, A. S., Ed.; Gordon and Breach Science Publishers: London, U.K., 1972; pp 455-467.
14. Eldefrawi, A. T.; Bakry, N. M.; Eldefrawi, M. E.; Tsai, M.-C.; Albuquerque, E. X. Nereistoxin interaction with the acetylcholine receptor-ionic channel complex. Mol. Pharmacol. 1980, 17, 172-179.
15. Sattelle, D. B.; Harrow, I. D.; David, J. A.; Pelhate, M.; Callec, J. J. ; Gepner, J. I.; Hall, L. M. Nereistoxin: actions on a CNS acetylcholine receptor/ion channel in the cockroach Periplaneta americana. J. Exp. Biol. 1985, 118, 37-52.
16. Sherby, S. M.; Eldefrawi, A. T.; David, J. A.; Sattelle, D. B.; Eldefrawi, M. E. Interactions of charatoxins and nereistoxin with the nicotinic acetylcholine receptors of insect CNS and Torpedo electric organ. Arch. Insect Biochem. Physiol. 1986, 3, 431-445.
17. Xie, Y.; Lane, W. V.; Loring, R. H. Nereistoxin: a naturally occurring toxin with redox effects on neuronal nicotinic acetylcholine receptors in chick retina. J. Pharmacol. Exp. Ther. 1993, 264, 689-694.
18. Tomizawa, M.; Otsuka, H.; Miyamoto, T.; Eldefrawi, M. E.; Yamamoto, I. Pharmacological characteristics of insect nicotinic acetylcholine receptor with its ion channel and the comparison of the effect of nicotinoids and neonicotinoids. J. Pestic. Sci. 1995, 20, 57-64.
19. Lee, S.-J.; Tomizawa, M.; Casida, J. E. Nereistoxin and cartap neurotoxicity attributable to direct block of the insect nicotinic receptor/channel. J. Agric. Food Chem. 2003, 51, 2646-2652.
20. Asahi, Y.; Yoshida, T. Kinetics of hydrolyses of insecticides: cartap hydrochloride and nereistoxin. Chem. Pharm. Bull. 1977, 25, 2211-2216.
21. Riddles, P. W.; Blakeley, R. L.; Zerner, B. Reassessment of Ellman's reagent. Methods Enzymol. 1983, 91, 49-60.
22. Roberts, T. R., Hutson, D. H., Eds. Cartap. In Metabolic Pathways of Agrochemicals, Part 2: Insecticides and Fungicides; The Royal Society of Chemistry: Cambridge, U.K., 1999; pp 129-133.