A possible mechanism for thiourea-based toxicities: Kinetics and mechanism of decomposition of thiourea dioxides in alkaline solutions

Journal of Physical Chemistry B

Volumn 105, Issue 50, 2001, Pages 12634-12643

  Svarovsky, Serge A ^a   Simoyi, Reuben H ^a   Makarov, Sergei V ^b  

^a WEST VIRGINIA UNIVERSITY   (United States)

^b IVANOVO STATE UNIVERSITY OF CHEMISTRY AND TECHNOLOGY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ANAEROBIC CONDITIONS;

CHEMICAL BONDS; DECOMPOSITION; NEGATIVE IONS; OXIDATION; OXYGEN; TOXICITY;

ORGANIC ACIDS;

EID: 0035924824     PISSN: 10895647     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0122474     Document Type: Article

References (49)

1. Part 2 (of 10) in the series of publications dedicated to the memory of Dr. Cordelia R. Chinake, 1965-1998.
2. Drabowicz, J.; Mikolaiczyk, M. Synthesis 1978, 8, 542.
3. Lang, E.S.; Comasseto, J.V. Synth. Commun. 1988, 18, 301.
4. Ferreira, J.T.B.; De Oliveira, A.R.M.; Comasseto, J.B. Synth. Commun. 1989, 19, 239.
5. Huang, W.Y.; Zhuang, J.L. Chin. Chem. Lett. 1990, 1, 191.
6. Abdel-Hafiz, S.A. J. Appl. Polym. Sci. 1995, 58, 2005.
7. Robertson, J.G.; Sparvero, L.J.; Villafranca, J.J. Protein Sci. 1992, 1, 1298.
8. Rabai, G.; Orban M.; Epstein, I.R. Acc. Chem. Res. 1990, 23, 258.
9. Jonnalagadda, S.B.; Chinake, C.R.; Simoyi, R.H. J. Phys. Chem. 1996, 100, 13521.
10. Simoyi, R.H.; Epstein, I.R.; Kustin, K. J. Phys. Chem. 1994, 98, 551.
11. Miller, A.E.; Bischoff; J.J.; Pae, K. Chem. Res. Toxicol. 1988, 1, 169.
12. Maryanoff, R.C.; Stanzione, R.C.; Plampin, J.N.; Mills, J.E. J. Org. Chem. 1986, 51, 1882.
13. Kim, K.; Lin, Y.-T.; Mosher, H.S. Tetrahedron Lett. 1988, 29, 3183.
14. Aitken, D.J.; Guillaume, D.; Hussen, H.-P. Tetrahedron Lett. 1993, 49, 6375.
15. Olah, G.A.; Burrichter, A.; Rasul, G.; Hachoumy, M.; Surya Prakash, G.K. J. Am. Chem. Soc. 1997, 119, 12929.
16. Poulsen, L.L.; Hyslop, R.M.; Ziegler, D.M. Arch. Biochem. Biophys. 1979, 198, 78.
17. Simoyi, R.H. J. Phys. Chem. 1986, 90, 2802.
18. Doona, C.J.; Blittersdorf, R.; Schneider, F.W. J. Phys. Chem. 1993, 97, 7258.
19. Martincigh, B.S.; Simoyi, R.H. Phys. Rev. E 1995, 52, 1606.
20. Mitchell, S. Biological Interactions of Sulfur Compounds; Taylor and Francis: London, 1996.
21. Ziegler, D.M. Metabolic Oxygenation of Organic Nitrogen and Sulfur Compounds in Drug Metabolism and Drug Toxicity; Mitchell, J.R., Homing, M.G., Eds.; Raven Press: New York, 1984; pp 33-53.
22. Freedman, R.B. FEBS Lett. 1997, 97, 201.
23. Ziegler, D.M. Drug Metab. Rev. 1988, 19, 1.
24. Ziegler, D.M. Annu. Rev. Pharmacol. Toxicol. 1993, 33, 179.
25. Darkwa, J.; Mundoma, C.; Simoyi, R.H. J. Chem. Soc., Faraday Trans. 1988, 94, 1971.
26. Ziegler, D.M. Microsomal Flavin-Containing Monooxygenase: Oxygenation of Nucleophilic Nitrogen and Sulfur Compounds in Enzymatic Basis of Detoxification; Jacoby, W.D., Ed.; Academic Press: New York, 1980; pp 210-227.
27. Neal, R.A. Microsomal Metabolism of Thiono-Sulfur Compounds: Mechanisms and Toxicological Significance in Reviews in Biochemical Toxicology; Hotgson, E., Bend, J.R., Philpot, R.M., Eds.; Elsevier: New York, 1980; pp 131-171.
28. Hollinger, M.A.; Gift, S.N.; Hwang, F. Drug Metab. Dispos. 1976, 4, 119.
29. Ishii, A.; Komiya, K.; Nakayama, J. J. Am. Chem. Soc. 1996, 118, 12836.
30. Lepentsiotis, V.; van Eldik, R.; Stulov, D.M.; Makarov, S.V. J. Chem. Soc., Dalton Trans. 1998, 17, 2915.
31. McGill, J.E.; Lindstrom, F. Anal. Chem. 1977, 49, 26.
32. Creutz, C.; Sutin, N. Inorg. Chem. 1974, 13, 2041.
33. Curtis, W.E.; Muldrow, M.E.; Parker, N.B.; Barkley, R.; Linas, S.L.; Repine, J.E. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 3422.
34. Lekhimena, K.; Makarov, S.V.; Budanov, V.V. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Technol. 1991, 34, 122.
35. McKenna, C.E.; Gutheil, W.G.; Song, W. Biochim. Biophys. Acta 1991, 1075, 109.
36. Linke, W.F., Ed. Solubilities of Inorganic and Metal-Organic Compounds; American Chemical Society: Washington, DC 1965; vol. 2, p 1914.
37. Svarovsky, S.A.; Simoyi, R.H.; Makarov, S.V. J. Chem. Soc., Faraday Trans. 2000, 511.
38. Duke, F.R.; Haas, T.W. J. Phys. Chem. 1961, 65, 304.
39. Budanov, V.V.; Makarov, S.V. Chemistry of Sulfur-Containing Reductants; Khimia: Moscow, 1994; p 140 (in Russian).
40. Blankenhorn, G.; Moore, E.G. J. Am. Chem. Soc. 1980, 102, 1092.
41. Fischer, M.; Warneck, P. J. Phys. Chem. 1996, 100, 15111.
42. Rowley, D.A.; Halliwell, B. FEBS Lett. 1982, 138, 33.
43. Yermakov, A.N.; Poskrebyshev, G.A.; Purmal, A.P. Prog. React. Kinet. 1997, 22, 141.
44. Kim, Y.H.; Yon, C.H.; Kim, H.J. Chem. Lett. 1984, 309.
45. Kelner, M.J.; Bagnell, R.; Welch, K.J. J. Biol. Chem. 1990, 265, 1306.
46. Calderwood, T.S.; Johlman, C.L.; Roberts, J.L.; Wilkins, C.L.; Sawyer, D.T. J. Am. Chem. Soc. 1984, 106, 4683.
47. Makarov, S.V.; Mundoma, C.; Svarovsky, S.A.; Shi, X.; Gannett, P.M.; Simoyi, R.H. Arch. Biochem. Biophys. 1999, 367(2), 289.
48. Beehler, C.J.; Ely, M.E.; Rutledge, S.; Simchuk, M.L.; Reiss, O.K.; Shanley, P.F.; Repine, J.E. J. Lab. Clin. Med. 1994, 123, 73.
49. Mundoma, C.; Shi, X.; Simoyi, R.H. J. Biol. Chem., submitted.