S-oxygenation of thiocarbamides V: Oxidation of tetramethylthiourea by chlorite in slightly acidic media

Journal of Physical Chemistry A

Volumn 118, Issue 31, 2014, Pages 5903-5914

  Chigwada, Tabitha ^a,c   Mbiya, Wilbes ^a   Chipiso, Kudzanai ^a   Simoyi, Reuben H ^a,b  

^a PORTLAND STATE UNIVERSITY   (United States)

^b UNIVERSITY OF KWAZULU NATAL   (South Africa)

^c WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMERS; METABOLISM; OXIDANTS; THIOUREAS; UREA;

CHLORINE DIOXIDES; CHLOROUS ACID; LOW MOLECULAR WEIGHT; QUANTITATIVE FORMATION; REACTION MECHANISM; STERIC GROUPS; SULFONIC ACID; TETRAMETHYLTHIOUREA;

OXIDATION;

CHLORIDE; CHLORINE DERIVATIVE; CHLORINE DIOXIDE; CHLORITE; DRUG COMBINATION; FREE RADICAL; ION; OIL; OXIDE; P & S LIQUID; PHENOL DERIVATIVE; TETRAMETHYLTHIOUREA; THIOUREA; WATER;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG COMBINATION; KINETICS; OXIDATION REDUCTION REACTION; SPECTROSCOPY; ULTRAVIOLET RADIATION;

CATALYSIS; CHLORIDES; CHLORINE COMPOUNDS; DRUG COMBINATIONS; FREE RADICALS; IONS; KINETICS; MOLECULAR STRUCTURE; OILS; OXIDATION-REDUCTION; OXIDES; PHENOLS; SPECTRUM ANALYSIS; THIOUREA; ULTRAVIOLET RAYS; WATER;

EID: 84905728425     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp504018k     Document Type: Article

References (42)

1. Guo, W. X.; Poulsen, L. L.; Ziegler, D. M. Use of Thiocarbamides as Selective Substrate Probes for Isoforms of Flavin-Containing Monooxygenases Biochem. Pharmacol. 1992, 44, 2029-2037
2. Chen, K.; Tan, Z.; He, M.; Li, J.; Tang, S.; Hewlett, I.; Yu, F.; Jin, Y.; Yang, M. Structure-Activity Relationships (SAR) Research of Thiourea Derivatives as Dual Inhibitors Targeting Both HIV-1 Capsid and Human Cyclophilin A Chem. Biol. Drug Des. 2010, 76, 25-33
3. Kim, S. G.; Kim, H. J.; Yang, C. H. Thioureas Differentially Induce Rat Hepatic Microsomal Epoxide Hydrolase and RGSTA2 Irrespective of Their Oxygen Radical Scavenging Effect: Effects on Toxicant-Induced Liver Injury Chem.-Biol. Interact. 1999, 117, 117-134 (Pubitemid 29076378)
4. Li, Z. G.; Chen, K. X.; Xie, H. Y.; Gao, J. R. Quantitative Structure-Activity Relationship Analysis of Some Thiourea Derivatives with Activities against HIV-1 (IIIB) QSAR Comb. Sci. 2009, 28, 89-97
5. McCord, J. M.; Fridovich, I. The Biology and Pathology of Oxygen Radicals Ann. Intern. Med. 1978, 89, 122-127 (Pubitemid 8365451)
6. Halliwell, B.; Gutteridge, J. M. Role of Free Radicals and Catalytic Metal Ions in Human Disease: An Overview Methods Enzymol. 1990, 186, 1-85 (Pubitemid 20279941)
7. Bruck, R.; Aeed, H.; Shirin, H.; Matas, Z.; Zaidel, L.; Avni, Y.; Halpern, Z. The Hydroxyl Radical Scavengers Dimethylsulfoxide and Dimethylthiourea Protect Rats Against Thioacetamide-Induced Fulminant Hepatic Failure J. Hepatol. 1999, 31, 27-38 (Pubitemid 29287606)
8. Pieper, G. M.; Siebeneich, W.; Roza, A. M.; Jordan, M.; Adams, M. B. Chronic Treatment in Vivo with Dimethylthiourea, a Hydroxyl Radical Scavenger, Prevents Diabetes-Induced Endothelial Dysfunction J. Cardiovasc. Pharmacol. 1996, 28, 741-745 (Pubitemid 26412484)
9. Bolli, R. Oxygen-Derived Free Radicals and Postischemic Myocardial Dysfunction ("Stunned Myocardium") J. Am. Coll. Cardiol. 1988, 12, 239-249
10. Kinugawa, S.; Tsutsui, H.; Hayashidani, S.; Ide, T.; Suematsu, N.; Satoh, S.; Utsumi, H.; Takeshita, A. Treatment with Dimethylthiourea Prevents Left Ventricular Remodeling and Failure after Experimental Myocardial Infarction in Mice: Role of Oxidative Stress Circ. Res. 2000, 87, 392-398
11. Pattanaik, U.; Prasad, K. Reactive Oxygen Species and Endotoxic Shock: Effect of Dimethylthiourea J. Cardiovasc. Pharmacol. Ther. 2001, 6, 273-285 (Pubitemid 34296590)
12. Portz, S. J.; Lesnefsky, E. J.; VanBenthuysen, K. M.; Repine, J. E.; Parker, N. B.; McMurtry, I. F.; Horwitz, L. D. Dimethylthiourea, but Not Dimethylsulfoxide, Reduces Canine Myocardial Infarct Size Free Radical Biol. Med. 1989, 7, 53-58 (Pubitemid 19165155)
13. Prasad, K.; Debnath, D.; Kalra, J.; Lee, P. Effects of Dimethylthiourea on the Cardiac Function and Oxyradical Status in Ischemia-Reperfusion Injury Ann. N.Y. Acad. Sci. 1994, 723, 375-379 (Pubitemid 24228169)
14. Kingma, J. G., Jr.; Yellon, D. M. Inability of Dimethylthiourea To Limit Tissue Necrosis during Acute Myocardial Infarction in Rabbits Free Radical Biol. Med. 1992, 12, 263-270
15. Fox, R. B. Prevention of Granulocyte-Mediated Oxidant Lung Injury in Rats by a Hydroxyl Radical Scavenger, Dimethylthiourea J. Clin. Invest. 1984, 74, 1456-1464 (Pubitemid 15200240)
16. Matsumoto, K.; Aizawa, H.; Inoue, H.; Koto, H.; Fukuyama, S.; Hara, N. Effect of Dimethylthiourea, a Hydroxyl Radical Scavenger, on Cigarette Smoke-Induced Bronchoconstriction in Guinea Pigs Eur. J. Pharmacol. 2000, 403, 157-161
17. Yuan, T.; Luo, B. L.; Wei, T. H.; Zhang, L.; He, B. M.; Niu, R. C. Salubrinal Protects against Cigarette Smoke Extract-Induced HBEpC Apoptosis Likely via Regulating the Activity of PERK-EIF2alpha Signaling Pathway Arch. Med. Res. 2012, 43, 522-529
18. Curtis, W. E.; Muldrow, M. E.; Parker, N. B.; Barkley, R.; Linas, S. L.; Repine, J. E. N, N '-Dimethylthiourea Dioxide Formation from N, N '-Dimethylthiourea Reflects Hydrogen Peroxide Concentrations in Simple Biological Systems Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 3422-3425
19. Teramoto, S.; Kaneda, M.; Aoyama, H.; Shirasu, Y. Correlation between the Molecular Structure of N -Alkylureas and N -Alkylthioureas and Their Teratogenic Properties Teratology 1981, 23, 335-342 (Pubitemid 11064700)
20. Chigwada, T. R.; Chikwana, E.; Simoyi, R. H. S-Oxygenation of Thiocarbamides I: Oxidation of Phenylthiourea by Chlorite in Acidic Media J. Phys. Chem. A 2005, 109, 1081-1093 (Pubitemid 40296745)
21. Chigwada, T. R.; Simoyi, R. H. S-Oxygenation of Thiocarbamides II: Oxidation of Trimethylthiourea by Chlorite and Chlorine Dioxide J. Phys. Chem. A 2005, 109, 1094-1104 (Pubitemid 40296746)
22. Chigwada, T. R.; Chikwana, E.; Ruwona, T.; Olagunju, O.; Simoyi, R. H. S-Oxygenation of Thiocarbamides. 3. Nonlinear Kinetics in the Oxidation of Trimethylthiourea by Acidic Bromate J. Phys. Chem. A 2007, 111, 11552-11561 (Pubitemid 350197597)
23. Ajibola, R. O.; Simoyi, R. H. S-Oxygenation of Thiocarbamides IV: Kinetics of Oxidation of Tetramethylthiourea by Aqueous Bromine and Acidic Bromate J. Phys. Chem. A 2011, 115, 2735-2744
24. Simoyi, R. H. Explosion with Sodium Chlorite Chem. Eng. News 1993, 71, 4
25. Kern, D.; Kim, C.-H. The Chlorite-Iodide Reaction J. Am. Chem. Soc. 1965, 87, 5309-5313
26. Darkwa, J.; Olojo, R.; Chikwana, E.; Simoyi, R. H. Antioxidant Chemistry: Oxidation of l -Cysteine and Its Metabolites by Chlorite and Chlorine Dioxide J. Phys. Chem. A 2004, 108, 5576-5587
27. Peintler, G.; Nagypal, I.; Epstein, I. R. Kinetics and Mechanism of the Reaction between Chlorite Ion and Hypochlorous Acid J. Phys. Chem. 1990, 94, 2954-2960
28. Doona, C. J.; Stanbury, D. M. Adventitious Catalysis in Oscillatory Reductions by Thiourea J. Phys. Chem. 1994, 98, 12630-12634
29. Hu, Z.; Du, H.; Man, W. L.; Leung, C. F.; Liang, H.; Lau, T. C. Catalytic Reactions of Chlorite with a Polypyridylruthenium(II) Complex: Disproportionation, Chlorine Dioxide Formation and Alcohol Oxidation Chem. Commun. 2012, 48, 1102-1104
30. Ishii, A.; Komiya, K.; Nakayama, J. Synthesis and Characterization of Thiophenetriptycene-8-Sulfenic Acid Phosphorus, Sulfur Silicon Relat. Elem. 1997, 120, 323-324
31. Ishii, A.; Komiya, K.; Nakayama, J. Synthesis of a Stable Sulfenic Acid by Oxidation of a Sterically Hindered Thiol (Thiophenetriptycene-8-Thiol) and Its Characterization J. Am. Chem. Soc. 1996, 118, 12836-12837 (Pubitemid 27042014)
32. Svarovsky, S. A.; Simoyi, R. H.; Makarov, S. V. A Possible Mechanism for Thiourea-Based Toxicities: Kinetics and Mechanism of Decomposition of Thiourea Dioxides in Alkaline Solutions J. Phys. Chem. B 2001, 105, 12634-12643 (Pubitemid 35338319)
33. Ojo, J. F.; Petersen, J. L.; Otoikhian, A.; Simoyi, R. H. Organosulfur Oxoacids. Part 1. Synthesis, Structure, and Reactivity of Dimethylaminoiminomethanesulfinic Acid (DMAIMSA) Can. J. Chem. 2006, 84, 825-830 (Pubitemid 44213468)
34. Song, J. S.; Kim, E. H.; Kang, S. K.; Yun, S. S.; Suh, I.-H.; Choi, S. S.; Lee, S. X-ray Crystal Structure for Thiourea Dioxide Bull. Korean Chem. Soc. 1996, 17, 201-205
35. Olagunju, O.; Siegel, P. A.; Olojo, R.; Simoyi, R. H. Oxyhalogen-Sulfur Chemistry: Kinetics and Mechanism of Oxidation of N -Acetylthiourea by Chlorite and Chlorine Dioxide J. Phys. Chem. A 2006, 110, 2396-2410
36. 2) Radical in Aqueous Solutions: First ESR Evidence of Formation of New Nitroxide Radicals Free Radical Biol. Med. 1996, 20, 837-841 (Pubitemid 26123858)
37. Azizi, F. The Safety and Efficacy of Antithyroid Drugs Expert Opin. Drug Saf. 2006, 5, 107-116 (Pubitemid 43056443)
38. Balkin, M. S.; Buchholtz, M.; Ortiz, J.; Green, A. J. Propylthiouracil (PTU)-Induced Agranulocytosis Treated with Recombinant Human Granulocyte Colony-Stimulating Factor (G-CSF) Thyroid 1993, 3, 305-309 (Pubitemid 24015325)
39. Greenstein, R. J.; Su, L.; Brown, S. T. The Thioamides Methimazole and Thiourea Inhibit Growth of M. avium Subspecies Paratuberculosis in Culture PLoS One 2010, 5 e11099
40. Kudrik, E. V.; Makarov, S. V.; Zahl, A.; van Eldik, R. Kinetics and Mechanism of the Iron Phthalocyanine Catalyzed Reduction of Nitrite by Dithionite and Sulfoxylate in Aqueous Solution Inorg. Chem. 2005, 44, 6470-6475 (Pubitemid 41323496)
41. Makarov, S. V.; Silaghi-Dumitrescu, R. Sodium Dithionite and Its Relatives: Past and Present J. Sulfur Chem. 2013, 34, 444-449
42. Autio, K.; von Wright, A.; Pyysalo, H. The Effect of Oxidation of the Sulfur Atom on the Mutagenicity of Ethylenethiourea Mutat. Res. 1982, 106, 27-31 (Pubitemid 12029407)