Oxyhalogen-sulfur chemistry: Kinetics and mechanism of oxidation of captopril by acidified bromate and aqueous bromine

Journal of Physical Chemistry A

Volumn 117, Issue 13, 2013, Pages 2704-2717

  Kapungu, G P ^a   Rukweza, G ^a   Tran, Thai ^b   Mbiya, Wilbes ^b   Adigun, Risikat ^b   Ndungu, Patrick ^c   Martincigh, Bice ^c   Simoyi, Reuben H ^b,c  

^a UNIVERSITY OF ZIMBABWE   (Zimbabwe)

^b PORTLAND STATE UNIVERSITY   (United States)

^c UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

BIMOLECULAR RATE CONSTANTS; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; IODOMETRIC TITRATION; KINETICS AND MECHANISM; OXIDIZING CONDITIONS; PHYSIOLOGICAL ENVIRONMENT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTIVE INTERMEDIATE;

BROMINE; COMPUTER SIMULATION; DRUG PRODUCTS; ELECTROSPRAY IONIZATION; MASS SPECTROMETRY; PHYSIOLOGY; RATE CONSTANTS; REACTION INTERMEDIATES; STOICHIOMETRY; SULFUR;

OXIDATION;

ANTIHYPERTENSIVE AGENT; BROMATE; BROMINE; CAPTOPRIL; SULFONIC ACID DERIVATIVE; THIOUREA; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; DOSE RESPONSE; ELECTROSPRAY MASS SPECTROMETRY; KINETICS; OXIDATION REDUCTION REACTION;

ANTIHYPERTENSIVE AGENTS; BROMATES; BROMINE; CAPTOPRIL; COMPUTER SIMULATION; DOSE-RESPONSE RELATIONSHIP, DRUG; KINETICS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFONIC ACIDS; THIOUREA; WATER;

EID: 84875861102     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp312672w     Document Type: Article

References (54)

1. Arima, H.; Murakami, Y.; Lam, T. H.; Kim, H. C.; Ueshima, H.; Woo, J.; Suh, I.; Fang, X.; Woodward, M. Effects of Prehypertension and Hypertension Subtype on Cardiovascular Disease in the Asia-Pacific Region Hypertension 2012, 59, 1118-1123
2. Bucher, B. S.; Tschumi, S.; Simonetti, G. D. Childhood's determinants for high blood pressure in adulthood Ther. Umsch. 2012, 295-298
3. Gray, L.; Lee, I. M.; Sesso, H. D.; Batty, G. D. Blood Pressure in Early Adulthood, Hypertension in Middle Age, and Future Cardiovascular Disease Mortality: HAHS (Harvard Alumni Health Study) J. Am. Coll. Cardiol. 2011, 58, 2396-2403
4. Guize, L.; Pannier, B.; Thomas, F.; Bean, K.; Jego, B.; Benetos, A. Recent Advances in Metabolic Syndrome and Cardiovascular Disease Arch. Cardiovasc. Dis. 2008, 101, 577-583
5. Holmes, J. S.; Arispe, I. E.; Moy, E. Heart Disease and Prevention: Race and Age Differences in Heart Disease Prevention, Treatment, and Mortality Med. Care 2005, 43, I33-I41
6. McNeill, A. M.; Katz, R.; Girman, C. J.; Rosamond, W. D.; Wagenknecht, L. E.; Barzilay, J. I.; Tracy, R. P.; Savage, P. J.; Jackson, S. A. Metabolic Syndrome and Cardiovascular Disease in Older People: The Cardiovascular Health Study J. Am. Geriatr. Soc. 2006, 54, 1317-1324
7. Ngo, D. H.; Ryu, B.; Vo, T. S.; Himaya, S. W. A.; Wijesekara, I.; Kim, S. K. Free Radical Scavenging and Angiotensin-I Converting Enzyme Inhibitory Peptides from Pacific Cod (Gadus macrocephalus) Skin Gelatin Int. J. Biol. Macromol. 2011, 49, 1110-1116
8. Wu, J. P.; Ding, X. L. Hypotensive and Physiological Effect of Angiotensin Converting Enzyme Inhibitory Peptides Derived from Soy Protein on Spontaneously Hypertensive Rats J. Agric. Food Chem. 2001, 49, 501-506
9. Cushman, D. W.; Ondetti, M. A. Design of Angiotensin converting Enzyme Inhibitors Nat. Med. 1999, 5, 1110-1113
10. Krapcho, J.; Turk, C.; Cushman, D. W.; Powell, J. R.; Deforrest, J. M.; Spitzmiller, E. R.; Karanewsky, D. S.; Duggan, M.; Rovnyak, G.; Schwartz, J. Angiotensin-Converting Enzyme-Inhibitors-Mercaptan, Carboxyalkyl Dipeptide, and Phosphinic Acid Inhibitors Incorporating 4-Substituted Prolines J. Med. Chem. 1988, 31, 1148-1160
11. Mukherjee, R.; McCaddon, A.; Smith, C. A.; Brasch, N. E. Synthesis, Synchrotron X-ray Diffraction, and Kinetic Studies on the Formation of a Novel Thiolatocobalamin of Captopril: Evidence for cis-trans Isomerization in the beta-Axial Ligand Inorg. Chem. 2009, 48, 9526-9534
12. Akif, M.; Masuyer, G.; Schwager, S. L. U.; Bhuyan, B. J.; Mugesh, G.; Isaac, R. E.; Sturrock, E. D.; Acharya, K. R. Structural Characterization of Angiotensin I-converting Enzyme in Complex with a Selenium Analogue of Captopril FEBS J. 2011, 278, 3644-3650
13. Brew, K. Structure of Human ACE gives New Insights into Inhibitor Binding and Design Trends Pharmacol. Sci. 2003, 24, 391-394
14. Gupta, A.; Prajapati, S. K.; Singh, M.; Balamurugan, M. Proniosomal pPowder of Captopril: Formulation and Evaluation Mol. Pharmaceutics 2007, 4, 596-599
15. Chang, J.; Yang, W.; Kahler, K. H.; Fellers, T.; Orloff, J.; Bensimon, A. G.; Yu, A. P.; Fan, C. P.; Wu, E. Q. Compliance, Persistence, Healthcare Resource Use, and Treatment Costs Associated with Aliskiren Plus ARB Versus ACE Inhibitor Plus ARB Combination Therapy: in US Patients with Hypertension Am. J. Cardiovasc. Drugs 2011, 11, 21-32
16. Gavras, I.; Rosenthal, T. Combination Therapy as First-Line Treatment for Hypertension Curr. Hypertens. Rep. 2004, 6, 267-272
17. Ruzicka, M.; Leenen, F. H. Combination Therapy as First-Line Treatment of Arterial Hypertension Can. J. Cardiol. 2002, 18, 1317-1327
18. Wu, S. L.; Du, X.; Xing, A. J.; Song, S. M.; Hou, G. S.; Yu, Q.; Liu, F. S.; Wang, G. L.; Wang, L. G.; Li, D. X.; Cao, Z. X.; Qi, R. P. Impact of Patient Compliance on the Outcomes in Hypertensive Patients Receiving Hydrochlorothiazide Based Combination Therapy with Spironolactone or Captopril] Zhonghua Xin. Xue. Guan. Bing. Za Zhi. 2008, 36, 1078-1082
19. Stevenson, J. G.; Chideckel, E. W. Evaluation of Cilazapril Versus Captopril in Patients with Mild to Moderate Essential Hypertension Clin. Exp. Hypertens. 1994, 16, 179-196
20. Wisenbaugh, T.; Sinovich, V.; Dullabh, A.; Sareli, P. Six Month Pilot Study of Captopril for Mildly Symptomatic, Severe Isolated Mitral and Isolated Aortic Regurgitation Journal of Heart Valve Disease 1994, 3, 197-204
21. Havelka, J.; Vetter, H.; Studer, A.; Greminger, P.; Luscher, T.; Wollnik, S.; Siegenthaler, W.; Vetter, W. Acute and Chronic Effects of the Angiotensin-Converting Enzyme Inhibitor Captopril in Severe Hypertension Am. J. Cardiol. 1982, 49, 1467-1474
22. Havelka, J.; Boerlin, H. J.; Studer, A.; Greminger, P.; Tenschert, W.; Luescher, T.; Siegenthaler, W.; Vetter, W.; Walger, P.; Vetter, H. Long-Term Experience with Captopril in Severe Hypertension Br. J. Clin. Pharmacol. 1982, 14, S71-S76
23. KotsakiKovatsi, V. P.; KoehlerSamouilidis, G.; Kovatsis, A.; Rozos, G. Fluctuation of Zinc, Copper, Magnesium and Calcium Concentrations in Guinea Pig Tissues after Administration of Captopril (SQ 14225) J. Trace Elem. Med. Biol. 1997, 11, 32-36
24. Small, W.; Molteni, A.; Kim, Y. T.; Taylor, J. M.; Ts'Ao, C. H.; Ward, W. F. Mechanism of Captopril Toxicity to a Human Mammary Ductal Carcinoma Cell Line in the Presence of Copper Breast Cancer Res. Treat. 1999, 55, 223-229
25. Barbagallo, M.; Dominguez, L. J.; Resnick, L. M. Protective Effects of Captopril Against Ischemic Stress-Role of Cellular Mg Hypertension 1999, 34, 958-963
26. Chopra, M.; Scott, N.; Mcmurray, J.; Mclay, J.; Bridges, A.; Smith, W. E.; Belch, J. J. F. Captopril-A Free-Radical Scavenger Br. J. Clin. Pharmacol. 1989, 27, 396-399
27. Engelman, R. M.; Rousou, J. A.; Iyengar, J.; Das, D. K. Captopril, An Ace Inhibitor, for Optimizing Reperfusion After Acute Myocardial-Infarction Annals of Thoracic Surgery 1991, 52, 918-926
28. De Cavanagh, E. M. V.; Inserra, F.; Ferder, L.; Fraga, C. G. Enalapril and Captopril Enhance Glutathione-Dependent Antioxidant Defenses in Mouse Tissues Am. J. Physiol.: Regul., Integr. Comp. Physiol. 2000, 278, R572-R577
29. Wieling, J.; Hendriks, G.; Tamminga, W. J.; Hempenius, J.; Mensink, C. K.; Oosterhuis, B.; Jonkman, J. H. G. Rational Experimental Design for Bioanalytical Methods Validation-Illustration using an Assay Method for Total Captopril in Plasma J. Chromatogr. A 1996, 730, 381-394
30. Drummer, O. H.; Kourtis, S. Bradykinin-Potentiating Activity of Captopril Disulfide Dimer (Sq-14,551) Eur. J. Pharmacol. 1988, 153, 11-17
31. Lin, B.; Zhan, X. C.; Li, L. L.; Li, C. R.; Qi, H. J.; Tao, J. L. Step Nonisothermal Method in Kinetics Studies of Captopril Oxidation under Compressed Oxygen Yakugaku Zasshi 2008, 128, 617-624
32. Dansette, P. M.; Libraire, J.; Bertho, G.; Mansuy, D. Metabolic Oxidative Cleavage of Thioesters: Evidence for the Formation of Sulfenic Acid Intermediates in the Bioactivation of the Antithrombotic Prodrugs Ticlopidine and Clopidogrel Chem. Res. Toxicol. 2009, 22, 369-373
33. Mansuy, D.; Valadon, P.; Erdelmeier, I.; Lopezgarcia, P.; Amar, C.; Girault, J. P.; Dansette, P. M. Thiophene S-Oxides As New Reactive Metabolites-Formation by Cytochrome-P450 Dependent Oxidation and Reaction with Nucleophiles 4 J. Am. Chem. Soc. 1991, 113, 7825-7826
34. Valadon, P.; Dansette, P. M.; Girault, J. P.; Amar, C.; Mansuy, D. Thiophene Sulfoxides as Reactive Metabolites: Formation upon Microsomal Oxidation of a 3-aroylthiophene and Fate in the Presence of Nucleophiles in Vitro and in Viv 2 Chem. Res. Toxicol. 1996, 9, 1403-1413
35. Tsikas, D.; Sandmann, J.; Luessen, P.; Savva, A.; Rossa, S.; Stichtenoth, D. O.; Frolich, J. C. S-Transnitrosylation of Albumin in Human Plasma and Blood in Vitro and in Vivo in the Rat Biochim. Biophys. Acta 2001, 1546, 422-434
36. Cushman, D. W.; Ondetti, M. A. Design of Angiotensin Converting Enzyme Inhibitors Nat. Med. 1999, 5, 1110-1112
37. Morakinyo, M. K.; Chikwana, E.; Simoyi, R. H. Oxyhalogen-Sulfur Chemistry-Kinetics and Mechanism of the Bromate Oxidation of Cysteamine Can. J. Chem. 2008, 86, 416-425
38. Darkwa, J.; Olojo, R.; Olagunju, O.; Otoikhian, A.; Simoyi, R. Oxyhalogen-Sulfur Chemistry: Oxidation of N-acetylcysteine by Chlorite and Acidic Bromate J. Phys. Chem. A 2003, 107, 9834-9845
39. Makarov, S. V.; Mundoma, C.; Svarovsky, S. A.; Shi, X.; Gannett, P. M.; Simoyi, R. H. Reactive Oxygen Species in the Aerobic Decomposition of Sodium Hydroxymethanesulfinate Arch. Biochem. Biophys. 1999, 367, 289-296
40. 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
41. Svarovsky, S. A.; Simoyi, R. H.; Makarov, S. V. Reactive Oxygen Species in Aerobic Decomposition of Thiourea Dioxides J. Chem. Soc., Dalton Trans. 2000, 511-514
42. Chanakira, A.; Chikwana, E.; Peyton, D.; Simoyi, R. Oxyhalogen-Sulfur Chemistry-Kinetics and Mechanism of the Oxidation of Cysteamine by Acidic Iodate and Iodine Can. J. Chem. 2006, 84, 49-57
43. Martincigh, B. S.; Mundoma, C.; Simoji, R. H. Antioxidant Chemistry: Hypotaurine-Taurine Oxidation by Chlorite J. Phys. Chem. A 1998, 102, 9838-9846
44. Darkwa, J.; Mundoma, C.; Simoyi, R. H. Antioxidant chemistry-Reactivity and Oxidation of DL-Cysteine by some Common Oxidants J. Chem. Soc., Faraday Trans. 1998, 94, 1971-1978
45. 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
46. Mrakavova, M.; Melichercik, M.; Olexova, A.; Treindl, L. The Autocatalytic Reduction of Ferriin by Malonic Acid with Regard to the Ferroin-Catalyzed Belousov-Zhabotinsky Reaction Collect. Czech. Chem. Commun. 2003, 68, 23-34
47. Sirimungkala, A.; Forsterling, H. D.; Dlask, V.; Field, R. J. Bromination Reactions Important in the Mechanism of the Belousov-Zhabotinsky System J. Phys. Chem. A 1999, 103, 1038-1043
48. Szalai, I.; Oslonovitch, J.; Forsterling, H. D. Oscillations in the Bromomalonic Acid/Bromate System Catalyzed by [Ru(phen)(3)](2+) J. Phys. Chem. A 2000, 104, 1495-1498
49. Chanakira, A.; Chikwana, E.; Peyton, D.; Simoyi, R. Oxyhalogen-Sulfur Chemistry-Kinetics and Mechanism of the Oxidation of Cysteamine by Acidic Iodate and Iodine Can. J. Chem. 2006, 84, 49-57
50. 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
51. Morakinyo, M. K.; Chikwana, E.; Simoyi, R. H. Oxyhalogen-Sulfur Chemistry-Kinetics and Mechanism of the Bromate Oxidation of Cysteamine Can. J. Chem. 2008, 86, 416-425
52. Chipinda, I.; Hettick, J. M.; Simoyi, R. H.; Siegel, P. D. Zinc Diethyldithiocarbamate Allergenicity: Potential Haptenation Mechanisms Contact Dermatitis 2008, 59, 79-89
53. Chipinda, I.; Zhang, X. D.; Simoyi, R. H.; Siegel, P. D. Mercaptobenzothiazole Allergenicity-Role of the Thiol Group Cutan. Ocul. Toxicol. 2008, 27, 103-116
54. Chipinda, I.; Hettick, J. M.; Simoyi, R. H.; Siegel, P. D. Oxidation of 2-mercaptobenzothiazole in Latex Gloves and its Possible Haptenation Pathway Chem. Res. Toxicol. 2007, 20, 1084-1092