Design, synthesis, and evaluation of thiol-activated sources of sulfur dioxide (SO 2) as antimycobacterial agents

Journal of Medicinal Chemistry

Volumn 55, Issue 1, 2012, Pages 553-557

  Malwal, Satish R ^a   Sriram, Dharmarajan ^b   Yogeeswari, Perumal ^b   Konkimalla, V Badireenath ^c   Chakrapani, Harinath ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

^b BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

^c NATIONAL INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DINITROPHENYLSULFONAMIDE; ANTIMYCOBACTERIAL AGENT; CYSTEINE; ISONIAZID; MYCOTHIOL; N BENZYL 2,4 DINITROBENZENESULFONAMIDE; SULFONAMIDE; SULFUR DIOXIDE; THIOL; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HALF LIFE TIME; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTITUBERCULAR AGENTS; CELL SURVIVAL; CYSTEINE; HEK293 CELLS; HUMANS; KINETICS; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; SULFONAMIDES; SULFUR DIOXIDE;

EID: 84855833527     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201023g     Document Type: Article

References (42)

1. Gandhi, N. R.; Moll, A.; Sturm, A. W.; Pawinski, R.; Govender, T.; Lalloo, U.; Zeller, K.; Andrews, J.; Friedland, G. Extensively drug-resistant tuberculosis as a cause of death in patients co-infected with tuberculosis and HIV in a rural area of South Africa Lancet 2006, 368, 1575-1580
2. Samandari, T.; Agizew, T. B.; Nyirenda, S.; Tedla, Z.; Sibanda, T.; Shang, N.; Mosimaneotsile, B.; Motsamai, O. I.; Bozeman, L.; Davis, M. K.; Talbot, E. A.; Moeti, T. L.; Moffat, H. J.; Kilmarx, P. H.; Castro, K. G.; Wells, C. D. Six-month versus 36-month isoniazid preventive treatment for tuberculosis in adults with HIV infection in Botswana: a randomised, double-blind, placebo-controlled trial Lancet 2011, 377, 1588-1598
3. Fauci, A. S. Multidrug-resistant and extensively drug-resistant tuberculosis: the National Institute of Allergy and Infectious Diseases Research agenda and recommendations for priority research J. Infect. Dis. 2008, 197, 1493-1498
4. Zhang, Y. The magic bullets and tuberculosis drug targets Annu. Rev. Pharmacol. Toxicol. 2005, 45, 529-564
5. Ginsberg, A. M; Spigelman, M. Challenges in tuberculosis drug research and development Nature Med. 2007, 13, 290-294
6. Singh, R.; Manjunatha, U.; Boshoff, H. I.; Ha, Y. H.; Niyomrattanakit, P.; Ledwidge, R.; Dowd, C. S.; Lee, I. Y.; Kim, P.; Zhang, L.; Kang, S.; Keller, T. H.; Jiricek, J.; Barry, C. E., III. PA-824 kills nonreplicating Mycobacterium tuberculosis by intracellular NO release Science 2008, 322, 1392-1395
7. Moncada, S.; Palmer, R. M.; Higgs, E. A. Nitric oxide: physiology, pathophysiology, and pharmacology Pharmacol. Rev. 1991, 43, 109-142
8. Ignarro, L. J.; Cirino, G.; Casini, A.; Napoli, C. Nitric oxide as a signaling molecule in the vascular system: an overview J. Cardiovasc. Pharmacol. 1999, 34, 879-886
9. Bonavida, B.; Khineche, S.; Huerta-Yepez, S.; Garban, H. Therapeutic potential of nitric oxide in cancer Drug Res. Updates 2006, 9, 157-173
10. Thatcher, G. R.; Bennett, B. M.; Reynolds, J. N. Nitric oxide mimetic molecules as therapeutic agents in Alzheimers disease Curr. Alzheimers Dis. 2005, 2, 171-182
11. King, S. B. Mechanisms and novel directions in the biological applications of nitric oxide donors Free Radical Biol. Med. 2004, 37, 735-736
12. Thatcher, G. R. J. An introduction to NO-related therapeutic agents Curr. Top. Med. Chem. 2005, 5, 597-601
13. Qin, G.; Meng, Z. Effect of sulfur dioxide inhalation on CYP1A1 and CYP1A2 in rat liver and lung Toxicol. Lett. 2005, 160, 34-42
14. Zhang, Q.; Meng, Z. The negative inotropic effects of gaseous sulfur dioxide and its derivatives in the isolated perfused rat heart Environ. Toxicol. 2010, 602, 117-123
15. Gunnison, A. F. Sulfite toxicity: a critical review of in vitro and in vivo data Food Cosmet. Toxicol. 1981, 19, 667-682
16. Shi, X.; Mao, Y. 8-Hydroxy-2′-deoxyguanosine formation and DNA damage induced by sulfur trioxide anion radicals Biochem. Biophys. Res. Commun. 1994, 205, 141-147
17. Wu, D.; Meng, Z. Effect of sulfur dioxide inhalation on the glutathione redox system in mice and protective role of sea buckthorn seed oil Arch. Environ. Contam. Toxicol. 2003, 45, 423-428
18. Rencuzogullari, E.; Ila, H. B.; Kayraldiz, A.; Topaktas, M. Chromosome aberrations and sister chromatid exchanges in cultured human lymphocytes treated with metabisulfite, a food preservative Mutat. Res. 2001, 490, 107-112
19. Armentia-Alvarez, A.; Fernández-Casero, A.; García-Moreno, C.; Peña-Egido, M. J. Residual levels of free and total sulphite in fresh and cooked burgers Food Addit. Contam. 1993, 10, 157-165
20. Pena-Egido, M. J.; Garcia-Alonso, B.; Garcia-Moreno, C. S -Sulfonate contents in raw and cooked meat products J. Agric. Food Chem. 2005, 53, 4198-4201 and references therein.
21. Amerine, M. A.; Berg, H. W.; Kunkee, R. E.; Ough, C. S.; Singleton, V. L.; Webb, A. D. Technology of Wine Making, 4th ed.; AVI Publishing Co., Inc.: Westport, CT, 1980.
22. Ough, C. S.; Crowell., E. A. Use of sulfur dioxide in wine making J. Food Sci. 1987, 52, 386-389
23. Wedzicha, B. L. Uses in food. In Chemistry of Sulphur Dioxide in Foods; Elsevier Applied Science: London, 1984; pp 275.
24. Li, R.; Meng, Z.; Xie, J. Effects of sulfur dioxide derivatives on four asthma-related gene expressions in human bronchial epithelial cells Toxicol. Lett. 2007, 175, 71-81
25. Izgöt-Uysal, V. N.; Köçökatay, V.; Bölböl, M.; Tan, R.; Yargiçoǧlu, P.; Aǧar, A. Effect of sulfite on macrophage functions of normal and sulfite oxidase-deficient rats Food Chem. Toxicol. 2005, 43, 599-605
26. Niknahad, H.; OBrien, P. J. Mechanism of sulfite cytotoxicity in isolated rat hepatocytes Chem.-Biol. Interact. 2008, 174, 147-154
27. Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. 2,4-Dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines Tetrahedron Lett. 1997, 38, 5831-5834
28. Chen, X.; Zhou, Y.; Peng, X.; Yoon, J. Fluorescent and colorimetric probes for detection of thiols Chem. Soc. Rev. 2010, 39, 2120-2135
29. Newton, G. L.; Arnold, K.; Price, M. S.; Sherrill, C.; Delcardayre, S. B.; Aharonowitz, Y.; Cohen, G.; Davies, J.; Fahey, R. C.; Davis, C. Distribution of thiols in microorganisms: mycothiol is a major thiol in most actinomycetes J. Bacteriol. 1996, 178, 1990-1995
30. Fang, F. C. Antimicrobial reactive oxygen and nitrogen species: concepts and controversies Nature Rev. Microbiol. 2004, 2, 820-832
31. Farhana, A.; Guidry, L.; Srivastava, A.; Singh, A.; Hondalus, M. K.; Steyn, A. J. Reductive Stress in Microbes: Implications for Understanding Mycobacterium tuberculosis Disease and Persistence Adv. Microb. Physiol. 2010, 57, 43-117
32. Garcia-Alonso, B.; Pena-Egido, M. J.; Garcia-Moreno, C. S -Sulfonate determination and formation in meat products J. Agric. Food Chem. 2001, 49, 423-429
33. Banks, J. G.; Board, R. G. Comparison of methods for the determination of free and bound sulphur dioxide in stored British fresh sausage J. Sci. Food Agric. 1982, 33, 197-303
34. Fazio, T.; Warner, C. R. A review of sulphites in foods: analytical methodology and reported findings Food Addit. Contam. 1990, 7, 443-454
35. Leinweber, F.-J.; Monty, K. J. Sulfite Determination: Fuchsin Method Methods Enzymol. 1987, 143, 15-17
36. Zhao, Z.; Koeplinger, K. A.; Conradi, R. A.; Burton, P. S.; Suarato, A.; Heinrikson, R. L.; Tomasselli, A. G. Mechanism, Structure-Activity Studies, and Potential Applications of Glutathione S -Transferase-Catalyzed Cleavage of Sulfonamides Drug Metab. Dispos. 1999, 27, 992-998
37. Our method was based on a reported procedure for sulfite analysis using an ion chromatograph equipped with an electrochemical detector: Paino-Campa, G.; Peña-Egido, M. J.; García-Moreno, C. Liquid Chromatographic Determination of Free and Total Sulphites in Fresh Sausages J. Sci. Food Agric. 1991, 56, 85-93
38. Hall, H. K., Jr. Correlation of the Base Strengths of Amines J. Am. Chem. Soc. 1957, 79, 5441-5444
39. Braude, E. A.; Nachod, F. C. Determination of Organic Structures by Physical Methods; Academic Press: New York, 1955.
40. Shami, P. J.; Saavedra, J. E.; Wang, L. Y.; Bonifant, C. L.; Diwan, B. A.; Singh, S. V.; Gu, Y.; Fox, S. D.; Buzard, G. S.; Citro, M. L.; Waterhouse, D. J.; Davies, K. M.; Ji, X.; Keefer, L. K. JS-K, a glutathione/glutathione S -transferase-activated nitric oxide donor of the diazeniumdiolate class with potent antineoplastic activity Mol. Cancer Ther. 2003, 2, 409-417
41. Maciag, A. E.; Saavedra, J. E.; Chakrapani, H. The nitric oxide prodrug JS-K and its structural analogues as cancer therapeutic agents Anticancer Agents Med. Chem. 2009, 9, 798-803
42. Li, J.; Meng, Z. The role of sulfur dioxide as an endogenous gaseous vasoactive factor in synergy with nitric oxide Nitric Oxide 2009, 20, 166-174