Growth inhibition of Mycobacterium bovis, Mycobacterium tuberculosis and Mycobacterium avium in vitro: Effect of 1-β-D-2′-arabinofuranosyl and 1-(2′-deoxy-2′-fluoro-β-D-2′-ribofuranosyl) pyrimidine nucleoside analogs

Journal of Medicinal Chemistry

Volumn 50, Issue 15, 2007, Pages 3696-3705

  Johar, Monika ^a   Manning, Tracey ^a   Tse, Christopher ^a   Desroches, Nancy ^a   Agrawal, B ^a   Kunimoto, Dennis Y ^a   Kumar, Rakesh ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2' DEOXY 2' FLUORO BETA DEXTRO RIBOFURANOSYL) 5 DODECYNYLURACIL; 1 (2' DEOXY 2' FLUORO BETA DEXTRO RIBOFURANOSYL) 5 TETRADECYNYLURACIL; 1 BETA DEXTRO 2' ARABINOFURANOSYL 5 DODECYNYLURACIL; PYRIMIDINE NUCLEOSIDE DERIVATIVE; RIFAMPICIN; UNCLASSIFIED DRUG; URACIL;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG EFFECT; DRUG POTENCY; DRUG SYNTHESIS; GROWTH INHIBITION; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM AVIUM; MYCOBACTERIUM BOVIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

ANIMALS; ARABINOFURANOSYLURACIL; CELL LINE; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; DRUG RESISTANCE, BACTERIAL; FLOXURIDINE; HUMANS; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM AVIUM; MYCOBACTERIUM BOVIS; MYCOBACTERIUM TUBERCULOSIS; PYRIMIDINE NUCLEOSIDES; RIFAMPIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34547557088     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0703901     Document Type: Article

References (50)

1. (a) Valadas, E.; Antunes, F. Tuberculosis a Re-emergent Disease. Eur. J. Radiol. 2005, 55, 154-157.
2. (b) World Health Organization Information Resource Center. HIV, Tuberculosis and Malaria WHO Fact Sheet No. 104; WHO: Geneva, Switzerland, 2004.
3. (a) Maher, D.; Raviglione, M. Global Epidemiology of Tuberculosis. Clin. Chest. 2005, 26, 168-182.
4. (b) Pilheu, J. A. Tuberculosis 2000: Problems and Solutions. Int. J. Tuberc. Lung Dis. 1998, 2, 696-703.
5. (a) World Health Organization. Global Tuberculosis Control: Surveillance, Planning, Financing; WHO: Geneva, Switzerland, 2004; Report.
6. (b) Raviglione, M. C.; Snider, D. E.; Kochi, A. Global Epidemiology of Tuberculosis. Morbidity and Mortality of a Worldwide Epidemic. J. Am. Med. Assoc. 1995, 273, 220-226.
7. (a) Willcox, P. A. Drug-Resistant Tuberculosis. Curr. Opin. Pulm. Med. 2000, 6, 198-202.
8. (b) Méndez, A. P.; Raviglione, M. C.; Laszlo, A.; Binkin, N.; Rieder, H. L.; Bustreo, F.; Cohn, D. L.; Weezenbeek, C. S. B. L.-van.; Kim, S. J.; Chaulet, P.; Nunn, P. Global Surveillance for Antituberculosis-Drug Resistance, 1994-1997. World Health Organization-International Union against Tuberculosis and Lung Disease Working Group on Anti-Tuberculosis Drug Resistance Surveillance. N. Engl. J. Med. 1998, 338, 1641-1649.
9. World Health Organization. Tuberculosis: WHO Report; WHO: Geneva, Switzerland, 2002.
10. (a) Guerrin-Tran, E.; Thiolet, J.-M.; Rousseau, C.; Henry, S.; Poirier, C.; Che, D.; Vinas, J.-M.; Jarlier, V.; Robert J. An Evaluation of Data Quality in a Network for Surveillance of Mycobacterium tuberculosis to Antituberculosis Drugs in France Region-2001-2002. Eur. J. Epidemiol. 2006, 21, 783-785.
11. (b) Frieden, T. R.; Sterling, T. R.; Munsiff, S. S.; Watt, C. J.; Dye, C. Tuberculosis Seminar. Lancet 2003, 162, 887-899.
12. Cohen, J. Extensively Drug-Resistant TB Gets Foothold in South Africa. Science 2006, 313, 1554.
13. Pozniak, A. Mycobacterial Diseases and HIV. J. HIV Ther. 2002, 7, 13-16.
14. (a) Zhang, Y. The Magic Bullets and Tuberculosis Drug Targets. Ann. Rev. Pharmacol. Toxicol. 2005, 45, 529-564.
15. (b) Nayyar, A.; Jain, R. Recent Advances in New Structural Classes of Antituberculosis Agents. Curr. Med. Chem. 2005, 12, 1873-1886.
16. Inderlied, C. B.; Kemper, C. A.; Bermudez, L. E. The Mycobacterium avium Complex. Clin. Microbiol. Rev. 1993, 6, 266-310.
17. Falkinham, J. O., III. Epidemiology of Infection by Nontuberculous Mycobacteria. Clin. Microbiol. Rev. 1996, 9, 177-215.
18. Dautzenberg, B. Clinical Trials in Mycobacterium avium Therapy: Lessons to Take Home. Res. Microbiol. 1994, 145, 197-206.
19. Ellner, J. J.; Goldberger, M. J.; Parenti, D. M. Mycobacterium avium Infection and AIDS: A Therapeutic Dilemma in Rapid Evolution. J. Infect. Dis. 1991, 163, 1326-1335.
20. (a) Espinal, M. A. The Global Situation of MDR-TB. Tuberculosis. 2003, 83, 44-51.
21. (b) Frieden, T. R.; Munsiff, S. S. The DOTS Strategy for Controlling the Global Tuberculosis Epidemic. Clin. Chest Med. 2005, 26, 197-205.
22. (c) Peloquin, C. A.; Berning, S. E. Infections Caused by Mycobacterium tuberculosis. Ann. Pharmacother. 1994, 28, 72-84.
23. (a) Murray, J. F. Tuberculosis and HIV Iinfection: A Global Perspective. Respiration 1998, 65, 335-342.
24. (b) Gordin, F. M.; Nelson, E. T.; Matts, J. P.; Cohn, D. L. J.; Benator, E. D.; Besch, C. L.; Crane, L. R.; Sampson, J. H.; Bragg, P. S.; El-Sadr, W. The Impact of HIV infection on Drug-Resistant Tuberculosis. Am. J. Resp. Crit. Care Med. 1996, 154, 1478-1483.
25. (c) Moss, A. R.; Alland. D.; Telzak, E.; Hewlett, D., Jr.; Sharp, V.; Chiliade, P.; LaBombardi, V.; Kabus, D.; Hanna, B.; Palumbo, L.; Brudney, K.; Weltman, A.; Stoeckle, K.; Chirgwin, K.; Simberkoff, M.; Moghazeh, S.; Eisner, W.; Lutfey, M.; Kreiswirth, B. A City-wide Outbreak of a Multiple-Drug-Resistant Strain of Mycobacterium tuberculosis in New York. Int. J. Tuberc. Lung Dis. 1997, 1, 115-121.
26. (d) National Survey of Tuberculosis in England and Wales. Commun. Dis. Rep. Weekly 1998, 8, 209-212.
27. XDR-TB-a Global Threat. Editorial. Lancet 2006, 368, 964.
28. Wright, A. Emergence of Mycobacterium tuberculosis with Extensive Resistance to Second-Line Drugs Worldwide, 2000-2004. Morbidity and Mortality Weekly Report (MMWR) 2006, 55, 301-305.
29. Colditz, G. A.; Brewer, T. F.; Berkey, C. S.; Wilson, M. E.; Burdick, E.; Fineberg, H. V.; Mosteller, F. Efficacy of BCG Vaccine in the Prevention of Tuberculosis. Meta-Analysis of the Published Literature. J. Am. Med. Assoc. 1994, 271, 698-702.
30. (a) Koehler, C. S. W. Consumption the Great Killer. Drug Discovery 2002, 47-49.
31. (b) Guerrero, A. Nosocomial Transmission of M. Bovis Resistant to 11 Drugs in People with Advanced HIV-1 Infection. Lancet 1997, 350, 1738-1742.
32. Cole, S. T.; Brosch, R.; Parkhill, J.; Garnier, T.; Churcher, C.; Harris, D.; Gordon, S. V.; Eiglmeier, K.; Gas, S.; Barry, C. E., III; Tekala, F.; Badcock, K.; Bashman, D.; Brown, D.; Chillingworth, T. R.; Connor, R.; et al. Deciphering the Biology of Mycobacterium tuberculosis from the Complete Genome Sequence. Nature 1998, 393, 537-544.
33. (a) Beres, J.; Bentrude, W. G.; Balzarini, J.; De Clercq, E.; Otvos, L. Synthesis and Antitumor and Antiviral Properties of 5-Alkyl-2′- deoxyuridines, 3′,5′-Cyclic Monophosphates, and Neutral Cyclic Triesters. J. Med. Chem. 1986, 29, 494-499.
34. (b) Herdewijn, P. A. 5-Substituted-2′-deoxyuridinesas Anti-HSV-1 Agents: Synthesis and Structure-Activity Relationships. Antiviral Chem. Chemother. 1994, 5, 131-146.
35. (c) Vincent, P.; Beaucourt, J. P.; Pichat, L. Alcynyl-5 desoxy-2′ Uridines par Couplages D'organozinciques Acetyleniques Avec L'iodo-5 O-3′,5′-bis(trimethylsilyl) desoxyuridine, Catalyzes Par des Complexes Organopalladies et de Nickel. Tetrahedron Lett. 1981, 22, 945-947.
36. Fillastre, J. P.; Godin, M.; Legallicier, B.; Chretien, P.; Bidault, R.; Gillotin, C.; Wooton, R.; Posner, J.; Peck, R. W. Pharmacokinetics of Netivudine, a Potent Anti-Varicella Zoster Virus Drug, in Patients with Renal Impairment. J. Antimicrob. Chemother. 1996, 37, 965-974.
37. (a) Machida, S.; Watanabe, Y.; Kano, F.; Sakata, S.; Kumagai, M.; Yamaguchi, T. Biochem. Pharmacol. 1995, 49, 763-766.
38. (b) Mercer, J. R.; Knaus, E. E.; Wiebe, L. I. Synthesis and Tumor Uptake of 5-Halo-1-(2′-fluoro-2′-deoxy-beta-D-ribofuranosyl)[2- 14C]uracils. J. Med. Chem. 1987, 30, 670-675.
39. Rai, D.; Johar, M.; Manning, T.; Agrawal, B.; Kunimoto, D. Y.; Kumar, R. Design and Studies of Novel 5-Substituted Alkynyl pyrimidine Nucleosides as Potent Inhibitors of Mycobacteria. J. Med. Chem. 2005, 48, 7012-7017.
40. Johar, M.; Manning, T.; Kunimoto, D. Y.; Kumar, R. Synthesis and In Vitro Anti-Mycobacterial Activity of 5-Substituted Pyrimidine Nucleosides. Bioorg. Med Chem. 2005, 13, 6663-6671.
41. Kumar, R.; Wiebe, L. I.; Knaus, E. E. Synthesis and Antiviral Activity of 1-β-D-Arabinofuranosyluracils and Uridines Containing 5-[2-Bromo-2-chloro(or bromo)-1-hydroxy(or methoxy)ethyl]substituents. Nucleosides Nucleotides 1993, 12, 537-545.
42. Kumar, R.; Wiebe, L. I.; Hall, T. W.; Knaus, E. E.; Tovell, D. R.; Tyrrell, D. L.; Allen, T. M.; Fathi-Afshar, R. Synthesis of 5-[1-Hydroxy(or methoxy)-2-bromo(or chloro)ethyl]-2′-deoxyuridines and Related Halohydrin Analogues with Antiviral and Cytotoxic Activity. J. Med. Chem. 1989, 32, 941-944.
43. Kumar, R.; Xu, L. H.; Knaus, E. E.; Wiebe, L. I.; Tovell, D. R.; Tyrrell, D. L.; Allen, T. M. Synthesis and Antiviral and Cytotoxic Activity of Iodohydrin and Iodomethoxy Derivatives of 5-Vinyl-2′-deoxyuridines, 2′-Fluoro-2′-deoxyuridine, and Uridine. J. Med. Chem. 1990, 33, 717-723.
44. Kumar, R.; Wiebe, L. I.; Knaus, E. E. A Mild and Efficient Methodology for the Synthesis of 5-Halogenouracil Nucleosides that Occurs via a 5-Halogeno-6-azido-5,6-dihydro Intermediate. Can. J. Chem. 1994, 72, 2005-2010.
45. Kumar, R.; Wiebe, L. I.; Knaus, E. E.; Allen, T. M.; Tempest M. L. Synthesis, Antiviral and Cytotoxic Activity of 2′-Deoxyuridines, 2′-Fluoro-2′-deoxyuridines, and 2′-Arabinouridines Containing 5-(1-Hydroxy-2-halo-2-ethoxycarbonylethyl)-, 5-(1-Hydroxy-2-iod-2-carboxyethyl)- and 5-(1-Hydroxy(or methoxy)-2-iodoethyl)- substituents. Drug Des. Dis. 1992, 8, 179-189.
46. Franzblau, S. G.; Witzig, R. S.; McLaughlin, J. C.; Torres, P.; Madico, G.; Hernandez, A.; Degnan, M. T.; Cook, M. B.; Quenzer, V. K.; Ferguson, R. M.; Gilman, R. H. Rapid, Low-technology MIC Determination with Clinical Mycobacterium tuberculosis Isolates by Using the Microplate Alamar Blue Assay. J. Clin. Microbiol. 1998, 36, 362-366.
47. Ryan, A. J.; Gray, N. M.; Lowe, P. N.; Chung, C. Effect of Detergent on Promiscuous Inhibitors. J. Med. Chem. 2003, 46, 3448-3451.
48. Neugebauer, J. M. Detergents: An Overview. Methods Enzymol. 1990, 182, 239-153.
49. Collins, L.; Franzblau, S .G. Microplate Alamar Blue Assay versus BACTEC 460 System for High-Throughput Screening of Compounds Against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents. Chemother. 1997, 41, 1004-1009.
50. Kumar, R. Synthesis and Enzymatic Transformations of 5-Halo-6-methoxy-5, 6-dihydro Derivatives of 5-[1-Methoxy-2-halo (or 2,2-dihalo) ethyl]-2′-deoxyuridines as Potential Herpes Simplex Virus Inhibitors. J. Enzyme Inhib. Med. Chem. 2003, 18, 273-278.