Pharmacophore insights into rpoB gene mutations in Mycobacterium tuberculosis rifampicin resistant isolates

European Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2012, Pages 186-193

  Figueiredo, Ricardo ^a,c   Ramos, Daniela F ^d   Moiteiro, Cristina ^c,e   Medeiros, Maria Augusta ^c   Marcelo Curto, Maria João ^c   Cardoso De Menezes, José ^a   Pando, Rogelio Hernandez ^e,f   Silva, Pedro E A ^d   Costa, Maria Do Céu ^b,c  

^a Instituto de Biotecnologia e Bioengenharia Lisboa   (Portugal)

^b UNIVERSITY OF MADEIRA   (Portugal)

^c LABORATÓRIO NACIONAL DE ENERGIA E GEOLOGIA   (Portugal)

^d FEDERAL UNIVERSITY OF RIO GRANDE   (Brazil)

^e UNIVERSITY OF LISBON   (Portugal)

^f INSTITUTO NACIONAL DE CIENCIAS MÉDICAS Y NUTRICIÓN SALVADOR ZUBIRÁN   (Mexico)

Author keywords

Clinical isolated mutants; In vivo efficacy; Multidrug resistant tuberculosis (MDR TB); Mycobacterium tuberculosis; Pharmacophore; Rifabutin analogs; rpoB

Indexed keywords

RIFABUTIN; RIFAMPICIN; RNA POLYMERASE BETA SUBUNIT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIUM ISOLATE; BRAZIL; CODON; CONTROLLED STUDY; GENE MUTATION; IN VIVO STUDY; MALE; MEXICO; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; TISSUE INJURY;

ANIMALS; ANTIBIOTICS, ANTITUBERCULAR; BACTERIAL PROTEINS; DRUG RESISTANCE, BACTERIAL; MALE; MICE; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MUTATION; MYCOBACTERIUM TUBERCULOSIS; PROTEIN CONFORMATION; RIFAMPIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84855807628     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.10.041     Document Type: Article

References (45)

1. K. Duncan Progress in TB drug development and what is still needed Tuberculosis 83 2003 201 207
2. NYC DOH, Bureau of Tuberculosis Control Clinical Policies and Protocols third ed. July 1999
3. S. Munsiff, D. Nilsen, S.D. Ahuja, and J.N. Burzynski Antiretroviral Drugs and the Treatment of Tuberculosis February 2007 NYC Department of Health & Mental Hygiene, Bureau of Tuberculosis Control
4. D.A. Mitchison, and A.J. Nunn Influence of initial drug resistance on the response to short-course chemotherapy of pulmonary tuberculosis Am. Rev. Respir. Dis. 133 1986 423 430
5. L. King, S.S. Munsiff, and S.D. Ahuja Achieving international targets for tuberculosis treatment success among HIV-positive patients in New York City Int. J. Tuberc. Lung Dis. 4 12 2010 1613 1620 (8)
6. W.J. Burman, and B.E. Jones Treatment of HIV-related tuberculosis in the era of effective antiretroviral therapy Am. J. Respir. Crit. Care 164 2001 7 12
7. G.R. Davies, S. Cerri, and L. Richeldi Rifabutin for Treating Pulmonary Tuberculosis (Review) 2010 John Wiley & Sons, Ltd The Cochrane Collaboration
8. M.X. Ho, B.P. Hudson, K. Das, E. Arnold, and R.H. Ebright Structures of RNA polymerase-antibiotic complexes Curr. Opin. Struct. Biol. 19 2009 715 723
9. P. Villain-Guillot, L. Bastide, M. Gualtieri, and J.P. Leonetti Progress in targeting bacterial transcription Drug Discov. Today 12 2007 200 208
10. E.A. Campbell, N. Korzheva, A. Mustaev, K. Murakami, S. Nair, A. Goldfarb, and S.A. Darst Structural mechanism for rifampicin inhibition of bacterial RNA polymerase Cell 104 2001 901 912
11. A. Carta, M. Palomba, I. Briguglio, P. Corona, S. Piras, D. Jabes, P. Guglierame, P. Molicotti, and S. Zanetti Synthesis and anti-mycobacterial activities of triazoloquinolones Eur. J. Med. Chem. 46 2010 320 326
12. R. Weis, J. Faist, U. di Vora, K. Schweiger, B. Brandner, A.J. Kungl, and W. Seebacher Antimycobacterial activity of diphenylpyraline derivatives Eur. J. Med. Chem. 43 2008 872 879
13. M. Kumar, S. Sharma, A. Srinivasan, T.P. Singh, and P. Kaur Structure-based in-silico rational design of a selective peptide inhibitor for thymidine monophosphate kinase of Mycobacterium tuberculosis J. Mol. Model. 17 2010 1173 1182
14. P.E. Almeida da Silva, D.F. Ramos, H.G. Bonacorso, A.I. de la Iglesia, M.R. Oliveira, T. Coelho, J. Navarini, H.R. Morbidoni, N. Zanatta, and M.A. Martins Synthesis and in vitro antimycobacterial activity of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-4,5-dihydro-1H-1-(isonicotinoyl) pyrazoles Int. J. Antimicrob. Agents 32 2008 139 144
15. J. Barluenga, F. Aznar, A.B. Garcia, M.P. Cabal, J.J. Palacios, and M.A. Menendez New rifabutin analogs: synthesis and biological activity against Mycobacterium tuberculosis Bioorg. Med. Chem. Lett. 16 2006 5717 5722
16. R. Figueiredo, C. Moiteiro, M.A. Medeiros, P.A. da Silva, D. Ramos, F. Spies, M.O. Ribeiro, M.C. Lourenco, I.N. Junior, M.M. Gaspar, M.E. Cruz, M.J. Curto, S.G. Franzblau, H. Orozco, D. Aguilar, R. Hernandez-Pando, and M.C. Costa Synthesis and evaluation of rifabutin analogs against Mycobacterium avium and H(37)Rv, MDR and NRP Mycobacterium tuberculosis Bioorg. Med. Chem. 17 2009 503 511
17. S.L. Moghazeh, X. Pan, T. Arain, C.K. Stover, J.M. Musser, and B.N. Kreiswirth Comparative antimycobacterial activities of rifampin, rifapentine, and KRM-1648 against a collection of rifampin-resistant Mycobacterium tuberculosis isolates with known rpoB mutations Antimicrob. Agents Chemother. 40 1996 2655 2657
18. L. Cellai, S. Cerrini, A. Segre, M. Brufani, W. Fedeli, and A. Vaciago Comparative study of the conformations of rifamycins in solution and in the solid state by proton nuclear magnetic resonance and X-rays J. Org. Chem. 47 13 1982 2652 2661
19. K. Arora Correlation of structure and activity in ansamycins: structure, conformation, and interactions of antibiotic rifamycin S J. Med. Chem. 28 8 1985 1099 1102
20. L. Santos, F. Fant, M.A. Medeiros, F.A.M. Borremans, M.C. Costa, and M.J.M. Curto Structural characterization by NMR of rifabutinol, a derivative of rifabutin Magn. Reson. Chem. 38 11 2000 937 945
21. A.R. Leach, V.J. Villet, R.A. Lewis, and R. Taylor Three-dimensional pharmacophore methods in drug discovery J. Med. Chem. 53 2010 539 558
22. I. Artsimovitch, M.N. Vassylyeva, D. Svetlov, V. Svetlov, A. Perederina, N. Igarashi, N. Matsugaki, S. Wakatsuki, T.H. Tahirov, and D.G. Vassylyev Allosteric modulation of the RNA polymerase catalytic reaction is an essential component of transcription control by rifamycins Cell 122 2005 351 363
23. T. Wichelhaus, V. Schafer, V. Brade, and B. Boddinghaus Differential effect of rpoB mutations on antibacterial activities of rifampicin and KRM-1648 against Staphylococcus aureus J. Antimicrob. Chemother. 47 2001 153 156
24. 2+ to the RNA polymerase active center Proc. Natl. Acad. Sci. U S A 105 2008 14820 14825
25. J.L. Knight, V. Mekler, J. Mukhopadhyay, R.H. Ebright, and R.M. Levy Distance-restrained docking of rifampicin and rifamycin SV to RNA polymerase using systematic FRET measurements: developing benchmarks of model quality and reliability Biophys. J. 88 2 2005 925 938
26. W.J. Burman, K. Gallicano, and C. Peloquin Comparative pharmacokinetics and pharmacodynamics of the rifamycin antibacterials Clin. Pharmacokinet. 40 2001 327 341
27. L.J. Gonzalez-Montaner, S. Natal, P. Yongchaiyuud, and P. Olliaro Rifabutin for the treatment of newly-diagnosed pulmonary tuberculosis: a multinational, randomized, comparative study versus rifampicina Tuber. Lung. Dis. 75 5 1994 341 347
28. G. Cocchiara, M.S. Benedetti, G.P. Vicario, M. Ballabio, B. Gioia, S. Vioglio, and A. Vigevani Urinary metabolites of rifabutin, a new antimycobacterial agent, in human volunteers Xenobiotica 19 1989 769 780
29. J.C. Palomino, A. Martin, M. Camacho, H. Guerra, J. Swings, and F. Portaels Resazurin microtiter assay plate: simple and inexpensive method for detection of drug resistance in Mycobacterium tuberculosis Antimicrob. Agents Chemother. 46 2002 2720 2722
30. J.D. van Embden, M.D. Cave, J.T. Crawford, J.W. Dale, K.D. Eisenach, B. Gicquel, P. Hermans, C. Martin, R. McAdam, and T.M. Shinnick Strain identification of Mycobacterium tuberculosis by DNA fingerprinting: recommendations for a standardized methodology J. Clin. Microbiol. 31 1993 406 409
31. A. Telenti, A.P. Imboden, F. Marchesi, D. Lowrie, S. Cole, M.J. Colston, L. Matter, K. Schopfer, and T. Bodmer Detection of rifampicin-resistance mutations in Mycobacterium tuberculosis Lancet 341 1993 647 650
32. R. Hernandez-Pando, H. Orozco, K. Arriaga, A. Sampieri, J. Larriva-Sahd, and V. Madrid-Marina Analysis of the local kinetics and localization of interleukin-1 alpha, tumour necrosis factor-alpha and transforming growth factor-beta, during the course of experimental pulmonary tuberculosis Immunology 90 1997 607 617
33. J.L. Jarnagin, and D.W. Luchsinger The use of fluorescein diacetate and ethidium bromide as a stain for evaluating viability of mycobacteria Stain. Technol. 55 1980 253 258
34. B.P. Kelly, S.K. Furney, M.T. Jessen, and I.M. Orme Low-dose aerosol infection model for testing drugs for efficacy against Mycobacterium tuberculosis Antimicrob. Agents Chemother. 40 1996 2809 2812
35. G. Aslan, S. Tezcan, M.S. Serin, and G. Emekdas Genotypic analysis of isoniazid and rifampin resistance in drug-resistant clinical Mycobacterium tuberculosis complex isolates in Southern Turkey Jpn. J. Infect. Dis. 61 2008 255 260
36. B. Yang, H. Koga, H. Ohno, K. Ogawa, M. Fukuda, Y. Hirakata, S. Maesaki, K. Tomono, T. Tashiro, and S. Kohno Relationship between antimycobacterial activities of rifampicin, rifabutin and KRM-1648 and rpoB mutations of Mycobacterium tuberculosis J. Antimicrob. Chemother. 42 1998 621 628
37. R.M. Anthony, A.R. Schuitema, I.L. Bergval, T.J. Brown, L. Oskam, and P.R. Klatser Acquisition of rifabutin resistance by a rifampicin resistant mutant of Mycobacterium tuberculosis involves an unusual spectrum of mutations and elevated frequency Ann. Clin. Microbiol. Antimicrob. 4 2005 9 (1-8)
38. C. Cavusoglu, Y. Karaca-Derici, and A. Bilgic In-vitro activity of rifabutin against rifampicin-resistant Mycobacterium tuberculosis isolates with known rpoB mutations Clin. Microbiol. Infect. 10 2004 662 665
39. N. Gonzalez, N.M.J. Torres, J.C. Palomares, and J. Aznar Characterization of the rpoB gene mutations in clinical isolates of rifampicin-resistant Mycobacterium tuberculosis Enferm. Infect. Microbiol. Clin. 16 1998 404 407
40. D.M. Spindola, A. Kritski, I. Filliol, C. Mabilat, G. Panteix, and E. Drouet Mutations in the rpoB gene of rifampicin-resistant Mycobacterium tuberculosis strains isolated in Brazil and France Mem. Inst. Oswaldo. Cruz. 96 2001 247 250
41. L. Santos, M.A. Medeiros, S. Santos, M.C. Costa, R. Tavares, and M.J.M. Curto NMR studies of some rifamycins J. Mol. Struct. 563-564 2001 61 78
42. S. Yoshida, K. Suzuki, K. Tsuyuguchi, M. Tomita, M. Okada, and M. Sakatani Comparison of rifabutin susceptibility and rpoB mutations in multi-drug-resistant Mycobacterium tuberculosis strains by DNA sequencing and the line probe assay J. Infect. Chemother. 16 5 2010 360 363
43. V. Sintchenko, W.K. Chew, P.J. Jelfs, and G.L. Gilbert Mutations in rpoB gene and rifabutin susceptibility of multidrug-resistant Mycobacterium tuberculosis strains isolated in Australia Pathology 31 1999 257 260
44. H.J. Boehm, S. Brode, U. Hesse, and G. Klebe Oxygen and nitrogen in competitive situations: which is the hydrogen-bond acceptor? Chem. - Eur. J. 2 1996 1509 1513
45. Y. Jin, S.K. Gill, P.D. Kirchhoff, B. Wand, S.G. Franzblau, G.A. Garcia, and H.D.H. Showalter Bioorg. Med. Chem. Lett. 21 2011 6094 6099