1H and13C NMR characterization of pyridinium-type isoniazid-NAD adducts as possible inhibitors of InhA reductase of Mycobacterium tuberculosis

Organic and Biomolecular Chemistry

Volumn 3, Issue 4, 2005, Pages 670-673

  Broussy, Sylvain ^a   Bernardes Génisson, Vania ^a   Coppel, Yannick ^a   Quémard, Annaïk ^b   Bernadou, Jean ^a   Meunier, Bernard ^a  

^a CNRS   (France)

^b INSTITUT DE PHARMACOLOGIE ET DE BIOLOGIE STRUCTURALE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; CHARACTERIZATION; CHEMOTHERAPY; DRUG PRODUCTS; ENZYME INHIBITION; FATTY ACIDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EPIMERIC STRUCTURES; MYCOBACTERIUM TUBERCULOSIS; PYRIDINIUM; REDUCTASE;

NITROGEN COMPOUNDS;

MYCOBACTERIUM; MYCOBACTERIUM TUBERCULOSIS;

ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; DRUG DERIVATIVE; INHA PROTEIN, MYCOBACTERIUM; ISONIAZID; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXIDOREDUCTASE; PYRIDINIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; METABOLISM; MYCOBACTERIUM TUBERCULOSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; ISONIAZID; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; NAD; OXIDOREDUCTASES; PYRIDINIUM COMPOUNDS; STEREOISOMERISM;

EID: 14544285436     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417698g     Document Type: Article

References (21)

1. K. Bartmann, H. Iwainski, H. H. Kleeberg, P. Mison, H. H. Offe, H. Ottea, D. Tettenborn, L. Trnka, in Antituberculosis drugs, ed. K. Bartmann, Springer-Verlag, Berlin, 1988.
2. J. S. Blanchard, Annu. Rev. Biochem., 1996, 65, 215-239.
3. B. K. Sinha, J. Biol. Chem., 1983, 258, 796-801.
4. Y. Zhang, B. Heym, B. Allen, D. Young and S. Cole, Nature, 1992, 358, 591-593.
5. K. Johnsson and P. G. Schultz, J. Am. Chem. Soc., 1994, 116, 7425-7426.
6. K. Johnsson, D. S. King and P. G. Schultz, J. Am. Chem. Soc., 1995, 117, 5009-5010.
7. D. A. Rozwarski, G. A. Grant, D. H. R. Barton, W. R. Jacobs Jr. and J. C. Sacchettini, Science, 1998, 279, 98-102.
8. M. Wilming and K. Johnsson, Angew. Chem., Int. Ed., 1999, 38, 2588-2590.
9. M. Nguyen, C. Claparols, J. Bernadou and B. Meunier, Chem-BioChem, 2001, 2, 877-883.
10. S. Broussy, Y. Coppel, M. Nguyen, J. Bernadou and B. Meunier, Chem. Eur. J., 2003, 9, 2034-2038.
11. S. Ducasse-Cabanot, M. Cohen-Gonsaud, H. Marrakchi, M. Nguyen, D. Zerbib, J. Bernadou, M. Daffe, G. Labesse and A. Quémard, Antimicrob. Agents Chemother., 2004, 48, 242-249.
12. A. Banerjee, E. Dubnau, A. Quémard, V. Balasubramanian, K. Sun Um, T. Wilson, D. Collins, G. de Lisle and W. R. Jacobs Jr., Science, 1994, 263, 227-230.
13. A. Quémard, A. Dessen, M. Sugantino, W R. Jacobs Jr., J. C. Sacchetini and J. S. Blanchard, J. Am. Chem. Soc., 1996, 118, 1561-1562.
14. K. Takayama, L. Wang and H. L. David, Antimicrob. Agents Chemother., 1972, 2, 29-35.
15. A. Quémard, C. Lacave and G. Lanéelle, Antimicrob. Agents Chemother., 1991, 35, 1035-1039.
16. C. Vilchèze, H. R. Morbidoni, T. R. Weisbrud, H. Iwamoto, M. Kuo, J. C. Sacchettini and W. R. Jacobs Jr., J. Bacterial., 2000, 182, 4059-4067.
17. B. Lei, C.-J. Wei and S.-C. Tu, J. Biol. Chem., 2000, 275, 2520-2526.
18. R. Rawat, A. Whitty and P. J. Tonge, Proc. Natl. Acad. Sci. U. S. A., 2003, 100, 13881-13886.
19. M. Nguyen, A. Quémard, S. Broussy, J. Bernadou and B. Meunier, Antimicrob. Agents Chemother., 2002, 46, 2137-2143.
20. S. Broussy, V. Bernardes-Génisson, H. Gornitzka, J. Bernadou and B. Meunier, Org. Biomol. Chem., 2005, DOI:10.1039/b415439h.
21. A. Quémard, J. C. Sacchettini, A. Dessen, C. Vilcheze, R. Bittman, W. R. Jacobs Jr. and J. S. Blanchard, Biochemistry, 1995, 34, 8235-8241.