Aminoglycoside multiacetylating activity of the enhanced intracellular survival protein from Mycobacterium smegmatis and its inhibition

Biochemistry

Volumn 51, Issue 24, 2012, Pages 4959-4967

  Chen, Wenjing ^a   Green, Keith D ^a   Tsodikov, Oleg V ^a   Garneau Tsodikova, Sylvie ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL TRANSFERASE; AMINO ACID RESIDUES; AMINOGLYCOSIDES; APRAMYCIN; CHEMICAL EQUATIONS; CLINICAL ISOLATES; GAIN INSIGHT; HYGROMYCIN; INTRACELLULAR SURVIVAL; KANAMYCIN A; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; PATHOGENIC MYCOBACTERIA; STRUCTURAL ORIGIN; SUBSTRATE SELECTIVITY; UP-REGULATION;

ACETYLATION; AMINO ACIDS; TUBES (COMPONENTS);

BACTERIA;

ACYLTRANSFERASE; AMINO ACID; APRAMYCIN; BACTERIAL PROTEIN; ENHANCED INTRACELLULAR SURVIVAL PROTEIN; HYGROMYCIN; PAROMOMYCIN; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CELL SURVIVAL; CONTROLLED STUDY; DRUG ACETYLATION; DRUG SELECTIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; SEQUENCE HOMOLOGY;

ACETYLATION; AMINO ACID SEQUENCE; AMINOGLYCOSIDES; BACTERIAL PROTEINS; BINDING, COMPETITIVE; CATALYTIC DOMAIN; KINETICS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MYCOBACTERIUM SMEGMATIS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84862510111     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi3004473     Document Type: Article

References (28)

1. Caminero, J. A. (2006) Treatment of multidrug-resistant tuberculosis: Evidence and controversies. Int. J. Tuberc. Lung Dis. 10, 829-837.
2. Chan, E. D., Laurel, V., Strand, M. J., Chan, J. F., Huynh, M. L., Goble, M., and Iseman, M. D. (2004) Treatment and outcome analysis of 205 patients with multidrug-resistant tuberculosis. Am. J. Respir. Crit. Care Med. 169, 1103-1109. (Pubitemid 38624789)
3. Ellner, J. J. (2008) The emergence of extensively drug-resistant tuberculosis: A global health crisis requiring new interventions: Part I: The origins and nature of the problem. Clin. Transl. Sci. 1, 249-254.
4. Banerjee, R., Schecter, G. F., Flood, J., and Porco, T. C. (2008) Extensively drug-resistant tuberculosis: New strains, new challenges. Expert Rev. Anti-Infect. Ther. 6, 713-724.
5. Udwadia, Z. F., Amale, R. A., Ajbani, K. K., and Rodrigues, C. (2012) Totally drug-resistant tuberculosis in India. Clin. Infect. Dis. 54, 579-581.
6. Shiloh, M. U., and DiGiuseppe Champion, P. A. (2010) To catch a killer. What can mycobacterial models teach us about Mycobacterium tuberculosis pathogenesis? Curr. Opin. Microbiol. 13, 86-92.
7. Reyrat, J. M., and Kahn, D. (2001) Mycobacterium smegmatis: An absurd model for tuberculosis? Trends Microbiol. 9, 472-474.
8. Tyagi, J. S., and Sharma, D. (2002) Mycobacterium smegmatis and tuberculosis. Trends Microbiol. 10, 68-69. (Pubitemid 34119341)
9. Cole, S. T., Brosch, R., Parkhill, J., Garnier, T., Churcher, C., Harris, D., Gordon, S. V., Eiglmeier, K., Gas, S., Barry, C. E., III, Tekaia, F., Badcock, K., Basham, D., Brown, D., Chillingworth, T., Connor, R., Davies, R., Devlin, K., Feltwell, T., Gentles, S., Hamlin, N., Holroyd, S., Hornsby, T., Jagels, K., Krogh, A., McLean, J., Moule, S., Murphy, L., Oliver, K., Osborne, J., Quail, M. A., Rajandream, M. A., Rogers, J., Rutter, S., Seeger, K., Skelton, J., Squares, R., Squares, S., Sulston, J. E., Taylor, K., Whitehead, S., and Barrell, B. G. (1998) Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. Nature 393, 537-544. (Pubitemid 28319235)
10. Fleischmann, R. D., Alland, D., Eisen, J. A., Carpenter, L., White, O., Peterson, J., DeBoy, R., Dodson, R., Gwinn, M., Haft, D., Hickey, E., Kolonay, J. F., Nelson, W. C., Umayam, L. A., Ermolaeva, M., Salzberg, S. L., Delcher, A., Utterback, T., Weidman, J., Khouri, H., Gill, J., Mikula, A., Bishai, W., Jacobs, W. R., Jr., Venter, J. C., and Fraser, C. M. (2002) Whole-genome comparison of Mycobacterium tuberculosis clinical and laboratory strains. J. Bacteriol. 184, 5479-5490. (Pubitemid 35024395)
11. Zaunbrecher, M. A., Sikes, R. D., Jr., Metchock, B., Shinnick, T. M., and Posey, J. E. (2009) Overexpression of the chromosomally encoded aminoglycoside acetyltransferase eis confers kanamycin resistance in Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. U.S.A. 106, 20004-20009.
12. Wei, J., Dahl, J. L., Moulder, J. W., Roberts, E. A., O'Gaora, P., Young, D. B., and Friedman, R. L. (2000) Identification of a Mycobacterium tuberculosis gene that enhances mycobacterial survival in macrophages. J. Bacteriol. 182, 377-384. (Pubitemid 30030121)
13. Chen, W., Biswas, T., Porter, V. R., Tsodikov, O. V., and Garneau-Tsodikova, S. (2011) Unusual regioversatility of acetyltransferase Eis, a cause of drug resistance in XDR-TB. Proc. Natl. Acad. Sci. U.S.A. 108, 9804-9808.
14. Green, K. D., Chen, W., and Garneau-Tsodikova, S. (2012) Identification and characterization of inhibitors of the aminoglycoside resistance acetyltransferase Eis from Mycobacterium tuberculosis. ChemMedChem 7, 73-77.
15. Green, K. D., Chen, W., Houghton, J. L., Fridman, M., and Garneau-Tsodikova, S. (2010) Exploring the substrate promiscuity of drug-modifying enzymes for the chemoenzymatic generation of N-acylated aminoglycosides. ChemBioChem 11, 119-126.
16. O'Connor, S., Lam, L. K. T., Jones, N. D., and Chaney, M. O. (1976) Apramycin, a unique aminocyclitol antibiotic. J. Org. Chem. 41, 2087-2092.
17. 13C NMR assignments and study of the solution conformation by ROESY measurements. Magn. Reson. Chem. 30, 107-117.
18. Williams, J. W., and Northrop, D. B. (1978) Kinetic mechanisms of gentamicin acetyltransferase I. Antibiotic-dependent shift from rapid to nonrapid equilibrium random mechanisms. J. Biol. Chem. 253, 5902-5907. (Pubitemid 9014221)
19. Magnet, S., Lambert, T., Courvalin, P., and Blanchard, J. S. (2001) Kinetic and mutagenic characterization of the chromosomally encoded Salmonella enterica AAC(6′)-Iy aminoglycoside N-acetyl-transferase. Biochemistry 40, 3700-3709. (Pubitemid 32242828)
20. Magalhaes, M. L., and Blanchard, J. S. (2005) The kinetic mechanism of AAC3-IV aminoglycoside acetyltransferase from Escherichia coli. Biochemistry 44, 16275-16283. (Pubitemid 41785826)
21. Martel, A., Masson, M., Moreau, N., and Le Goffic, F. (1983) Kinetic studies of aminoglycoside acetyltransferase and phosphotransferase from Staphylococcus aureus RPAL. Relationship between the two activities. Eur. J. Biochem. 133, 515-521. (Pubitemid 13060120)
22. Hegde, S. S., Javid-Majd, F., and Blanchard, J. S. (2001) Overexpression and mechanistic analysis of chromosomally encoded aminoglycoside 2′-N-acetyltransferase (AAC(2′)-Ic) from Mycobacterium tuberculosis. J. Biol. Chem. 276, 45876-45881.
23. Kim, C., Villegas-Estrada, A., Hesek, D., and Mobashery, S. (2007) Mechanistic characterization of the bifunctional aminoglycoside- modifying enzyme AAC(3)-Ib/AAC(6′)-Ib′ from Pseudomonas aeruginosa. Biochemistry 46, 5270-5282. (Pubitemid 46683023)
24. Kim, C., Hesek, D., Zajicek, J., Vakulenko, S. B., and Mobashery, S. (2006) Characterization of the bifunctional aminoglycosidemodifying enzyme ANT(3″)-Ii/AAC(6′)-IId from Serratia marcescens. Biochemistry 45, 8368-8377. (Pubitemid 44036543)
25. Draker, K. A., Northrop, D. B., and Wright, G. D. (2003) Kinetic mechanism of the GCN5-related chromosomal aminoglycoside acetyltransferase AAC(6′)-Ii from Enterococcus faecium: Evidence of dimer subunit cooperativity. Biochemistry 42, 6565-6574. (Pubitemid 36665832)
26. Han, Q., Zhao, Q., Fish, S., Simonsen, K. B., Vourloumis, D., Froelich, J. M., Wall, D., and Hermann, T. (2005) Molecular recognition by glycoside pseudo base pairs and triples in an apramycin-RNA complex. Angew. Chem., Int. Ed. 44, 2694-2700. (Pubitemid 40689568)
27. Hermann, T., Tereshko, V., Skripkin, E., and Patel, D. J. (2007) Apramycin recognition by the human ribosomal decoding site. Blood Cells, Mol., Dis. 38, 193-198. (Pubitemid 46518168)
28. Kondo, J., Francois, B., Urzhumtsev, A., and Westhof, E. (2006) Crystal structure of the Homo sapiens cytoplasmic ribosomal decoding site complexed with apramycin. Angew. Chem., Int. Ed. 45, 3310-3314. (Pubitemid 44098997)