Unexpected N-acetylation of capreomycin by mycobacterial Eis enzymes

Journal of Antimicrobial Chemotherapy

Volumn 68, Issue 4, 2013, Pages 800-805

  Houghton, Jacob L ^a   Green, Keith D ^a   Pricer, Rachel E ^a   Mayhoub, Abdelrahman S ^a,b   Garneau Tsodikova, Sylvie ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b Al Azhar University   (Egypt)

Author keywords

Anti tuberculosis drugs; Antibiotic resistance; Mechanisms of resistance

Indexed keywords

ACETYL AMYLOID BETA PROTEIN FRAGMENT 15 20 AMIDE; BACTERIAL ENZYME; CAPREOMYCIN; CIPROFLOXACIN; DI LYSINE; EIS PROTEIN; ISONIAZID; LISINOPRIL; LYSINE; NEUROGRANIN FRAGMENT 28 43; NISIN; PYRAZINAMIDE; TETRA LYSINE; THYMOPOIETIN II PEPTIDE FRAGMENT; THYMULIN; TRI LYSINE; TUBERCULOSTATIC AGENT; TUFTSIN; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; DRUG DETERMINATION; ENZYME INACTIVATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PREDICTOR VARIABLE; THIN LAYER CHROMATOGRAPHY;

ACETYLATION; ANTIGENS, BACTERIAL; ANTITUBERCULAR AGENTS; BACTERIAL PROTEINS; CAPREOMYCIN; MAGNETIC RESONANCE SPECTROSCOPY; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS;

EID: 84875278075     PISSN: 03057453     EISSN: 14602091     Source Type: Journal    
DOI: 10.1093/jac/dks497     Document Type: Article

References (27)

1. Campbell PJ, Morlock GP, Sikes RD et al. Molecular detection of mutations associated with first- and second-line drug resistance compared with conventional drug susceptibility testing of Mycobacterium tuberculosis. Antimicrob Agents Chemother 2011; 55: 2032-41.
2. Zaunbrecher MA, Sikes RD Jr, Metchock B et al. Overexpression of the chromosomally encoded aminoglycoside acetyltransferase eis confers kanamycin resistance in Mycobacterium tuberculosis. Proc Natl Acad Sci USA 2009; 106: 20004-9.
3. Chen W, Biswas T, Porter VR et al. Unusual regioversatility of acetyltransferase Eis, a cause of drug resistance in XDR-TB. Proc Natl Acad Sci USA 2011; 108: 9804-8.
4. Chen W, Green KD, Tsodikov OV et al. Aminoglycoside multiacetylating activity of the enhanced intracellular survival protein from Mycobacterium smegmatis and its inhibition. Biochemistry 2012; 51: 4959-67.
5. Kim KH, An DR, Song J et al. Mycobacterium tuberculosis Eis protein initiates suppression of host immune responses by acetylation of DUSP16/MKP-7. Proc Natl Acad Sci USA 2012; 109: 7729-34.
6. Pricer RE, Houghton JL, Green KD et al. Biochemical and structural analysis of aminoglycoside acetyltransferase Eis from Anabaena variabilis. Mol Biosyst 2012; 8: 3305-13.
7. Green KD, Chen W, Garneau-Tsodikova S. Identification and characterization of inhibitors of the aminoglycoside resistance acetyltransferase Eis from Mycobacterium tuberculosis. ChemMedChem2012; 7: 73-7.
8. Lella RK, Sharma C. Eis (enhanced intracellular survival) protein of Mycobacterium tuberculosis disturbs the cross regulation of T-cells. J Biol Chem 2007; 282: 18671-5.
9. Roberts EA, Clark A, Mcbeth S et al. Molecular characterization of the eis promoter of Mycobacterium tuberculosis. J Bacteriol 2004; 186: 5410-7.
10. Samuel LP, Song CH, Wei J et al. Expression, production and release of the Eis protein by Mycobacterium tuberculosis during infection of macrophages and its effect on cytokine secretion. Microbiology 2007; 153: 529-40.
11. Shin DM, Jeon BY, Lee HM et al. Mycobacterium tuberculosis Eis regulates autophagy, inflammation, and cell death through redox-dependent signaling. PLoS Pathog 2010; 6: e1001230.
12. Wei J, Dahl JL, Moulder JW et al. Identification of a Mycobacterium tuberculosis gene that enhances mycobacterial survival in macrophages. J Bacteriol 2000; 182: 377-84.
13. Vetting MW, Park CH, Hegde SS et al. Mechanistic and structural analysis of aminoglycoside N-acetyltransferase AAC(6')-Ib and its bifunctional, fluoroquinolone-active AAC(6')-Ib-cr variant. Biochemistry 2008; 47: 9825-35.
14. Verdonk ML, Cole JC, Hartshorn MJ et al. Improved protein-ligand docking using GOLD. Proteins 2003; 52: 609-23.
15. Simpson AJ, Brown SA. Purge NMR: effective and easy solvent suppression. J Magn Reson 2005; 175: 340-6.
16. Sim E, Walters K, Boukouvala S. Arylamine N-acetyltransferases: from structure to function. Drug Metab Rev 2008; 40: 479-510.
17. Georghiou SB, Magana M, Garfein RS et al. Evaluation of genetic mutations associated with Mycobacterium tuberculosis resistance to amikacin, kanamycin and capreomycin: a systematic review. PLoS One 2012; 7: e33275.
18. Skinner RH, Cundliffe E. Resistance to the antibiotics viomycin and capreomycin in the Streptomyces species which produce them. J Gen Microbiol 1980; 120: 95-104.
19. Stanley RE, Blaha G, Grodzicki RL et al. The structures of the anti-tuberculosis antibiotics viomycin and capreomycin bound to the 70S ribosome. Nat Struct Mol Biol 2010; 17: 289-93.
20. Ermolenko DN, Spiegel PC, Majumdar ZK et al. The antibiotic viomycin traps the ribosome in an intermediate state of translocation. Nat Struct Mol Biol 2007; 14: 493-7.
21. Marrero P, Cabanas MJ, Modolell J. Induction of translational errors (misreading) by tuberactinomycins and capreomycins. Biochem Biophys Res Commun 1980; 97: 1047-42.
22. Modolell J, Vazquez D. The inhibition of ribosomal translocation by viomycin. Eur J Biochem 1977; 81: 491-7.
23. Peske F, Savelsbergh A, Katunin VI et al. Conformational changes of the small ribosomal subunit during elongation factor G-dependent tRNA-mRNA translocation. J Mol Biol 2004; 343: 1183-94.
24. Nomoto S, Shiba T. Syntheses of capreomycin analogs in relation to their antibacterial activities. Bull Chem Soc Jpn 1979; 52: 1709-15.
25. Shiloh MU, Digiuseppe Champion PA. To catch a killer. What can mycobacterial models teach us about Mycobacterium tuberculosis pathogenesis? Curr Opin Microbiol 2010; 13: 86-92.
26. Tyagi JS, Sharma D. Mycobacterium smegmatis and tuberculosis. Trends Microbiol 2002; 10: 68-9.
27. Reyrat JM, Kahn D. Mycobacterium smegmatis: an absurd model for tuberculosis? Trends Microbiol 2001; 9: 472-4.