Inhibitors of aminoglycoside resistance activated in cells

ACS Chemical Biology

Volumn 7, Issue 3, 2012, Pages 470-475

  Vong, Kenward ^a   Tam, Ingrid S ^a   Yan, Xuxu ^a   Auclair, Karine ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLTRANSFERASE; AMINOGLYCOSIDE ANTIBIOTIC AGENT; COENZYME A; KANAMYCIN A; PANTETHEINE;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL CELL; BACTERIAL STRAIN; DRUG SYNTHESIS; ENTEROCOCCUS FAECIUM; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL;

ACETYLTRANSFERASES; AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; COENZYME A; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG RESISTANCE, BACTERIAL; ENTEROCOCCUS FAECIUM; KANAMYCIN; PANTETHEINE; PRODRUGS; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS); ENTEROCOCCUS FAECIUM;

EID: 84858643163     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb200366u     Document Type: Article

References (26)

1. Wright, G. D., Berghuis, A. M., and Mobashery, S. (1998) Aminoglycoside Antibiotics: Structures, Functions, and Resistance, in Resolving the Antibiotic Paradox (Rosen, B. P. and Mobashery, S., Ed.), pp 27-69, Kluwer Academic/Plenum, New York.
2. Vakulenko, S. B. and Mobashery, S. (2003) Versatility of aminoglycosides and prospects for their future Clin. Microbiol. Rev. 16, 430-450 (Pubitemid 36871315)
3. Kotra, L. P., Haddad, J., and Mobashery, S. (2000) Aminoglycosides: perspectives on mechanisms of action and resistance and strategies to counter resistance Antimicrob. Agents Chemother. 44, 3249-3256 (Pubitemid 33009480)
4. Davies, J. and Wright, G. D. (1997) Bacterial resistance to aminoglycoside antibiotics Trends Microbiol. 5, 234-240 (Pubitemid 27348681)
5. Wright, G. D. (1999) Aminoglycoside-modifying enzymes Curr. Opin. Microbiol. 2, 499-503 (Pubitemid 29477176)
6. Shakya, T. and Wright, G. D. (2007) Mechanisms of Aminoglycoside Antibiotic Resistance, in Aminoglycoside Antibiotics: From Chemical Biology to Drug Discovery (Arya, D. P., Ed.), pp 119-140, John Wiley & Sons, Inc., New Jersey.
7. Gao, F., Yan, X., Baettig, O. M., Berghuis, A. M., and Auclair, K. (2005) Regio- and chemoselective 6′-N-derivatization of amino-glycosides: Bisubstrate inhibitors as probes to study aminoglycoside 6′-N- acetyltransferase Angew. Chem., Int. Ed. 44, 6859-6862 (Pubitemid 41546528)
8. Gao, F., Yan, X., Zahr, O., Larsen, A., Vong, K., and Auclair, K. (2008) Synthesis and use of sulfonamide-, sulfoxide-, or sulfone-containing aminoglycoside-CoA bisubstrates as mechanistic probes for aminoglycoside N-6′-acetyltransferase Bioorg. Med. Chem. Lett. 18, 5518-5522
9. Gao, F., Yan, X., and Auclair, K. (2009) Synthesis of a phosphonate-linked aminoglycoside-coenzyme A bisubstrate and use in mechanistic studies of an enzyme involved in aminoglycoside resistance Chem.-Eur. J. 15, 2064-2070
10. Magalhaes, M. L. B., Vetting, M. W., Gao, F., Freiburger, L., Auclair, K., and Blanchard, J. S. (2008) Kinetic and structural analysis of bisubstrate inhibition of the Salmonella enterica aminoglycoside 6′-N- acetyltransferase Biochemistry 47, 579-584 (Pubitemid 351195429)
11. Gao, F., Yan, X., Shakya, T., Baettig, O. M., Ait-Mohand-Brunet, S., Berghuis, A. M., Wright, G. D., and Auclair, K. (2006) Synthesis and structure-activity relationships of truncated bisubstrate inhibitors of aminoglycoside 6′-N-acetyltransferases J. Med. Chem. 49, 5273-5281 (Pubitemid 44260222)
12. Mishra, P. K. and Drueckhammer, D. G. (2000) Coenzyme A analogues and derivatives: Synthesis and applications as mechanistic probes of coenzyme A ester-utilizing enzymes Chem. Rev. 100, 3283-3309
13. Begley, T. P., Kinsland, C., and Strauss, E. (2001) The biosynthesis of coenzyme A in bacteria Vitam. Horm. 61, 157-171 (Pubitemid 33805694)
14. Vallari, D. S. and Rock, C. O. (1985) Pantothenate transport in Escherichia coli J. Bacteriol. 162, 1156-1161 (Pubitemid 15012276)
15. Jackowski, S. and Rock, C. O. (1984) Metabolism of 4′- phosphopantetheine in Escherichia coli J. Bacteriol. 158, 115-120
16. Strauss, E. and Begley, T. P. (2002) The antibiotic activity of N-pentylpantothenamide results from its conversion to ethyldethia-coenzyme A, a coenzyme A antimetabolite J. Biol. Chem. 277, 48205-48209 (Pubitemid 35470771)
17. Meier, J. L., Mercer, A. C., Rivera, H., Jr., and Burkart, M. D. (2006) Synthesis and evaluation of bioorthogonal pantetheine analogues for in vivo protein modification J. Am. Chem. Soc. 128, 12174-12184 (Pubitemid 44413849)
18. Clarke, K. M., Mercer, A. C., La Clair, J. J., and Burkart, M. D. (2005) In vivo reporter labeling of proteins via metabolic delivery of coenzyme A analogues J. Am. Chem. Soc. 127, 11234-11235 (Pubitemid 41176871)
19. Song, W. J. and Jackowski, S. (1992) Cloning, sequencing, and expression of the pantothenate kinase (coaA) gene of Escherichia coli J. Bacteriol. 174, 6411-6417
20. Geerlof, A., Lewendon, A., and Shaw, W. V. (1999) Purification and characterization of phosphopantetheine adenylyltransferase from Escherichia coli J. Biol. Chem. 274, 27105-27111
21. Mishra, P. K., Park, P. K., and Drueckhammer, D. G. (2001) Identification of yacE (coaE) as the structural gene for dephosphocoenzyme A kinase in Escherichia coli K-12 J. Bacteriol. 183, 2774-2778 (Pubitemid 32319279)
22. Murray, B. E. (1990) The life and times of the Enterococcus Clin. Microbiol. Rev. 3, 46-65 (Pubitemid 20078774)
23. Jackowski, S. and Rock, C. O. (1981) Regulation of coenzyme A biosynthesis J. Bacteriol. 148, 926-932 (Pubitemid 12178526)
24. Davies, J. and Davies, D. (2010) Origins and evolution of antibiotic resistance Microbiol. Mol. Biol. Rev. 74, 417-433
25. Nazi, I., Koteva, K. P., and Wright, G. D. (2004) One-pot chemoenzymatic preparation of coenzyme A analogues Anal. Biochem. 324, 100-105 (Pubitemid 37491129)
26. Worthington, A. S. and Burkart, M. D. (2006) One-pot chemo-enzymatic synthesis of reporter-modified proteins Org. Biomol. Chem. 4, 44-46