Plazomicin Retains Antibiotic Activity against Most Aminoglycoside Modifying Enzymes

ACS Infectious Diseases

Volumn 4, Issue 6, 2018, Pages 980-987

  Cox, Georgina ^a   Ejim, Linda ^a   Stogios, Peter J ^b   Koteva, Kalinka ^a   Bordeleau, Emily ^a   Evdokimova, Elena ^b   Sieron, Arthur O ^a   Savchenko, Alexei ^b,c   Serio, Alisa W ^d   Krause, Kevin M ^d   Wright, Gerard D ^a  

^a MCMASTER UNIVERSITY   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c UNIVERSITY OF CALGARY   (Canada)

^d Achaogen   (United States)

Author keywords

aminoglycoside modifying enzymes; antibiotic resistance; Enterobacteriaceae; plazomicin

Indexed keywords

AMINOGLYCOSIDE ACYLTRANSFERASE; AMINOGLYCOSIDE DERIVATIVE; AMINOGLYCOSIDE MODIFYING ENZYME; AMINOGLYCOSIDE PHOSPHOTRANSFERASE; BACTERIAL ENZYME; METHYLTRANSFERASE; PHOSPHOTRANSFERASE; PLAZOMICIN; RNA 16S; SISOMICIN; UNCLASSIFIED DRUG; 6'-(HYDROXYLETHYL)-1-(HABA)-SISOMICIN; ACYLTRANSFERASE; AMINOGLYCOSIDE; AMINOGLYCOSIDE ACETYLTRANSFERASE; ANTIINFECTIVE AGENT;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIBIOTIC SENSITIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CHEMICAL MODIFICATION; COMPLEX FORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG STRUCTURE; ENTEROBACTERIACEAE; ENTEROCOCCUS; ENZYME SUBSTRATE; ESCHERICHIA COLI; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROVIDENCIA STUARTII; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; ENZYMOLOGY; HUMAN; MASS SPECTROMETRY; METABOLISM; MICROBIAL SENSITIVITY TEST; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION;

ACETYLTRANSFERASES; AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; ESCHERICHIA COLI; HUMANS; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SISOMICIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 85048305151     PISSN: None     EISSN: 23738227     Source Type: Journal    
DOI: 10.1021/acsinfecdis.8b00001     Document Type: Article

References (33)

1. Brown, E. D. and Wright, G. D. (2016) Antibacterial drug discovery in the resistance era. Nature 529 (7586), 336-343, 10.1038/nature17042
2. Pawlowski, A. C., Johnson, J. W., and Wright, G. D. (2016) Evolving medicinal chemistry strategies in antibiotic discovery. Curr. Opin. Biotechnol. 42, 108-117, 10.1016/j.copbio.2016.04.006
3. Garneau-Tsodikova, S. and Labby, K. J. (2016) Mechanisms of Resistance to Aminoglycoside Antibiotics: Overview and Perspectives. MedChemComm 7 (1), 11-27, 10.1039/C5MD00344J
4. Armstrong, E. S. and Miller, G. H. (2010) Combating evolution with intelligent design: the neoglycoside ACHN-490. Curr. Opin. Microbiol. 13 (5), 565-573, 10.1016/j.mib.2010.09.004
5. Bacot-Davis, V. R., Bassenden, A. V., and Berghuis, A. M. (2016) Drug-target networks in aminoglycoside resistance: hierarchy of priority in structural drug design. MedChemComm 7 (1), 103-113, 10.1039/C5MD00384A
6. Shaw, K. J., Rather, P. N., Hare, R. S., and Miller, G. H. (1993) Molecular genetics of aminoglycoside resistance genes and familial relationships of the aminoglycoside-modifying enzymes. Microbiol. Rev. 57 (1), 138-163
7. Wright, G. D. (1999) Aminoglycoside-modifying enzymes. Curr. Opin. Microbiol. 2 (5), 499-503, 10.1016/S1369-5274(99)00007-7
8. Ramirez, M. S. and Tolmasky, M. E. (2010) Aminoglycoside modifying enzymes. Drug Resist. Updates 13 (6), 151-171, 10.1016/j.drup.2010.08.003
9. Liou, G. F., Yoshizawa, S., Courvalin, P., and Galimand, M. (2006) Aminoglycoside resistance by ArmA-mediated ribosomal 16S methylation in human bacterial pathogens. J. Mol. Biol. 359 (2), 358-364, 10.1016/j.jmb.2006.03.038
10. Perichon, B., Courvalin, P., and Galimand, M. (2007) Transferable resistance to aminoglycosides by methylation of G1405 in 16S rRNA and to hydrophilic fluoroquinolones by QepA-mediated efflux in Escherichia coli. Antimicrob. Agents Chemother. 51 (7), 2464-2469, 10.1128/AAC.00143-07
11. Doi, Y., Wachino, J. I., and Arakawa, Y. (2016) Aminoglycoside Resistance: The Emergence of Acquired 16S Ribosomal RNA Methyltransferases. Infect. Dis. Clin. North. Am. 30 (2), 523-537, 10.1016/j.idc.2016.02.011
12. Husain, N., Obranic, S., Koscinski, L., Seetharaman, J., Babic, F., Bujnicki, J. M., Maravic-Vlahovicek, G., and Sivaraman, J. (2011) Structural basis for the methylation of A1408 in 16S rRNA by a panaminoglycoside resistance methyltransferase NpmA from a clinical isolate and analysis of the NpmA interactions with the 30S ribosomal subunit. Nucleic Acids Res. 39 (5), 1903-1918, 10.1093/nar/gkq1033
13. Wachino, J., Shibayama, K., Kurokawa, H., Kimura, K., Yamane, K., Suzuki, S., Shibata, N., Ike, Y., and Arakawa, Y. (2007) Novel plasmid-mediated 16S rRNA m1A1408 methyltransferase, NpmA, found in a clinically isolated Escherichia coli strain resistant to structurally diverse aminoglycosides. Antimicrob. Agents Chemother. 51 (12), 4401-4409, 10.1128/AAC.00926-07
14. Aggen, J. B., Armstrong, E. S., Goldblum, A. A., Dozzo, P., Linsell, M. S., Gliedt, M. J., Hildebrandt, D. J., Feeney, L. A., Kubo, A., Matias, R. D., Lopez, S., Gomez, M., Wlasichuk, K. B., Diokno, R., Miller, G. H., and Moser, H. E. (2010) Synthesis and spectrum of the neoglycoside ACHN-490. Antimicrob. Agents Chemother. 54 (11), 4636-4642, 10.1128/AAC.00572-10
15. Weinstein, M. J., Marquez, J. A., Testa, R. T., Wagman, G. H., Oden, E. M., and Waitz, J. A. (1970) Antibiotic 6640, a new Micromonospora-produced aminoglycoside antibiotic. J. Antibiot. 23 (11), 551-554, 10.7164/antibiotics.23.551
16. Cox, G., Sieron, A., King, A. M., De Pascale, G., Pawlowski, A. C., Koteva, K., and Wright, G. D. (2017) A Common Platform for Antibiotic Dereplication and Adjuvant Discovery. Cell chem. biol. 24 (1), 98-109, 10.1016/j.chembiol.2016.11.011
17. López, M. C., Picazo, J. J., Simaluiza, J. R., Rodríguez-Avial, I., and Culebras, E. (April 25-28, 2015) Plazomicin has potent in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA) isolates carrying different aminoglycoside-modifying enzymes. In ECCMID Conference Programme, Copenhagen, Denmark.
18. Shakya, T., Stogios, P. J., Waglechner, N., Evdokimova, E., Ejim, L., Blanchard, J. E., McArthur, A. G., Savchenko, A., and Wright, G. D. (2011) A small molecule discrimination map of the antibiotic resistance kinome. Chem. Biol. 18 (12), 1591-1601, 10.1016/j.chembiol.2011.10.018
19. Haidar, G., Alkroud, A., Cheng, S., Churilla, T. M., Churilla, B. M., Shields, R. K., Doi, Y., Clancy, C. J., and Nguyen, M. H. (2016) Association between the Presence of Aminoglycoside-Modifying Enzymes and In Vitro Activity of Gentamicin, Tobramycin, Amikacin, and Plazomicin against Klebsiella pneumoniae Carbapenemase- and Extended-Spectrum-beta-Lactamase-Producing Enterobacter Species. Antimicrob. Agents Chemother. 60 (9), 5208-5214, 10.1128/AAC.00869-16
20. Lopez Diaz, M. C., Rios, E., Rodriguez-Avial, I., Simaluiza, R. J., Picazo, J. J., and Culebras, E. (2017) In-vitro activity of several antimicrobial agents against methicillin-resistant Staphylococcus aureus (MRSA) isolates expressing aminoglycoside-modifying enzymes: potency of plazomicin alone and in combination with other agents. Int. J. Antimicrob. Agents 50 (2), 191-196, 10.1016/j.ijantimicag.2017.01.039
21. Lopez-Diaz, M. D., Culebras, E., Rodriguez-Avial, I., Rios, E., Vinuela-Prieto, J. M., Picazo, J. J., and Rodriguez-Avial, C. (2017) Plazomicin Activity against 346 Extended-Spectrum-beta-Lactamase/AmpC-Producing Escherichia coli Urinary Isolates in Relation to Aminoglycoside-Modifying Enzymes. Antimicrob. Agents Chemother. 61 (2), AAC.02454-16, 10.1128/AAC.02454-16
22. Macinga, D. R. and Rather, P. N. (1999) The chromosomal 2'- N-acetyltransferase of Providencia stuartii: physiological functions and genetic regulation. Front. Biosci., Landmark Ed. 4, D132-140, 10.2741/Macinga
23. Swiatlo, E. and Kocka, F. E. (1987) Inducible expression of an aminoglycoside-acetylating enzyme in Providencia stuartii. J. Antimicrob. Chemother. 19 (1), 27-30, 10.1093/jac/19.1.27
24. Payie, K. G., Rather, P. N., and Clarke, A. J. (1995) Contribution of gentamicin 2'- N-acetyltransferase to the O-acetylation of peptidoglycan in Providencia stuartii. J. Bacteriol. 177 (15), 4303-4310, 10.1128/jb.177.15.4303-4310.1995
25. Kaplan, E., Guichou, J. F., Chaloin, L., Kunzelmann, S., Leban, N., Serpersu, E. H., and Lionne, C. (2016) Aminoglycoside binding and catalysis specificity of aminoglycoside 2'-phosphotransferase IVa: A thermodynamic, structural and kinetic study. Biochim. Biophys. Acta, Gen. Subj. 1860 (4), 802-813, 10.1016/j.bbagen.2016.01.016
26. Shi, K., Houston, D. R., and Berghuis, A. M. (2011) Crystal structures of antibiotic-bound complexes of aminoglycoside 2'-phosphotransferase IVa highlight the diversity in substrate binding modes among aminoglycoside kinases. Biochemistry 50 (28), 6237-6244, 10.1021/bi200747f
27. Thompson, P. R., Boehr, D. D., Berghuis, A. M., and Wright, G. D. (2002) Mechanism of aminoglycoside antibiotic kinase APH(3′)-IIIa: role of the nucleotide positioning loop. Biochemistry 41 (22), 7001-7007, 10.1021/bi0256680
28. Tsai, S. F., Zervos, M. J., Clewell, D. B., Donabedian, S. M., Sahm, D. F., and Chow, J. W. (1998) A new high-level gentamicin resistance gene, aph(2')-Id, in Enterococcus spp. Antimicrob. Agents Chemother. 42 (5), 1229-1232
29. CLSI. (2015) Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard, Tenth ed., Document M07-A10, Clinical and Laboratory Standards Institute, Wayne, PA.
30. Kabsch, W. (2010) Xds. Acta Crystallogr., Sect. D: Biol. Crystallogr. 66 (Pt 2), 125-132, 10.1107/S0907444909047337
31. Winn, M. D., Ballard, C. C., Cowtan, K. D., Dodson, E. J., Emsley, P., Evans, P. R., Keegan, R. M., Krissinel, E. B., Leslie, A. G., McCoy, A., McNicholas, S. J., Murshudov, G. N., Pannu, N. S., Potterton, E. A., Powell, H. R., Read, R. J., Vagin, A., and Wilson, K. S. (2011) Overview of the CCP4 suite and current developments. Acta Crystallogr., Sect. D: Biol. Crystallogr. 67 (Pt 4), 235-242, 10.1107/S0907444910045749
32. Adams, P. D., Afonine, P. V., Bunkoczi, G., Chen, V. B., Davis, I. W., Echols, N., Headd, J. J., Hung, L. W., Kapral, G. J., Grosse-Kunstleve, R. W., McCoy, A. J., Moriarty, N. W., Oeffner, R., Read, R. J., Richardson, D. C., Richardson, J. S., Terwilliger, T. C., and Zwart, P. H. (2010) PHENIX: a comprehensive Python-based system for macromolecular structure solution. Acta Crystallogr., Sect. D: Biol. Crystallogr. 66 (Pt 2), 213-221, 10.1107/S0907444909052925
33. Emsley, P. and Cowtan, K. (2004) Coot: model-building tools for molecular graphics. Acta Crystallogr., Sect. D: Biol. Crystallogr. 60 (Pt 12), 2126-2132, 10.1107/S0907444904019158