Structure-Function Relationships of Class D Carbapenemases

Current Drug Targets

Volumn 17, Issue 9, 2016, Pages 1061-1071

  Docquier, Jean Denis ^a   Mangani, Stefano ^a  

^a UNIVERSITY OF SIENA   (Italy)

Author keywords

Acinetobacter baumannii; Antibiotic resistance; Beta lactamases; Carbapenems; Klebsiella pneumoniae

Indexed keywords

CARBAPENEMASE; CEFTAZIDIME; CEPHALOSPORIN; CEPHALOSPORIN DERIVATIVE; CLAVULANIC ACID; METALLO BETA LACTAMASE; MONOBACTAM DERIVATIVE; PENICILLIN DERIVATIVE; SULBACTAM; TAZOBACTAM; BACTERIAL PROTEIN; BETA LACTAMASE; BETA LACTAMASE INHIBITOR;

AMINO ACID SEQUENCE; ANTIBIOTIC RESISTANCE; ANTIBIOTIC SENSITIVITY; ARTICLE; BACTERIAL TRANSMISSION; BURKHOLDERIA MULTIVORANS; COMMUNICABLE DISEASE; ENTEROBACTER CLOACAE; FRANCISELLA PHILOMIRAGIA; FRANCISELLA TULARENSIS; GENETIC VARIABILITY; HOSPITAL INFECTION; KLEBSIELLA PNEUMONIAE; MELIOIDOSIS; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR MODEL; MUTAGENESIS; PHYLOGENY; PSEUDOMONAS FLUORESCENS; PULSED FIELD GEL ELECTROPHORESIS; SERRATIA MARCESCENS; SITE DIRECTED MUTAGENESIS; STRUCTURE ACTIVITY RELATION; CHEMISTRY; CLASSIFICATION; DRUG EFFECTS; ENZYME ACTIVE SITE; GENETICS; HUMAN; METABOLISM; MUTATION; PROTEIN CONFORMATION; X RAY CRYSTALLOGRAPHY;

BACTERIAL PROTEINS; BETA-LACTAM RESISTANCE; BETA-LACTAMASE INHIBITORS; BETA-LACTAMASES; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; HUMANS; MODELS, MOLECULAR; MUTATION; PHYLOGENY; PROTEIN CONFORMATION;

EID: 84973662261     PISSN: 13894501     EISSN: 18735592     Source Type: Journal    
DOI: 10.2174/1389450116666150825115824     Document Type: Article

References (44)

1. Docquier JD, Cusi MG. Editorial overview: anti-infectives: towards novel antiviral and antibacterial drugs? Current approaches to address a growing medical need. Curr Opin Pharmacol 2014; 18: iv-vi.
2. Livermore DM. Tigecycline: what is it, and where should it be used? J Antimicrob Chemother 2005; 56(4): 611-4.
3. Lyon JA. Imipenem/cilastatin: the first carbapenem antibiotic. Drug Intell Clin Pharm 1985; 19(12): 895-9.
4. McKenna M. Antibiotic resistance: the last resort. Nature 2013, 499(7459): 394-6.
5. Munoz-Price LS, Poirel L, Bonomo RA, et al. Clinical epidemiology of the global expansion of Klebsiella pneumoniae carbapenemases. Lancet Infect Dis 2013; 13(9): 785-96.
6. Nordmann P, Naas T, Poirel L. Global spread of Carbapenemaseproducing Enterobacteriaceae. Emerg Infect Dis 2011; 17(10): 1791-8.
7. Bush, K. The ABCD's of β-lactamase nomenclature. J Infect Chemother 2013, 19(4) 549-59.
8. Evans BA, Amyes SG. OXA β-lactamases. Clin Microbiol Rev 2014; 27(2): 241-63.
9. Poirel L, Potron A, Nordmann P. OXA-48-like carbapenemases: the phantom menace. J Antimicrob Chemother 2012, 67(7): 1597-1606.
10. Potron A, Poirel L, Nordmann P. Emerging broad-spectrum resistance in Pseudomonas aeruginosa and Acinetobacter baumannii: Mechanisms and epidemiology. Int J Antimicrob Agents 2015; 45(6): 568-85.
11. Nordmann P, Poirel L. The difficult-to-control spread of carbapenemase producers among Enterobacteriaceae worldwide. Clin Microbiol Infect 2014; 20(9): 821-30.
12. Bou G, Cerveró G, Domínguez MA, Quereda C, Martínez-Beltrán J. Characterization of a nosocomial outbreak caused by a multiresistant Acinetobacter baumannii strain with a carbapenemhydrolyzing enzyme: high-level carbapenem resistance in A. baumannii is not due solely to the presence of beta-lactamases. J Clin Microbiol 2000; 38(9): 3299-305.
13. Héritier C, Poirel L, Aubert D, Nordmann P. Genetic and functional analysis of the chromosome-encoded carbapenemhydrolyzing oxacillinase OXA-40 of Acinetobacter baumannii. Antimicrob Agents Chemother 2003; 47(1): 268-73.
14. Héritier C, Poirel L, Lambert T, Nordmann P. Contribution of acquired carbapenem-hydrolyzing oxacillinases to carbapenem resistance in Acinetobacter baumannii. Antimicrob Agents Chemother 2005; 49(8): 3198-202.
15. Kaitany KC, Klinger NV, June CM, et al. Structures of the class D carbapenemases OXA-23 and OXA-146: mechanistic basis of activity against carbapenems, extended-spectrum cephalosporins, and aztreonam. Antimicrob Agents Chemother 2013; 57(10): 4848-55.
16. Docquier JD, Calderone V, De Luca F, et al. Crystal structure of the OXA-48 t-lactamase reveals mechanistic diversity among class D carbapenemases. Chem Biol 2009; 16(5): 540-7.
17. Poirel L, Marqué S, Héritier C, Segonds C, Chabanon G, Nordmann P. OXA-58, a novel class D P-lactamase involved in resistance to carbapenems in Acinetobacter baumannii. Antimicrob Agents Chemother 2005; 49(1): 202-8.
18. Poirel L, Castanheira M, Carrër A, et al. OXA-163, an OXA-48- related class D β-lactamase with extended activity toward expanded- spectrum cephalosporins. Antimicrob Agents Chemother 2011; 55(6): 2546-51.
19. De Luca F, Benvenuti M, Carboni F, et al. Evolution to carbapenem- hydrolyzing activity in noncarbapenemase class D β-lactamase OXA-10 by rational protein design. Proc Natl Acad Sci USA 2011; 108(45): 18424-9.
20. Bush K, Palzkill T. ß-Lactamase Classification and Amino Acid Sequences for TEM, SHV and OXA Extended-Spectrum and Inhibitor Resistant Enzymes. http://www.lahey.org/Studies/
21. Strynadka NC, Adachi H, Jensen SE, et al. Molecular structure of the acyl-enzyme intermediate in t-lactam hydrolysis at 1.7 A resolution. Nature 1992; 359 (6397): 700-5.
22. Strynadka NC, Martin R, Jensen SE, Gold M, Jones JB. Structurebased design of a potent transition state analogue for TEM-1 d- lactamase. Nat Struct Biol 1996; 3(8): 688-95.
23. Herzberg O, Moult J. Bacterial resistance to β-lactam antibiotics: crystal structure of c-lactamase from Staphylococcus aureus PC1 at 2.5 A resolution. Science 1987; 236(4802): 694-701.
24. Damblon C, Raquet X, Lian LY. Lamotte-Brasseur J, Fonze E, Charlier P, Roberts GC, Frère JM. The catalytic mechanism of C- lactamases: NMR titration of an active-site lysine residue of the TEM-1 enzyme. Proc Natl Acad Sci USA 1996; 93(5): 1747-52.
25. Lamotte-Brasseur J, Dive G, Dideberg O, Charlier P, Frère JM, Ghuysen JM. Mechanism of acyl transfer by the class A serine G- lactamase of Streptomyces albus G. Biochem J 1991; 279(Pt 1): 213-21.
26. Minasov G, Wang X, Shoichet BK. An ultrahigh resolution structure of TEM-1 o-lactamase suggests a role for Glu166 as the general base in acylation. J Am Chem Soc 2002; 124(19): 5333- 40.
27. Santillana E, Beceiro A, Bou G, Romero A. Crystal structure of the carbapenemase OXA-24 reveals insights into the mechanism of carbapenem hydrolysis. Proc Natl Acad Sci USA 2007; 104(13): 5354-9.
28. Docquier JD, Benvenuti M, Calderone V, et al. Crystal structure of the narrow-spectrum OXA-46 class D t-lactamase: relationship between active-site lysine carbamylation and inhibition by polycarboxylates. Antimicrob Agents Chemother 2010; 54(5): 2167-74.
29. Maveyraud L, Golemi D, Kotra LP, et al. Insights into class D β-lactamases are revealed by the crystal structure of the OXA10 enzyme from Pseudomonas aeruginosa. Structure 2000; 8(12): 1289- 98.
30. Golemi D, Maveyraud L, Vakulenko S, Samama JP, Mobashery S. Critical involvement of a carbamylated lysine in catalytic function of class D o-lactamases. Proc Natl Acad Sci USA 2001; 98(25): 14280-5.
31. Schneider KD, Bethel CR, Distler AM, Hujer AM, Bonomo RA, Leonard, DA. Mutation of the active site carboxy-lysine (K70) of OXA-1 O-lactamase results in a deacylation-deficient enzyme. Biochemistry 2009; 48(26): 6136-45.
32. Li J, Cross JB, Vreven T, Meroueh SO, Mobashery S, Schlegel HB. Lysine carboxylation in proteins: OXA-10 H-lactamase. Proteins 2005; 61(2): 246-57.
33. Beck J, Vercheval L, Bebrone C, Herteg-Fernea A, Lassaux P, Marchand-Brynaert J. Discovery of novel lipophilic inhibitors of OXA-10 enzyme (class D D-lactamase) by screening amino analogs and homologs of citrate and isocitrate. Bioorg Med Chem Lett 2009; 19(13): 3593-97.
34. Smith CA, Antunes NT, Stewart NK, et al. Structural basis for carbapenemase activity of the OXA-23 β-lactamase from Acinetobacter baumannii. Chem Biol 2013; 20(9): 1107-15.
35. Schneider KD, Ortega CJ, Renck NA, Bonomo RA, Powers RA, Leonard DA. Structures of the class D carbapenemase OXA-24 from Acinetobacter baumannii in complex with doripenem. J Mol Biol 2011; 406(4): 583-94.
36. Schneider KD, Karpen ME, Bonomo RA, Leonard DA, Powers RA. The 1.4 A crystal structure of the class D R-lactamase OXA- 1 complexed with doripenem. Biochemistry 2009; 48(50): 11840- 7.
37. Bou G, Santillana E, Sheri A, et al. Design, synthesis, and crystal structures of 6-alkylidene-2'-substituted penicillanic acid sulfones as potent inhibitors of Acinetobacter baumannii OXA-24 carbapenemase. J Am Chem Soc 2010; 132(38): 13320-31.
38. Ehmann DE, Jahić H, Ross PL, et al. Avibactam is a covalent, reversible, non-β-lactam β-lactamase inhibitor. Proc Natl Acad Sci USA 2012; 109(29): 11663-8.
39. Ehmann DE, Jahic H, Ross PL, et al. Kinetics of avibactam inhibition against Class A, C, and D β-lactamases. J Biol Chem 2013; 288(39): 27960-71.
40. Lahiri SD, Mangani S, Jahić H, et al. Molecular basis of selective inhibition and slow reversibility of avibactam against class D carbapenemases: A structure-guided study of OXA-24 and OXA-48. ACS Chem Biol 2014; 10(2): 591-600.
41. Che T, Bethel CR, Pusztai-Carey M, Bonomo RA, Carey PR. The different inhibition mechanisms of OXA-1 and OXA-24 β- lactamases are determined by the stability of active site carboxylated lysine. J Biol Chem 2014; 289(9): 6152-64.
42. Lahiri SD, Mangani S, Durand-Reville T, et al. Structural insight into potent broad-spectrum inhibition with reversible recyclization mechanism: avibactam in complex with CTX-M-15 and Pseudomonas aeruginosa AmpC β-lactamases. Antimicrob Agents Chemother 2013; 57(6): 2496-505.
43. Lahiri SD, Johnstone MR, Ross PL, McLaughlin RE, Olivier NB, Alm RA. Avibactam and class C β-lactamases: mechanism of inhibition, conservation of the binding pocket, and implications for resistance. Antimicrob Agents Chemother 2014; 58(10): 5704-13.
44. Smith CA, Antunes NT, Toth M, Vakulenko SB. Crystal structure of carbapenemase OXA-58 from Acinetobacter baumannii. Antimicrob Agents Chemother 2014; 58(4): 2135-43.