Inactivation of the lipopeptide antibiotic daptomycin by hydrolytic mechanisms

Antimicrobial Agents and Chemotherapy

Volumn 56, Issue 2, 2012, Pages 757-764

  D'Costa, Vanessa M ^a   Mukhtar, Tariq A ^a   Patel, Tejal ^a   Koteva, Kalinka ^a   Waglechner, Nicholas ^a   Hughes, Donald W ^b   Wright, Gerard D ^a   De Pascale, Gianfranco ^a  

^a MCMASTER UNIVERSITY   (Canada)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DAPTOMYCIN; ESTER; SERINE PROTEINASE;

ANTIBIOTIC RESISTANCE; ARTICLE; CONTROLLED STUDY; COVALENT BOND; DEACYLATION; DRUG HYDROLYSIS; DRUG INACTIVATION; IN VIVO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHENOTYPE; PRIORITY JOURNAL; PROTEIN DEGRADATION; STREPTOMYCES;

ACTINOBACTERIA; ANTI-BACTERIAL AGENTS; DAPTOMYCIN; DRUG RESISTANCE, BACTERIAL; HYDROLYSIS; LIPOPEPTIDES; MICROBIAL SENSITIVITY TESTS; SERINE PROTEASES; SOIL MICROBIOLOGY; STREPTOMYCES;

EID: 84856070939     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.05441-11     Document Type: Article

References (45)

1. Altschul SF, et al. 1997. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res. 25:3389-3402. (Pubitemid 27359211)
2. Ball LJ, Goult CM, Donarski JA, Micklefield J, Ramesh V. 2004. NMR structure determination and calcium binding effects of lipopeptide antibiotic daptomycin. Org. Biomol. Chem. 2:1872-1878.
3. Baltz RH, Miao V, Wrigley SK. 2005. Natural products to drugs: daptomycin and related lipopeptide antibiotics. Nat. Prod. Rep. 22:717-741. (Pubitemid 41830839)
4. Barry AL, Fuchs PC, Brown SD. 2001. In vitro activities of daptomycin against 2,789 clinical isolates from 11 North American medical centers. Antimicrob. Agents Chemother. 45:1919-1922. (Pubitemid 32466376)
5. Bastian S, Brossier F, Wichlacz C, Jarlier V, Veziris N. 2010. Daptomycin is not active against rapidly growing mycobacteria. J. Med. Microbiol. 59:135-136.
6. Boeck LD, Fukuda DS, Abbott BJ, Debono M. 1988. Deacylation of A21978C, an acidic lipopeptide antibiotic complex, by Actinoplanes utahensis. J. Antibiot. (Tokyo) 41:1085-1092.
7. Boeck LD, Fukuda DS, Abbott BJ, Debono M. 1989. Deacylation of echinocandin B by Actinoplanes utahensis. J. Antibiot. (Tokyo) 42:382-388. (Pubitemid 19088955)
8. Bourne DG, Riddles P, Jones GJ, Smith W, Blakeley RL. 2001. Characterisation of a gene cluster involved in bacterial degradation of the cyanobacterial toxin microcystin LR. Environ. Toxicol. 16:523-534. (Pubitemid 33130332)
9. Chater KF, Biro S, Lee KJ, Palmer T, Schrempf H. 2010. The complex extracellular biology of Streptomyces. FEMS Microbiol. Rev. 34:171-198.
10. Chittum HS, et al. 1998. Rabbit beta-globin is extended beyond its UGA stop codon by multiple suppressions and translational reading gaps. Biochemistry 37:10866-10870. (Pubitemid 28368910)
11. Clinical and Laboratory Standards Institute. 2009. Methods for dilution antimicrobial susceptibility tests for bacteria thatgrowaerobically; approved standard M07-A8. Clinical and Laboratory Standards Institute, Wayne, PA.
12. Critchley IA, et al. 2003. Activity of daptomycin against susceptible and multidrug-resistant Gram-positive pathogens collected in the SECURE study (Europe) during 2000-2001. J. Antimicrob. Chemother. 51:639-649. (Pubitemid 36336158)
13. Davies J. 1994. Inactivation of antibiotics and the dissemination of resistance genes. Science 264:375-382. (Pubitemid 24178900)
14. D'Costa VM, McGrann KM, Hughes DW, Wright GD. 2006. Sampling the antibiotic resistome. Science 311:374-377. (Pubitemid 43132661)
15. D'Costa VM, Wright GD. 2009. Biochemical logic of antibiotic inactivation and modification. In Mayers DL, Lerner SA, Ouellette M, Sobel JD (ed), Antimicrobial drug resistance, vol 1. Humana Press, New York, NY.
16. Debono M, et al. 1988. Enzymatic and chemical modifications of lipopeptide antibiotic A21978C: the synthesis and evaluation of daptomycin (LY146032). J. Antibiot. (Tokyo) 41:1093-1105.
17. Dubin G. 2002. Extracellular proteases of Staphylococcus spp. Biol. Chem. 383:1075-1086. (Pubitemid 35215052)
18. Fleischmann RD, et al. 1995. Whole-genome random sequencing and assembly of Haemophilus influenzae Rd. Science 269:496-512.
19. Goldstein EJ, et al. 2003. In vitro activities of daptomycin, vancomycin, quinupristin-dalfopristin, linezolid, and five other antimicrobials against 307 gram-positive anaerobic and 31 Corynebacterium clinical isolates. Antimicrob. Agents Chemother. 47:337-341. (Pubitemid 36074932)
20. Grunewald J, et al. 2005. Fluorescence resonance energy transfer as a probe of peptide cyclization catalyzed by nonribosomal thioesterase domains. Chem. Biol. 12:873-881. (Pubitemid 41206801)
21. Guardabassi L, Christensen H, Hasman H, Dalsgaard A. 2004. Members of the genera Paenibacillus and Rhodococcus harbor genes homologous to enterococcal glycopeptide resistance genes vanA and vanB. Antimicrob. Agents Chemother. 48:4915-4918. (Pubitemid 39577707)
22. Heinzel P, Werbitzky O, Distler J, Piepersberg W. 1988. A second streptomycin resistance gene from Streptomyces griseus codes for streptomycin-3″-phosphotransferase. Relationships between antibiotic and protein kinases. Arch. Microbiol. 150:184-192.
23. Ho SW, et al. 2008. Effect of divalent cations on the structure of the antibiotic daptomycin. Eur. Biophys. J. 37:421-433. (Pubitemid 351423116)
24. Hong HJ, Paget MS, Buttner MJ. 2002. A signal transduction system in Streptomyces coelicolor that activates the expression of a putative cell wall glycan operon in response to vancomycin and other cell wall-specific antibiotics. Mol. Microbiol. 44:1199-1211. (Pubitemid 34595753)
25. Hyder SL, Streitfeld MM. 1973. Inducible and constitutive resistance to macrolide antibiotics and lincomycin in clinically isolated strains of Streptococcus pyogenes. Antimicrob. Agents Chemother. 4:327-331.
26. Kato H, Tsuji K, Harada K. 2009. Microbial degradation of cyclic peptides produced by bacteria. J. Antibiot. (Tokyo) 62:181-190.
27. Kreuzman AJ, et al. 2000. Membrane-associated echinocandin B deacylase of Actinoplanes utahensis: purification, characterization, heterologous cloning and enzymatic deacylation reaction. J. Ind. Microbiol. Biotechnol. 24:173-180. (Pubitemid 30262235)
28. Lai CC, et al. 2009. Comparative in vitro activities of nemonoxacin, doripenem, tigecycline and 16 other antimicrobials against Nocardia brasiliensis, Nocardia asteroides and unusual Nocardia species. J. Antimicrob. Chemother. 64:73-78.
29. Low DE, Keller N, Barth A, Jones RN. 2001. Clinical prevalence, antimicrobial susceptibility, and geographic resistance patterns of enterococci: results from the SENTRY Antimicrobial Surveillance Program, 1997-1999. Clin. Infect. Dis. 32(Suppl. 2):S133-S145. (Pubitemid 32424267)
30. Marshall CG, Lessard IA, Park I, Wright GD. 1998. Glycopeptide antibiotic resistance genes in glycopeptide-producing organisms. Antimicrob. Agents Chemother. 42:2215-2220. (Pubitemid 28420352)
31. Muangsiri W, Kirsch LE. 2001. The kinetics of the alkaline degradation of daptomycin. J. Pharm. Sci. 90:1066-1075.
32. Oliynyk M, et al. 2007. Complete genome sequence of the erythromycin-producing bacterium Saccharopolyspora erythraea NRRL23338. Nat. Biotechnol. 25:447-453. (Pubitemid 46572853)
33. Richter SS, et al. 2003. The in vitro activity of daptomycin against Staphylococcus aureus and Enterococcus species. J. Antimicrob. Chemother. 52:123-127. (Pubitemid 36850098)
34. Robbel L, Marahiel MA. 2010. Daptomycin, a bacterial lipopeptide synthesized by a nonribosomal machinery. J. Biol. Chem. 285:27501-27508.
35. Roberts MC, et al. 1999. Nomenclature for macrolide and macrolidelincosamide-streptogramin B resistance determinants. Antimicrob. Agents Chemother. 43:2823-2830.
36. Rodriguez MM, et al. 2004. Chromosome-encoded CTX-M-3 from Kluyvera ascorbata: a possible origin of plasmid-borne CTX-M-1-derived cefotaximases. Antimicrob. Agents Chemother. 48:4895-4897. (Pubitemid 39577703)
37. Rybak MJ, Hershberger E, Moldovan T, Grucz RG. 2000. In vitro activities of daptomycin, vancomycin, linezolid, and quinupristindalfopristin against staphylococci and enterococci, including vancomycin-intermediate and -resistant strains. Antimicrob. Agents Chemother. 44:1062-1066. (Pubitemid 30165292)
38. Silverman JA, Perlmutter NG, Shapiro HM. 2003. Correlation of daptomycin bactericidal activity and membrane depolarization in Staphylococcus aureus. Antimicrob. Agents Chemother. 47:2538-2544. (Pubitemid 36919456)
39. Streit JM, Jones RN, Sader HS. 2004. Daptomycin activity and spectrum: a worldwide sample of 6737 clinical Gram-positive organisms. J. Antimicrob. Chemother. 53:669-674. (Pubitemid 38499788)
40. Styers D, Sheehan DJ, Hogan P, Sahm DF. 2006. Laboratory-based surveillance of current antimicrobial resistance patterns and trends among Staphylococcus aureus: 2005 status in the United States. Ann. Clin. Microbiol. Antimicrob. 5:2.
41. Tsentalovich YP, Snytnikova OA, Sherin PS, Forbes MD. 2005. Photochemistry of kynurenine, a tryptophan metabolite: properties of the triplet state. J. Phys. Chem. A 109:3565-3568. (Pubitemid 40643948)
42. Tsukiura H, Konishi M, Saka M, Naito T, Kawaguchi H. 1969. Studies on cirramycin A1. 3. Structure of cirramycin A1. J. Antibiot. (Tokyo) 22:89-99.
43. Wise R, Andrews JM, Ashby JP. 2001. Activity of daptomycin against Gram-positive pathogens: a comparison with other agents and the determination of a tentative breakpoint. J. Antimicrob. Chemother. 48:563-567. (Pubitemid 33040701)
44. Zerbino DR, Birney E. 2008. Velvet: algorithms for de novo short read assembly using de Bruijn graphs. Genome Res. 18:821-829. (Pubitemid 351645072)
45. Ziebandt AK, et al. 2001. Extracellular proteins of Staphylococcus aureus and the role of SarA and sigma B. Proteomics 1:480-493.