β-Lactam and glycopeptide antibiotics: First and last line of defense?

Trends in Biotechnology

Volumn 28, Issue 12, 2010, Pages 596-604

  Jovetic, Srdjan ^a   Zhu, Yang ^b,c   Marcone, Giorgia Letizia ^d   Marinelli, Flavia ^d   Tramper, Johannes ^c  

^a Actygea Srl   (Italy)

^b TNO   (Netherlands)

^c WAGENINGEN UNIVERSITY   (Netherlands)

^d UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL CELLS; BACTERIAL RESISTANCE; GLYCOPEPTIDE ANTIBIOTICS; GLYCOPEPTIDES; MICROBIAL DIVERSITY; NOVEL STRATEGIES; PHARMACEUTICAL COMPANY; SCREENING STRATEGY; STRUCTURE-FUNCTION RELATIONSHIP;

AMIDES; ANTIBIOTICS;

BACTERIOLOGY;

A 40926; A47934; AMINOGLYCOSIDE ANTIBIOTIC AGENT; ANTIBIOTIC AGENT; BETA LACTAM ANTIBIOTIC; CARBAPENEM DERIVATIVE; CEFTAROLINE; CEFTOBIPROLE; CEPHALOSPORIN; CEPHALOSPORIN DERIVATIVE; DALBAVANCIN; DAPTOMYCIN; ERYTHROMYCIN; GYRASE INHIBITOR; LINEZOLID; METICILLIN; ORITAVANCIN; PENICILLIN DERIVATIVE; PENICILLIN G; POLYPEPTIDE ANTIBIOTIC AGENT; QUINOLINE DERIVED ANTIINFECTIVE AGENT; QUINOLONE DERIVATIVE; RAZUPENEM; STREPTOGRAMIN DERIVATIVE; TEICOPLANIN; TEICOPLANIN DERIVATIVE; TELAVANCIN; TETRACYCLINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; BACTERIAL CELL WALL; BACTERIAL INFECTION; BACTERIAL STRAIN; BIOSYNTHESIS; CLOSTRIDIUM DIFFICILE; DRUG DESIGN; DRUG EFFICACY; DRUG INDUSTRY; DRUG INHIBITION; DRUG MANUFACTURE; DRUG SCREENING; FOOD AND DRUG ADMINISTRATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOSPITAL INFECTION; HOST RESISTANCE; HUMAN; MASS SPECTROMETRY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS INFECTION; MICROBIAL DIVERSITY; MULTIDRUG RESISTANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PATHOGENESIS; PENICILLIN RESISTANCE; PHARMACOGENOMICS; PRIORITY JOURNAL; REVIEW; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS INFECTION; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; BACTERIA; BACTERIAL INFECTIONS; BETA-LACTAMS; CELL WALL; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; DRUG RESISTANCE, BACTERIAL; GLYCOPEPTIDES; HUMANS;

BACTERIA (MICROORGANISMS);

EID: 78149466664     PISSN: 01677799     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tibtech.2010.09.004     Document Type: Review

References (83)

1. Walsh C. Antibiotics: Actions, Origins, Resistance 2003, American Society for Microbiology.
2. Tramper J., et al. Biocatalytic production of semi-synthetic cephalosporins: process technology and integration. Synthesis of β-Lactam Antibiotics - Chemistry, Biocatalysis and Process Integration 2001, 207-249. Kluwer Academic Publishers. A. Bruggink (Ed.).
3. Demain A.L., Elander R.P. The beta-lactam antibiotics: past, present, and future. Antonie Van Leeuwenhoek 1999, 75:5-19.
4. Demain A.L., Sanchez S. Microbial drug discovery: 80 years of progress. J. Antibiot. 2009, 62:5-16.
5. Lyon B.R., Skurray R. Antimicrobial resistance of Staphylococcus aureus: genetic basis. Microbiol. Rev. 1987, 51:88-134.
6. Gaisford W.C., Reynolds P.E. Methicillin resistance in Staphylococcus epidermidis. Eur. J. Biochem. 1989, 185:211-218.
7. Chambers H.F. Methicillin resistance in staphylococci: molecular and biochemical basis and clinical implications. Clin. Microbiol. Rev. 1997, 10:781-791.
8. Holden M., et al. Complete genomes of two clinical Staphylococcus aureus strains: evidence for the rapid evolution of virulence and drug resistance. Proc. Natl. Acad. Sci. U. S. A. 2004, 101:9786-9791.
9. Fuda C., et al. The basis for resistance to -lactam antibiotics by penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus. J. Biol. Chem. 2004, 279:40802-40806.
10. Chambers H.F., DeLeo F.R. Waves of resistance: Staphylococcus aureus in the antibiotic era. Nat. Rev. Microbiol. 2009, 7:629-641.
11. DeLeo F.R., et al. Community-associated methicillin-resistant Staphylococcus aureus. Lancet 2010, 375:1557-1568.
12. Ito T., et al. Classification of staphylococcal cassette chromosome mec (SCCmec): guidelines for reporting novel SCCmec elements. Antimicrob. Agents Chemother. 2009, 53:4961-4967.
13. Tsubakishita S., et al. The origin and molecular evolution of the determinant of methicillin-resistance in staphylococci. Antimicrob. Agents Chemother. 2010, 54:4352-4359.
14. Rice L.B. The clinical consequences of antimicrobial resistance. Curr. Opin. Microbiol. 2009, 12:476-481.
15. Grundmann H., et al. Emergence and resurgence of methicillin-resistant Staphylococcus aureus as a public-health threat. Lancet 2006, 368:874-885.
16. Courvalin P. Vancomycin resistance in Gram-positive cocci. Clin. Infect. Dis. 2006, 42:S25-S34.
17. Salmond G.P.C., Welch M. Antibiotic resistance: adaptive evolution. Lancet 2008, 372:S97-S103.
18. Liñares J., et al. Changes in antimicrobial resistance, serotypes, and genotypes in Streptococcus pneumoniae over a thirty-year period. Clin. Microbiol. Infect. 2010, 16:402-410.
19. Huang H., et al. Antimicrobial resistance in Clostridium difficile. Int. J. Antimicrob. Agents 2009, 34:516-522.
20. Courvalin P. Predictable and unpredictable evolution of antibiotic resistance. J. Intern. Med. 2008, 264:4-16.
21. Leclercq R., et al. Transferable vancomycin and teicoplanin resistance in Enterococcus faecium. Antimicrob. Agents Chemother. 1989, 33:10-15.
22. Larkin M. Antibacterial resistance deemed a public-health crisis. Lancet Infect. Dis. 2003, 3:322-1322.
23. Hiramatsu K., et al. Methicillin-resistant Staphylococcus aureus clinical strain with reduced vancomycin susceptibility. J. Antimicrob. Chemother. 1997, 40:135-136.
24. Chang S., et al. Infection with vancomycin-resistant Staphylococcus aureus containing the vanA resistance gene. N. Engl. J. Med. 2003, 348:1342-1347.
25. Tenover F.C., et al. Vancomycin-resistant Staphylococcus aureus isolate from a patient in Pennsylvania. Antimicrob. Agents Chemother. 2004, 48:275-280.
26. Weigel L.M., et al. Genetic analysis of a high-level vancomycin-resistant isolate of Staphylococcus aureus. Science 2003, 302:1569-1571.
27. Walsh C., et al. Bacterial resistance to vancomycin: five genes and one missing hydrogen bond tell the story. Chem. Biol. 1996, 3:21-28.
28. Perichon B., Courvalin P. VanA-type vancomycin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 2009, 53:4580-4587.
29. Kahne D., et al. Glycopeptide and lipoglycopeptide antibiotics. Chem. Rev. 2005, 105:425-448.
30. Wright G.D. The antibiotic resistome: the nexus of chemical and genetic diversity. Nat. Rev. Microbiol. 2007, 5:175-186.
31. Beltrametti F., et al. Resistance to glycopeptide antibiotics in the teicoplanin producer is mediated by van gene homologue expression directing the synthesis of a modified cell wall peptidoglycan. Antimicrob. Agents Chemother. 2007, 51:1135-1141.
32. Marshall C.G., et al. Glycopeptide antibiotic resistance genes in glycopeptide-producing organisms. Antimicrob. Agents Chemother. 1998, 42:2215-2220.
33. Marcone G., et al. Novel mechanism of glycopeptide resistance in the A40926 producer Nonomuraea sp. ATCC 39727. Antimicrob. Agents Chemother. 2010, 54:2465-2472.
34. Foucault M.L., et al. Fitness cost of vanA-type vancomycin resistance in methicillin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 2009, 53:2354-2359.
35. Wichelhaus T.A., et al. Biological cost of rifampin resistance from the perspective of Staphylococcus aureus. Antimicrob. Agents Chemother. 2002, 46:3381-3385.
36. Gillespie S.H., McHugh T.D. The biological cost of antimicrobial resistance. Trends Microbiol. 1997, 5:337-339.
37. Martinez J.L., et al. Predicting antibiotic resistance. Nat. Rev. Microbiol. 2007, 5:958-965.
38. Sievert D., et al. Vancomycin resistant Staphylococcus aureus in the United States, 2002-2006. Clin. Infect. Dis. 2008, 46:668-674.
39. Saha B., et al. Identification and characterization of a vancomycin-resistant Staphylococcus aureus isolated from Kolkata (South Asia). J. Med. Microbiol. 2008, 57:72-79.
40. Jabalameli M.A.M.E.F., Sedaght S.S.H.D.H. Emergence of high-level vancomycin-resistant Staphylococcus aureus in the Imam Khomeini Hospital in Tehran. Med. Princ. Pract. 2008, 17:432-434.
41. Ender M., et al. Fitness cost of SCCmec and methicillin resistance levels in Staphylococcus aureus. Antimicrob. Agents Chemother. 2004, 48:2295-2297.
42. Fischbach M.A., Walsh C.T. Antibiotics for emerging pathogens. Science 2009, 325:1089-1093.
43. Demain A.L. Antibiotics: natural products essential to human health. Med. Res. Rev. 2009, 29:821-842.
44. Overbye K.M., Barrett J.F. Antibiotics: where did we go wrong. Drug Discov. Today 2005, 10:45-52.
45. Barrett J.F. Can biotech deliver new antibiotics?. Curr. Opin. Microbiol. 2005, 8:498-503.
46. Payne D.J., et al. Drugs for bad bugs: confronting the challenges of antibacterial discovery. Nat. Rev. Drug Discov. 2007, 6:29-40.
47. Koehn F.E. New strategies and methods in the discovery of natural product anti-infective agents: the mannopeptimycins. J. Med. Chem. 2008, 51:2613-2617.
48. Schneider T., Sahl H.G. Lipid II and other bactoprenol-bound cell wall precursors as drug targets. Curr. Opin. Investig. Drugs 2010, 11:157-164.
49. Leung S.S.F., et al. Vancomycin analogs: Seeking improved binding of d-Ala-d-Ala and d-Ala-d-Lac peptides by side-chain and backbone modifications. Bioorg. Med. Chem. 2009, 17:5874-5886.
50. Leung S.S.F., et al. Vancomycin resistance: modeling backbone variants with D-Ala-D-Ala and D-Ala-D-Lac peptides. Bioorg. Med. Chem. Lett. 2009, 19:1236-1239.
51. Castiglione F., et al. A novel lantibiotic acting on bacterial cell wall synthesis produced by the uncommon actinomycete Planomonospora sp. Biochemistry 2007, 46:5884-5895.
52. Castiglione F., et al. Determining the structure and mode of action of microbisporicin, a potent lantibiotic active against multiresistant pathogens. Chem. Biol. 2008, 15:22-31.
53. Ciabatti R., et al. Synthesis and preliminary biological characterization of new semisynthetic derivatives of ramoplanin. J. Med. Chem. 2007, 50:3077-3085.
54. Shang W., et al. Effects of ceftobiprole and oxacillin on mecA expression in methicillin-resistant Staphylococcus aureus clinical isolates. Antimicrob. Agents Chemother. 2010, 54:956-959.
55. Cornaglia G., Rossolini G.M. Forthcoming therapeutic perspectives for infections due to multidrug-resistant Gram-positive pathogens. Clin. Microbiol. Infect. 2009, 15:218-223.
56. Guskey M.T., Tsuji B.T. A comparative review of the lipoglycopeptides: oritavancin, dalbavancin, and telavancin. Pharmacotherapy 2010, 30:80-94.
57. Abbanat D., et al. New agents in development for the treatment of bacterial infections. Curr. Opin. Pharmacol. 2008, 8:582-592.
58. Gandolfi R., et al. Biotransformations of lipoglycopeptides to obtain novel antibiotics. J. Antibiot. 2007, 60:265-271.
59. Shi R., et al. Structure and function of the glycopeptide N-methyltransferase MtfA, a tool for the biosynthesis of modified glycopeptide antibiotics. Chem. Biol. 2009, 16:401-410.
60. Howard-Jones A., et al. Kinetic analysis of teicoplanin glycosyltransferases and acyltransferase reveal ordered tailoring of aglycone scaffold to reconstitute mature teicoplanin. J. Am. Chem. Soc. 2007, 129:10082-10083.
61. Zou Y., et al. Crystal structures of lipoglycopeptide antibiotic deacetylases: implications for the biosynthesis of A40926 and teicoplanin. Chem. Biol. 2008, 15:533-545.
62. Bick M., et al. Crystal structures of the glycopeptide sulfotransferase Teg12 in a complex with the teicoplanin aglycone. Biochemistry 2010, 49:4159-4168.
63. Boakes S., et al. Organization of the genes encoding the biosynthesis of actagardine and engineering of a variant generation system. Mol. Microbiol. 2009, 72:1126-1136.
64. Appleyard A.N., et al. Dissecting structural and functional diversity of the lantibiotic mersacidin. Chem. Biol. 2009, 16:490-498.
65. Foulston L., Bibb M. Microbisporicin gene cluster reveals unusual features of lantibiotic biosynthesis in actinomycetes. Proc. Natl. Acad. Sci. U. S. A. 2010, 107:13461-13466.
66. Somma S., et al. Gardimycin, a new antibiotic inhibiting peptidoglycan synthesis. Antimicrob. Agents Chemother. 1977, 11:396-401.
67. Marcone G.L., et al. Protoplast preparation and reversion to the normal filamentous growth in antibiotic-producing uncommon actinomycetes. J. Antibiot. 2010, 63:83-88.
68. Hasper H., et al. An alternative bactericidal mechanism of action for lantibiotic peptides that target lipid II. Science 2006, 313:1636-1637.
69. Schneider T., Sahl H.G. An oldie but a goodie - cell wall biosynthesis as antibiotic target pathway. Int. J. Med. Microbiol. 2010, 300:161-169.
70. Ruzin A., et al. Mechanism of action of the mannopeptimycins, a novel class of glycopeptide antibiotics active against vancomycin-resistant Gram-positive bacteria. Antimicrob. Agents Chemother. 2004, 48:728-738.
71. Cavalleri B., et al. A-16686, a new antibiotic from actinoplanes. 1. Fermentation, isolation and preliminary physico-chemical characteristics. J. Antibiot. 1984, 37:309-317.
72. Shah D., et al. Clostridium difficile infection: update on emerging antibiotic treatment options and antibiotic resistance. Expert Rev. Anti-Infect. Ther. 2010, 8:555-564.
73. Hamburger J.B., et al. A crystal structure of a dimer of the antibiotic ramoplanin illustrates membrane positioning and a potential lipid II docking interface. Proc. Natl. Acad. Sci. U. S. A. 2009, 106:13759-13764.
74. Cottarel G., Wierzbowski J. Combination drugs, an emerging option for antibacterial therapy. Trends Biotechnol. 2007, 25:547-555.
75. Fox P.M., et al. Successful therapy of experimental endocarditis caused by vancomycin-resistant Staphylococcus aureus with a combination of vancomycin and beta-lactam antibiotics. Antimicrob. Agents Chemother. 2006, 50:2951-2956.
76. Arnusch C.J., et al. The vancomycin-nisin(1-12) hybrid restores activity against vancomycin resistant enterococci. Biochemistry 2008, 47:12661-12663.
77. Deresinski S. Bacteriophage therapy: exploiting smaller fleas. Clin. Infect. Dis. 2009, 48:1096-1101.
78. Fischetti V. Bacteriophage lysins as effective antibacterials. Curr. Opin. Microbiol. 2008, 11:393-400.
79. Kutateladze M., Adamia R. Bacteriophages as potential new therapeutics to replace or supplement antibiotics. Trends Biotechnol. 2010, 28:591-595.
80. Richter S.S., et al. Changing epidemiology of antimicrobial resistant Streptococcus pneumoniae in the United States, 2004-2005. Clin. Infect. Dis. 2009, 48:e23-e33.
81. McCormick M.H., et al. Vancomycin, a new antibiotic. I. Chemical and biologic properties. Antibiot. Annu. 1955, 3:606-611.
82. Somma S., et al. Teicoplanin, a new antibiotic from Actinoplanes teichomyceticus nov. sp. Antimicrob. Agents Chemother. 1984, 26:917-923.
83. Nitanai Y., et al. Crystal structures of the complexes between vancomycin and cell-wall precursor analogs. J. Mol. Biol. 2009, 385:1422-1432.