Mechanism of action of oritavancin and related glycopeptide antibiotics

FEMS Microbiology Reviews

Volumn 26, Issue 5, 2003, Pages 511-532

  Allen, Norris E ^a,b   Nicas, Thalia I ^a  

^a ELI LILLY AND COMPANY   (United States)

^b NONE   (United States)

Author keywords

Alkyl glycopeptide; Dimerization; Membrane anchoring; Oritavancin; Peptidoglycan biosynthesis; Transglycosylation

Indexed keywords

ANTIBIOTIC AGENT; CHLOROORIENTICIN A; LY 191145; LY 307599; LY 377502; ORITAVANCIN; PEPTIDOGLYCAN; TEICOPLANIN; UNCLASSIFIED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIBIOTIC SENSITIVITY; BACTERIAL CELL WALL; BACTERIAL INFECTION; BACTERIUM ISOLATE; BINDING AFFINITY; BIOSYNTHESIS; CYTOPLASM; DIMERIZATION; DOSE RESPONSE; DRUG EFFECT; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; GLYCOSYLATION; GRAM POSITIVE BACTERIUM; MICROANGIOPATHY; NONHUMAN; REVIEW;

ANTI-BACTERIAL AGENTS; DRUG RESISTANCE, MICROBIAL; GLYCOPEPTIDES; GRAM-POSITIVE BACTERIA; GRAM-POSITIVE BACTERIAL INFECTIONS; HUMANS; MODELS, MOLECULAR; PEPTIDOGLYCAN; VANCOMYCIN; VANCOMYCIN RESISTANCE;

BACTERIA (MICROORGANISMS); POSIBACTERIA;

EID: 0037266399     PISSN: 01686445     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0168-6445(02)00144-4     Document Type: Review

References (146)

1. McCormick, M.H., Stark, W.M., Pittenger, G.E., Pittenger, R.C. and McGuire, J.M. (1956) Vancomycin, a new antibiotic. I. Chemical and biological properties. Antibiot. Annu. 1955-1956, 606-611.
2. Courvalin P. Resistance of enterococci to glycopeptides. Antimicrob. Agents Chemother. 34:1990;2291-2296.
3. Leclerq R., Derlot E., Duval J., Courvalin P. Plasmid-mediated resistance to vancomycin and teicoplanin in Enterococcus faecium. N. Engl. J. Med. 319:1988;157-161.
4. Uttley A.H.C., Collins C.H., Naidoo J., George R.C. Vancomycin-resistant enterococci. Lancet. 1:1988;57-58.
5. Nicas, T.I. and Allen, N.E. (1994) In: Glycopeptide Antibiotics (Nagarajan, R., Ed.), pp. 219-241. Marcel Dekker, New York.
6. Reynolds P.E. Structure, biochemistry and mechanism of action of glycopeptide antibiotics. Eur. J. Clin. Microbiol. Infect. Dis. 8:1989;943-950.
7. Arthur M., Reynolds P., Courvalin P. Glycopeptide resistance in enterococci. Trends Microbiol. 4:1996;401-407.
8. Walsh C.T., Fisher S.L., Park I.S., Prahalad M., Wu Z. Bacterial resistance to vancomycin: five genes and one missing hydrogen bond tell the story. Chem. Biol. 3:1996;21-28.
9. Wright G.D., Walsh C.T. D-Alanyl-D-alanine ligases and the molecular mechanism of vancomycin resistance. Acc. Chem. Res. 25:1992;468-473.
10. Arthur M., Courvalin P. Genetics and mechanisms of glycopeptide resistance in enterococci. Antimicrob. Agents Chemother. 37:1993;1563-1571.
11. Yao, R.C. and Crandall, L.W. (1994) In: Glycopeptide Antibiotics (Nagarajan, R., Ed.). pp. 1-27. Marcel Dekker, New York.
12. Kleinkauf H., Von Dohren H. A nonribosomal system of peptide biosynthesis. Eur. J. Biochem. 236:1996;335-351.
13. Nicolaou K.C., Boddy C.N.C., Brase S., Winssinger N. Chemistry, biology, and medicine of the glycopeptide antibiotics. Angew. Chem. Int. Ed. 38:1999;2097-2152.
14. Nagarajan, R. (1994) In: Glycopeptide Antibiotics (Nagarajan, R., Ed.), pp. 195-218. Marcel Dekker, New York.
15. Nicas T.I., Mullen D.L., Flokowitsch J.E., Preston D.A., Snyder N.J., Stratford R.E., Cooper R.D.D. Activities of the semisynthetic glycopeptide LY191145 against vancomycin-resistant enterococci and other gram-positive bacteria. Antimicrob. Agents Chemother. 39:1995;285-287.
16. Rodriguez M.J., et al. Novel glycopeptide antibiotics: N-alkylated derivatives active against vancomycin-resistant enterococci. J. Antibiot. 51:1998;560-569.
17. Nagarajan R. Structure-activity relationships of vancomycin-type glycopeptide antibiotics. J. Antibiot. 46:1993;1181-1195.
18. Cooper R.D.G., et al. Reductive alkylation of glycopeptide antibiotics: synthesis and antibacterial activity. J. Antibiot. 49:1996;575-581.
19. Nicas T.I., et al. Semisynthetic glycopeptide antibiotics derived from LY264826 active against vancomycin-resistant enterococci. Antimicrob. Agents Chemother. 40:1996;2194-2199.
20. Rupp M.E., Fey P.D., Longo G.M. Effect of LY333328 against vancomycin-resistant Enterococcus faecium in a rat central venous catheter-associated infection model. J. Antimicrob. Chemother. 47:2001;705-707.
21. Baltch A.L., Smith R.P., Ritz W.J., Bopp L.H. Comparison of inhibitory and bactericidal activities and postantibiotic effects of LY333328 and ampicillin used singly and in combination against vancomycin-resistant Enterococcus faecium. Antimicrob. Agents Chemother. 42:1998;2564-2568.
22. Perkins H.R., Nieto M. The chemical basis for the action of the vancomycin group of antibiotics. Ann. N.Y. Acad. Sci. 235:1974;348-363.
23. Reynolds P. Studies on the mode of action of vancomycin. Biochim. Biophys. Acta. 52:1961;403-405.
24. Hammes W.P., Neuhaus F.C. On the mechanism of action of vancomycin: inhibition of peptidoglycan synthesis in Gaffkya homai. Antimicrob. Agents Chemother. 6:1974;722-728.
25. Anderson J.S., Matsuhashi M., Haskin M.A., Strominger J.L. Biosynthesis of the peptidoglycan of bacterial cell walls. II. Phospholipid carriers in the reaction sequence. J. Biol. Chem. 242:1967;3180-3190.
26. Jordan D.C. Effect of vancomycin on the synthesis of the cell wall mucopeptide of Staphylococcus aureus. Biochem. Biophys. Res. Commun. 6:1961;167-170.
27. Williams D.H., Waltho J.P. Molecular basis of the activity of antibiotics of the vancomycin group. Biochem. Pharmacol. 37:1988;133-141.
28. Barna J.C.J., Williams D.H. The structure and mode of action of glycopeptide antibiotics of the vancomycin group. Annu. Rev. Microbiol. 38:1984;339-357.
29. Cristofaro M.F., Beauregard D.A., Yan H., Osborn N.J., Williams D.H. Cooperativity between non-polar and ionic forces in the binding of bacterial cell wall analogues by vancomycin in aqueous solution. J. Antibiot. 48:1995;805-810.
30. Nieto M., Perkins R., Reynolds P.E. Reversal by a specific peptide (diacetyl-αγ-L-diaminobutyryl-D-alanyl-D-alanine) of vancomycin inhibition in intact bacteria and cell-free preparations. Biochem. J. 126:1972;139-149.
31. Allen N.E., LeTourneau D.L., Hobbs J.N. Jr. Molecular interactions of a semisynthetic glycopeptide antibiotic with D-alanyl-D-alanine and D-alanyl-D-lactate residues. Antimicrob. Agents Chemother. 41:1997;66-71.
32. Beauregard D.A., Williams D.H., Gwynn M.N., Knowles D.J. Dimerization and membrane anchors in extracellular targeting of vancomycin group antibiotics. Antimicrob. Agents Chemother. 39:1995;781-785.
33. Williams D.H., Westwell M.S. The fight against antibiotic-resistant bacteria. Chemtech. 26:1996;17-23.
34. Beauregard D.A., Maguire A.J., Williams D.H., Reynolds P.E. Semiquantitation of cooperativity in binding of vancomycin-group antibiotics to vancomycin-susceptible and -resistant organisms. Antimicrob. Agents Chemother. 41:1997;2418-2423.
35. 2 and vancomycin against staphylococci and enterococci. Antimicrob. Agents Chemother. 21:1982;504-505.
36. 2. Antimicrob. Agents Chemother. 23:1983;497-499.
37. Mackay J.P., Gerhard U., Beauregard D.A., Westwell M.S., Searle M.S., Williams D.H. Glycopeptide antibiotic activity and the possible role of dimerization: a model for biological signalling. J. Am. Chem. Soc. 116:1994;4581-4590.
38. Mackay J.P., Gerhard U., Beauregard D.A., Maplestone R.A., Williams D.H. Dissection of the contributions towards dimerization of glycopeptide antibiotics. J. Am. Chem. Soc. 116:1994;4573-4580.
39. Groves P., Searle M.S., Mackay J.P., Williams D.H. The structure of an asymmetric dimer relevant to the mode of action of the glycopeptide antibiotics. Structure (London). 2:1994;747-754.
40. Gerhard U., Mackay J.P., Maplestone R.A., Williams D.H. The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics. J. Am. Chem. Soc. 115:1993;232-237.
41. Cho Y.R., Maguire A.J., Try A.C., Westwell M.S., Groves P., Williams D.H. Cooperativity and anti-cooperativity between ligand binding and the dimerization of ristocetin A: asymmetry of a homodimer complex and implications for signal transduction. Chem. Biol. 3:1996;207-215.
42. Williams D.H., Bardsley B. The vancomycin group of antibiotics and the fight against resistant bacteria. Angew. Chem. Int. Ed. 38:1999;1172-1193.
43. Arthur M., Molinas C., Courvalin P. The vanS-vanR two-component regulatory system controls synthesis of depsipeptide peptidoglycan precursors in Enterococcus faecium BM4147. J. Bacteriol. 174:1992;2582-2591.
44. Arthur M., Molinas C., Dutka-Malen S., Courvalin P. Structural relationship between the vancomycin resistance protein VanH and 2-hydroxycarboxylic acid dehydrogenases. Gene. 103:1991;133-134.
45. Bugg T.D.H., Wright G.D., Dutka-Malen S., Arthur M., Courvalin P., Walsh C.T. Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins vanH and vanA. Biochemistry. 30:1991;10408-10415.
46. Bugg T.D.H., Dutka-Malen S., Arthur M., Courvalin P., Walsh D.T. Identification of vancomycin resistance protein vanA as a D-alanine:D-alanine ligase of altered substrate specificity. Biochemistry. 30:1991;2017-2021.
47. Reynolds P.E., Depardieu F., Dutka-Malen S., Arthur M., Courvalin P. Glycopeptide resistance mediated by enterococcal transposon Tn1546 requires production of VanX for hydrolysis of D-alanyl-D-alanine. Mol. Microbiol. 13:1994;1065-1070.
48. Wu Z., Wright G.D., Walsh C.T. Overexpression, purification, and characterization of vanX, a D,D-dipeptidase which is essential for vancomycin resistance in Enterococcus faecium BM4147. Biochemistry. 34:1995;2455-2463.
49. Arthur M., Depardieu F., Snaith H.A., Reynolds P., Courvalin P. Contribution of vanY D,D-carboxypeptidase to glycopeptide resistance in Enterococcus faecalis by hydrolysis of peptidoglycan precursors. Antimicrob. Agents Chemother. 38:1994;1899-1903.
50. Wright G.D., Molinas C., Arthur M., Courvalin P., Walsh C.T. Characterization of vanY, a DD-carboxypeptidase from vancomycin-resistant Enterococcus faecium BM4147. Antimicrob. Agents Chemother. 36:1992;1514-1518.
51. Gutmann L., Billot-Klein D., Al-Obeid S., Klare I., Francoual S., Collatz E., van Heijenoort J. Inducible carboxypeptidase activity in vancomycin-resistant enterococci. Antimicrob. Agents Chemother. 36:1992;77-80.
52. Arthur M., Depardieu F., Reynolds P., Courvalin P. Quantitative analysis of the metabolism of soluble cytoplasmic precursors of glycopeptide-resistant enterococci. Mol. Microbiol. 21:1996;33-44.
53. Reynolds P.E. Control of peptidoglycan synthesis in vancomycin-resistant enterococci: D,D-peptidases and D,D-carboxypeptidases. Cell. Mol. Life Sci. 54:1998;325-331.
54. Rasmussen J.R., Strominger J.L. Utilization of a depsipeptide substrate for trapping acyl-enzyme intermediates of penicillin-sensitive D-alanine carboxypeptidases. Proc. Natl. Acad. Sci. USA. 75:1978;84-88.
55. Allen N.E., Hobbs J.N. Jr., Richardson J.M., Riggin R.M. Biosynthesis of modified peptidoglycan precursors by vancomycin-resistant Enterococcus faecium. FEMS Microbiol. Lett. 98:1992;109-116.
56. Reynolds P.E., Snaith H.A., Maguire A.J., Dutka-Malen S., Courvalin P. Analysis of peptidoglycan precursors in vancomycin-resistant Enterococcus gallinarum. Biochem. J. 301:1994;5-8.
57. Billot-Klein D., Blanot D., Gutmann L., van Heijenoort J. Association constants for the binding of vancomycin and teicoplainin to N-acetyl-D-alanyl-D-alanine and N-acetyl-D-alanyl-D-serine. Biochem. J. Lett. 304:1994;1021-1022.
58. Billot-Klein D., Gutmann L., Sable S., Guittet E., van Heijenoort J. Modification of peptidoglycan precursors is a common feature of the low-level vancomycin-resistant vanB-type enterococcus D366 and of the naturally glycopeptide-resistant species Lactobacillus casei, Pediococcus pentosaceus, Leuconostoc mesenteroides, and Enterococcus gallinarum. J. Bacteriol. 176:1994;2398-2405.
59. Park I.-S., Lin H.-L., Walsh C.T. Bacterial resistance to vancomycin: overproduction, purification, and characterization of vanC2 from Enterococcus casseliflavus as a D-Ala-D-Ser ligase. Proc. Natl. Acad. Sci. USA. 94:1997;10040-10044.
60. Navarro F., Courvalin P. Analysis of genes encoding D-alanine:D-alanine ligase related enzymes in Enterococcus casseliflavus and Enterococcus flavescens. Antimicrob. Agents Chemother. 38:1994;1788-1793.
61. Handwerger S., Pucci M.J., Volk K.J., Liu J., Lee M.S. Vancomycin-resistant Leuconostoc mesenteroides and Lactobacillus casei synthesize cytoplasmic precursors that terminate in lactate. J. Bacteriol. 176:1994;260-264.
62. Hiramatsu K. Vancomycin resistance in staphylococci. Drug Resist. Updates. 1:1998;135-150.
63. Cui L., Murakami H., Kuwahara-Arai K., Hanaki H., Hiramatsu K. Contribution of a thickened cell wall and its glutamine nonamidated component to the vancomycin resistance expressed by Staphylococcus aureus Mu50. Antimicrob. Agents Chemother. 44:2000;2276-2285.
64. Hanaki H., Kuwahara-Arai K., Boyle-Vavra S., Daum R.S., Labischinski H., Hiramatsu K. Activated cell-wall synthesis is associated with vancomycin resistance in methicillin-resistant Staphylococcus aureus clinical strains Mu3 and Mu50. J. Antimicrob. Chemother. 42:1998;199-209.
65. Sieradzki K., Tomasz A. Inhibition of cell wall turnover and autolysis by vancomycin in a highly vancomycin-resistant mutant of Staphylococcus aureus. J. Bacteriol. 179:1997;2557-2566.
66. Sieradzki K., Pinho M., Tomasz A. Inactivated pbp4 in highly glycopeptide-resistant laboratory mutants of Staphylococcus aureus. J. Biol. Chem. 274:1999;18942-18946.
67. Noble W.C., Virani Z., Cree R.G. Co-transfer of vancomycin and other resistance genes from Enterococcus faecalis NCTC 12201 to Staphylococcus aureus. FEMS Microbiol. Lett. 72:1992;195-198.
68. Sievert D.M., et al. Staphylococcus aureus resistant to vancomycin. Morb. Mort. Weekly Rep. 51:2002;565-567.
69. Barrett J.F. Oritavancin Eli Lilly&Co. Curr. Opin. Invest. Drugs. 2:2001;1039-1044.
70. Johnson A.P. LY-333328 Eli Lilly. Curr. Opin. Anti-Infect. Invest. Drugs. 1:1999;87-95.
71. Muller-Serieys, C., Vallee, E., Pangon, B., Chachaty, E. and Decre, E. (1997) In vitro activity of oritavancin, a new glycopeptide, against gram-positive cocci. In: Abstracts, 37th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Toronto, ON, September 28-October 1, F-3, p. 146.
72. Harland S., Tebbs S.E., Elliott T.S. Evaluation of the in-vitro activity of the glycopeptide antibiotic LY333328 in comparison with vancomycin and teicoplanin. J. Antimicrob. Chemother. 41:1998;273-276.
73. Biavasco F., Vignaroli C., Lupidi R., Manso E., Facinelli B., Varaldo P.E. In vitro antibacterial activity of LY333328, a new semisynthetic glycopeptide. Antimicrob. Agents Chemother. 41:1997;2165-2172.
74. Patel R., Rouse M.S., Piper K.E., Cockerill F.R., Steckelberg J.M. In vitro activity of LY333328 against vancomycin-resistant enterococci, methicillin-resistant Staphylococcus aureus, and penicillin-resistant Streptococcus pneumoniae. Diagn. Microbiol. Infect. Dis. 30:1998;89-92.
75. Canton R., Mir N., Sanchez M., Baquero F. MIC distribution and inoculum effect of LY333328: a study of vancomycin-susceptible and VanA-type and VanC-type enterococci obtained from intensive care unit patient surveillance cultures. Clin. Microbiol. Infect. 5:1999;554-559.
76. Garcia-Garrote F., Cercenado E., Alcala L., Bouza E. In vitro activity of the new glycopeptide LY333328 against multiply resistant gram-positive clinical isolates. Antimicrob. Agents Chemother. 42:1998;2452-2455.
77. Jones R.N., Barrett M.S., Erwin M.E. In vitro activity and spectrum of LY333328, a novel glycopeptide derivative. Antimicrob. Agents Chemother. 41:1997;488-493.
78. Zeckel M.L., Preston D.A., Allen B.S. In vitro activities of LY333328 and comparative agents against nosocomial gram-positive pathogens collected in a 1997 global surveillance study. Antimicrob. Agents Chemother. 44:2000;1370-1374.
79. Fasola E., Spangler S.K., Ednie L.M., Jacobs M.R., Bajaksouzian S., Appelbaum P.C. Comparative activities of LY 333328, a new glycopeptide, against penicillin-susceptible and -resistant pneumococci. Antimicrob. Agents Chemother. 40:1996;2661-2663.
80. Verhaegen J., Verbist L. In-vitro activities of 16 non-beta-lactam antibiotics against penicillin-susceptible and penicillin-resistant Streptococcus pneumoniae. J. Antimicrob. Chemother. 43:1999;563-567.
81. Reynolds, P. (1997) High-level glycopeptide-resistant Staphylococcus aureus is susceptible to glycopeptide, oritavancin. In: Abstracts, 37th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Toronto, ON, September 28-October 1, C-165, p. 74.
82. Sillerstrom E., Wahlund E., Nord C.E. In vitro activity of LY 333328 against anaerobic Gram-positive bacteria. J. Chemother. (Firenze). 11:1999;90-92.
83. Heine, H.S., Dicks, R. and Andres, G. (2001) In vitro activity of LY333328 (oritavancin), levofloxacin, meropenem, GAR936, and linezolid against strains of Bacillus anthracis. In: Abstracts, 41st Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Chicago, IL, September 22-25, E-524, p. 173.
84. Nicas, T.I., Mullen, D.L., Flokowitsch, J.E. and Preston, D.A. (1996) Bactericidal activity against enterococci of the semisynthetic glycopeptide oritavancin. In: Abstracts, 36th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), New Orleans, LA, September 15-18, F198, p. 134.
85. Boylan, C.J. et al. (1995) Efficacy of semisynthetic glycopeptides active against vancomycin-resistant enterococci in a mouse infection model. In: Abstracts, 35th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), New Orleans, LA, September 17-20, F255, p. 157.
86. Mercier R.-C., Penzak S.R., Rybak M.J. In vitro activities of an investigational quinolone, glycylcycline, glycopeptide, streptogramin, and oxazolidinone tested alone and in combinations against vancomycin-resistant Enterococcus faecium. Antimicrob. Agents Chemother. 41:1997;2573-2575.
87. Mercier R.-C., Houlihan H.H., Rybak M.J. Pharmacodynamic evaluation of a new glycopeptide, LY333328, and in vitro activity against Staphylococcus aureus and Enterococcus faecium. Antimicrob. Agents Chemother. 41:1997;1307-1312.
88. Zelenitsky S.A., Karlowsky J.A., Zhanel G.G., Hoban D.J., Nicas T. Time-kill curves for a semisynthetic glycopeptide, LY333328, against vancomycin-sensitive and vancomycin-resistant Enterococcus faecium strains. J. Antimicrob. Chemother. 41:1997;1407-1408.
89. Schwalbe R.S., McIntosh A.C., Qaiyumi S., Johnson J.A., Johnson R.J., Furness K.M., Holloway W.J., Steele-Moore L. In vitro activity of LY3333328, an investigational glycopeptide antibiotic, against enterococci and staphylococci. Antimicrob. Agents Chemother. 40:1996;2416-2419.
90. Donabedian, S., Perri, M.B., Thal, L.A. and Zervos, M.J. (1996) Comparative in-vitro and bactericidal activity of oritavancin against multi-drug resistant enterococci. In: Abstracts, 36th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), New Orleans, LA, September 15-18, F204, p. 135.
91. Cheron, M. and Boisivon, A. (1997) In vitro bactericidal effect of LY 333328 against vancomycin resistant and susceptible Enterococcus faecium. In: Abstracts, 37th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Toronto, ON, September 28-October 1, F-8, p. 147.
92. Nicas, T.I. et al. (1995) Semisynthetic glycopeptides active against vancomycin-resistant enterococci: activity against staphylococci and streptococci in vitro and in vivo. In: Abstracts, 35th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), New Orleans, LA, September 17-20, F248, p. 156.
93. Sloos, J.H., Van de Klundert, J.A.M., Seymonson, G. and Vanboven, C.P. (1997) Susceptibility of coagulase-negative staphylococci to a new glycopeptide (oritavancin). In: Abstracts, 37th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Toronto, ON, September 28-October 1, F-6, p. 147.
94. Hershberger E., Aeschlimann J.R., Moldovan T., Rybak M.J. Evaluation of bactericidal activities of LY333328, vancomycin, teicoplanin, ampicillin-sulbactam, trovafloxacin, and RP59500 alone or in combination with rifampin or gentamicin against different strains of vancomycin-intermediate Staphylococcus aureus by time-kill curve methods. Antimicrob. Agents Chemother. 43:1999;717-721.
95. Coyle E.A., Rybak M.J. Activity of oritavancin (LY333328), an investigational glycopeptide, compared to that of vancomycin against multidrug-resistant Streptococcus pneumoniae in an in vitro pharmacodynamic model. Antimicrob. Agents Chemother. 45:2001;706-709.
96. Cha R., Rybak M.J. Characterization of the activities of linezolid, oritavancin, levofloxacin and vancomycin against vancomycin-tolerant Streptococcus pneumoniae. Pharmacotherapy. 21:2001;347-352.
97. Loll P.J., Kaplan J., Selinsky B.S., Axelsen P.H. Vancomycin binding to low-affinity ligands: delineating a minimum set of interactions necessary for high-affinity binding. J. Med. Chem. 42:1999;4714-4719.
98. Arthur M., Depardieu F., Reynolds P., Courvalin P. Moderate-level resistance to glycopeptide LY333328 mediated by genes of the vanA and vanB clusters in enterococci. Antimicrob. Agents Chemother. 43:1999;1875-1880.
99. Wilson P. An LY333328-dependent strain of Enterococcus faecalis isolated from a blood culture. J. Antimicrob. Chemother. 42:1998;406-407.
100. Allen N.E., Hobbs J.N. Jr., Nicas T.I. Inhibition of peptidoglycan biosynthesis in vancomycin-susceptible and -resistant bacteria by a semisynthetic glycopeptide antibiotic. Antimicrob. Agents Chemother. 40:1996;2356-2362.
101. Allen N.E., Hobbs J.N. Jr., Alborn W.E. Jr. Inhibition of peptidoglycan biosynthesis in gram-positive bacteria by LY146032. Antimicrob. Agents Chemother. 31:1987;1093-1099.
102. Hammes W.P., Neuhaus F.C. Biosynthesis of peptidoglycan in Gaffkya homari: role of the peptide subunit of uridine diphosphate-N-acetyl-muramyl-pentapeptide. J. Bacteriol. 120:1974;210-218.
103. Ge M., et al. Vancomycin derivatives that inhibit peptidoglycan biosynthesis without binding D-Ala-D-Ala. Science (Washington, DC). 284:1999;507-511.
104. Roy R.S., et al. Direct interaction of a vancomycin derivative with bacterial enzymes involved in cell wall biosynthesis. Chem. Biol. 8:2001;1095-1106.
105. Allen N.E., LeTourneau D.L., Hobbs J.N. Jr. The role of hydrophobic side chains as determinants of antibacterial activity of semisynthetic glycopeptide antibiotics. J. Antibiot. 50:1997;677-684.
106. Gale, E.F., Cundliffe, E., Reynolds, P.E., Richmond, M.H. and Waring, M.J. (1981) The molecular basis of antibiotic action. Wiley, New York.
107. Goldman R.C., Baizman E.R., Longley C.B., Branstrom A.A. Chlorobiphenyl-desleucyl-vancomycin inhibits the transglycosylation process required for peptidoglycan synthesis in bacteria in the absence of dipeptide binding. FEMS Microbiol. Lett. 183:2000;209-214.
108. Kerns R., Dong S.D., Fukuzawa S., Carbeck J., Kohler J., Silver L., Kahne D. The role of hydrophobic substituents in the biological activity of glycopeptide antibiotics. J. Am. Chem. Soc. 122:2000;12608-12609.
109. Pavlov A.Y., et al. Synthesis of hydrophobic N′-mono and N′,N″-double alkylated eremomycins inhibiting the transglycosylation stage of bacterial cell wall biosynthesis. J. Antibiot. 54:2001;455-459.
110. Printsevskaya S.S., et al. Synthesis and mode of action of hydrophobic derivatives of the glycopeptide antibiotic eremomycin and des-(N-methyl-D-leucyl)eremomycin against glycopeptide-sensitive and -resistant bacteria. J. Med. Chem. 45:2002;1340-1347.
111. Perkins H.R. Vancomycin and related antibiotics. Pharmacol. Ther. 16:1982;181-197.
112. Chu Y.-H., Avila L.Z., Gao J., Whitesides G.M. Affinity capillary electrophoresis. Acc. Chem. Res. 28:1995;461-468.
113. Good V.M., Gwynn M.N., Knowles D.J.C. MM45289, a potent glycopeptide antibiotic which interacts weakly with diacetyl-L-lysyl-D-alanyl-D-alanine. J. Antibiot. 43:1990;550-555.
114. Sharman, G.J. and Williams, D.H. (1997) Common factors in the mode of action of vancomycin group antibiotics active against resistant bacteria. Chem. Commun. (Cambridge) 1997, 723-724.
115. Nieto M., Perkins H.R. Physiochemical properties of vancomycin and iodovancomycin and their complexes with diacetyl-L-lysyl-D-alanyl-D-alanine. Biochem. J. 123:1971;773-787.
116. Prowse W.G., Kline A.D., Skelton M.A., Loncharich R.J. Conformation of A82846B, a glycopeptide antibiotic, complexed with its cell wall fragment: an asymmetric homodimer determined using NMR spectroscopy. Biochemistry. 34:1995;9632-9644.
117. LeTourneau D.L., Allen N.E. Use of capillary electrophoresis to measure dimerization of glycopeptide antibiotics. Anal. Biochem. 246:1997;62-66.
118. Rao J., Whitesides G.M. Tight binding of a dimeric derivative of vancomycin with dimeric L-Lys-D-Ala-D-Ala. J. Am. Chem. Soc. 119:1997;10286-10290.
119. Sundram U.N., Griffin J.H., Nicas T.I. Novel vancomycin dimers with activity against vancomycin-resistant enterococci. J. Am. Chem. Soc. 118:1996;13107-13108.
120. Staroske T., Williams D.H. Synthesis of covalent head-to-tail dimers of vancomycin. Tetrahedron Lett. 39:1998;4917-4920.
121. Nicolaou K.C., Hughes R., Cho S.Y., Winssinger N., Labischinski H., Endermann R. Synthesis and biological evaluation of vancomycin dimers with potent activity against vancomycin-resistant bacteria: target-accelerated combinatorial synthesis. Chem. Eur. J. 7:2001;3824-3843.
122. Stack, D.R., LeTourneau, D.L., Mullen, D.L., Butler, T.F., Allen, N.E., Kline, A.D., Nicas, T.I. and Thompson, R.C. (1997) Covalent glycopeptide dimers: synthesis, physical characterization, and antibacterial activity. In: Abstracts, 37th Interscience Conference on Antimicrobial Agents and Chemotherapy, Toronto, ON, September 28-October 1, F-1.
123. Cooper M.A., Williams D.H., Cho Y.R. Surface plasmon resonance analysis of glycopeptide antibiotic activity at a model membrane surface. J. Chem. Soc. Chem. Commun. 1997:1997;1625-1626.
124. Cooper M.A., Williams D.H. Binding of glycopeptide antibiotics to a model of a vancomycin-resistant bacterium. Chem. Biol. 6:1999;891-899.
125. Sharman G.J., et al. The roles of dimerization and membrane anchoring in activity of glycopeptide antibiotics against vancomycin-resistant bacteria. J. Am. Chem. Soc. 119:1997;12041-12047.
126. Westwell M.S., Bardsley B., Dancer R.J., Try C., Williams D.H. Cooperativity in ligand binding expressed at a model cell membrane by the vancomycin group antibiotics. J. Chem. Soc. Chem. Commun. 1996:1996;589-590.
127. Searle M.S., et al. Enthalpic (electrostatic) contribution to the chelate effect: a correlation between ligand binding constant and a specific hydrogen bond strength in complexes of glycopeptide antibiotics with cell wall analogs. J. Chem. Soc. Perkin Trans. 1:1996;2781-2786.
128. Williams D.H., Maguire A.J., Tsuzuki W., Westwell M.S. An analysis of the origins of a cooperative binding energy of dimerization. Science. 280:1998;711-714.
129. Linsdell H., Toiron C., Bruix M., Rivas G., Menendez M. Dimerization of A82846B, vancomycin and ristocetin: influence on antibiotic complexation with cell wall model peptides. J. Antibiot. 49:1996;181-193.
130. Jencks W.P. On the attribution and additivity of binding energies. Proc. Natl. Acad. Sci. USA. 78:1981;4046-4050.
131. Try A.C., Sharman G.J., Dancer R.J., Bardsley B., Entress R.M.H., Williams D.H. Use of model cell membranes to demonstrate templated binding of vancomycin group antibiotics. J. Chem. Soc. Perkin Trans. 1:1997;2911-2917.
132. Entress R.M.H., Dancer R.J., O'Brien D.P., Try A.C., Cooper M.A., Williams D.H. 19F NMR in the measurement of binding affinities of chloroeremomycin to model bacterial cell-wall surfaces that mimic VanA and VanB resistance. Chem. Biol. 5:1998;329-337.
133. Allen N.E., LeTourneau D.L., Hobbs J.N. Jr., Thompson R.C. Hexapeptide derivatives of glycopeptide antibiotics: tools for mechanism of action studies. Antimicrob. Agents Chemother. 46:2002;2344-2348.
134. Wilkie, S.C., LeTourneau, D.L., Mullen, D.L., Butler, T.F., Allen, N.E., Nicas, T.I. and Thompson, R.C. (1998) N-terminal modification of glycopeptide antibiotics: synthesis, antibacterial activity and mechanism of action. In: Abstracts, 38th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego, CA, September 24-27, F-115.
135. Williams D.H. The glycopeptide story - How to kill the deadly 'superbugs'. Nat. Prod. Res. 13:1996;469-477.
136. Goldman R.C., Gange D. Inhibition of transglycosylation involved in bacterial peptidoglycan synthesis. Curr. Med. Chem. 7:2000;801-820.
137. Chen H.Y., Hill R.L.R., Kirk M., Casewell M.W., Beighton D. Differential antimicrobial susceptibility between human and chicken isolates of vancomycin-resistant and sensitive Enterococcus faecium. Int. J. Antimicrob. Agents. 19:2002;39-46.
138. Frank U., Jonas D., Lupke T., Ribeiro-Ayeh E., Schmidt-Eisenlohr E., Daschner F.D., Resistance T.N.R.C.S.G.f.A. Antimicrobial susceptibilities among nosocomial pathogens isolated in intensive care units in Germany. Eur. J. Clin. Microbiol. Infect. Dis. 19:2000;888-891.
139. Hoban, D., Cox, L., Palatnick, L., Weshnoweski, B., Kabani, A., Zelenitsky, S., Karlowsky, J. and Zhanel, G. (1997) Comparative in vitro activity of oritavancin, a new glycopeptide, against Enterococcus gallinarum and Enterococcus casseliflavus. In: Abstracts, 37th Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Toronto, ON, September 28-October 1, F-7, p. 24.
140. Mezzatesta M.L., Bonfiglio G., De Angelis L., Stefani S., Russo G. Study on the in-vitro activity of LY333328 against gram-positive cocci. J. Antimicrob. Chemother. 42:1998;266-268.
141. Noviello S., Ianniello F., Esposito S. In vitro activity of LY333328 (oritavancin) against gram-positive aerobic cocci and synergy with ciprofloxacin against enterococci. J. Antimicrob. Chemother. 48:2001;283-286.
142. Schouten M.A., Voss A., Hoogkamp-Korstanje J.A. Antimicrobial susceptibility patterns of enterococci causing infections in Europe. The European VRE Study Group. Antimicrob. Agents Chemother. 43:1999;2542-2546.
143. Sanchez-Silos R.M., Perez-Giraldo C., Blanco M.T., Moran F.J., Hurtado C., Gomez-Garcia A.C. Resistance to vancomycin, LY333328, ciprofloxacin and trovafloxacin of community-acquired and nosocomial strains of Enterococcus faecalis isolated in Badajoz (Spain) with and without high-level resistance to streptomycin and gentamicin. Chemotherapy (Basel). 47:2001;415-420.
144. Struwig M.C., Botha P.L., Chalkley L.J. In vitro activities of 15 antimicrobial agents against clinical isolates of South African enterococci. Antimicrob. Agents Chemother. 42:1998;2752-2755.
145. Candiani G., Abbondi M., Borgonovi M., Romano G., Parenti F. In-vitro and in-vivo antibacterial activity of BI 397, a new semi-synthetic glycopeptide antibiotic. J. Antimicrob. Chemother. 44:1999;179-192.
146. Fraise A.P., Andrews J., Wise R. Activity of a new glycopeptide antibiotic (LY333328) against enterococci and other resistant gram-positive organisms. J. Antimicrob. Chemother. 40:1997;423-425.