메뉴 건너뛰기




Volumn 50, Issue 8, 1997, Pages 677-684

The role of hydrophobic side chains as determinants of antibacterial activity of semisynthetic glycopeptide antibiotics

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; CHLOROORIENTICIN A; DRUG DERIVATIVE; GLYCOPEPTIDE; LY 191145; LY 307599; LY 377502; ORITAVANCIN; UNCLASSIFIED DRUG; VANCOMYCIN;

EID: 0030866228     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.50.677     Document Type: Article
Times cited : (94)

References (38)
  • 1
    • 0027177994 scopus 로고
    • Structure-activity relationships of vancomycin-type glycopeptide antibiotics
    • NAGARAJAN, R.: Structure-activity relationships of vancomycin-type glycopeptide antibiotics. J. Antibiotics 46: 1181-1195, 1993
    • (1993) J. Antibiotics , vol.46 , pp. 1181-1195
    • Nagarajan, R.1
  • 2
    • 0017865395 scopus 로고
    • Teichomycins, new antibiotics from Actinoplanes teichomyceticus nov. sp. I. Description of the producer strain, fermentation studies and biological properties
    • PARENTI, F.; G. BERETTA, M. BERTI & V. ARIOLI: Teichomycins, new antibiotics from Actinoplanes teichomyceticus nov. sp. I. Description of the producer strain, fermentation studies and biological properties. J. Antibiotics 31: 276-283, 1978
    • (1978) J. Antibiotics , vol.31 , pp. 276-283
    • Parenti, F.1    Beretta, G.2    Berti, M.3    Arioli, V.4
  • 3
    • 0021154432 scopus 로고
    • The structure and mode of action of glycopeptide antibiotics of the vancomycin group
    • BARNA, J. C. J. & D. H. WILLIAMS: The structure and mode of action of glycopeptide antibiotics of the vancomycin group. Ann. Rev. Microbiol. 38: 339-357, 1984
    • (1984) Ann. Rev. Microbiol. , vol.38 , pp. 339-357
    • Barna, J.C.J.1    Williams, D.H.2
  • 4
    • 0001805081 scopus 로고
    • Resistance and mode of action
    • Ed., R. NAGARAJAN, Marcel Dekker, New York
    • NICAS, T. I. & N. E. ALLEN: Resistance and mode of action. In Glycopeptide Antibiotics. Ed., R. NAGARAJAN, pp. 219-241, Marcel Dekker, New York, 1994
    • (1994) Glycopeptide Antibiotics , pp. 219-241
    • Nicas, T.I.1    Allen, N.E.2
  • 5
    • 0024355483 scopus 로고
    • Structure, biochemistry and mechanism of action of glycopeptide antibiotics
    • REYNOLDS, P. E.: Structure, biochemistry and mechanism of action of glycopeptide antibiotics. Eur. J. Clin. Microbiol. Infect. Dis. 8: 943-950, 1989
    • (1989) Eur. J. Clin. Microbiol. Infect. Dis. , vol.8 , pp. 943-950
    • Reynolds, P.E.1
  • 6
    • 0016175191 scopus 로고
    • The chemical basis for the action of the vancomycin group of antibiotics
    • PERKINS, H. R. & M. NIETO: The chemical basis for the action of the vancomycin group of antibiotics. Ann. N.Y. Acad. Sci. 235: 348-363, 1974
    • (1974) Ann. N.Y. Acad. Sci. , vol.235 , pp. 348-363
    • Perkins, H.R.1    Nieto, M.2
  • 7
    • 0023856535 scopus 로고
    • Molecular basis of the activity of antibiotics of the vancomycin group
    • WILLIAMS, D. H. & J. P. WALTHO: Molecular basis of the activity of antibiotics of the vancomycin group. Biochemical Pharmacology 37: 133-141, 1988
    • (1988) Biochemical Pharmacology , vol.37 , pp. 133-141
    • Williams, D.H.1    Waltho, J.P.2
  • 8
    • 0001935537 scopus 로고
    • Structure-activity relationships of vancomycin antibiotics
    • Ed., R. NAGARAJAN, Marcel Dekker, New York
    • NAGARAJAN, R.: Structure-activity relationships of vancomycin antibiotics. In Glycopeptide Antibiotics. Ed., R. NAGARAJAN, pp. 195-218. Marcel Dekker, New York, 1994
    • (1994) Glycopeptide Antibiotics , pp. 195-218
    • Nagarajan, R.1
  • 10
    • 0025059822 scopus 로고
    • In vitro activity of LY264826, a new glycopeptide antibiotic, against Gram-positive bacteria isolated from patients with cancer
    • ROLSTON, K. V. I.; H. NGUYEN & M. MESSER: In vitro activity of LY264826, a new glycopeptide antibiotic, against Gram-positive bacteria isolated from patients with cancer. Antimicrob. Agents Chemother. 34: 2137-2141, 1990
    • (1990) Antimicrob. Agents Chemother. , vol.34 , pp. 2137-2141
    • Rolston, K.V.I.1    Nguyen, H.2    Messer, M.3
  • 11
    • 0031038392 scopus 로고    scopus 로고
    • Molecular interactions of a semisynthetic glycopeptide antibiotic with D-alanyl-D-alanine and D-alanyl-D-lactate residues
    • ALLEN, N. E.; D. L. LETOURNEAU & J. N. HOBBS, Jr.: Molecular interactions of a semisynthetic glycopeptide antibiotic with D-alanyl-D-alanine and D-alanyl-D-lactate residues. Antimicrob. Agents Chemother. 41: 66-71, 1997
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 66-71
    • Allen, N.E.1    Letourneau, D.L.2    Hobbs Jr., J.N.3
  • 13
    • 0024600303 scopus 로고
    • Conversion of antibiotic A82846B to orienticin A and structural relationships of related antibiotics
    • NAGARAJAN, R.; D. M. BERRY, A. H. HUNT, J. L. OCCOLOWITZ & A. A. SCHABEL: Conversion of antibiotic A82846B to orienticin A and structural relationships of related antibiotics. J. Org. Chem. 54: 983-986, 1988
    • (1988) J. Org. Chem. , vol.54 , pp. 983-986
    • Nagarajan, R.1    Berry, D.M.2    Hunt, A.H.3    Occolowitz, J.L.4    Schabel, A.A.5
  • 14
    • 0025360337 scopus 로고
    • MM 45289, a potent glycopeptide antibiotic which interacts weakly with diacetyl-L-lysyl-D-alanyl-D-alanine
    • GOOD, V. M.; M. N. GWYNN & D. J. C. KNOWLES: MM 45289, a potent glycopeptide antibiotic which interacts weakly with diacetyl-L-lysyl-D-alanyl-D-alanine. J. Antibiotics 43: 550-555, 1990
    • (1990) J. Antibiotics , vol.43 , pp. 550-555
    • Good, V.M.1    Gwynn, M.N.2    Knowles, D.J.C.3
  • 15
    • 0000005481 scopus 로고
    • Aspects of molecular recognition: Solvent exclusion and dimerisation of the antibiotic ristocetin when bound to a model bacterial cell-wall precursor
    • WALTHO, J. P. & D. H. WILLIAMS: Aspects of molecular recognition: Solvent exclusion and dimerisation of the antibiotic ristocetin when bound to a model bacterial cell-wall precursor. J. Am. Chem. Soc. 111: 2475-2480, 1989
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2475-2480
    • Waltho, J.P.1    Williams, D.H.2
  • 16
    • 0015101180 scopus 로고
    • Physiochemical properties of vancomycin and iodovancomycin and their complexes with diacetyl-L-lysyl-D-alanyl-D-alanine
    • NIETO, M. & H. R. PERKINS: Physiochemical properties of vancomycin and iodovancomycin and their complexes with diacetyl-L-lysyl-D-alanyl-D-alanine. Biochem. J. 123: 773-787, 1971
    • (1971) Biochem. J. , vol.123 , pp. 773-787
    • Nieto, M.1    Perkins, H.R.2
  • 17
    • 0027401261 scopus 로고
    • The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics
    • GERHARD, U.; J. P. MACKAY, R. A. MAPLESTONE & D. H. WILLIAMS: The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics. J. Am. Chem. Soc. 115: 232-237, 1993
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 232-237
    • Gerhard, U.1    Mackay, J.P.2    Maplestone, R.A.3    Williams, D.H.4
  • 18
    • 0029877781 scopus 로고    scopus 로고
    • Dimerization of A82846B, vancomycin and ristocetin: Influence on antibiotic complexation with cell wall model peptides
    • LINSDELL, H.; C. TOIRON, M. BRUIX, G. RIVAS & M. MENÉNDEZ: Dimerization of A82846B, vancomycin and ristocetin: influence on antibiotic complexation with cell wall model peptides. J. Antibiotics 49: 181-193, 1996
    • (1996) J. Antibiotics , vol.49 , pp. 181-193
    • Linsdell, H.1    Toiron, C.2    Bruix, M.3    Rivas, G.4    Menéndez, M.5
  • 19
    • 0028942365 scopus 로고
    • Dimerization and membrane anchors in extracellular targeting of vancomycin group antibiotics
    • BEAUREGARD, D. A.; D. H. WILLIAMS, M. N. GWYNN & D. J. C. KNOWLES: Dimerization and membrane anchors in extracellular targeting of vancomycin group antibiotics. Antimicrob. Agents Chemother. 39: 781-785, 1995
    • (1995) Antimicrob. Agents Chemother. , vol.39 , pp. 781-785
    • Beauregard, D.A.1    Williams, D.H.2    Gwynn, M.N.3    Knowles, D.J.C.4
  • 20
    • 0028774039 scopus 로고
    • The structure of an asymmetric dimer relevant to the mode of action of the glycopeptide antibiotics
    • GROVES, P.; M. S. SEARLE, J. P. MACKAY & D. H. WILLIAMS: The structure of an asymmetric dimer relevant to the mode of action of the glycopeptide antibiotics. Structure 2: 747-754, 1994
    • (1994) Structure , vol.2 , pp. 747-754
    • Groves, P.1    Searle, M.S.2    Mackay, J.P.3    Williams, D.H.4
  • 21
    • 0027936628 scopus 로고
    • Glycopeptide antibiotic activity and the possible role of dimerization: A model for biological signaling
    • MACKAY, J. P.; U. GERHARD, D. A. BEAUREGARD, M. S. WESTWELL, M. S. SEARLE & D. H. WILLIAMS: Glycopeptide antibiotic activity and the possible role of dimerization: a model for biological signaling. J. Am. Chem. Soc. 116: 4581-4590, 1994
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4581-4590
    • Mackay, J.P.1    Gerhard, U.2    Beauregard, D.A.3    Westwell, M.S.4    Searle, M.S.5    Williams, D.H.6
  • 24
    • 0026748911 scopus 로고
    • Affinity capillary electrophoresis can simultaneously measure binding constants of multiple peptides to vancomycin
    • CHU, Y.-H. & G. M. WHITESIDES: Affinity capillary electrophoresis can simultaneously measure binding constants of multiple peptides to vancomycin. J. Org. Chem. 57: 3524-3525, 1992
    • (1992) J. Org. Chem. , vol.57 , pp. 3524-3525
    • Chu, Y.-H.1    Whitesides, G.M.2
  • 25
    • 0028451165 scopus 로고
    • Determination of binding constants of ligands to proteins by affinity capillary electrophoresis: Compensation for electroosmotic flow
    • GOMEZ, F. A.; L. Z. AVILA, Y.-H. CHU & G. M. WHITESIDES: Determination of binding constants of ligands to proteins by affinity capillary electrophoresis: compensation for electroosmotic flow. Anal. Chem. 66: 1785-1791, 1994
    • (1994) Anal. Chem. , vol.66 , pp. 1785-1791
    • Gomez, F.A.1    Avila, L.Z.2    Chu, Y.-H.3    Whitesides, G.M.4
  • 26
    • 0031106867 scopus 로고    scopus 로고
    • Use of capillary electrophoresis to measure dimerization of glycopeptide antibiotics
    • LETOURNEAU, D. L. & N. E. ALLEN: Use of capillary electrophoresis to measure dimerization of glycopeptide antibiotics. Anal. Biochemistry 246: 62-66, 1997
    • (1997) Anal. Biochemistry , vol.246 , pp. 62-66
    • Letourneau, D.L.1    Allen, N.E.2
  • 27
    • 0015765613 scopus 로고
    • New procedure for the isolation of membrane vesicles of Bacillus subtilis and an electron microscopy study of their ultrastructure
    • KONINGS, W. N.; A. BISSCHOP, M. VEENHUIS & C. A. VERMEULEN: New procedure for the isolation of membrane vesicles of Bacillus subtilis and an electron microscopy study of their ultrastructure. J. Bacteriol. 116: 1456-1465, 1973
    • (1973) J. Bacteriol. , vol.116 , pp. 1456-1465
    • Konings, W.N.1    Bisschop, A.2    Veenhuis, M.3    Vermeulen, C.A.4
  • 28
    • 0029797308 scopus 로고    scopus 로고
    • Inhibition of peptidoglycan biosynthesis in vancomycin-susceptible and -resistant bacteria by a semisynthetic glycopeptide antibiotic
    • ALLEN, N. E.; J. N. HOBBS, Jr. & T. I. NICAS: Inhibition of peptidoglycan biosynthesis in vancomycin-susceptible and -resistant bacteria by a semisynthetic glycopeptide antibiotic. Antimicrob. Agents Chemother. 40: 2356-2362, 1996
    • (1996) Antimicrob. Agents Chemother. , vol.40 , pp. 2356-2362
    • Allen, N.E.1    Hobbs Jr., J.N.2    Nicas, T.I.3
  • 29
    • 0024361589 scopus 로고
    • Characterization of vancomycin resistance in Enterococcus faecium and Enterococcus faecalis
    • NICAS, T. I.; C. Y. E. WU, J. N. HOBBS, Jr. & N. E. ALLEN: Characterization of vancomycin resistance in Enterococcus faecium and Enterococcus faecalis. Antimicrobial Agents and Chemother. 33: 1121-1124, 1989
    • (1989) Antimicrobial Agents and Chemother. , vol.33 , pp. 1121-1124
    • Nicas, T.I.1    Wu, C.Y.E.2    Hobbs Jr., J.N.3    Allen, N.E.4
  • 30
    • 0028855994 scopus 로고
    • Two conformers of the glycopeptide antibiotic teicoplanin with distinct ligand binding sites
    • WESTWELL, M. S.; U. GERHARD & D. H. WILLIAMS: Two conformers of the glycopeptide antibiotic teicoplanin with distinct ligand binding sites. J. Antibiotics 48: 1292-1298, 1995
    • (1995) J. Antibiotics , vol.48 , pp. 1292-1298
    • Westwell, M.S.1    Gerhard, U.2    Williams, D.H.3
  • 31
    • 0026658231 scopus 로고
    • The cytoplasmic peptidoglycan precursor of vancomycin-resistant Enterococcus faecalis terminates in lactate
    • HANDWERGER, S.; M. J. PUCCI, K. J. VOLK, J. LIU & M. S. LEE: The cytoplasmic peptidoglycan precursor of vancomycin-resistant Enterococcus faecalis terminates in lactate. J. Bacteriol. 174: 5982-5984, 1992
    • (1992) J. Bacteriol. , vol.174 , pp. 5982-5984
    • Handwerger, S.1    Pucci, M.J.2    Volk, K.J.3    Liu, J.4    Lee, M.S.5
  • 32
    • 0026468195 scopus 로고
    • Biosynthesis of modified peptidoglycan precursors by vancomycin-resistant Enterococcus faecium
    • ALLEN, N. E.; J. N. HOBBS, Jr., J. M. RICHARDSON & R. M. RIGGIN: Biosynthesis of modified peptidoglycan precursors by vancomycin-resistant Enterococcus faecium. FEMS Microbiol. Lett. 98: 109-116, 1992
    • (1992) FEMS Microbiol. Lett. , vol.98 , pp. 109-116
    • Allen, N.E.1    Hobbs Jr., J.N.2    Richardson, J.M.3    Riggin, R.M.4
  • 33
    • 0026892270 scopus 로고
    • Modified peptidoglycan precursors produced by glycopeptide-resistant enterococci
    • MESSER, J. & P. E. REYNOLDS: Modified peptidoglycan precursors produced by glycopeptide-resistant enterococci. FEMS Microbiol. Lett. 94: 195-200, 1992
    • (1992) FEMS Microbiol. Lett. , vol.94 , pp. 195-200
    • Messer, J.1    Reynolds, P.E.2
  • 34
    • 0026355435 scopus 로고
    • Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: Biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins vanH and vanA
    • BUGG, T. D. H.; G. D. WRIGHT, S. DUTKA-MALEN, M. ARTHUR, P. COURVALIN & C. T. WALSH: Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins vanH and vanA. Biochemistry 30: 10408-10415, 1991
    • (1991) Biochemistry , vol.30 , pp. 10408-10415
    • Bugg, T.D.H.1    Wright, G.D.2    Dutka-Malen, S.3    Arthur, M.4    Courvalin, P.5    Walsh, C.T.6
  • 35
    • 0028018443 scopus 로고
    • Binding studies of vancomycin to the cytoplasmic peptidoglycan precursors by affinity capillary electrophoresis
    • LIU, J.; K. J. VOLK, M. S. LEE, M. PUCCI & S. HANDWERGER: Binding studies of vancomycin to the cytoplasmic peptidoglycan precursors by affinity capillary electrophoresis. Anal. Chem. 66: 2412-2416, 1994
    • (1994) Anal. Chem. , vol.66 , pp. 2412-2416
    • Liu, J.1    Volk, K.J.2    Lee, M.S.3    Pucci, M.4    Handwerger, S.5
  • 36
    • 0029872767 scopus 로고    scopus 로고
    • Cooperatively in ligand binding expressed at a model cell membrane by the vancomycin group antibiotics
    • WESTWELL, M. S.; B. BARDSLEY, R. J. DANCER, A. C. TRY & D. H. WILLIAMS: Cooperatively in ligand binding expressed at a model cell membrane by the vancomycin group antibiotics. Chem. Commun. 1996: 589-590, 1996
    • (1996) Chem. Commun. , vol.1996 , pp. 589-590
    • Westwell, M.S.1    Bardsley, B.2    Dancer, R.J.3    Try, A.C.4    Williams, D.H.5
  • 37
    • 0019407381 scopus 로고
    • On the attribution and additivity of binding energies
    • JENCKS, W. P.: On the attribution and additivity of binding energies. Proc. Natl. Acad. Sci. U.S.A. 78: 4046-4050, 1981
    • (1981) Proc. Natl. Acad. Sci. U.S.A. , vol.78 , pp. 4046-4050
    • Jencks, W.P.1
  • 38
    • 0031051359 scopus 로고    scopus 로고
    • In vitro activity and spectrum of LY333328, a novel glycopeptide derivative
    • JONES, R. D.; M. S. BARRETT & M. E. ERWIN: In vitro activity and spectrum of LY333328, a novel glycopeptide derivative. Antimicrob. Agents Chemother. 41: 488-493, 1996
    • (1996) Antimicrob. Agents Chemother. , vol.41 , pp. 488-493
    • Jones, R.D.1    Barrett, M.S.2    Erwin, M.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.