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Volumn 46, Issue 23, 2003, Pages 4904-4909

Multivalent Antibiotics via Metal Complexes: Potent Divalent Vancomycins against Vancomycin-Resistant Enterococci

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN DERIVATIVE; DIMER; DRUG RECEPTOR; LIGAND; METAL COMPLEX; VANCOMYCIN DERIVATIVE;

EID: 0242331083     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030417q     Document Type: Article
Times cited : (51)

References (49)
  • 1
    • 0026760182 scopus 로고
    • The Crisis in Antibiotic-Resistance
    • Neu, H. C. The Crisis in Antibiotic-Resistance. Science 1992, 257, 1064-1073.
    • (1992) Science , vol.257 , pp. 1064-1073
    • Neu, H.C.1
  • 2
    • 0033579207 scopus 로고    scopus 로고
    • Use of the cell wall precursor lipid II by a pore-forming peptide antibiotic
    • Breukink, E.; Wiedemann, I.; van Kraaij, C.; Kuipers, O. P.; Sahl, H. G. et al. Use of the cell wall precursor lipid II by a pore-forming peptide antibiotic. Science 1999, 286, 2361-2364.
    • (1999) Science , vol.286 , pp. 2361-2364
    • Breukink, E.1    Wiedemann, I.2    Van Kraaij, C.3    Kuipers, O.P.4    Sahl, H.G.5
  • 3
    • 0035943435 scopus 로고    scopus 로고
    • Selective Celavage of D-Ala-D-Lac by Small Molecules: Re-Sensitizing Resistant Bacteria to Vancomycin
    • Chiosis, G.; Boneca, I. G. Selective Celavage of D-Ala-D-Lac by Small Molecules: Re-Sensitizing Resistant Bacteria to Vancomycin. Science 2001, 293, 1484-1487.
    • (2001) Science , vol.293 , pp. 1484-1487
    • Chiosis, G.1    Boneca, I.G.2
  • 4
    • 0033574743 scopus 로고    scopus 로고
    • Vancomycin derivatives that inhibit peptidoglycan biosynthesis without binding D-Ala-D-Ala
    • Ge, M.; Chen, Z.; Onishi, H. R.; Kohler, J.; Silver, L. L. et al. Vancomycin derivatives that inhibit peptidoglycan biosynthesis without binding D-Ala-D-Ala. Science 1999, 284, 507-511.
    • (1999) Science , vol.284 , pp. 507-511
    • Ge, M.1    Chen, Z.2    Onishi, H.R.3    Kohler, J.4    Silver, L.L.5
  • 5
    • 0037043734 scopus 로고    scopus 로고
    • Biomimetic synthesis and optimization of cyclic peptide antibiotics
    • Kohli, R. M.; Walsh, C. T.; Burkart, M. D. Biomimetic synthesis and optimization of cyclic peptide antibiotics. Nature 2002, 418, 658-661.
    • (2002) Nature , vol.418 , pp. 658-661
    • Kohli, R.M.1    Walsh, C.T.2    Burkart, M.D.3
  • 6
    • 0034648798 scopus 로고    scopus 로고
    • Peptide cyclization catalysed by the thioesterase domain of tyrocidine synthetase
    • Trauger, J. W.; Kohli, R. M.; Mootz, H. D.; Marahiel, M. A.; Walsh, C. T. Peptide cyclization catalysed by the thioesterase domain of tyrocidine synthetase. Nature 2000, 407, 215-218.
    • (2000) Nature , vol.407 , pp. 215-218
    • Trauger, J.W.1    Kohli, R.M.2    Mootz, H.D.3    Marahiel, M.A.4    Walsh, C.T.5
  • 7
    • 0033897809 scopus 로고    scopus 로고
    • Emerging themes in medicinal glycoscience
    • Koeller, K. M.; Wong, C. H. Emerging themes in medicinal glycoscience. Nat. Biotech. 2000, 18, 835-841.
    • (2000) Nat. Biotech. , vol.18 , pp. 835-841
    • Koeller, K.M.1    Wong, C.H.2
  • 8
    • 0035840941 scopus 로고    scopus 로고
    • An efficient chemoenzymatic strategy for the synthesis of wild-type and vancomycin-resistant bacterial cell-wall precursors: UDP-N-acetylmuramyl-peptides
    • Liu, H. T.; Sadamoto, R.; Sears, P. S.; Wong, C. H. An efficient chemoenzymatic strategy for the synthesis of wild-type and vancomycin-resistant bacterial cell-wall precursors: UDP-N-acetylmuramyl-peptides. J. Am. Chem. Soc. 2001, 123, 9916-9917.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9916-9917
    • Liu, H.T.1    Sadamoto, R.2    Sears, P.S.3    Wong, C.H.4
  • 9
    • 0032476812 scopus 로고    scopus 로고
    • Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors
    • Mammen, M.; Choi, S. K.; Whitesides, G. M. Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors. Angew. Chem., Int. Ed. 1998, 37, 2755-2794.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2755-2794
    • Mammen, M.1    Choi, S.K.2    Whitesides, G.M.3
  • 10
    • 0033485286 scopus 로고    scopus 로고
    • Binding of glycopeptide antibiotics to a model of a vancomycin-resistant bacterium
    • Cooper, M. A.; Williams, D. H. Binding of glycopeptide antibiotics to a model of a vancomycin-resistant bacterium. Chem. Biol. 1999, 6, 891-899.
    • (1999) Chem. Biol. , vol.6 , pp. 891-899
    • Cooper, M.A.1    Williams, D.H.2
  • 11
    • 0032076568 scopus 로고    scopus 로고
    • A trivalent system from vancomycin center dot D-Ala-D-Ala with higher affinity than avidin center dot biotin
    • Rao, J. H.; Lahiri, J.; Isaacs, L.; Weis, R. M.; Whitesides, G. M. A trivalent system from vancomycin center dot D-Ala-D-Ala with higher affinity than avidin center dot biotin. Science 1998, 280, 708-711.
    • (1998) Science , vol.280 , pp. 708-711
    • Rao, J.H.1    Lahiri, J.2    Isaacs, L.3    Weis, R.M.4    Whitesides, G.M.5
  • 12
    • 0033599497 scopus 로고    scopus 로고
    • Using surface plasmon resonance to study the binding of vancomycin and its dimer to self-assembled monolayers presenting D-Ala-D-Ala
    • Rao, J.; Yan, L.; Xu, B.; Whitesides, G. M. Using surface plasmon resonance to study the binding of vancomycin and its dimer to self-assembled monolayers presenting D-Ala-D-Ala. J. Am. Chem. Soc. 1999, 121, 2629-2630.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2629-2630
    • Rao, J.1    Yan, L.2    Xu, B.3    Whitesides, G.M.4
  • 13
    • 0034728565 scopus 로고    scopus 로고
    • Design, synthesis, and characterization of a high-affinity trivalent system derived from vancomycin and L-Lys-D-Ala-D-Ala
    • Rao, J. H.; Lahiri, J.; Weis, R. M.; Whitesides, G. M. Design, synthesis, and characterization of a high-affinity trivalent system derived from vancomycin and L-Lys-D-Ala-D-Ala. J. Am. Chem. Soc. 2000, 122, 2698-2710.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2698-2710
    • Rao, J.H.1    Lahiri, J.2    Weis, R.M.3    Whitesides, G.M.4
  • 14
    • 0033150261 scopus 로고    scopus 로고
    • Binding of a dimeric derivative of vancomycin to L-Lys-D-Ala-D-Lact in solution and at a surface
    • Rao, J. H.; Yan, L.; Lahiri, J.; Whitesides, G. M.; Weis, R. M. et al. Binding of a dimeric derivative of vancomycin to L-Lys-D-Ala-D-Lact in solution and at a surface. Chem. Biol. 1999, 6, 353-359.
    • (1999) Chem. Biol. , vol.6 , pp. 353-359
    • Rao, J.H.1    Yan, L.2    Lahiri, J.3    Whitesides, G.M.4    Weis, R.M.5
  • 15
    • 0035801386 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of vancomycin dimers with potent activity against vancomycin-resistant bacteria: Target- accelerated combinatorial synthesis
    • Nicolaou, K. C.; Hughes, R.; Cho, S. Y.; Winssinger, N.; Labischinski, H. et al. Synthesis and biological evaluation of vancomycin dimers with potent activity against vancomycin-resistant bacteria: target- accelerated combinatorial synthesis. Chem. Eur. J. 2001, 7, 3824-3843.
    • (2001) Chem. Eur. J. , vol.7 , pp. 3824-3843
    • Nicolaou, K.C.1    Hughes, R.2    Cho, S.Y.3    Winssinger, N.4    Labischinski, H.5
  • 16
    • 0034602053 scopus 로고    scopus 로고
    • Target-accelerated combinatorial synthesis and discovery of highly potent antibiotics effective against vancomycin-resistant bacteria
    • Nicolaou, K. C.; Hughes, R.; Cho, S. Y.; Winssinger, N.; Smethurst, C. et al. Target-accelerated combinatorial synthesis and discovery of highly potent antibiotics effective against vancomycin-resistant bacteria. Angew. Chem., Int. Ed. 2000, 39, 3823-3828.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3823-3828
    • Nicolaou, K.C.1    Hughes, R.2    Cho, S.Y.3    Winssinger, N.4    Smethurst, C.5
  • 17
    • 0030479181 scopus 로고    scopus 로고
    • Novel vancomycin dimers with activity against vancomycin-resistant enterococci
    • Sundram, U. N.; Griffin, J. H.; Nicas, T. I. Novel vancomycin dimers with activity against vancomycin-resistant enterococci. J. Am. Chem. Soc. 1996, 118, 13107-13108.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 13107-13108
    • Sundram, U.N.1    Griffin, J.H.2    Nicas, T.I.3
  • 18
    • 0037009079 scopus 로고    scopus 로고
    • Novel glycodendrimers self-assemble to nanoparticles which function as polyvalent ligands in vitro and in vivo
    • Thoma, G.; Katopodis, A. G.; Voelcker, N.; Duthaler, R. O.; Streiff, M. B. Novel glycodendrimers self-assemble to nanoparticles which function as polyvalent ligands in vitro and in vivo. Angew. Chem., Int. Ed. 2002, 41, 3195-3198.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3195-3198
    • Thoma, G.1    Katopodis, A.G.2    Voelcker, N.3    Duthaler, R.O.4    Streiff, M.B.5
  • 23
    • 0033542413 scopus 로고    scopus 로고
    • Emergence of vancomycin tolerance in Streptococcus pneumoniae
    • Novak, R.; Henriques, B.; Charpentier, E.; Normark, S.; Tuomanen, E. Emergence of vancomycin tolerance in Streptococcus pneumoniae. Nature 1999, 399, 590-593.
    • (1999) Nature , vol.399 , pp. 590-593
    • Novak, R.1    Henriques, B.2    Charpentier, E.3    Normark, S.4    Tuomanen, E.5
  • 24
    • 0034680167 scopus 로고    scopus 로고
    • Molecular mechanisms that confer antibacterial drug resistance
    • Walsh, C. Molecular mechanisms that confer antibacterial drug resistance. Nature 2000, 406, 775-781.
    • (2000) Nature , vol.406 , pp. 775-781
    • Walsh, C.1
  • 25
    • 0027488684 scopus 로고
    • Vancomycin Resistance - Decoding the Molecular Logic (Vol 261, Pg 469, 1993)
    • Walsh, C. T. Vancomycin Resistance - Decoding the Molecular Logic (Vol 261, Pg 469, 1993). Science 1993, 262, 164-164.
    • (1993) Science , vol.262 , pp. 164-164
    • Walsh, C.T.1
  • 26
    • 0033574766 scopus 로고    scopus 로고
    • Microbiology - Deconstructing vancomycin
    • Walsh, C. Microbiology - Deconstructing vancomycin. Science 1999, 284, 442-443.
    • (1999) Science , vol.284 , pp. 442-443
    • Walsh, C.1
  • 30
    • 0032076269 scopus 로고    scopus 로고
    • An analysis of the origins of a cooperative binding energy of dimerization
    • Williams, D. H.; Maguire, A. J.; Tsuzuki, W.; Westwell, M. S. An analysis of the origins of a cooperative binding energy of dimerization. Science 1998, 280, 711-714.
    • (1998) Science , vol.280 , pp. 711-714
    • Williams, D.H.1    Maguire, A.J.2    Tsuzuki, W.3    Westwell, M.S.4
  • 32
    • 0025886180 scopus 로고
    • Toward the Semiquantitative Estimation of Binding Constants - Guides for Peptide Peptide Binding in Aqueous-Solution
    • Williams, D. H.; Cox, J. P. L.; Doig, A. J.; Gardner, M.; Gerhard, U. et al. Toward the Semiquantitative Estimation of Binding Constants - Guides for Peptide Peptide Binding in Aqueous-Solution. J. Am. Chem. Soc. 1991, 113, 7020-7030.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7020-7030
    • Williams, D.H.1    Cox, J.P.L.2    Doig, A.J.3    Gardner, M.4    Gerhard, U.5
  • 33
    • 0033519259 scopus 로고    scopus 로고
    • The vancomycin group of antibiotics and the fight against resistant bacteria
    • Williams, D. H.; Bardsley, B. The vancomycin group of antibiotics and the fight against resistant bacteria. Angew. Chem., Int. Ed. 1999, 38, 1173-1193.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1173-1193
    • Williams, D.H.1    Bardsley, B.2
  • 34
    • 12444297125 scopus 로고    scopus 로고
    • Multivalen Drug Design. Synthesis and In Vitro Analysis of an Array of Vancomycin Dimers
    • Griffin, J. H.; Linsell, M. S.; Nodwell, M. B.; Chen, Q.; Pace, J. L. et al. Multivalen Drug Design. Synthesis and In Vitro Analysis of an Array of Vancomycin Dimers. J. Am. Chem. Soc. 2003, 125, 6517-6531.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6517-6531
    • Griffin, J.H.1    Linsell, M.S.2    Nodwell, M.B.3    Chen, Q.4    Pace, J.L.5
  • 36
    • 0000598486 scopus 로고    scopus 로고
    • Using a convenient, quantitative model for torsional entropy to establish qualitative trends for molecular processes that restrict conformational freedom
    • Mammen, M.; Shakhnovich, E. I.; Whitesides, G. M. Using a convenient, quantitative model for torsional entropy to establish qualitative trends for molecular processes that restrict conformational freedom. J. Org. Chem. 1998, 63, 3168-3175.
    • (1998) J. Org. Chem. , vol.63 , pp. 3168-3175
    • Mammen, M.1    Shakhnovich, E.I.2    Whitesides, G.M.3
  • 37
    • 9644258919 scopus 로고
    • The cost of conformational order: Entropy changes in Molecular associations
    • Searle, M. S.; Williams, D. H. The cost of conformational order: entropy changes in Molecular associations. J. Am. Chem. Soc. 1992, 114, 10690-10697.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10690-10697
    • Searle, M.S.1    Williams, D.H.2
  • 39
    • 0001403845 scopus 로고
    • Multivalent Carbohydrate Ligands Assembled on a Metal Template
    • Sakai, S.; Sasaki, T. Multivalent Carbohydrate Ligands Assembled on a Metal Template. J. Am. Chem. Soc. 1994, 116, 1587-1588.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1587-1588
    • Sakai, S.1    Sasaki, T.2
  • 40
    • 0027458868 scopus 로고
    • Design of a Metallo Bzip-Protein That Discriminates between Cre and Ap1 Target Sites - Selection against Ap1
    • Cuenoud, B.; Schepartz, A. Design of a Metallo Bzip-Protein That Discriminates between Cre and Ap1 Target Sites - Selection against Ap1. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1154-1159.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 1154-1159
    • Cuenoud, B.1    Schepartz, A.2
  • 41
    • 0027339727 scopus 로고
    • Altered Specificity of DNA-Binding Proteins with Transition- Metal Dimerization Domains
    • Cuenoud, B.; Schepartz, A. Altered Specificity of DNA-Binding Proteins with Transition- Metal Dimerization Domains. Science 1993, 259, 510-513.
    • (1993) Science , vol.259 , pp. 510-513
    • Cuenoud, B.1    Schepartz, A.2
  • 42
    • 0026795211 scopus 로고
    • Sequence-Specific Oxidative Cleavage of DNA by a Designed Metalloprotein, Ni(Ii).Ggh(Hin139-190)
    • Mack, D. P.; Dervan, P. B. Sequence-Specific Oxidative Cleavage of DNA by a Designed Metalloprotein, Ni(Ii).Ggh(Hin139-190). Biochemistry 1992, 31, 9399-9405.
    • (1992) Biochemistry , vol.31 , pp. 9399-9405
    • Mack, D.P.1    Dervan, P.B.2
  • 44
    • 0037132667 scopus 로고    scopus 로고
    • Hydrophobic Interaction and Hydrogen Bonding Cooperatively Confer a Vancomycin Hydrogel: A Potential Candidate for Biomaterials
    • Xing, B.; Yu, C.-W.; Chow, K.-H.; Ho, P.-L.; Fu, D. et al. Hydrophobic Interaction and Hydrogen Bonding Cooperatively Confer a Vancomycin Hydrogel: A Potential Candidate for Biomaterials. J. Am. Chem. Soc. 2002, 124, 14846-14847.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14846-14847
    • Xing, B.1    Yu, C.-W.2    Chow, K.-H.3    Ho, P.-L.4    Fu, D.5
  • 45
    • 0141796263 scopus 로고    scopus 로고
    • Presenting Vancomycin on Nanoparticles to Enhance Antimicrobial Activities
    • Gu, H.; Ho, P. L.; Tong, E.; Xu, C.; Xu, B. Presenting Vancomycin on Nanoparticles to Enhance Antimicrobial Activities. Nano Lett. 2003, 3, 1261-1263.
    • (2003) Nano Lett. , vol.3 , pp. 1261-1263
    • Gu, H.1    Ho, P.L.2    Tong, E.3    Xu, C.4    Xu, B.5
  • 46
    • 0043236522 scopus 로고    scopus 로고
    • Self-Assembled Multivalent Vancomycin on Cell Surfaces Against Vancomycin-Resistant Enterococci (VRE)
    • Xing, B.; Ho, P. L.; Yu, C.-W.; Chow, K.-H.; Gu, H. et al. Self-Assembled Multivalent Vancomycin on Cell Surfaces Against Vancomycin-Resistant Enterococci (VRE). Chem. Commun. 2003, 2224-2225.
    • (2003) Chem. Commun. , pp. 2224-2225
    • Xing, B.1    Ho, P.L.2    Yu, C.-W.3    Chow, K.-H.4    Gu, H.5
  • 47
    • 0037025968 scopus 로고    scopus 로고
    • Structural requirements for VanA activity of vancomycin analogues
    • Chen, Z.; Eggert, U. S.; Dong, S. D.; Shaw, S. J.; Sun, B. Y. et al. Structural requirements for VanA activity of vancomycin analogues. Tetrahedron 2002, 58, 6585-6594.
    • (2002) Tetrahedron , vol.58 , pp. 6585-6594
    • Chen, Z.1    Eggert, U.S.2    Dong, S.D.3    Shaw, S.J.4    Sun, B.Y.5
  • 48
    • 0037018918 scopus 로고    scopus 로고
    • Rotational-echo double resonance characterization of vancomycin binding sites in Staphylococcus aureus
    • Kim, S. J.; Cegelski, L.; Studelska, D. R.; O'Connor, R. D.; Mehta, A. K. et al. Rotational-echo double resonance characterization of vancomycin binding sites in Staphylococcus aureus. Biochemistry 2002, 41, 6967-6977.
    • (2002) Biochemistry , vol.41 , pp. 6967-6977
    • Kim, S.J.1    Cegelski, L.2    Studelska, D.R.3    O'Connor, R.D.4    Mehta, A.K.5
  • 49
    • 0037195278 scopus 로고    scopus 로고
    • Rotational-echo double resonance characterization of the effects of vancomycin on cell wall synthesis in Staphylococcus aureus
    • Cegelski, L.; Kim, S. J.; Hing, A. W.; Studelska, D. R.; O'Connor, R. D. et al. Rotational-echo double resonance characterization of the effects of vancomycin on cell wall synthesis in Staphylococcus aureus. Biochemistry 2002, 41, 13053-13058.
    • (2002) Biochemistry , vol.41 , pp. 13053-13058
    • Cegelski, L.1    Kim, S.J.2    Hing, A.W.3    Studelska, D.R.4    O'Connor, R.D.5


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