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Volumn 6, Issue 4, 2015, Pages 455-460

Azolylthioacetamide: A highly promising scaffold for the development of metallo-β-lactamase inhibitors

Author keywords

Antibiotic resistance; azolylthioacetamide; ImiS; inhibitor; metallo lactamase; subclass B2

Indexed keywords

ASPARAGINE; BACTERIAL PROTEIN; BETA LACTAMASE INHIBITOR; CARBOXYL GROUP; CEFALEXIN; IMIPENEM; LYSINE; METALLO BETA LACTAMASE; METALLO BETA LACTAMASE INHIBITOR; PROTEIN CCRA; PROTEIN CPHA; PROTEIN IMIS; PYRROLE DERIVATIVE; THIOACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

EID: 84927600380     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml500534c     Document Type: Article
Times cited : (49)

References (36)
  • 2
    • 33746312394 scopus 로고    scopus 로고
    • A new approach to the inhibition of metallo-beta-lactamases
    • Spencer, J.; Walsh, T. R. A new approach to the inhibition of metallo-beta-lactamases Angew. Chem., Int. Ed. 2006, 45, 1022-6
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1022-1026
    • Spencer, J.1    Walsh, T.R.2
  • 3
    • 77149165713 scopus 로고    scopus 로고
    • Updated functional classification of beta-lactamases
    • Bush, K.; Jacoby, G. A. Updated functional classification of beta-lactamases Antimicrob. Agents Chemother. 2010, 54, 969-76
    • (2010) Antimicrob. Agents Chemother. , vol.54 , pp. 969-976
    • Bush, K.1    Jacoby, G.A.2
  • 4
    • 16644379888 scopus 로고    scopus 로고
    • Metallo-beta-lactamase inhibitors: Promise for the future?
    • Toney, J. H.; Moloughney, J. G. Metallo-beta-lactamase inhibitors: promise for the future? Curr. Opin. Investig. Drugs 2004, 5, 823-6
    • (2004) Curr. Opin. Investig. Drugs , vol.5 , pp. 823-826
    • Toney, J.H.1    Moloughney, J.G.2
  • 6
    • 74249108028 scopus 로고    scopus 로고
    • Three decades of beta-lactamase inhibitors
    • Drawz, S. M.; Bonomo, R. A. Three decades of beta-lactamase inhibitors Clin. Microbiol. Rev. 2010, 23, 160-201
    • (2010) Clin. Microbiol. Rev. , vol.23 , pp. 160-201
    • Drawz, S.M.1    Bonomo, R.A.2
  • 7
    • 84904514434 scopus 로고    scopus 로고
    • Recent advances in the discovery of metallo-beta-lactamase inhibitors for beta-lactam antibiotic-resistant reversing agents
    • Guo, Z.; Ma, S. Recent advances in the discovery of metallo-beta-lactamase inhibitors for beta-lactam antibiotic-resistant reversing agents Curr. Drug Targets 2014, 15, 689-702
    • (2014) Curr. Drug Targets , vol.15 , pp. 689-702
    • Guo, Z.1    Ma, S.2
  • 9
    • 0034681922 scopus 로고    scopus 로고
    • Crystal structure of the IMP-1 metallo beta-lactamase from Pseudomonas aeruginosa and its complex with a mercaptocarboxylate inhibitor: Binding determinants of a potent, broad-spectrum inhibitor
    • Concha, N. O.; Janson, C. A.; Rowling, P.; Pearson, S.; Cheever, C. A.; Clarke, B. P.; Lewis, C.; Galleni, M.; Frere, J. M.; Payne, D. J.; Bateson, J. H.; Abdel-Meguid, S. S. Crystal structure of the IMP-1 metallo beta-lactamase from Pseudomonas aeruginosa and its complex with a mercaptocarboxylate inhibitor: binding determinants of a potent, broad-spectrum inhibitor Biochemistry 2000, 39, 4288-98
    • (2000) Biochemistry , vol.39 , pp. 4288-4298
    • Concha, N.O.1    Janson, C.A.2    Rowling, P.3    Pearson, S.4    Cheever, C.A.5    Clarke, B.P.6    Lewis, C.7    Galleni, M.8    Frere, J.M.9    Payne, D.J.10    Bateson, J.H.11    Abdel-Meguid, S.S.12
  • 10
    • 68349152498 scopus 로고    scopus 로고
    • Metallo-beta-lactamase inhibitory activity of phthalic acid derivatives
    • Hiraiwa, Y.; Morinaka, A.; Fukushima, T.; Kudo, T. Metallo-beta-lactamase inhibitory activity of phthalic acid derivatives Bioorg. Med. Chem. Lett. 2009, 19, 5162-5
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 5162-5165
    • Hiraiwa, Y.1    Morinaka, A.2    Fukushima, T.3    Kudo, T.4
  • 15
    • 84864417937 scopus 로고    scopus 로고
    • N-heterocyclic dicarboxylic acids: Broad-spectrum inhibitors of metallo-beta-lactamases with co-antibacterial effect against antibiotic-resistant bacteria
    • Feng, L.; Yang, K. W.; Zhou, L. S.; Xiao, J. M.; Yang, X.; Zhai, L.; Zhang, Y. L.; Crowder, M. W. N-heterocyclic dicarboxylic acids: broad-spectrum inhibitors of metallo-beta-lactamases with co-antibacterial effect against antibiotic-resistant bacteria Bioorg. Med. Chem. Lett. 2012, 22, 5185-9
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 5185-5189
    • Feng, L.1    Yang, K.W.2    Zhou, L.S.3    Xiao, J.M.4    Yang, X.5    Zhai, L.6    Zhang, Y.L.7    Crowder, M.W.8
  • 16
    • 0032553559 scopus 로고    scopus 로고
    • The crystal structure of the L1 metallo-beta-lactamase from Stenotrophomonas maltophilia at 1.7 A resolution
    • Ullah, J. H.; Walsh, T. R.; Taylor, I. A.; Emery, D. C.; Verma, C. S.; Gamblin, S. J.; Spencer, J. The crystal structure of the L1 metallo-beta-lactamase from Stenotrophomonas maltophilia at 1.7 A resolution J. Mol. Biol. 1998, 284, 125-36
    • (1998) J. Mol. Biol. , vol.284 , pp. 125-136
    • Ullah, J.H.1    Walsh, T.R.2    Taylor, I.A.3    Emery, D.C.4    Verma, C.S.5    Gamblin, S.J.6    Spencer, J.7
  • 17
    • 80051672898 scopus 로고    scopus 로고
    • Crystal Structure of Serratia fonticola Sfh-I: Activation of the Nucleophile in Mono-Zinc Metallo-β-Lactamases
    • Fonseca, F.; Bromley, E. H. E.; Saavedra, M. J.; Correia, A.; Spencer, J. Crystal Structure of Serratia fonticola Sfh-I: Activation of the Nucleophile in Mono-Zinc Metallo-β-Lactamases J. Mol. Biol. 2011, 411, 951-9
    • (2011) J. Mol. Biol. , vol.411 , pp. 951-959
    • Fonseca, F.1    Bromley, E.H.E.2    Saavedra, M.J.3    Correia, A.4    Spencer, J.5
  • 18
    • 46049100791 scopus 로고    scopus 로고
    • Conformational changes in the metallo-beta-lactamase ImiS during the catalytic reaction: An EPR spectrokinetic study of Co(II)-spin label interactions
    • Sharma, N.; Hu, Z.; Crowder, M. W.; Bennett, B. Conformational changes in the metallo-beta-lactamase ImiS during the catalytic reaction: an EPR spectrokinetic study of Co(II)-spin label interactions J. Am. Chem. Soc. 2008, 130, 8215-22
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8215-8222
    • Sharma, N.1    Hu, Z.2    Crowder, M.W.3    Bennett, B.4
  • 19
    • 33750970568 scopus 로고    scopus 로고
    • X-ray absorption spectroscopy of the zinc-binding sites in the class B2 metallo-beta-lactamase ImiS from Aeromonas veronii bv. Sobria
    • Costello, A. L.; Sharma, N. P.; Yang, K. W.; Crowder, M. W.; Tierney, D. L. X-ray absorption spectroscopy of the zinc-binding sites in the class B2 metallo-beta-lactamase ImiS from Aeromonas veronii bv. sobria Biochemistry 2006, 45, 13650-8
    • (2006) Biochemistry , vol.45 , pp. 13650-13658
    • Costello, A.L.1    Sharma, N.P.2    Yang, K.W.3    Crowder, M.W.4    Tierney, D.L.5
  • 20
    • 33748274756 scopus 로고    scopus 로고
    • Mechanistic studies on the mononuclear ZnII-containing metallo-beta-lactamase ImiS from Aeromonas sobria
    • Sharma, N. P.; Hajdin, C.; Chandrasekar, S.; Bennett, B.; Yang, K. W.; Crowder, M. W. Mechanistic studies on the mononuclear ZnII-containing metallo-beta-lactamase ImiS from Aeromonas sobria Biochemistry 2006, 45, 10729-38
    • (2006) Biochemistry , vol.45 , pp. 10729-10738
    • Sharma, N.P.1    Hajdin, C.2    Chandrasekar, S.3    Bennett, B.4    Yang, K.W.5    Crowder, M.W.6
  • 21
    • 16444387315 scopus 로고    scopus 로고
    • Spectroscopic studies on cobalt(II)-substituted metallo-beta-lactamase ImiS from Aeromonas veronii bv. Sobria
    • Crawford, P. A.; Yang, K. W.; Sharma, N.; Bennett, B.; Crowder, M. W. Spectroscopic studies on cobalt(II)-substituted metallo-beta-lactamase ImiS from Aeromonas veronii bv. sobria Biochemistry 2005, 44, 5168-76
    • (2005) Biochemistry , vol.44 , pp. 5168-5176
    • Crawford, P.A.1    Yang, K.W.2    Sharma, N.3    Bennett, B.4    Crowder, M.W.5
  • 23
    • 84931830225 scopus 로고    scopus 로고
    • Diaryl-Substituted Azolylthioacetamides: Inhibitor Discovery of New Delhi Metallo-beta-Lactamase-1 (NDM-1)
    • Zhang, Y. L.; Yang, K. W.; Zhou, Y. J.; LaCuran, A. E.; Oelschlaeger, P.; Crowder, M. W. Diaryl-Substituted Azolylthioacetamides: Inhibitor Discovery of New Delhi Metallo-beta-Lactamase-1 (NDM-1) ChemMedChem 2014, 9, 2445-8
    • (2014) ChemMedChem , vol.9 , pp. 2445-2448
    • Zhang, Y.L.1    Yang, K.W.2    Zhou, Y.J.3    Lacuran, A.E.4    Oelschlaeger, P.5    Crowder, M.W.6
  • 24
    • 84882239083 scopus 로고    scopus 로고
    • The ABCDs of beta-lactamase nomenclature
    • Bush, K. The ABCDs of beta-lactamase nomenclature J. Infect. Chemother. 2013, 19, 549-59
    • (2013) J. Infect. Chemother. , vol.19 , pp. 549-559
    • Bush, K.1
  • 26
    • 84861641797 scopus 로고    scopus 로고
    • Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents
    • Patel, R. V.; Patel, P. K.; Kumari, P.; Rajani, D. P.; Chikhalia, K. H. Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents Eur. J. Med. Chem. 2012, 53, 41-51
    • (2012) Eur. J. Med. Chem. , vol.53 , pp. 41-51
    • Patel, R.V.1    Patel, P.K.2    Kumari, P.3    Rajani, D.P.4    Chikhalia, K.H.5
  • 27
    • 0032575621 scopus 로고    scopus 로고
    • Purification, characterization, and kinetic studies of a soluble Bacteroides fragilis metallo-beta-lactamase that provides multiple antibiotic resistance
    • Wang, Z.; Benkovic, S. J. Purification, characterization, and kinetic studies of a soluble Bacteroides fragilis metallo-beta-lactamase that provides multiple antibiotic resistance J. Biol. Chem. 1998, 273, 22402-8
    • (1998) J. Biol. Chem. , vol.273 , pp. 22402-22408
    • Wang, Z.1    Benkovic, S.J.2
  • 30
    • 0031978726 scopus 로고    scopus 로고
    • Overexpression, purification, and characterization of the cloned metallo-beta-lactamase L1 from Stenotrophomonas maltophilia
    • Crowder, M. W.; Walsh, T. R.; Banovic, L.; Pettit, M.; Spencer, J. Overexpression, purification, and characterization of the cloned metallo-beta-lactamase L1 from Stenotrophomonas maltophilia Antimicrob. Agents Chemother. 1998, 42, 921-6
    • (1998) Antimicrob. Agents Chemother. , vol.42 , pp. 921-926
    • Crowder, M.W.1    Walsh, T.R.2    Banovic, L.3    Pettit, M.4    Spencer, J.5
  • 35
    • 84855757480 scopus 로고    scopus 로고
    • 2013.08; Chemical Computing Group Inc. Montreal, Canada
    • Molecular Operating Environment (MOE), 2013.08; Chemical Computing Group Inc.: Montreal, Canada, 2014.
    • (2014) Molecular Operating Environment (MOE)
  • 36
    • 84885172034 scopus 로고    scopus 로고
    • New b-phospholactam as a carbapenem transition state analog: Synthesis of a broad-spectrum inhibitor of metallo-b-lactamases
    • Yang, K. W.; Feng, L.; Yang, S. K.; Aitha, M.; LaCuran, A. E.; Oelschlaeger, P.; Crowder, M. W. New b-phospholactam as a carbapenem transition state analog: Synthesis of a broad-spectrum inhibitor of metallo-b-lactamases Bioorg. Med. Chem. Lett. 2013, 23, 5855-9
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 5855-5859
    • Yang, K.W.1    Feng, L.2    Yang, S.K.3    Aitha, M.4    Lacuran, A.E.5    Oelschlaeger, P.6    Crowder, M.W.7


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