메뉴 건너뛰기




Volumn 57, Issue 21, 2014, Pages 8947-8959

Design, synthesis, and antibacterial properties of dual-ligand inhibitors of acetyl-CoA carboxylase

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL COENZYME A CARBOXYLASE; BIOTIN; CARBOXYLASE; CARBOXYLTRANSFERASE; FATTY ACID; HYDROCARBON; LIGASE INHIBITOR; 2-AMINO-N,N-DIBENZYLOXAZOLE-5-CARBOXAMIDE; ANTIINFECTIVE AGENT; ENZYME INHIBITOR; OXAZOLE DERIVATIVE; TRANSFERASE;

EID: 84923793605     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501082n     Document Type: Article
Times cited : (24)

References (44)
  • 1
    • 84884597711 scopus 로고    scopus 로고
    • CDC. U.S. Department of Health and Human Services, Centers for Disease Control and Prevention: Atlanta, GA
    • CDC. Antibiotic Resistance Threats in the United States, 2013; U.S. Department of Health and Human Services, Centers for Disease Control and Prevention: Atlanta, GA, 2013; http://www.cdc.gov/drugresistance/threat-report-2013/.
    • (2013) Antibiotic Resistance Threats in the United States, 2013
  • 2
    • 3042764816 scopus 로고    scopus 로고
    • Fatty acid biosynthesis as a target for novel antibacterials
    • Heath, R. J.; Rock, C. O. Fatty acid biosynthesis as a target for novel antibacterials Curr. Opin. Investig. Drugs 2004, 5, 146-153
    • (2004) Curr. Opin. Investig. Drugs , vol.5 , pp. 146-153
    • Heath, R.J.1    Rock, C.O.2
  • 3
    • 33745817391 scopus 로고    scopus 로고
    • Inhibiting bacterial fatty acid synthesis
    • Zhang, Y. M.; White, S. W.; Rock, C. O. Inhibiting bacterial fatty acid synthesis J. Biol. Chem. 2006, 281, 17541-17544
    • (2006) J. Biol. Chem. , vol.281 , pp. 17541-17544
    • Zhang, Y.M.1    White, S.W.2    Rock, C.O.3
  • 4
    • 0034780806 scopus 로고    scopus 로고
    • Bacterial fatty acid biosynthesis: Targets for antibacterial drug discovery
    • Campbell, J. W.; Cronan, J. E., Jr. Bacterial fatty acid biosynthesis: targets for antibacterial drug discovery Annu. Rev. Microbiol. 2001, 55, 305-332
    • (2001) Annu. Rev. Microbiol. , vol.55 , pp. 305-332
    • Campbell, J.W.1    Cronan, J.E.2
  • 5
    • 0036018143 scopus 로고    scopus 로고
    • Multi-subunit acetyl-CoA carboxylases
    • Cronan, J. E., Jr.; Waldrop, G. L. Multi-subunit acetyl-CoA carboxylases Prog. Lipid Res. 2002, 41, 407-435
    • (2002) Prog. Lipid Res. , vol.41 , pp. 407-435
    • Cronan, J.E.1    Waldrop, G.L.2
  • 6
    • 0016830820 scopus 로고
    • Acetyl-coenzyme-A carboxylase from rat liver. Subunit structure and proteolytic modification
    • Tanabe, T.; Wada, K.; Okazaki, T.; Numa, S. Acetyl-coenzyme-A carboxylase from rat liver. Subunit structure and proteolytic modification Eur. J. Biochem. 1975, 57, 15-24
    • (1975) Eur. J. Biochem. , vol.57 , pp. 15-24
    • Tanabe, T.1    Wada, K.2    Okazaki, T.3    Numa, S.4
  • 7
    • 0030581109 scopus 로고    scopus 로고
    • Escherichia coli as a model for the regulation of dissociable (type II) fatty acid biosynthesis
    • Rock, C. O.; Cronan, J. E. Escherichia coli as a model for the regulation of dissociable (type II) fatty acid biosynthesis Biochim. Biophys. Acta 1996, 1302, 1-16
    • (1996) Biochim. Biophys. Acta , vol.1302 , pp. 1-16
    • Rock, C.O.1    Cronan, J.E.2
  • 8
    • 0036247948 scopus 로고    scopus 로고
    • Inhibitors of fatty acid synthesis as antimicrobial chemotherapeutics
    • Heath, R. J.; White, S. W.; Rock, C. O. Inhibitors of fatty acid synthesis as antimicrobial chemotherapeutics Appl. Microbiol. Biotechnol. 2002, 58, 695-703
    • (2002) Appl. Microbiol. Biotechnol. , vol.58 , pp. 695-703
    • Heath, R.J.1    White, S.W.2    Rock, C.O.3
  • 11
    • 0001282462 scopus 로고
    • Andrimid and moiramides A-C, metabolites produced in culture by a marine isolate of the bacterium Pseudomonas fluorescens: Structure elucidation and biosynthesis
    • Needham, J.; Kelly, M. T.; Ishige, M.; Andersen, R. J. Andrimid and moiramides A-C, metabolites produced in culture by a marine isolate of the bacterium Pseudomonas fluorescens: Structure elucidation and biosynthesis J. Org. Chem. 1994, 59, 2058-2063
    • (1994) J. Org. Chem. , vol.59 , pp. 2058-2063
    • Needham, J.1    Kelly, M.T.2    Ishige, M.3    Andersen, R.J.4
  • 12
    • 2942718769 scopus 로고    scopus 로고
    • Identification and characterization of the first class of potent bacterial acetyl-CoA carboxylase inhibitors with antibacterial activity
    • Freiberg, C.; Brunner, N. A.; Schiffer, G.; Lampe, T.; Pohlmann, J.; Brands, M.; Raabe, M.; Habich, D.; Ziegelbauer, K. Identification and characterization of the first class of potent bacterial acetyl-CoA carboxylase inhibitors with antibacterial activity J. Biol. Chem. 2004, 279, 26066-26073
    • (2004) J. Biol. Chem. , vol.279 , pp. 26066-26073
    • Freiberg, C.1    Brunner, N.A.2    Schiffer, G.3    Lampe, T.4    Pohlmann, J.5    Brands, M.6    Raabe, M.7    Habich, D.8    Ziegelbauer, K.9
  • 14
    • 0032563087 scopus 로고    scopus 로고
    • Overexpression and kinetic characterization of the carboxyltransferase component of acetyl-CoA carboxylase
    • The activity of carboxyltransferase is measured in the reverse or non-physiological direction where malonyl-CoA and biocytin (a biotin analogue) are the substrates. The formation of the product acetyl-CoA is detected using the coupling enzymes, citrate synthase and malate dehydrogenase: Blanchard, C. Z.; Waldrop, G. L. Overexpression and kinetic characterization of the carboxyltransferase component of acetyl-CoA carboxylase J. Biol. Chem. 1998, 273, 19140-19145
    • (1998) J. Biol. Chem. , vol.273 , pp. 19140-19145
    • Blanchard, C.Z.1    Waldrop, G.L.2
  • 15
    • 0027389215 scopus 로고
    • Growth rate regulation of Escherichia coli acetyl coenzyme A carboxylase, which catalyzes the first committed step of lipid biosynthesis
    • Li, S. J.; Cronan, J. E., Jr. Growth rate regulation of Escherichia coli acetyl coenzyme A carboxylase, which catalyzes the first committed step of lipid biosynthesis J. Bacteriol. 1993, 175, 332-340
    • (1993) J. Bacteriol. , vol.175 , pp. 332-340
    • Li, S.J.1    Cronan, J.E.2
  • 16
    • 33845894155 scopus 로고    scopus 로고
    • Multi-targeting by monotherapeutic antibacterials
    • Silver, L. L. Multi-targeting by monotherapeutic antibacterials Nat. Rev. Drug Discovery 2007, 6, 41-55
    • (2007) Nat. Rev. Drug Discovery , vol.6 , pp. 41-55
    • Silver, L.L.1
  • 17
    • 77955967899 scopus 로고    scopus 로고
    • Dual-acting hybrid antibiotics: A promising strategy to combat bacterial resistance
    • Pokrovskaya, V.; Baasov, T. Dual-acting hybrid antibiotics: a promising strategy to combat bacterial resistance Expert Opin. Drug Discovery 2010, 5, 883-902
    • (2010) Expert Opin. Drug Discovery , vol.5 , pp. 883-902
    • Pokrovskaya, V.1    Baasov, T.2
  • 19
    • 84872712864 scopus 로고    scopus 로고
    • Multitarget ligands in antibacterial research: Progress and opportunities
    • East, S. P.; Silver, L. L. Multitarget ligands in antibacterial research: progress and opportunities Expert Opin. Drug Discovery 2013, 8, 143-156
    • (2013) Expert Opin. Drug Discovery , vol.8 , pp. 143-156
    • East, S.P.1    Silver, L.L.2
  • 20
    • 84877743578 scopus 로고    scopus 로고
    • Complex formation and regulation of Escherichia coli acetyl-CoA carboxylase
    • Broussard, T. C.; Price, A. E.; Laborde, S. M.; Waldrop, G. L. Complex formation and regulation of Escherichia coli acetyl-CoA carboxylase Biochemistry 2013, 52, 3346-3357
    • (2013) Biochemistry , vol.52 , pp. 3346-3357
    • Broussard, T.C.1    Price, A.E.2    Laborde, S.M.3    Waldrop, G.L.4
  • 21
    • 72049109416 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of N -benzyl- N -(X-2-hydroxybenzyl)- N -phenylureas and thioureas as antitumor agents
    • Li, H. Q.; Yan, T.; Yang, Y.; Shi, L.; Zhou, C. F.; Zhu, H. L. Synthesis and structure-activity relationships of N -benzyl- N -(X-2-hydroxybenzyl)- N -phenylureas and thioureas as antitumor agents Bioorg. Med. Chem. 2010, 18, 305-313
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 305-313
    • Li, H.Q.1    Yan, T.2    Yang, Y.3    Shi, L.4    Zhou, C.F.5    Zhu, H.L.6
  • 23
    • 0025835960 scopus 로고
    • A convenient diastereoselective total synthesis of andrimid
    • Rama Rao, A. V.; Singh, A. K.; Varaprasad, C. V. N. S. A convenient diastereoselective total synthesis of andrimid Tetrahedron Lett. 1991, 32, 4393-4396
    • (1991) Tetrahedron Lett. , vol.32 , pp. 4393-4396
    • Rama Rao, A.V.1    Singh, A.K.2    Varaprasad, C.V.N.S.3
  • 26
    • 0005692691 scopus 로고
    • Selectivity of radical formation in the reaction of carbonyl-compounds with manganese (III) acetate
    • Midgley, G.; Thomas, C. B. Selectivity of radical formation in the reaction of carbonyl-compounds with manganese (III) acetate J. Chem. Soc., Perkin Trans. 2 1987, 1103-1108
    • (1987) J. Chem. Soc., Perkin Trans. 2 , pp. 1103-1108
    • Midgley, G.1    Thomas, C.B.2
  • 27
    • 0037471511 scopus 로고    scopus 로고
    • Spiro cyclisations of N- acyliminium ions involving an aromatic π-nucleophile
    • Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Spiro cyclisations of N- acyliminium ions involving an aromatic π-nucleophile Tetrahedron Lett. 2003, 59, 3369-3378
    • (2003) Tetrahedron Lett. , vol.59 , pp. 3369-3378
    • Bailey, P.D.1    Morgan, K.M.2    Smith, D.I.3    Vernon, J.M.4
  • 29
    • 14944338677 scopus 로고    scopus 로고
    • Total synthesis and properties of the crambescidin core zwitterionic acid and crambescidin 359
    • Aron, Z. D.; Overman, L. E. Total synthesis and properties of the crambescidin core zwitterionic acid and crambescidin 359 J. Am. Chem. Soc. 2005, 127, 3380-3390
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 3380-3390
    • Aron, Z.D.1    Overman, L.E.2
  • 30
    • 0034720932 scopus 로고    scopus 로고
    • Solid-phase synthesis of new S-glycoamino acid building blocks
    • Jobron, L.; Hummel, G. Solid-phase synthesis of new S-glycoamino acid building blocks Org. Lett. 2000, 2, 2265-2267
    • (2000) Org. Lett. , vol.2 , pp. 2265-2267
    • Jobron, L.1    Hummel, G.2
  • 31
    • 49449098967 scopus 로고    scopus 로고
    • Effect of hapten structures on specific and sensitive enzyme-linked immunosorbent assays for N -methylcarbamate insecticide metolcarb
    • Zhang, Q.; Wu, Y.; Wang, L.; Hu, B.; Li, P.; Liu, F. Effect of hapten structures on specific and sensitive enzyme-linked immunosorbent assays for N -methylcarbamate insecticide metolcarb Anal. Chim. Acta 2008, 625, 87-94
    • (2008) Anal. Chim. Acta , vol.625 , pp. 87-94
    • Zhang, Q.1    Wu, Y.2    Wang, L.3    Hu, B.4    Li, P.5    Liu, F.6
  • 34
    • 46249112774 scopus 로고    scopus 로고
    • In vitro evaluation of CBR-2092, a novel rifamycin-quinolone hybrid antibiotic: Microbiology profiling studies with staphylococci and streptococci
    • Robertson, G. T.; Bonventre, E. J.; Doyle, T. B.; Du, Q.; Duncan, L.; Morris, T. W.; Roche, E. D.; Yan, D.; Lynch, A. S. In vitro evaluation of CBR-2092, a novel rifamycin-quinolone hybrid antibiotic: microbiology profiling studies with staphylococci and streptococci Antimicrob. Agents Chemother. 2008, 52, 2324-2334
    • (2008) Antimicrob. Agents Chemother. , vol.52 , pp. 2324-2334
    • Robertson, G.T.1    Bonventre, E.J.2    Doyle, T.B.3    Du, Q.4    Duncan, L.5    Morris, T.W.6    Roche, E.D.7    Yan, D.8    Lynch, A.S.9
  • 35
    • 0033040998 scopus 로고    scopus 로고
    • Effects of NorA inhibitors on in vitro antibacterial activities and postantibiotic effects of levofloxacin, ciprofloxacin, and norfloxacin in genetically related strains of Staphylococcus aureus
    • Aeschlimann, J. R.; Dresser, L. D.; Kaatz, G. W.; Rybak, M. J. Effects of NorA inhibitors on in vitro antibacterial activities and postantibiotic effects of levofloxacin, ciprofloxacin, and norfloxacin in genetically related strains of Staphylococcus aureus Antimicrob. Agents Chemother. 1999, 43, 335-340
    • (1999) Antimicrob. Agents Chemother. , vol.43 , pp. 335-340
    • Aeschlimann, J.R.1    Dresser, L.D.2    Kaatz, G.W.3    Rybak, M.J.4
  • 36
    • 0021257420 scopus 로고
    • Susceptibility of Gram-negative bacteria to polymyxin B nonapeptide
    • Viljanen, P.; Vaara, M. Susceptibility of Gram-negative bacteria to polymyxin B nonapeptide Antimicrob. Agents Chemother. 1984, 25, 701-705
    • (1984) Antimicrob. Agents Chemother. , vol.25 , pp. 701-705
    • Viljanen, P.1    Vaara, M.2
  • 37
    • 0036840627 scopus 로고    scopus 로고
    • Modulation of the hydrophobic domain of polymyxin B nonapeptide: Effect on outer-membrane permeabilization and lipopolysaccharide neutralization
    • Tsubery, H.; Ofek, I.; Cohen, S.; Eisenstein, M.; Fridkin, M. Modulation of the hydrophobic domain of polymyxin B nonapeptide: effect on outer-membrane permeabilization and lipopolysaccharide neutralization Mol. Pharmacol. 2002, 62, 1036-1042
    • (2002) Mol. Pharmacol. , vol.62 , pp. 1036-1042
    • Tsubery, H.1    Ofek, I.2    Cohen, S.3    Eisenstein, M.4    Fridkin, M.5
  • 38
    • 36448983944 scopus 로고    scopus 로고
    • Polymyxin B for the treatment of multidrug-resistant pathogens: A critical review
    • Zavascki, A. P.; Goldani, L. Z.; Li, J.; Nation, R. L. Polymyxin B for the treatment of multidrug-resistant pathogens: a critical review J. Antimicrob. Chemother. 2007, 60, 1206-1215
    • (2007) J. Antimicrob. Chemother. , vol.60 , pp. 1206-1215
    • Zavascki, A.P.1    Goldani, L.Z.2    Li, J.3    Nation, R.L.4
  • 39
    • 84900839248 scopus 로고    scopus 로고
    • Teaching old polymyxins new tricks: New-generation lipopeptides targeting Gram-negative superbugs
    • Velkov, T.; Roberts, K. D.; Nation, R. L.; Wang, J.; Thompson, P. E.; Li, J. Teaching old polymyxins new tricks: new-generation lipopeptides targeting Gram-negative superbugs ACS Chem. Biol. 2014, 9, 1172-1177
    • (2014) ACS Chem. Biol. , vol.9 , pp. 1172-1177
    • Velkov, T.1    Roberts, K.D.2    Nation, R.L.3    Wang, J.4    Thompson, P.E.5    Li, J.6
  • 40
    • 0037083238 scopus 로고    scopus 로고
    • Restricting the selection of antibiotic-resistant mutant bacteria: Measurement and potential use of the mutant selection window
    • Zhao, X.; Drlica, K. Restricting the selection of antibiotic-resistant mutant bacteria: measurement and potential use of the mutant selection window J. Infect. Dis. 2002, 185, 561-565
    • (2002) J. Infect. Dis. , vol.185 , pp. 561-565
    • Zhao, X.1    Drlica, K.2
  • 41
    • 0038639673 scopus 로고    scopus 로고
    • The mutant selection window and antimicrobial resistance
    • Drlica, K. The mutant selection window and antimicrobial resistance J. Antimicrob. Chemother. 2003, 52, 11-17
    • (2003) J. Antimicrob. Chemother. , vol.52 , pp. 11-17
    • Drlica, K.1
  • 42
    • 84899532843 scopus 로고    scopus 로고
    • Computational redesign of bacterial biotin carboxylase inhibitors using structure-based virtual screening of combinatorial libraries
    • Brylinski, M.; Waldrop, G. L. Computational redesign of bacterial biotin carboxylase inhibitors using structure-based virtual screening of combinatorial libraries Molecules 2014, 19, 4021-4045
    • (2014) Molecules , vol.19 , pp. 4021-4045
    • Brylinski, M.1    Waldrop, G.L.2
  • 43
    • 0018735516 scopus 로고
    • Statistical analysis of enzyme kinetic data
    • Cleland, W. W. Statistical analysis of enzyme kinetic data Methods Enzymol. 1979, 63, 103-138
    • (1979) Methods Enzymol. , vol.63 , pp. 103-138
    • Cleland, W.W.1
  • 44
    • 84923805537 scopus 로고    scopus 로고
    • Clinical and Laboratory Standards Institute 7 th ed. Clinical and Laboratory Standards Institute: Wayne, PA, CLSI document M7-A7
    • Clinical and Laboratory Standards Institute. Methods fordilution antimicrobial susceptibility tests for bacteria that growaerobically, approved standard, 7 th ed.; Clinical and Laboratory Standards Institute: Wayne, PA, 2006; CLSI document M7-A7, Vol. 26, no. 2.
    • (2006) Methods Fordilution Antimicrobial Susceptibility Tests for Bacteria That Growaerobically, Approved Standard , vol.26 , Issue.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.