메뉴 건너뛰기




Volumn 6, Issue 5, 2011, Pages

New classes of alanine racemase inhibitors identified by high-throughput screening show antimicrobial activity against mycobacterium tuberculosis

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE RACEMASE; ALANINE DEHYDROGENASE; ANTIINFECTIVE AGENT; ENZYME INHIBITOR;

EID: 79957558426     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0020374     Document Type: Article
Times cited : (38)

References (36)
  • 1
    • 36549054073 scopus 로고    scopus 로고
    • WHO Fact Sheet: Tuberculosis 2007
    • Organization WH, 2007
    • Organization WH (2007) WHO Fact Sheet: Tuberculosis 2007. http://wwwwhoint/mediacentre/factsheets/fs104/en/indexhtml, 2007.
    • (2007)
  • 2
    • 78449274705 scopus 로고    scopus 로고
    • Drugs in development for tuberculosis
    • Ginsberg AM, (2010) Drugs in development for tuberculosis. Drugs 70: 2201-2214.
    • (2010) Drugs , vol.70 , pp. 2201-2214
    • Ginsberg, A.M.1
  • 3
    • 0012746992 scopus 로고    scopus 로고
    • The growing burden of tuberculosis: global trends and interactions with the HIV epidemic
    • Corbett EL, Watt CJ, Walker N, Maher D, Williams BG, et al. (2003) The growing burden of tuberculosis: global trends and interactions with the HIV epidemic. Arch Intern Med 163: 1009-1021.
    • (2003) Arch Intern Med , vol.163 , pp. 1009-1021
    • Corbett, E.L.1    Watt, C.J.2    Walker, N.3    Maher, D.4    Williams, B.G.5
  • 4
    • 34248181891 scopus 로고    scopus 로고
    • Barriers to reaching the targets for tuberculosis control: multidrug-resistant tuberculosis
    • discussion 391-384
    • Blondal K, (2007) Barriers to reaching the targets for tuberculosis control: multidrug-resistant tuberculosis. Bull World Health Organ 85: 387-390; discussion 391-384.
    • (2007) Bull World Health Organ , vol.85 , pp. 387-390
    • Blondal, K.1
  • 5
    • 34248640281 scopus 로고    scopus 로고
    • Key issues in multidrug-resistant tuberculosis
    • Chakrabarti B, Davies PD, (2007) Key issues in multidrug-resistant tuberculosis. Future Microbiol 2: 51-61.
    • (2007) Future Microbiol , vol.2 , pp. 51-61
    • Chakrabarti, B.1    Davies, P.D.2
  • 6
    • 0031195996 scopus 로고    scopus 로고
    • Multidrug-resistant tuberculosis in Denmark 1993-1995
    • Viskum K, Kok-Jensen A, (1997) Multidrug-resistant tuberculosis in Denmark 1993-1995. Int J Tuberc Lung Dis 1: 299-301.
    • (1997) Int J Tuberc Lung Dis , vol.1 , pp. 299-301
    • Viskum, K.1    Kok-Jensen, A.2
  • 7
    • 77951796544 scopus 로고    scopus 로고
    • Extensively drug-resistant tuberculosis: "there must be some kind of way out of here"
    • Cegielski JP, (2010) Extensively drug-resistant tuberculosis: "there must be some kind of way out of here". Clin Infect Dis 50 (Suppl 3): S195-200.
    • (2010) Clin Infect Dis , vol.50 , Issue.SUPPL. 3 , pp. 195-200
    • Cegielski, J.P.1
  • 8
    • 77952545901 scopus 로고    scopus 로고
    • Tuberculosis drug development: progress, challenges, and the road ahead
    • Ginsberg AM, (2010) Tuberculosis drug development: progress, challenges, and the road ahead. Tuberculosis (Edinb) 90: 162-167.
    • (2010) Tuberculosis (Edinb) , vol.90 , pp. 162-167
    • Ginsberg, A.M.1
  • 9
    • 33947710631 scopus 로고    scopus 로고
    • New tuberculosis drugs in development
    • Laughon BE, (2007) New tuberculosis drugs in development. Curr Top Med Chem 7: 463-473.
    • (2007) Curr Top Med Chem , vol.7 , pp. 463-473
    • Laughon, B.E.1
  • 10
    • 33847704942 scopus 로고    scopus 로고
    • Challenges in tuberculosis drug research and development
    • Ginsberg A, Spigelman M, (2007) Challenges in tuberculosis drug research and development. Nature Medicine 13: 290-294.
    • (2007) Nature Medicine , vol.13 , pp. 290-294
    • Ginsberg, A.1    Spigelman, M.2
  • 11
    • 0001794737 scopus 로고
    • D-cycloserine and O-carbamyl-D-serine
    • In: Gottlieb D, Shaw P, editors, Heidelbaerg, Springer-Verlag
    • Neuhaus F, (1967) D-cycloserine and O-carbamyl-D-serine. In: Gottlieb D, Shaw P, editors. Antibiotics, mechanisms of action Heidelbaerg Springer-Verlag.
    • (1967) Antibiotics, Mechanisms of Action
    • Neuhaus, F.1
  • 12
    • 0345701347 scopus 로고    scopus 로고
    • Genes required for mycobacterial growth defined by high density mutagenesis
    • Sassetti CM, Boyd DH, Rubin EJ, (2003) Genes required for mycobacterial growth defined by high density mutagenesis. Mol Microbiol 48: 77-84.
    • (2003) Mol Microbiol , vol.48 , pp. 77-84
    • Sassetti, C.M.1    Boyd, D.H.2    Rubin, E.J.3
  • 13
    • 36549035341 scopus 로고    scopus 로고
    • The alanine racemase of Mycobacterium smegmatis is essential for growth in the absence of D-alanine
    • Milligan DL, Tran SL, Strych U, Cook GM, Krause KL, (2007) The alanine racemase of Mycobacterium smegmatis is essential for growth in the absence of D-alanine. J Bacteriol 189: 8381-8386.
    • (2007) J Bacteriol , vol.189 , pp. 8381-8386
    • Milligan, D.L.1    Tran, S.L.2    Strych, U.3    Cook, G.M.4    Krause, K.L.5
  • 14
    • 0024561489 scopus 로고
    • Enzymes in the D-alanine branch of bacterial cell wall peptidoglycan assembly
    • Walsh CT, (1989) Enzymes in the D-alanine branch of bacterial cell wall peptidoglycan assembly. J Biol Chem 264: 2393-2396.
    • (1989) J Biol Chem , vol.264 , pp. 2393-2396
    • Walsh, C.T.1
  • 15
    • 0015351329 scopus 로고
    • Mechanism of D-cycloserine action: alanine racemase from Escherichia coli W
    • Lambert MP, Neuhaus FC, (1972) Mechanism of D-cycloserine action: alanine racemase from Escherichia coli W. J Bacteriol 110: 978-987.
    • (1972) J Bacteriol , vol.110 , pp. 978-987
    • Lambert, M.P.1    Neuhaus, F.C.2
  • 16
    • 77956798944 scopus 로고
    • Biosynthesis of bacterial peptidoglycan unit
    • In: Ghuysen J, Hakenbeck R, editors, Amsterdam, Elsevier Medical Press
    • van Heijenoort J, (1994) Biosynthesis of bacterial peptidoglycan unit. In: Ghuysen J, Hakenbeck R, editors. Bacterial Cell Wall Amsterdam Elsevier Medical Press pp. 39-54.
    • (1994) Bacterial Cell Wall , pp. 39-54
    • van Heijenoort, J.1
  • 17
    • 13444274582 scopus 로고    scopus 로고
    • The 1.9 A crystal structure of alanine racemase from Mycobacterium tuberculosis contains a conserved entryway into the active site
    • LeMagueres P, Im H, Ebalunode J, Strych U, Benedik MJ, et al. (2005) The 1.9 A crystal structure of alanine racemase from Mycobacterium tuberculosis contains a conserved entryway into the active site. Biochemistry 44: 1471-1481.
    • (2005) Biochemistry , vol.44 , pp. 1471-1481
    • LeMagueres, P.1    Im, H.2    Ebalunode, J.3    Strych, U.4    Benedik, M.J.5
  • 18
    • 0001794737 scopus 로고
    • D-cycloserine and O-carbamyl-D-serine;
    • In: D G, P S, editors, Heidelbaerg, Springer-Verlag
    • Neuhaus F, (1967) D-cycloserine and O-carbamyl-D-serine; In: D G, P S, editors. Heidelbaerg Springer-Verlag.
    • (1967)
    • Neuhaus, F.1
  • 19
    • 0019766646 scopus 로고
    • Inhibition of cell wall biosynthesis by analogues and alanine
    • Neuhaus FC, Hammes WP, (1981) Inhibition of cell wall biosynthesis by analogues and alanine. Pharmacol Ther 14: 265-319.
    • (1981) Pharmacol Ther , vol.14 , pp. 265-319
    • Neuhaus, F.C.1    Hammes, W.P.2
  • 20
    • 0027197907 scopus 로고
    • Adverse neurological reactions in patients with multidrug-resistant pulmonary tuberculosis after coadministration of cycloserine and ofloxacin
    • Yew WW, Wong CF, Wong PC, Lee J, Chau CH, (1993) Adverse neurological reactions in patients with multidrug-resistant pulmonary tuberculosis after coadministration of cycloserine and ofloxacin. Clin Infect Dis 17: 288-289.
    • (1993) Clin Infect Dis , vol.17 , pp. 288-289
    • Yew, W.W.1    Wong, C.F.2    Wong, P.C.3    Lee, J.4    Chau, C.H.5
  • 21
    • 0345700229 scopus 로고    scopus 로고
    • N(2)-substituted D,L-cycloserine derivatives: synthesis and evaluation as alanine racemase inhibitors
    • Kim MG, Strych U, Krause K, Benedik M, Kohn H, (2003) N(2)-substituted D,L-cycloserine derivatives: synthesis and evaluation as alanine racemase inhibitors. J Antibiot (Tokyo) 56: 160-168.
    • (2003) J Antibiot (Tokyo) , vol.56 , pp. 160-168
    • Kim, M.G.1    Strych, U.2    Krause, K.3    Benedik, M.4    Kohn, H.5
  • 22
    • 0942301251 scopus 로고    scopus 로고
    • Evaluation of Amino-substituted Heterocyclic Derivatives as Alanine Racemase Inhibitors
    • Kim MG, Strych U, Krause K, Benedik M, Kohn H, (2003) Evaluation of Amino-substituted Heterocyclic Derivatives as Alanine Racemase Inhibitors. Medicinal Chemistry Research 12: 130-138.
    • (2003) Medicinal Chemistry Research , vol.12 , pp. 130-138
    • Kim, M.G.1    Strych, U.2    Krause, K.3    Benedik, M.4    Kohn, H.5
  • 23
    • 0023764098 scopus 로고
    • Inhibition of alanine racemase by alanine phosphonate: detection of an imine linkage to pyridoxal 5′-phosphate in the enzyme-inhibitor complex by solid-state 15N nuclear magnetic resonance
    • Copie V, Faraci WS, Walsh CT, Griffin RG, (1988) Inhibition of alanine racemase by alanine phosphonate: detection of an imine linkage to pyridoxal 5′-phosphate in the enzyme-inhibitor complex by solid-state 15N nuclear magnetic resonance. Biochemistry 27: 4966-4970.
    • (1988) Biochemistry , vol.27 , pp. 4966-4970
    • Copie, V.1    Faraci, W.S.2    Walsh, C.T.3    Griffin, R.G.4
  • 24
    • 0023657752 scopus 로고
    • 1-Aminocyclopropanephosphonate: time-dependent inactivation of 1-aminocyclopropanecarboxylate deaminase and Bacillus stearothermophilus alanine racemase by slow dissociation behavior
    • Erion MD, Walsh CT, (1987) 1-Aminocyclopropanephosphonate: time-dependent inactivation of 1-aminocyclopropanecarboxylate deaminase and Bacillus stearothermophilus alanine racemase by slow dissociation behavior. Biochemistry 26: 3417-3425.
    • (1987) Biochemistry , vol.26 , pp. 3417-3425
    • Erion, M.D.1    Walsh, C.T.2
  • 25
    • 0021769535 scopus 로고
    • Inactivation of the dadB Salmonella typhimurium alanine racemase by D and L isomers of beta-substituted alanines: kinetics, stoichiometry, active site peptide sequencing, and reaction mechanism
    • Badet B, Roise D, Walsh CT, (1984) Inactivation of the dadB Salmonella typhimurium alanine racemase by D and L isomers of beta-substituted alanines: kinetics, stoichiometry, active site peptide sequencing, and reaction mechanism. Biochemistry 23: 5188-5194.
    • (1984) Biochemistry , vol.23 , pp. 5188-5194
    • Badet, B.1    Roise, D.2    Walsh, C.T.3
  • 26
    • 0037952855 scopus 로고    scopus 로고
    • A side reaction of alanine racemase: transamination of cycloserine
    • Fenn TD, Stamper GF, Morollo AA, Ringe D, (2003) A side reaction of alanine racemase: transamination of cycloserine. Biochemistry 42: 5775-5783.
    • (2003) Biochemistry , vol.42 , pp. 5775-5783
    • Fenn, T.D.1    Stamper, G.F.2    Morollo, A.A.3    Ringe, D.4
  • 27
    • 0032555181 scopus 로고    scopus 로고
    • Reaction of alanine racemase with 1-aminoethylphosphonic acid forms a stable external aldimine
    • Stamper GF, Morollo AA, Ringe D, (1998) Reaction of alanine racemase with 1-aminoethylphosphonic acid forms a stable external aldimine. Biochemistry 37: 10438-10445.
    • (1998) Biochemistry , vol.37 , pp. 10438-10445
    • Stamper, G.F.1    Morollo, A.A.2    Ringe, D.3
  • 28
    • 9744235147 scopus 로고    scopus 로고
    • Reaction specificity in pyridoxal phosphate enzymes
    • Toney MD, (2005) Reaction specificity in pyridoxal phosphate enzymes. Arch Biochem Biophys 433: 279-287.
    • (2005) Arch Biochem Biophys , vol.433 , pp. 279-287
    • Toney, M.D.1
  • 29
    • 0141891817 scopus 로고    scopus 로고
    • Molecular dynamics studies of alanine racemase: a structural model for drug design
    • Mustata GI, Soares TA, Briggs JM, (2003) Molecular dynamics studies of alanine racemase: a structural model for drug design. Biopolymers 70: 186-200.
    • (2003) Biopolymers , vol.70 , pp. 186-200
    • Mustata, G.I.1    Soares, T.A.2    Briggs, J.M.3
  • 30
    • 0034816313 scopus 로고    scopus 로고
    • A model for enzyme-substrate interaction in alanine racemase
    • Ondrechen MJ, Briggs JM, McCammon JA, (2001) A model for enzyme-substrate interaction in alanine racemase. J Am Chem Soc 123: 2830-2834.
    • (2001) J Am Chem Soc , vol.123 , pp. 2830-2834
    • Ondrechen, M.J.1    Briggs, J.M.2    McCammon, J.A.3
  • 31
    • 0037499658 scopus 로고    scopus 로고
    • A structure-based design approach for the identification of novel inhibitors: application to an alanine racemase
    • Mustata GI, Briggs JM, (2002) A structure-based design approach for the identification of novel inhibitors: application to an alanine racemase. J Comput Aided Mol Des 16: 935-953.
    • (2002) J Comput Aided Mol Des , vol.16 , pp. 935-953
    • Mustata, G.I.1    Briggs, J.M.2
  • 33
    • 0022536214 scopus 로고
    • Biosynthetic alanine racemase of Salmonella typhimurium: purification and characterization of the enzyme encoded by the alr gene
    • Esaki N, Walsh CT, (1986) Biosynthetic alanine racemase of Salmonella typhimurium: purification and characterization of the enzyme encoded by the alr gene. Biochemistry 25: 3261-3267.
    • (1986) Biochemistry , vol.25 , pp. 3261-3267
    • Esaki, N.1    Walsh, C.T.2
  • 34
    • 0033003760 scopus 로고    scopus 로고
    • A Simple Statistical Parameter for Use in Evaluation and Validation of High Throughput Screening Assays
    • Zhang JH, Chung TD, Oldenburg KR, (1999) A Simple Statistical Parameter for Use in Evaluation and Validation of High Throughput Screening Assays. J Biomol Screen 4: 67-73.
    • (1999) J Biomol Screen , vol.4 , pp. 67-73
    • Zhang, J.H.1    Chung, T.D.2    Oldenburg, K.R.3
  • 35
    • 77955347387 scopus 로고    scopus 로고
    • In vitro antituberculosis activities of ACH-702, a novel isothiazoloquinolone, against quinolone-susceptible and quinolone-resistant isolates
    • Pucci MJ, Ackerman M, Thanassi JA, Shoen CM, Cynamon MH, (2010) In vitro antituberculosis activities of ACH-702, a novel isothiazoloquinolone, against quinolone-susceptible and quinolone-resistant isolates. Antimicrob Agents Chemother 54: 3478-3480.
    • (2010) Antimicrob Agents Chemother , vol.54 , pp. 3478-3480
    • Pucci, M.J.1    Ackerman, M.2    Thanassi, J.A.3    Shoen, C.M.4    Cynamon, M.H.5
  • 36
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ, (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46: 3-26.
    • (2001) Adv Drug Deliv Rev , vol.46 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.