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Volumn 22, Issue 1, 2013, Pages 134-146

γ-Amino butyric acid analogs as novel potent GABA-AT inhibitors: Molecular docking, synthesis, and biological evaluation

Author keywords

AutoDock 4.0.1; Docking simulation; GABA; GABA AT inhibitor; IC50; Lamarckian genetic algorithm

Indexed keywords

3 [(1,4,5,8 TETRACHLORO 10 OXO 9,10 DIHYDROANTHRACENE 9 YLIDENE)AMINO]BENZOIC ACID; 3 [(10 OXO 9,10 DIHYDROANTHRACENE 9 YLIDENE)AMINO]BENZOIC ACID; 3 [(10 OXO 9,10 DIHYDROPHENANTHRENE 9 YLIDENE)AMINO]BENZOIC ACID; 3 [(2 ETHYL 10 OXO 9,10 DIHYDROANTHRACENE 9 YLIDENE)AMINO]BENZOIC ACID; 3 [(2,3,5,6 TETRAMETHYL 4 OXOCYCLOHEXA 2,5 DIEN 1 YLIDENE)AMINO]BENZOIC ACID; 3 AMINO N' (2,3,5,6 TETRACHLORO 4 OXOCYCLOHEXA 2,5 DIEN 1 YLIDENE)BENZOHYDRAZIDE; 3 AMINO N' [1 (3 CHLOROPHENYL)ETHYLIDENE]BENZOHYDRAZIDE; 3 AMINO N' [1, 2 DIHYDROXY 10 OXO 9,10 DIHYDROANTHRACENE 9 YLIDENE]BENZOHYDRAZIDE; 3 AMINO N' [2 CHLORO 10 OXO 9,10 DIHYDROANTHRACENE 9 YLIDENE]BENZOHYDRAZIDE; 3 AMINO N' [4 CHLOROPHENYL(PHENYL)METHYLIDENE]BENZOHYDRAZIDE; 4 [(1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YLIDENE)AMINO]BUTANOIC ACID; 4 [(1,5 DIPHENYLPENTA 1,4 DIEN 3 YLIDENE)AMINO]BUTANOIC ACID; 4 [(10 OXO 9,10 DIHYDROPHENANTHRENE 9 YLIDENE)AMINO]BUTANOIC ACID; 4 [(2 METHYL 4 OXOCYCLOHEXA 2,5 DIEN 1 YLIDENE)AMINO]BUTANOIC ACID; 4 [[1 (NAPHTHALEN 2 YL)ETHYLIDENE]AMINO]BUTANOIC ACID; 4 AMINO N [1 (2 BROMOPHENYL)ETHYLIDENE]BUTANEHYDRAZIDE; 4 AMINO N' (10 OXO 9, 10 DIHYDROANTHRACENE 9 YLIDENE)BUTANEHYDRAZIDE; 4 AMINO N' [1 (2 BROMOPHENYL)ETHYLIDENE]BUTANEHYDRAZIDE; 4 AMINO N' [1 (3 CHLOROPHENYL)ETHYLIDENE]BUTANEHYDRAZIDE; 4 AMINO N' [1, 2, 3, 4 TETRAHYDRONAPHTHALENE 2 YLIDENE]BUTANEHYDRAZIDE; 4 AMINO N' [1,2,3,4 TETRAHYDRONAPHTHALEN 1 YLIDENE]BUTANEHYDRAZIDE; 4 AMINO N' [2 IODOPHENYLMETHYLIDENE]BUTANEHYDRAZIDE; 4 AMINO N' [2 METHYL 10 OXO 9,10 DIHYDROANTHRACENE 9 YLIDENE]BUTANEHYDRAZIDE; 4 AMINO N' [2 OXO 1, 2 DIPHENYLETHYLIDENE]BUTANEHYDRAZIDE; 4 AMINO N' [3 IODOPHENYLMETHYLIDENE]BUTANEHYDRAZIDE; 4 AMINO N' [4 BROMOPHENYL(PHENYL)METHYLIDENE]BUTANEHYDRAZIDE; 4 AMINOBUTYRIC ACID; SCHIFF BASE; UNCLASSIFIED DRUG; VIGABATRIN;

EID: 84872044582     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0023-0     Document Type: Article
Times cited : (13)

References (33)
  • 1
    • 0023837924 scopus 로고    scopus 로고
    • Simulation of the diffusion-controlled reaction between superoxide and superoxide dismutase II: Detailed models
    • 10.1002/bip.360270207
    • Allison SA, Bacquet RJ, McCammon JA (1998) Simulation of the diffusion-controlled reaction between superoxide and superoxide dismutase II: detailed models. Biopolymers 27:251-269
    • (1998) Biopolymers , vol.27 , pp. 251-269
    • Allison, S.A.1    Bacquet, R.J.2    McCammon, J.A.3
  • 2
    • 84866395677 scopus 로고    scopus 로고
    • Novel GABA-AT inhibitors: QSAR and docking based virtual screening of phenyl-substituted β-phenyl ethylidene hydrazine analogs
    • Bansal SK, Sinha BN, Khosa RL, Olson AJ (2010) Novel GABA-AT inhibitors: QSAR and docking based virtual screening of phenyl-substituted β-phenyl ethylidene hydrazine analogs. Med Chem Res 19:S114
    • (2010) Med Chem Res , vol.19 , pp. 114
    • Bansal, S.K.1    Sinha, B.N.2    Khosa, R.L.3    Olson, A.J.4
  • 3
    • 80052036339 scopus 로고    scopus 로고
    • QSAR and docking-based computational chemistry approach to novel GABA-AT inhibitors: KNN-MFA based 3DQSAR model for phenyl-substituted analogs of β-phenylethylidene hydrazine
    • 10.1007/s00044-010-9350-1 1:CAS:528:DC%2BC3cXktVahs7g%3D
    • Bansal SK, Sinha BN, Khosa RL (2011a) QSAR and docking-based computational chemistry approach to novel GABA-AT inhibitors: kNN-MFA based 3DQSAR model for phenyl-substituted analogs of β-phenylethylidene hydrazine. Med Chem Res 20:549-553
    • (2011) Med Chem Res , vol.20 , pp. 549-553
    • Bansal, S.K.1    Sinha, B.N.2    Khosa, R.L.3
  • 4
    • 84866359901 scopus 로고    scopus 로고
    • Docking based virtual screening of schiff's bases of GABA - A prospective to novel GABA-AT inhibitors
    • doi: 10.1007/s00044-011-9843-6
    • Bansal SK, Sinha BN, Khosa RL (2011b) Docking based virtual screening of schiff's bases of GABA- a prospective to novel GABA-AT inhibitors. Med Chem Res. doi: 10.1007/s00044-011-9843-6
    • (2011) Med Chem Res
    • Bansal, S.K.1    Sinha, B.N.2    Khosa, R.L.3
  • 5
    • 84856226862 scopus 로고    scopus 로고
    • Novel GABA-AT inhibitors: QSAR and docking based virtual screening of phenyl-substituted β-phenyl ethylidene hydrazine analogs
    • 10.1007/s00044-010-9390-6 1:CAS:528:DC%2BC3cXpt1yisrs%3D
    • Bansal SK, Sinha BN, Khosa RL, Olson AJ (2011c) Novel GABA-AT inhibitors: QSAR and docking based virtual screening of phenyl-substituted β-phenyl ethylidene hydrazine analogs. Med Chem Res 20:1482-1489
    • (2011) Med Chem Res , vol.20 , pp. 1482-1489
    • Bansal, S.K.1    Sinha, B.N.2    Khosa, R.L.3    Olson, A.J.4
  • 6
    • 13444250001 scopus 로고    scopus 로고
    • New anticonvulsant agents
    • 10.2174/1568026053386944
    • Barbara M (2005) New anticonvulsant agents. Curr Top Med Chem 5:69-85
    • (2005) Curr Top Med Chem , vol.5 , pp. 69-85
    • Barbara, M.1
  • 7
    • 0017184389 scopus 로고
    • Rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principle of dye binding
    • 942051 10.1016/0003-2697(76)90527-3 1:CAS:528:DyaE28XksVehtrY%3D
    • Bradford MM (1976) Rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principle of dye binding. Anal Biochem 72:248-254
    • (1976) Anal Biochem , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 8
    • 49149147973 scopus 로고
    • Iterative partial equalization of orbital electronegativity - A rapid access to atomic charges
    • 10.1016/0040-4020(80)80168-2 1:CAS:528:DyaL3MXhslCjtbs%3D
    • Gasteiger J, Marsili M (1980) Iterative partial equalization of orbital electronegativity-a rapid access to atomic charges. Tetrahedron 36:3219-3228
    • (1980) Tetrahedron , vol.36 , pp. 3219-3228
    • Gasteiger, J.1    Marsili, M.2
  • 9
    • 77957258627 scopus 로고    scopus 로고
    • Antiepileptic drug discovery and development: What have we learned and where are we going?
    • 10.3390/ph3092884 1:CAS:528:DC%2BC3cXhtFWktLvE
    • Gerlach AC, Krajewski JL (2010) Antiepileptic drug discovery and development: what have we learned and where are we going? Pharmaceuticals 3:2884-2899
    • (2010) Pharmaceuticals , vol.3 , pp. 2884-2899
    • Gerlach, A.C.1    Krajewski, J.L.2
  • 10
    • 0021871375 scopus 로고
    • A computational procedure for determining energetically favorable binding sites on biologically important macromolecules
    • 3892003 10.1021/jm00145a002 1:CAS:528:DyaL2MXktVeit7c%3D
    • Goodford PJ (1985) A computational procedure for determining energetically favorable binding sites on biologically important macromolecules. J Med Chem 28:849-857
    • (1985) J Med Chem , vol.28 , pp. 849-857
    • Goodford, P.J.1
  • 11
    • 0025135112 scopus 로고
    • Automated docking of substrates to proteins by simulated annealing
    • 2281083 10.1002/prot.340080302 1:CAS:528:DyaK3MXhsFKntbg%3D
    • Goodsell DS, Olson AJ (1990) Automated docking of substrates to proteins by simulated annealing. Proteins Struct Funct Genet 8:195-202
    • (1990) Proteins Struct Funct Genet , vol.8 , pp. 195-202
    • Goodsell, D.S.1    Olson, A.J.2
  • 13
    • 33744852461 scopus 로고
    • Enzymes of γ-aminobutyrate metabolism
    • Jakoby WB (1962) Enzymes of γ-aminobutyrate metabolism. Methods Enzymol 5:771-774
    • (1962) Methods Enzymol , vol.5 , pp. 771-774
    • Jakoby, W.B.1
  • 14
    • 0016201652 scopus 로고
    • Effect of convulsive agent 3-mercaptopropionic acid on the levels of GABA other amino acids and glutamate decarboxylase in different regions of rat brain
    • 4154755 10.1016/0006-2952(74)90281-0 1:CAS:528:DyaE2MXhtF2mtr0%3D
    • Karlsson A, Fonnum F, Malthe-Sorenssen D, Storm-Mathisen J (1974) Effect of convulsive agent 3-mercaptopropionic acid on the levels of GABA other amino acids and glutamate decarboxylase in different regions of rat brain. Biochem Pharmacol 23:3053-3061
    • (1974) Biochem Pharmacol , vol.23 , pp. 3053-3061
    • Karlsson, A.1    Fonnum, F.2    Malthe-Sorenssen, D.3    Storm-Mathisen, J.4
  • 15
    • 1542602473 scopus 로고    scopus 로고
    • Inhibitory effects of the fragrance inhalation of essential oil from Acorus gramineus on central nervous system
    • 12843622 10.1248/bpb.26.978 1:CAS:528:DC%2BD3sXmsFWnsbk%3D
    • Koo BS, Park KS, Ha JH, Park JH, Lim JC, Lee DU (2003) Inhibitory effects of the fragrance inhalation of essential oil from Acorus gramineus on central nervous system. Biol Pharm Bull 26:978-982
    • (2003) Biol Pharm Bull , vol.26 , pp. 978-982
    • Koo, B.S.1    Park, K.S.2    Ha, J.H.3    Park, J.H.4    Lim, J.C.5    Lee, D.U.6
  • 16
    • 0019839152 scopus 로고
    • Gamma-aminobutyric acid agonists antagonists and uptake inhibitors Design and therapeutic aspects
    • 6118436 10.1021/jm00144a001 1:CAS:528:DyaL3MXlvVSgur4%3D
    • Krogsgaard-Larsen P (1981) Gamma-aminobutyric acid agonists antagonists and uptake inhibitors Design and therapeutic aspects. J Med Chem 24:1377-1383
    • (1981) J Med Chem , vol.24 , pp. 1377-1383
    • Krogsgaard-Larsen, P.1
  • 17
    • 0026774619 scopus 로고
    • Brain 4-aminobutyrate aminotransferase: Isolation and sequence of a cDNA encoding the enzyme
    • 1559966 1:CAS:528:DyaK38Xks1Gntbk%3D
    • Kwon OS, Park J, Churchich JE (1992) Brain 4-aminobutyrate aminotransferase: isolation and sequence of a cDNA encoding the enzyme. J Biol Chem 267:7215-7216
    • (1992) J Biol Chem , vol.267 , pp. 7215-7216
    • Kwon, O.S.1    Park, J.2    Churchich, J.E.3
  • 18
    • 0030203710 scopus 로고    scopus 로고
    • Distributed automated docking of flexible ligands to proteins: Parallel applications of Autodock 2.4
    • 8877701 10.1007/BF00124499 1:CAS:528:DyaK28XlsVOhsL0%3D
    • Morris GM, Goodsell DS, Huey R, Olson AJ (1996) Distributed automated docking of flexible ligands to proteins: parallel applications of Autodock 2.4. J Comput Aided Mol Des 10:293-304
    • (1996) J Comput Aided Mol des , vol.10 , pp. 293-304
    • Morris, G.M.1    Goodsell, D.S.2    Huey, R.3    Olson, A.J.4
  • 20
    • 70349315220 scopus 로고    scopus 로고
    • Molecular docking: Theoretical background, practical applications and perspectives
    • 10.1016/j.mencom.2009.09.001 1:CAS:528:DC%2BD1MXhtlOit7fO
    • Novikov FN, Chilov GG (2009) Molecular docking: theoretical background, practical applications and perspectives. Mendeleev Commun 19:237-242
    • (2009) Mendeleev Commun , vol.19 , pp. 237-242
    • Novikov, F.N.1    Chilov, G.G.2
  • 22
    • 33646466675 scopus 로고    scopus 로고
    • Inhibition of rabbit brain 4-aminobutyrate transaminase by some taurine analogues: A kinetic analysis
    • 16540097 10.1016/j.bcp.2006.02.007 1:CAS:528:DC%2BD28Xjs1Gls7c%3D
    • Ricci L, Frosini M, Gaggelli N, Valensin G, Machetti F, Sgaragli G, Valoti M (2006) Inhibition of rabbit brain 4-aminobutyrate transaminase by some taurine analogues: a kinetic analysis. Biochem Pharm 71:1510-1519
    • (2006) Biochem Pharm , vol.71 , pp. 1510-1519
    • Ricci, L.1    Frosini, M.2    Gaggelli, N.3    Valensin, G.4    MacHetti, F.5    Sgaragli, G.6    Valoti, M.7
  • 23
    • 84965093141 scopus 로고
    • Soluble γ-aminobutyric-glutamic transaminase from Pseudomonas fluorescens
    • 13654294 1:CAS:528:DyaG1MXnt1yksA%3D%3D
    • Scott EM, Jakoby WB (1959) Soluble γ-aminobutyric-glutamic transaminase from Pseudomonas fluorescens. J Biol Chem 234:932-936
    • (1959) J Biol Chem , vol.234 , pp. 932-936
    • Scott, E.M.1    Jakoby, W.B.2
  • 24
    • 0023364022 scopus 로고
    • Computer simulations of the diffusion of a substrate to an active site of an enzyme
    • 3589666 10.1126/science.3589666 1:CAS:528:DyaL2sXltFWksLg%3D
    • Sharp K, Fine R, Honig B (1987) Computer simulations of the diffusion of a substrate to an active site of an enzyme. Science 236:1460-1463
    • (1987) Science , vol.236 , pp. 1460-1463
    • Sharp, K.1    Fine, R.2    Honig, B.3
  • 25
    • 43549118378 scopus 로고    scopus 로고
    • Synthesis and evaluation of novel aromatic substrates and competitive inhibitors of GABA aminotransferase
    • 17988865 10.1016/j.bmcl.2007.10.060
    • Silverman RB, Clift MD (2008) Synthesis and evaluation of novel aromatic substrates and competitive inhibitors of GABA aminotransferase. Bioorg Med Chem Lett 18:3122-3125
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 3122-3125
    • Silverman, R.B.1    Clift, M.D.2
  • 26
    • 0022872451 scopus 로고
    • 4-Amino-2-(substituted methyl)-2-butenoic acids: Substrates and potent inhibitors of gamma-aminobutyric acid aminotransferase
    • 3701787 10.1021/jm00155a029 1:CAS:528:DyaL28Xhsl2ksb8%3D
    • Silverman RB, Durkee SC, Invergo BJ (1986) 4-Amino-2-(substituted methyl)-2-butenoic acids: substrates and potent inhibitors of gamma-aminobutyric acid aminotransferase. J Med Chem 29:764-770
    • (1986) J Med Chem , vol.29 , pp. 764-770
    • Silverman, R.B.1    Durkee, S.C.2    Invergo, B.J.3
  • 27
    • 1542577769 scopus 로고    scopus 로고
    • A receptor pharmacology and functional responses
    • 12937886 10.1007/s00216-003-2172-y 1:CAS:528:DC%2BD3sXot1ersb8%3D
    • A receptor pharmacology and functional responses. Anal Bioanal Chem 377:843-851
    • (2003) Anal Bioanal Chem , vol.377 , pp. 843-851
    • Smith, A.J.1    Simpson, P.B.2
  • 28
    • 0019525292 scopus 로고
    • Minimization by random search techniques
    • 10.1287/moor.6.1.19
    • Solis FJ, Wets RJ-B (1981) Minimization by random search techniques. Math Oper Res 6:19-30
    • (1981) Math Oper Res , vol.6 , pp. 19-30
    • Solis, F.J.1    Wets, R.-B.2
  • 29
    • 20444500516 scopus 로고    scopus 로고
    • Design and biological evaluation of phenyl-substituted analogs of β-phenyl ethylidene hydrazine
    • 15927473 10.1016/j.bmc.2005.04.072 1:CAS:528:DC%2BD2MXlt1Sktb4%3D
    • Sowa B, Rauw G, Davood A, Fassihi A, Knaus EE, Baker GB (2005) Design and biological evaluation of phenyl-substituted analogs of β-phenyl ethylidene hydrazine. Bioorg Med Chem 13:4389-4395
    • (2005) Bioorg Med Chem , vol.13 , pp. 4389-4395
    • Sowa, B.1    Rauw, G.2    Davood, A.3    Fassihi, A.4    Knaus, E.E.5    Baker, G.B.6
  • 30
    • 0033529338 scopus 로고    scopus 로고
    • Crystal structure of GABA aminotransferase a target for antiepileptic drug therapy
    • 10393538 10.1021/bi990478j 1:CAS:528:DyaK1MXjsFCqsbo%3D
    • Storici P, Capitani G, Baise DD, Moser M, John RA, Jansonius JN, Schirmer T (1999) Crystal structure of GABA aminotransferase a target for antiepileptic drug therapy. Biochemistry 38:8628-8634
    • (1999) Biochemistry , vol.38 , pp. 8628-8634
    • Storici, P.1    Capitani, G.2    Baise, D.D.3    Moser, M.4    John, R.A.5    Jansonius, J.N.6    Schirmer, T.7
  • 31
    • 0347052772 scopus 로고    scopus 로고
    • Structure of γ-amino butyric acid (GABA) aminotransferase a pyridoxal 5′-phosphate and [2Fe-2S] cluster-containing enzyme complexed with γ-ethynyl-GABA and with the antiepilepsy drug vigabatrin
    • 10.1074/jbc.M305884200
    • Storici P, Baise DD, Bossa F, Bruno S, Mozzarelli A, Peneff C, Silverman RB, Schirmer T (2005) Structure of γ-amino butyric acid (GABA) aminotransferase a pyridoxal 5′-phosphate and [2Fe-2S] cluster-containing enzyme complexed with γ-ethynyl-GABA and with the antiepilepsy drug vigabatrin. J Biol Chem 279:363-373
    • (2005) J Biol Chem , vol.279 , pp. 363-373
    • Storici, P.1    Baise, D.D.2    Bossa, F.3    Bruno, S.4    Mozzarelli, A.5    Peneff, C.6    Silverman, R.B.7    Schirmer, T.8
  • 32
    • 0028783806 scopus 로고
    • Active site model for γ-amino butyrate aminotransferase explains substrate specificity and inhibitor reactivities
    • 8563634 10.1002/pro.5560041115 1:CAS:528:DyaK2MXpsVGqt7w%3D
    • Toney MD, Pascarella S, Baise DD (1995) Active site model for γ-amino butyrate aminotransferase explains substrate specificity and inhibitor reactivities. Protein Sci 4:2366-2374
    • (1995) Protein Sci , vol.4 , pp. 2366-2374
    • Toney, M.D.1    Pascarella, S.2    Baise, D.D.3


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