메뉴 건너뛰기




Volumn 309, Issue 2, 2004, Pages 677-683

Enantioselectivity of α-Benzyl-α-methyl-γ -butyrolactone-Mediated Modulation of Anticonvulsant Activity and GABA A Receptor Function

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; 4 AMINOBUTYRIC ACID A RECEPTOR; ALKYL GROUP; ALPHA BENZYL ALPHA METHYL GAMMA BUTYROLACTONE; ANTICONVULSIVE AGENT; GAMMA BUTYROLACTONE DERIVATIVE; LACTONE DERIVATIVE; PENTETRAZOLE; PICROTOXIN; RECOMBINANT RECEPTOR; TERT BUTYLBICYCLOPHOSPHOROTHIOATE; UNCLASSIFIED DRUG;

EID: 2142810127     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.103.063008     Document Type: Article
Times cited : (14)

References (38)
  • 1
    • 0000958405 scopus 로고
    • Chiral aggregation phenomena. 4. A search for stereospecific interactions between highly purified enantiomeric and racemic dipalmitoyl phosphatidylcholines and other chiral surfactants in monolayers, vesicles and gels
    • Arnett EM and Gold JM (1986) Chiral aggregation phenomena. 4. A search for stereospecific interactions between highly purified enantiomeric and racemic dipalmitoyl phosphatidylcholines and other chiral surfactants in monolayers, vesicles and gels. J Am Chem Soc 104:636-639.
    • (1986) J Am Chem Soc , vol.104 , pp. 636-639
    • Arnett, E.M.1    Gold, J.M.2
  • 2
    • 0022537169 scopus 로고
    • Demonstration of a receptor in Torpedo synaptic vesicles for the acetylcholine storage blocker L-trans-2-(4-phenyl[3,4-3H]-piperidino)cyclohexanol
    • Bahr BA and Parsons SM (1986) Demonstration of a receptor in Torpedo synaptic vesicles for the acetylcholine storage blocker L-trans-2-(4-phenyl[3,4-3H]-piperidino)cyclohexanol. Proc Natl Acad Sci USA 83:2267-2270.
    • (1986) Proc Natl Acad Sci USA , vol.83 , pp. 2267-2270
    • Bahr, B.A.1    Parsons, S.M.2
  • 5
    • 0026563082 scopus 로고
    • Triethylamine/aluminum chloride promoted aminolysis of lactones: A useful method for the preparation of ω-hydroxy amides
    • Bigg DCH and Lesimple P (1992) Triethylamine/aluminum chloride promoted aminolysis of lactones: a useful method for the preparation of ω-hydroxy amides. Synthesis 277-278.
    • (1992) Synthesis , pp. 277-278
    • Bigg, D.C.H.1    Lesimple, P.2
  • 7
    • 0025913905 scopus 로고
    • Synthesis and structure-activity studies of alkyl-substituted γ-butyrolactones and γ-thiobutyrolactones: Ligands for the picrotoxin receptor
    • Canney DJ, Holland KD, Levine JA, McKeon AC, Ferrendelli JA, and Covey DF (1991) Synthesis and structure-activity studies of alkyl-substituted γ-butyrolactones and γ-thiobutyrolactones: ligands for the picrotoxin receptor. J Med Chem 34:1460-1467.
    • (1991) J Med Chem , vol.34 , pp. 1460-1467
    • Canney, D.J.1    Holland, K.D.2    Levine, J.A.3    McKeon, A.C.4    Ferrendelli, J.A.5    Covey, D.F.6
  • 9
  • 10
    • 0035666443 scopus 로고    scopus 로고
    • Recent developments in structure-activity relationships for steroid modulators of GABA(A) receptors
    • Covey DF, Evers AS, Mennerick S, Zorumski CF, and Purdy RH (2001) Recent developments in structure-activity relationships for steroid modulators of GABA(A) receptors. Brain Res Brain Res Rev 37:91-97.
    • (2001) Brain Res Brain Res Rev , vol.37 , pp. 91-97
    • Covey, D.F.1    Evers, A.S.2    Mennerick, S.3    Zorumski, C.F.4    Purdy, R.H.5
  • 12
    • 0030250038 scopus 로고    scopus 로고
    • Gamma hydroxybutyrate is not a GABA agonist
    • Feigenbaum JJ and Howard SG (1996) Gamma hydroxybutyrate is not a GABA agonist. Prog Neurobiol 50:1-7.
    • (1996) Prog Neurobiol , vol.50 , pp. 1-7
    • Feigenbaum, J.J.1    Howard, S.G.2
  • 14
    • 0021074081 scopus 로고
    • Phosphatidylcholine and cholesterol interactions in model membranes
    • Guyer W and Block K (1983) Phosphatidylcholine and cholesterol interactions in model membranes. Chem Phys Lipids 33:313-322.
    • (1983) Chem Phys Lipids , vol.33 , pp. 313-322
    • Guyer, W.1    Block, K.2
  • 17
    • 0032509817 scopus 로고    scopus 로고
    • Stereoselective actions of halothane at GABA(A) receptors
    • Harris BD, Moody EJ, and Skolnick P (1998) Stereoselective actions of halothane at GABA(A) receptors. Eur J Pharmacol 341:349-352.
    • (1998) Eur J Pharmacol , vol.341 , pp. 349-352
    • Harris, B.D.1    Moody, E.J.2    Skolnick, P.3
  • 20
    • 0025438389 scopus 로고
    • Physiological regulation of the picrotoxin receptor by gamma-butyrolactones and gamma-thiobutyrolactones in cultured hippocampal neurons
    • Holland KD, Ferrendelli JA, Covey DF, and Rothman SM (1990a) Physiological regulation of the picrotoxin receptor by gamma-butyrolactones and gamma-thiobutyrolactones in cultured hippocampal neurons. J Neurosci 10:1719-1727.
    • (1990) J Neurosci , vol.10 , pp. 1719-1727
    • Holland, K.D.1    Ferrendelli, J.A.2    Covey, D.F.3    Rothman, S.M.4
  • 23
    • 0025007643 scopus 로고
    • Binding interactions of convulsant and anticonvulsant gamma-butyrolactones and gamma-thiobutyrolactones with the picrotoxin receptor
    • Holland KD, McKeon AC, Covey DF, and Ferrendelli JA (1990b) Binding interactions of convulsant and anticonvulsant gamma-butyrolactones and gamma-thiobutyrolactones with the picrotoxin receptor. J Pharmacol Exp Ther 254:578-583.
    • (1990) J Pharmacol Exp Ther , vol.254 , pp. 578-583
    • Holland, K.D.1    McKeon, A.C.2    Covey, D.F.3    Ferrendelli, J.A.4
  • 24
    • 0026099495 scopus 로고
    • Gamma-butyrolactone antagonism of the picrotoxin receptor: Comparison of a pure antagonist and a mixed antagonist/inverse agonist
    • Holland KD, Yoon KW, Ferrendelli JA, Covey DF, and Rothman SM (1991) Gamma-butyrolactone antagonism of the picrotoxin receptor: comparison of a pure antagonist and a mixed antagonist/inverse agonist. Mol Pharmacol 39:79-84.
    • (1991) Mol Pharmacol , vol.39 , pp. 79-84
    • Holland, K.D.1    Yoon, K.W.2    Ferrendelli, J.A.3    Covey, D.F.4    Rothman, S.M.5
  • 25
    • 0005871619 scopus 로고
    • Determination of enantiomeric purity of chiral lactones. A general method using nuclear magnetic resonance
    • Jakovac IJ and Jones JB (1979) Determination of enantiomeric purity of chiral lactones. A general method using nuclear magnetic resonance. J Org Chem 44:2165-2168.
    • (1979) J Org Chem , vol.44 , pp. 2165-2168
    • Jakovac, I.J.1    Jones, J.B.2
  • 26
    • 0019943406 scopus 로고
    • Anticonvulsant properties of α, γ and α,γ -substituted γ-butyrolactones
    • Klunk WE, Covey DF, and Ferrendelli JA (1982a) Anticonvulsant properties of α, γ and α,γ-substituted γ-butyrolactones. Mol Pharmacol 22:438-443.
    • (1982) Mol Pharmacol , vol.22 , pp. 438-443
    • Klunk, W.E.1    Covey, D.F.2    Ferrendelli, J.A.3
  • 27
    • 0019982612 scopus 로고
    • Comparison of epileptogenic properties of unsubstituted and beta-alkyl-substituted gamma-butyrolactones
    • Klunk WE, Covey DF, and Ferrendelli JA (1982b) Comparison of epileptogenic properties of unsubstituted and beta-alkyl-substituted gamma-butyrolactones. Mol Pharmacol 22:431-437.
    • (1982) Mol Pharmacol , vol.22 , pp. 431-437
    • Klunk, W.E.1    Covey, D.F.2    Ferrendelli, J.A.3
  • 28
    • 0031967619 scopus 로고    scopus 로고
    • Propofol and other intravenous anesthetics have sites of action on the gamma-aminobutyric acid type A receptor distinct from that for isoflurane
    • Krasowski MD, Koltchine VV, Rick CE, Ye Q, Finn SE, and Harrison NL (1998) Propofol and other intravenous anesthetics have sites of action on the gamma-aminobutyric acid type A receptor distinct from that for isoflurane. Mol Pharmacol 53:530-538.
    • (1998) Mol Pharmacol , vol.53 , pp. 530-538
    • Krasowski, M.D.1    Koltchine, V.V.2    Rick, C.E.3    Ye, Q.4    Finn, S.E.5    Harrison, N.L.6
  • 29
    • 0022407542 scopus 로고
    • Convulsant and anti-convulsant gammabutyrolactones bind at the picrotoxinin/T-butylbicyclophosphorothionate (TBPS) receptor
    • Levine JA, Ferrendelli JA, and Covey DF (1985) Convulsant and anti-convulsant gammabutyrolactones bind at the picrotoxinin/T-butylbicyclophosphorothionate (TBPS) receptor. Biochem Pharmacol 34:4187-4190.
    • (1985) Biochem Pharmacol , vol.34 , pp. 4187-4190
    • Levine, J.A.1    Ferrendelli, J.A.2    Covey, D.F.3
  • 31
    • 0037304550 scopus 로고    scopus 로고
    • Effects of natural and enantiomeric cholesterol on the thermotropic phase behavior and structure of egg sphingomyelin bilayer membranes
    • Mannock DA, McIntosh TJ, Jiang X, Covey DF, and McElhaney RN (2003) Effects of natural and enantiomeric cholesterol on the thermotropic phase behavior and structure of egg sphingomyelin bilayer membranes. Biophys J 84:1038-1046.
    • (2003) Biophys J , vol.84 , pp. 1038-1046
    • Mannock, D.A.1    McIntosh, T.J.2    Jiang, X.3    Covey, D.F.4    McElhaney, R.N.5
  • 33
    • 33751554472 scopus 로고
    • The asymmetric synthesis of 2,2-dialkyl carboxylic esters and 2,2-disubstituted dihydronapthalenes
    • Meyers AI, Wallace RH, Harre M, and Garland R (1990) The asymmetric synthesis of 2,2-dialkyl carboxylic esters and 2,2-disubstituted dihydronapthalenes. J Org Chem 55:3137-3143.
    • (1990) J Org Chem , vol.55 , pp. 3137-3143
    • Meyers, A.I.1    Wallace, R.H.2    Harre, M.3    Garland, R.4
  • 34
    • 0028796049 scopus 로고
    • Evolutionary history of the ligand-gated ion-channel superfamily of receptors
    • Ortells MO and Lunt GG (1995) Evolutionary history of the ligand-gated ion-channel superfamily of receptors. Trends Neurosci 18:121-127.
    • (1995) Trends Neurosci , vol.18 , pp. 121-127
    • Ortells, M.O.1    Lunt, G.G.2
  • 36
    • 0346435104 scopus 로고    scopus 로고
    • Cholesterol depletion results in site-specific increases in EGF receptor phosphorylation due to membrane level effects: Studies with cholesterol enantiomers
    • Westover EJ, Covey DF, Brockman HL, Brown RE, and Pike LJ (2003) Cholesterol depletion results in site-specific increases in EGF receptor phosphorylation due to membrane level effects: studies with cholesterol enantiomers. J Biol Chem 278:51125-51133.
    • (2003) J Biol Chem , vol.278 , pp. 51125-51133
    • Westover, E.J.1    Covey, D.F.2    Brockman, H.L.3    Brown, R.E.4    Pike, L.J.5
  • 38
    • 0027158425 scopus 로고
    • Multiple mechanisms of picrotoxin block of GABA-induced currents in rat hippocampal neurons
    • Yoon KW, Covey DF, and Rothman SM (1993) Multiple mechanisms of picrotoxin block of GABA-induced currents in rat hippocampal neurons. J Physiol (Lond) 464:423-439.
    • (1993) J Physiol (Lond) , vol.464 , pp. 423-439
    • Yoon, K.W.1    Covey, D.F.2    Rothman, S.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.