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Volumn 41, Issue 14, 1998, Pages 2604-2613

Neurosteroid analogues. 6. The synthesis and GABA(A) receptor pharmacology of enantiomers of dehydroepiandrosterone sulfate, pregnenolone sulfate, and (3α,5β)-3-hydroxypregnan-20-one sulfate

Author keywords

[No Author keywords available]

Indexed keywords

3 (SULFOOXY)ANDROST 5 EN 17 ONE AMMONIUM; 3 (SULFOOXY)PREGN 5 EN 20 ONE AMMONIUM; 3 (SULFOOXY)PREGNAN 20 ONE AMMONIUM; 3 HYDROXYPREGNAN 20 ONE SULFATE; 4 AMINOBUTYRIC ACID A RECEPTOR; NEUROSTEROID; PRASTERONE SULFATE; PREGNENOLONE SULFATE; UNCLASSIFIED DRUG;

EID: 0032474840     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980148h     Document Type: Article
Times cited : (67)

References (47)
  • 1
    • 0026509649 scopus 로고
    • A Receptor. Mechanism of Action and Physiological Significance
    • A Receptor. Mechanism of Action and Physiological Significance. Prog. Neurobiol. (Oxford) 1992, 38, 379-395.
    • (1992) Prog. Neurobiol. (Oxford) , vol.38 , pp. 379-395
    • Majewska, M.D.1
  • 6
    • 0028213566 scopus 로고
    • Neurosteroids Modulate Calcium Currents in Hippocampal CA1 Neurons via a Pertussis Toxin-sensitive G-Protein-coupled Mechanism
    • (c) ffrench-Mullen, J. M. H.; Danks, P.; Spence, K. T. Neurosteroids Modulate Calcium Currents in Hippocampal CA1 Neurons via a Pertussis Toxin-sensitive G-Protein-coupled Mechanism. J. Neurosci. 1994, 14, 1963-1977.
    • (1994) J. Neurosci. , vol.14 , pp. 1963-1977
    • Ffrench-Mullen, J.M.H.1    Danks, P.2    Spence, K.T.3
  • 7
    • 0025995802 scopus 로고
    • Pregnenolone Sulfate: A Positive Allosteric Modulator at the N-Methyl-D-aspartate Receptor
    • (a) Wu, F.-S.; Gibbs, T. T.; Farb, D. H. Pregnenolone Sulfate: A Positive Allosteric Modulator at the N-Methyl-D-aspartate Receptor. Mol. Pharmacol. 1991, 40, 333-336.
    • (1991) Mol. Pharmacol. , vol.40 , pp. 333-336
    • Wu, F.-S.1    Gibbs, T.T.2    Farb, D.H.3
  • 8
    • 0027155274 scopus 로고
    • Pregnenolone Sulfate Potentiation of N-Methyl-D-aspartate Receptor Channels in Hippocampal Neurons
    • (b) Bowlby, M. R. Pregnenolone Sulfate Potentiation of N-Methyl-D-aspartate Receptor Channels in Hippocampal Neurons. Mol. Pharmacol. 1993, 43, 813-819.
    • (1993) Mol. Pharmacol. , vol.43 , pp. 813-819
    • Bowlby, M.R.1
  • 10
    • 0028167701 scopus 로고
    • 3α-Hydroxy-5β-pregnan-20-one Sulfate: A Negative Modulator of the NMDA-induced Current in Cultured Neurons
    • (d) Park-Chung, M.; Wu, F.-S.; Farb, D. H. 3α-Hydroxy-5β-pregnan-20-one Sulfate: A Negative Modulator of the NMDA-induced Current in Cultured Neurons. Mol. Pharmacol. 1994, 46, 146-150.
    • (1994) Mol. Pharmacol. , vol.46 , pp. 146-150
    • Park-Chung, M.1    Wu, F.-S.2    Farb, D.H.3
  • 11
    • 0031467726 scopus 로고    scopus 로고
    • Distinct Sites for Inverse Modulation of N-Methyl-D-aspartate Receptors by Sulfated Steroids
    • (e) Park-Chung, M.; Wu, F.-S.; Purdy, R. H.; Malayev, A. A.; Gibbs, T. T.; Farb, D. H. Distinct Sites for Inverse Modulation of N-Methyl-D-aspartate Receptors by Sulfated Steroids. Mol. Pharmacol. 1997, 52, 1113-1123.
    • (1997) Mol. Pharmacol. , vol.52 , pp. 1113-1123
    • Park-Chung, M.1    Wu, F.-S.2    Purdy, R.H.3    Malayev, A.A.4    Gibbs, T.T.5    Farb, D.H.6
  • 13
    • 0030010448 scopus 로고    scopus 로고
    • Potentiation of Neuronal NMDA Response Induced by Dehydroepiandrosterone and its Suppression by Progesterone: Effects Mediated via Sigma Receptors
    • (b) Bergeron, R.; de Montigny, C.; Debonnel, G. Potentiation of Neuronal NMDA Response Induced by Dehydroepiandrosterone and its Suppression by Progesterone: Effects Mediated via Sigma Receptors. J. Neurosci. 1996, 16, 1193-1202.
    • (1996) J. Neurosci. , vol.16 , pp. 1193-1202
    • Bergeron, R.1    De Montigny, C.2    Debonnel, G.3
  • 14
    • 0025329137 scopus 로고
    • Inverse Modulation of γ-Aminobutyric Acid- And Glycine-induced Currents by Progesterone
    • (a) Wu, F.-S.; Gibbs, T. T.; Farb, D. H. Inverse Modulation of γ-Aminobutyric Acid- and Glycine-induced Currents by Progesterone. Mol. Pharmacol. 1990, 37, 597-602.
    • (1990) Mol. Pharmacol. , vol.37 , pp. 597-602
    • Wu, F.-S.1    Gibbs, T.T.2    Farb, D.H.3
  • 15
    • 0031052768 scopus 로고    scopus 로고
    • Competitive Inhibition of the Glycine-induced Current by Pregnenolone Sulfate in Cultured Chick Spinal Cord Neurons
    • (b) Wu, F.-S.; Chen, S.-C.; Tsai, J.-J. Competitive Inhibition of the Glycine-induced Current by Pregnenolone Sulfate in Cultured Chick Spinal Cord Neurons. Brain Res. 1997, 750, 318-320.
    • (1997) Brain Res. , vol.750 , pp. 318-320
    • Wu, F.-S.1    Chen, S.-C.2    Tsai, J.-J.3
  • 16
    • 0022483382 scopus 로고
    • Steroid Hormone Metabolites are Barbiturate-like Modulators of the GABA Receptor
    • (a) Majewska, M. D.; Harrison, N. L.; Schwartz, R. D.; Barker, J. L.; Paul, S. M. Steroid Hormone Metabolites are Barbiturate-like Modulators of the GABA Receptor. Science 1986, 232, 1004-1007.
    • (1986) Science , vol.232 , pp. 1004-1007
    • Majewska, M.D.1    Harrison, N.L.2    Schwartz, R.D.3    Barker, J.L.4    Paul, S.M.5
  • 18
    • 0024517220 scopus 로고
    • Steroid anesthetics and Naturally Occurring Analogs Modulate the γ-Aminobutyric Acid Receptor Complex at a Site Distinct from Barbiturates
    • (c) Turner, D. M.; Ransom, R. W.; Yang, S.-J.; Olsen, R. W. Steroid anesthetics and Naturally Occurring Analogs Modulate the γ-Aminobutyric Acid Receptor Complex at a Site Distinct from Barbiturates. J. Pharmacol. Exp. Ther. 1989 248, 960-966.
    • (1989) J. Pharmacol. Exp. Ther. , vol.248 , pp. 960-966
    • Turner, D.M.1    Ransom, R.W.2    Yang, S.-J.3    Olsen, R.W.4
  • 19
    • 0014232652 scopus 로고
    • Steroids. CCCX. Structure-Activity Relationship of Some Steroidal Hypnotic Agents
    • (a) Gyermek, L.; Iriarte, J.; Crabbé, P. Steroids. CCCX. Structure-Activity Relationship of Some Steroidal Hypnotic Agents. J. Med. Chem. 1968, 11, 117-125.
    • (1968) J. Med. Chem. , vol.11 , pp. 117-125
    • Gyermek, L.1    Iriarte, J.2    Crabbé, P.3
  • 20
    • 0016806065 scopus 로고
    • Structure-Activity Relationships in Steroidal Anaesthetics
    • (b) Phillips, G. H. Structure-Activity Relationships in Steroidal Anaesthetics. J. Steroid Biochem. 1975, 6, 607-613.
    • (1975) J. Steroid Biochem. , vol.6 , pp. 607-613
    • Phillips, G.H.1
  • 22
    • 0025353194 scopus 로고
    • Synthesis, Metabolism, and Pharmacological Activity of 3α-Hydroxy Steroids Which Potentiate GABA-Receptor-Mediated Chloride Ion Uptake in Rat Cerebral Cortical Synaptoneurosomes
    • (d) Purdy, R. H.; Morrow, A. L.; Blinn, J. R.; Paul, S. M. Synthesis, Metabolism, and Pharmacological Activity of 3α-Hydroxy Steroids Which Potentiate GABA-Receptor-Mediated Chloride Ion Uptake in Rat Cerebral Cortical Synaptoneurosomes. J. Med. Chem. 1990, 33, 1572-1581.
    • (1990) J. Med. Chem. , vol.33 , pp. 1572-1581
    • Purdy, R.H.1    Morrow, A.L.2    Blinn, J.R.3    Paul, S.M.4
  • 28
    • 0023114555 scopus 로고
    • Pregnenolone-sulfate: An Endogenous antagonist of the γ-Aminobutyric Acid Receptor Complex in Brain
    • Majewska, M. D.; Schwartz, R. D. Pregnenolone-sulfate: An Endogenous antagonist of the γ-Aminobutyric Acid Receptor Complex in Brain. Brain Res. 1987, 404, 355-360.
    • (1987) Brain Res. , vol.404 , pp. 355-360
    • Majewska, M.D.1    Schwartz, R.D.2
  • 29
    • 0023940075 scopus 로고
    • Neurosteroid Pregnenolone Sulfate Antagonizes Electrophysiological Responses to GABA in Neurons
    • Majewska, M. D.; Mienville, J.-M.; Vicini, S. Neurosteroid Pregnenolone Sulfate Antagonizes Electrophysiological Responses to GABA in Neurons. Neurosci. Lett. 1988, 90, 279-284.
    • (1988) Neurosci. Lett. , vol.90 , pp. 279-284
    • Majewska, M.D.1    Mienville, J.-M.2    Vicini, S.3
  • 33
    • 0030854871 scopus 로고    scopus 로고
    • A Receptor Complex Reveals that it May Act via the Picrotoxin Site
    • A Receptor Complex Reveals that it May Act via the Picrotoxin Site. J. Pharmacol. Exp. Ther. 1997, 282, 827-833.
    • (1997) J. Pharmacol. Exp. Ther. , vol.282 , pp. 827-833
    • Sousa, A.1    Ticku, M.J.2
  • 34
    • 0028204425 scopus 로고
    • A Receptors in Ventral Midbrain Neurons by a Neurosteroid Dehydroepiandrosterone Sulfate
    • A Receptors in Ventral Midbrain Neurons by a Neurosteroid Dehydroepiandrosterone Sulfate. Synapse 1994, 16, 113-122.
    • (1994) Synapse , vol.16 , pp. 113-122
    • Spivak, C.1
  • 35
    • 0026577401 scopus 로고
    • Synthesis of enf-Cholesterol, the Unnatural Enantiomer
    • Rychnovsky, S. D.; Mickus, D. E. Synthesis of enf-Cholesterol, the Unnatural Enantiomer. J. Org. Chem. 1992, 57, 2732-2736.
    • (1992) J. Org. Chem. , vol.57 , pp. 2732-2736
    • Rychnovsky, S.D.1    Mickus, D.E.2
  • 36
    • 0020615392 scopus 로고
    • Structural and Configurational Dependence of the Sensory Process in Steroids
    • Ohloff, G.; Maurer, B.; Winter, B.; Giersch, W. Structural and Configurational Dependence of the Sensory Process in Steroids. Helv. Chim. Acta 1983, 66, 192-217.
    • (1983) Helv. Chim. Acta , vol.66 , pp. 192-217
    • Ohloff, G.1    Maurer, B.2    Winter, B.3    Giersch, W.4
  • 37
    • 12644286921 scopus 로고
    • 4-3-Oxo Steroid Isomerase of Pseudomonas Testosteroni
    • 4-3-Oxo Steroid Isomerase of Pseudomonas Testosteroni. Can. J. Chem. 1969, 47, 4459-4466.
    • (1969) Can. J. Chem. , vol.47 , pp. 4459-4466
    • Jones, J.B.1    Wigfield, D.C.2
  • 38
    • 0014305416 scopus 로고
    • Steroid conjugates IV. the Preparation of Steroid Sulfates with Triethylamine-sulfur Trioxide
    • Dusza, J. P.; Joseph, J. P.; Bernstein, S. Steroid conjugates IV. The Preparation of Steroid Sulfates with Triethylamine-sulfur Trioxide. Steroids 1968, 12, 49-61.
    • (1968) Steroids , vol.12 , pp. 49-61
    • Dusza, J.P.1    Joseph, J.P.2    Bernstein, S.3
  • 39
    • 0001675758 scopus 로고
    • The Hydration of Unsaturated Steroids by the Brown Hydroboration Reaction
    • Nussim, M.; Mazur, Y.; Sondheimer, F. The Hydration of Unsaturated Steroids by the Brown Hydroboration Reaction, J. Org. Chem. 1964, 29, 1120-1131.
    • (1964) J. Org. Chem. , vol.29 , pp. 1120-1131
    • Nussim, M.1    Mazur, Y.2    Sondheimer, F.3
  • 41
    • 0019441262 scopus 로고
    • Improved Patch-clamp Techniques for High Resolution Current Recordings from Cells and Cell-Free Membrane Patches
    • Hamill, O. P.; Marty, A.; Neher, E.; Sakmann, B.; Sigworth, F. J. Improved Patch-clamp Techniques for High Resolution Current Recordings from Cells and Cell-Free Membrane Patches. Pfluegers Arch. 1981, 391, 85-100.
    • (1981) Pfluegers Arch. , vol.391 , pp. 85-100
    • Hamill, O.P.1    Marty, A.2    Neher, E.3    Sakmann, B.4    Sigworth, F.J.5
  • 43
    • 0026542895 scopus 로고
    • Memory-enhancing Effects in Male Mice of Pregnenolone and Steroids Metabolically Derived from it
    • (a) Flood, J. F.; Morley, J. E.; Roberts, E. Memory-enhancing Effects in Male Mice of Pregnenolone and Steroids Metabolically Derived from it. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 1567-1571.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 1567-1571
    • Flood, J.F.1    Morley, J.E.2    Roberts, E.3
  • 44
    • 0030445549 scopus 로고    scopus 로고
    • The Neurosteroid Pregnenolone Sulfate Blocks Deficits Induced by a Competitive NMDA Antagonist in Active Avoidance and Lever-press Learning Tasks in Mice
    • (b) Mathis, C.; Vogel, E.; Cagniard, B.; Criscuolo, F.; Ungerer, A. The Neurosteroid Pregnenolone Sulfate Blocks Deficits Induced by a Competitive NMDA Antagonist in Active Avoidance and Lever-press Learning Tasks in Mice. Neuropharmacology 1996, 35, 1057-1064.
    • (1996) Neuropharmacology , vol.35 , pp. 1057-1064
    • Mathis, C.1    Vogel, E.2    Cagniard, B.3    Criscuolo, F.4    Ungerer, A.5
  • 45
    • 12644271203 scopus 로고    scopus 로고
    • Neuroprotective Activity of a New Class of Steroidal Inhibitors of the N-Methyl-D-aspartate Receptor
    • (a) Weaver, C. E., Jr.; Marek, P.; Park-Chung, M.; Tam, W. S.; Farb, D. H. Neuroprotective Activity of a New Class of Steroidal Inhibitors of the N-Methyl-D-aspartate Receptor. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10450-10454.
    • (1997) Proc. Natl. Acad. Sci. U.S.A. , vol.94 , pp. 10450-10454
    • Weaver Jr., C.E.1    Marek, P.2    Park-Chung, M.3    Tam, W.S.4    Farb, D.H.5
  • 46
    • 0031467726 scopus 로고    scopus 로고
    • Distinct Sites for Inverse Modulation of N-Methyl-D-aspartate Receptors by Sulfated Steroids
    • (b) Park-Chung, M.; Wu, F.-S.; Purdy, R. H.; Malayev, A. A.; Gibbs, T. T.; Farb, D. H. Distinct Sites for Inverse Modulation of N-Methyl-D-aspartate Receptors by Sulfated Steroids. Mol. Pharmacol. 1997, 52, 1113-1123.
    • (1997) Mol. Pharmacol. , vol.52 , pp. 1113-1123
    • Park-Chung, M.1    Wu, F.-S.2    Purdy, R.H.3    Malayev, A.A.4    Gibbs, T.T.5    Farb, D.H.6
  • 47
    • 0028868292 scopus 로고
    • Passive and Synaptic Properties of Hippocampal Neurons Grown in Microcultures and in Mass Cultures
    • Mennerick, S.; Que, J.; Benz, A.; Zorumski, C. F. Passive and Synaptic Properties of Hippocampal Neurons Grown in Microcultures and in Mass Cultures. J. Neurophysiol. 1995, 73, 320-332.
    • (1995) J. Neurophysiol. , vol.73 , pp. 320-332
    • Mennerick, S.1    Que, J.2    Benz, A.3    Zorumski, C.F.4


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