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Volumn 49, Issue 1, 2006, Pages 307-317

Design and synthesis of photoaffinity-labeling ligands of the L-prolyl-L-leucylglycinamide binding site involved in the allosteric modulation of the dopamine receptor

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; DOPAMINE 2 RECEPTOR; GAMMA LACTAM DERIVATIVE; HYDROXYL GROUP; LIGAND; PROLYLLEUCYLGLYCINAMIDE; PROPYLNORAPOMORPHINE;

EID: 30444456827     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050644n     Document Type: Article
Times cited : (34)

References (30)
  • 2
  • 3
    • 0021273822 scopus 로고
    • Effects of L-prolyl-L-leucyl-glycinamide and cyclo(leucyl-glycine) on the supersensitivity of dopamine receptors in brain induced by chronic administration of haloperidol to rats
    • Bhargava, H. N. Effects of L-Prolyl-L-Leucyl-Glycinamide and Cyclo(Leucyl-Glycine) on the Supersensitivity of Dopamine Receptors in Brain Induced by Chronic Administration of Haloperidol to Rats. Neuropharmacology 1984, 23, 439-444.
    • (1984) Neuropharmacology , vol.23 , pp. 439-444
    • Bhargava, H.N.1
  • 4
    • 0018168469 scopus 로고
    • Potentiation of apomorphine action in rats by L-prolyl-L-leucyl-glycine amide
    • Kostrzewa, R. M.; Kastin, A. J.; Sobrian, S. K. Potentiation of Apomorphine Action in Rats by L-Prolyl-L-Leucyl-Glycine Amide. Pharmacol. Biochem. Behav. 1978, 9, 375-378.
    • (1978) Pharmacol. Biochem. Behav. , vol.9 , pp. 375-378
    • Kostrzewa, R.M.1    Kastin, A.J.2    Sobrian, S.K.3
  • 6
    • 0020691136 scopus 로고
    • Binding studies of L-prolyl-L-leucyl-glycinamide (PLG), a novel antiparkinsonian agent, in normal human brain
    • Chiu, S.; Wong, Y. W.; Ferris, J. A.; Johnson, R. L.; Mishra, R. M. Binding Studies of L-Prolyl-L-Leucyl-Glycinamide (PLG), a Novel Antiparkinsonian Agent, in Normal Human Brain. Pharmacol. Res. Commun. 1983, 15, 41-51.
    • (1983) Pharmacol. Res. Commun. , vol.15 , pp. 41-51
    • Chiu, S.1    Wong, Y.W.2    Ferris, J.A.3    Johnson, R.L.4    Mishra, R.M.5
  • 7
    • 0021024260 scopus 로고
    • Are the pharmacological effects of L-prolyl-L-leucyl-glycinamide (PLG) mediated through specific receptor mechanisms?
    • Chiu, S.; Wong, Y. W.; Wan, Y. P.; Chiu, P.; Mishra, R. K. Are the Pharmacological Effects of L-Prolyl-L-Leucyl-Glycinamide (PLG) Mediated Through Specific Receptor Mechanisms? Prog. Neuro-Psychopharmacol. Biol. Psychiat. 1983, 7, 739-742.
    • (1983) Prog. Neuro-Psychopharmacol. Biol. Psychiat. , vol.7 , pp. 739-742
    • Chiu, S.1    Wong, Y.W.2    Wan, Y.P.3    Chiu, P.4    Mishra, R.K.5
  • 10
    • 0033516588 scopus 로고    scopus 로고
    • Modulation of agonist stimulated adenylyl cylcase and GTPase activity by L-pro-L-leu-glycinamide and its peptidomimetic analogue in rat striatal membranes
    • Mishra, R. K.; Makman, M. H.; Costain, W. J.; Nair, V. D.; Johnson, R. L. Modulation of Agonist Stimulated Adenylyl Cylcase and GTPase Activity by L-Pro-L-Leu-Glycinamide and Its Peptidomimetic Analogue in Rat Striatal Membranes. Neurosci. Lett. 1999, 269, 21-24.
    • (1999) Neurosci. Lett. , vol.269 , pp. 21-24
    • Mishra, R.K.1    Makman, M.H.2    Costain, W.J.3    Nair, V.D.4    Johnson, R.L.5
  • 11
    • 0037303584 scopus 로고    scopus 로고
    • Pro-leu-glycinamide and its peptidomimetic, PAOPA, attenuate haloperidol induced vacuous chewing movements in rat: A model of human tardive dyskinesia
    • Sharma, S.; Paladino, P.; Gabriele, J.; Saeedi, H.; Henry, P.; Chang, M.; Mishra, R. K.; Johnson, R. L. Pro-Leu-glycinamide and its Peptidomimetic, PAOPA, Attenuate Haloperidol Induced Vacuous Chewing Movements in Rat: A Model of Human Tardive Dyskinesia. Peptides 2003, 24, 313-319.
    • (2003) Peptides , vol.24 , pp. 313-319
    • Sharma, S.1    Paladino, P.2    Gabriele, J.3    Saeedi, H.4    Henry, P.5    Chang, M.6    Mishra, R.K.7    Johnson, R.L.8
  • 12
    • 0034026258 scopus 로고    scopus 로고
    • L-prolyl-L-leucyl-glycinamide and its peptidomimetic analog 3(R)-[(2(S)pyrrolidylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide (PAOPA) attenuate haloperidol-induced c-fos expression in the striatum
    • Ott, M. C.; Costain, W. J.; Mishra, R. K.; Johnson, R. L. L-Prolyl-L-Leucyl-Glycinamide and its Peptidomimetic Analog 3(R)-[(2(S) pyrrolidylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide (PAOPA) Attenuate Haloperidol-Induced c-fos Expression in the Striatum. Peptides 2000, 21, 301-308.
    • (2000) Peptides , vol.21 , pp. 301-308
    • Ott, M.C.1    Costain, W.J.2    Mishra, R.K.3    Johnson, R.L.4
  • 13
    • 0032552918 scopus 로고    scopus 로고
    • β-analogs of PLG (L-prolyl-L-leucyl-glycinamide): Ex-chiral pool syntheses and dopamine Ü2 receptor modulating effects
    • Thomas, C.; Ohnmacht, U.; Niger, M.; Gmeiner, P. β-Analogs of PLG (L-Prolyl-L-Leucyl-Glycinamide): Ex-Chiral Pool Syntheses and Dopamine Ü2 Receptor Modulating Effects. Bioorg. Med. Chem. Lett. 1998, 8, 2885-2890.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2885-2890
    • Thomas, C.1    Ohnmacht, U.2    Niger, M.3    Gmeiner, P.4
  • 16
    • 33947091497 scopus 로고
    • Photogenerated reagents for biological receptor-site labeling
    • Knowles, J. R. Photogenerated Reagents for Biological Receptor-Site Labeling. Acc. Chem. Res. 1972, 5, 155-160.
    • (1972) Acc. Chem. Res. , vol.5 , pp. 155-160
    • Knowles, J.R.1
  • 17
    • 0000906980 scopus 로고
    • Iodination of phenols using chloramine T and sodium iodide
    • Kometani, T.; Watt, D. S.; Ji, T. Iodination of Phenols using Chloramine T and Sodium Iodide. Tetrahedron Lett. 1985, 26, 2043-2046.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2043-2046
    • Kometani, T.1    Watt, D.S.2    Ji, T.3
  • 18
    • 0001456037 scopus 로고
    • An asymmetrical disulfide-containing photoreactive heterobifunctional reagent designed to introduce radioactive labeling into biological receptors
    • Dupuis, G. An Asymmetrical Disulfide-Containing Photoreactive Heterobifunctional Reagent Designed to Introduce Radioactive Labeling Into Biological Receptors. Can. J. Chem. 1987, 65, 2450-2453.
    • (1987) Can. J. Chem. , vol.65 , pp. 2450-2453
    • Dupuis, G.1
  • 19
    • 0028067715 scopus 로고
    • Synthesis of conformationally constrained DTPA analogues. Incorporation of the ethylenediamine units as aminopyrrolidines
    • Williams, M. A.; Rapoport, H. Synthesis of Conformationally Constrained DTPA Analogues. Incorporation of the Ethylenediamine Units as Aminopyrrolidines. J. Org. Chem. 1994, 59, 3616-3625.
    • (1994) J. Org. Chem. , vol.59 , pp. 3616-3625
    • Williams, M.A.1    Rapoport, H.2
  • 20
    • 0025831274 scopus 로고
    • Conformationally restricted arginine analogues
    • Webb, T. R.; Eigenbrot, C. Conformationally Restricted Arginine Analogues. J. Org. Chem. 1991, 56, 3009-3016.
    • (1991) J. Org. Chem. , vol.56 , pp. 3009-3016
    • Webb, T.R.1    Eigenbrot, C.2
  • 21
    • 0035953043 scopus 로고    scopus 로고
    • The conversion of alcohols to halides using a filterable phosphine source
    • Pollastri, M. P.; Sagal, J. F.; Chang, G. The Conversion of Alcohols to Halides Using a Filterable Phosphine Source. Tetrahedron Lett. 2001, 42, 2459-2460.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2459-2460
    • Pollastri, M.P.1    Sagal, J.F.2    Chang, G.3
  • 23
    • 0037468419 scopus 로고    scopus 로고
    • Synthesis and sopamie receptor modulating activity of 3-substituted λ-lactam peptidomimetics of L-prolyl-L-leucyl-glycinamide
    • Dolbeare, K.; Pontoriero, G. F.; Gupta, S. K.; Mishra, R. K.; Johnson, R. L. Synthesis and Sopamie Receptor Modulating Activity of 3-Substituted λ-Lactam Peptidomimetics of L-Prolyl-L-leucyl-glycinamide. J. Med. Chem. 2003, 46, 727-733.
    • (2003) J. Med. Chem. , vol.46 , pp. 727-733
    • Dolbeare, K.1    Pontoriero, G.F.2    Gupta, S.K.3    Mishra, R.K.4    Johnson, R.L.5
  • 24
    • 33646825288 scopus 로고
    • Protected lactam-bridged dipeptides for use as conformational constraints in peptides
    • Freidinger, R. M.; Perlow, D. S.; Veber, D. F. Protected Lactam-Bridged Dipeptides for Use as Conformational Constraints in Peptides. J. Org. Chem. 1982, 47, 104-109.
    • (1982) J. Org. Chem. , vol.47 , pp. 104-109
    • Freidinger, R.M.1    Perlow, D.S.2    Veber, D.F.3
  • 26
    • 33845549989 scopus 로고
    • Mixed anhydrides in peptide synthesis. Reduction of urethane formation and racemization using W-methylpiperidine as the tertiary amine base
    • Chen, F. M. F.; Steinauer, R.; Benoiton, N. L. Mixed Anhydrides in Peptide Synthesis. Reduction of Urethane Formation and Racemization Using W-Methylpiperidine as the Tertiary Amine Base. J. Org. Chem. 1983, 48, 2939-2941.
    • (1983) J. Org. Chem. , vol.48 , pp. 2939-2941
    • Chen, F.M.F.1    Steinauer, R.2    Benoiton, N.L.3
  • 27
    • 0022054206 scopus 로고
    • Utilization of 1-hydroxybenzotriazole in mixed anhydride coupling reactions
    • Prasad, K. U.; Iqbal, M. A. Urry, D. W. Utilization of 1-Hydroxybenzotriazole in Mixed Anhydride Coupling Reactions. Int. J. Pept. Protein Res. 1985, 25, 408-413.
    • (1985) Int. J. Pept. Protein Res. , vol.25 , pp. 408-413
    • Prasad, K.U.1    Iqbal, M.A.2    Urry, D.W.3
  • 28
    • 84987478892 scopus 로고
    • Monoprotection of μ,ω-alkanediamines with N-benzyloxycarbonyl group
    • Atwell, G. J.; Denny, W. A. Monoprotection of μ,ω-Alkanediamines with N-Benzyloxycarbonyl Group. Synthesis 1984, 1032-1033.
    • (1984) Synthesis , pp. 1032-1033
    • Atwell, G.J.1    Denny, W.A.2
  • 29
    • 0042090281 scopus 로고    scopus 로고
    • iso-lactam and reduced amide analogues of the peptidomimetic dopamine receptor modulator 3(R)-[2(S)-pyrrolidinylcarbonylamino]-2-oxo-1- pyrrolidineacetamide
    • Dolbeare, K.; Pontoriero, G. F.; Gupta, S. K.; Mishra, R. K.; Johnson, R. L. iso-Lactam and Reduced Amide Analogues of the Peptidomimetic Dopamine Receptor Modulator 3(R)-[(2(S)-Pyrrolidinylcarbonylamino]-2-oxo-1- pyrrolidineacetamide. Bioorg. Med. Chem. 2003, 11, 4103-4112.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 4103-4112
    • Dolbeare, K.1    Pontoriero, G.F.2    Gupta, S.K.3    Mishra, R.K.4    Johnson, R.L.5
  • 30
    • 0000117881 scopus 로고    scopus 로고
    • On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding
    • 1H NMR spectrum of the methyl ester did not possess the NH peak at 6.53, which is in agreement with the intermolecular H-bond complex, as it could not form with the methyl ester structure. For examples of this phenomenon, see: Marcovici-Mizrahi, D.; Gottlieb, H. E.; Marks, V.; Nudelman, A. On the Stabilization of the Syn-Rotamer of Amino Acid Carbamate Derivatives by Hydrogen Bonding. J. Org. Chem. 1996, 61, 8402-8406.
    • (1996) J. Org. Chem. , vol.61 , pp. 8402-8406
    • Marcovici-Mizrahi, D.1    Gottlieb, H.E.2    Marks, V.3    Nudelman, A.4


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