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Volumn 54, Issue 19, 2011, Pages 6538-6547

Synthesis, biological evaluation, and automated docking of constrained analogues of the opioid peptide H-Dmt-d-Ala-Phe-Gly-NH 2 using the 4- or 5-methyl substituted 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one scaffold

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO1,24,5 TETRAHYDRO 2 BENZAZEPIN 3 ONE; BENZAZEPINE DERIVATIVE; DERMORPHIN DERIVATIVE; MU OPIATE RECEPTOR AGONIST; OPIATE PEPTIDE; PHENYLALANINE; SIGMA OPIATE RECEPTOR; TETRAPEPTIDE; UNCLASSIFIED DRUG;

EID: 80053898753     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2003574     Document Type: Article
Times cited : (11)

References (79)
  • 1
    • 0033825829 scopus 로고    scopus 로고
    • Opioid receptors: From genes to mice
    • Kieffer, B. L. Opioid receptors: from genes to mice J. Pain 2000, 1, 45-50
    • (2000) J. Pain , vol.1 , pp. 45-50
    • Kieffer, B.L.1
  • 2
    • 1242314868 scopus 로고    scopus 로고
    • Recent Advances in Selective Opioid Receptor Agonists and Antagonists
    • DOI 10.1002/med.10059
    • Eguchi, M. Recent advances in selective opioid receptor agonists and antagonists Med. Res. Rev. 2004, 24, 182-212 (Pubitemid 38230679)
    • (2004) Medicinal Research Reviews , vol.24 , Issue.2 , pp. 182-212
    • Eguchi, M.1
  • 3
    • 42149181885 scopus 로고    scopus 로고
    • Structural diversity of G protein-coupled receptors and significance for drug discovery
    • Lagerström, M. C.; Schiöth, H. B. Structural diversity of G protein-coupled receptors and significance for drug discovery Nat. Rev. Drug Discovery 2008, 7, 339-357
    • (2008) Nat. Rev. Drug Discovery , vol.7 , pp. 339-357
    • Lagerström, M.C.1    Schiöth, H.B.2
  • 5
    • 0035336676 scopus 로고    scopus 로고
    • Activation of rhodopsin: New insights from structural and biochemical studies
    • DOI 10.1016/S0968-0004(01)01799-6, PII S0968000401017996
    • Okada, T.; Ernst, O. P.; Palczewski, K.; Hofmann, K. P. Activation of rhodopsin: new insights from structural and biochemical studies Trends Biochem. Sci. 2001, 26, 318-324 (Pubitemid 32436382)
    • (2001) Trends in Biochemical Sciences , vol.26 , Issue.5 , pp. 318-324
    • Okada, T.1    Ernst, O.P.2    Palczewski, K.3    Hofmann, K.P.4
  • 6
    • 6344248639 scopus 로고    scopus 로고
    • Structure of bovine rhodopsin in a trigonal crystal form
    • DOI 10.1016/j.jmb.2004.08.090, PII S0022283604010903
    • Li, J.; Edwards, P. C.; Burghammer, M.; Villa, C.; Schertler, G. F. X. Structure of bovine rhodopsin in a trigonal crystal form J. Mol. Biol. 2004, 343, 1409-1438 (Pubitemid 39387834)
    • (2004) Journal of Molecular Biology , vol.343 , Issue.5 , pp. 1409-1438
    • Li, J.1    Edwards, P.C.2    Burghammer, M.3    Villa, C.4    Schertler, G.F.X.5
  • 13
    • 0028089275 scopus 로고
    • Human μ opiate receptor: CDNA and genomic clones, pharmacologic characterization and chromosomal assignment
    • DOI 10.1016/0014-5793(94)80368-4
    • Wang, J. B.; Johnson, P. S.; Persico, A. M.; Hawkins, A. L.; Griffin, C. A.; Uhl, G. R. Human mu-opiate receptor: cDNA and genomic clones, pharmacological characterization and chromosomal assignment FEBS Lett. 1994, 338, 217-222 (Pubitemid 24064969)
    • (1994) FEBS Letters , vol.338 , Issue.2 , pp. 217-222
    • Wang, J.-B.1    Johnson, P.S.2    Persico, A.M.3    Hawkins, A.L.4    Griffin, C.A.5    Uhl, G.R.6
  • 15
    • 0028670235 scopus 로고
    • The human delta-opioid receptor: Genomic organization, cDNA cloning, functional expression, and distribution in human brain
    • Simonin, F.; Befort, K.; Gaveriauxruff, C.; Matthes, H.; Nappey, V.; Lannes, B.; Micheletti, G.; Kieffer, B. The human delta-opioid receptor: genomic organization, cDNA cloning, functional expression, and distribution in human brain Mol. Pharmacol. 1994, 46, 1015-1021
    • (1994) Mol. Pharmacol. , vol.46 , pp. 1015-1021
    • Simonin, F.1    Befort, K.2    Gaveriauxruff, C.3    Matthes, H.4    Nappey, V.5    Lannes, B.6    Micheletti, G.7    Kieffer, B.8
  • 16
    • 0028983787 scopus 로고
    • Kappa-opioid receptor in humans: CDNA and genomic cloning, chromosomal assignment, functional expression, pharmacology, and expression pattern in the central-nervous-system
    • Simonin, F.; Gaveriauxruff, C.; Befort, K.; Matthes, H.; Lannes, B.; Micheletti, G.; Mattei, M. G.; Charron, G.; Bloch, B.; Kieffer, B. Kappa-opioid receptor in humans: cDNA and genomic cloning, chromosomal assignment, functional expression, pharmacology, and expression pattern in the central-nervous-system Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7006-7010
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 7006-7010
    • Simonin, F.1    Gaveriauxruff, C.2    Befort, K.3    Matthes, H.4    Lannes, B.5    Micheletti, G.6    Mattei, M.G.7    Charron, G.8    Bloch, B.9    Kieffer, B.10
  • 19
    • 30644458763 scopus 로고    scopus 로고
    • Homology modeling of opioid receptor-ligand complexes using experimental constraints
    • Pogozheva, I. D.; Przydzial, M. J.; Mosberg, H. I. Homology modeling of opioid receptor-ligand complexes using experimental constraints AAPS J. 2005, 7, E434-E448
    • (2005) AAPS J. , vol.7
    • Pogozheva, I.D.1    Przydzial, M.J.2    Mosberg, H.I.3
  • 20
    • 0027503898 scopus 로고
    • Molecular cloning of a rat κ opioid receptor reveals sequence similarities to the μ and δ opioid receptors
    • Chen, Y.; Mestek, A.; Liu, J.; Yu, L. Molecular-cloning of a rat kappa-opioid receptor reveals sequence similarities to the mu-opioid and delta-opioid receptors Biochem. J. 1993, 295, 625-628 (Pubitemid 23323479)
    • (1993) Biochemical Journal , vol.295 , Issue.3 , pp. 625-628
    • Chen, Y.1    Mestek, A.2    Liu, J.3    Yu, L.4
  • 21
    • 78049502261 scopus 로고    scopus 로고
    • Recent progress in the structure determination of GPCRs, a membrane protein family with high potential as pharmaceutical targets
    • Cherezov, V.; Abola, E.; Stevens, R. C. Recent progress in the structure determination of GPCRs, a membrane protein family with high potential as pharmaceutical targets Methods Mol. Biol. 2010, 654, 141-168
    • (2010) Methods Mol. Biol. , vol.654 , pp. 141-168
    • Cherezov, V.1    Abola, E.2    Stevens, R.C.3
  • 24
    • 0034948696 scopus 로고    scopus 로고
    • Structural mimicry in G protein-coupled receptors: Implications of the high-resolution structure of rhodopsin for structure-function analysis of rhodopsin-like receptors
    • Ballesteros, J. A.; Shi, L.; Javitch, J. A. Structural mimicry in G-protein-coupled receptors: implications of high-resolution structure of rhodopsin for structure-function analysis of rhodopsin-like receptors Mol. Pharmacol. 2001, 60, 1-19 (Pubitemid 32595228)
    • (2001) Molecular Pharmacology , vol.60 , Issue.1 , pp. 1-19
    • Ballesteros, J.A.1    Shi, L.2    Javitch, J.A.3
  • 25
    • 71749112086 scopus 로고    scopus 로고
    • Customizing G protein-coupled receptor models for structure-based virtual screening
    • de Graaf, C.; Rognan, D. Customizing G protein-coupled receptor models for structure-based virtual screening Curr. Pharm. Des. 2009, 15, 4026-4048
    • (2009) Curr. Pharm. Des. , vol.15 , pp. 4026-4048
    • De Graaf, C.1    Rognan, D.2
  • 26
    • 10844246435 scopus 로고    scopus 로고
    • Complex of an active μ-opioid receptor with a cyclic peptide agonist modeled from experimental constraints
    • DOI 10.1021/bi048413q
    • Fowler, C. B.; Pogozheva, I. D.; Lomize, A. L.; LeVine, H.; Mosberg, H. I. Complex of an active mu-opioid receptor with a cyclic peptide agonist modeled from experimental constraints Biochemistry 2004, 43, 15796-15810 (Pubitemid 39665079)
    • (2004) Biochemistry , vol.43 , Issue.50 , pp. 15796-15810
    • Fowler, C.B.1    Pogozheva, I.D.2    Lomize, A.L.3    LeVine III, H.4    Mosberg, H.I.5
  • 27
    • 3042772949 scopus 로고    scopus 로고
    • Refinement of a homology model of the μ-opioid receptor using distance constraints from intrinsic and engineered zinc-binding sites
    • DOI 10.1021/bi036067r
    • Fowler, C. B.; Pogozheva, I. D.; LeVine, H.; Mosberg, H. I. Refinement of a homology model of the mu-opioid receptor using distance constraints from intrinsic and engineered zinc-binding sites Biochemistry 2004, 43, 8700-8710 (Pubitemid 38880040)
    • (2004) Biochemistry , vol.43 , Issue.27 , pp. 8700-8710
    • Fowler, C.B.1    Pogozheva, I.D.2    LeVine III, H.3    Mosberg, H.I.4
  • 28
    • 0033523062 scopus 로고    scopus 로고
    • Asp147 in the third transmembrane helix of the rat μ opioid receptor forms ion-pairing with morphine and naltrexone
    • PII S0024320599002349
    • Li, J. G.; Chen, C. G.; Yin, J. L.; Rice, K.; Zhang, Y.; Matecka, D.; de Riel, J. K.; DesJarlais, R. L.; Liu-Chen, L. Y. Asp147 in the third transmembrane helix of the rat mu opioid receptor forms ion-pairing with morphine and naltrexone Life Sci. 1999, 65, 175-185 (Pubitemid 29292820)
    • (1999) Life Sciences , vol.65 , Issue.2 , pp. 175-185
    • Li, J.-G.1    Chen, C.2    Yin, J.3    Rice, K.4    Zhang, Y.5    Matecka, D.6    De Riel, J.K.7    DesJarlais, R.L.8    Liu-Chen, L.-Y.9
  • 29
    • 0028170438 scopus 로고
    • Mu opiate receptor: Charged transmembrane domain amino-acids are critical for agonist recognition and intrinsic activity
    • Surratt, C. K.; Johnson, P. S.; Moriwaki, A.; Seidleck, B. K.; Blaschak, C. J.; Wang, J. B.; Uhl, G. R. Mu opiate receptor: charged transmembrane domain amino-acids are critical for agonist recognition and intrinsic activity J. Biol. Chem. 1994, 269, 20548-20553
    • (1994) J. Biol. Chem. , vol.269 , pp. 20548-20553
    • Surratt, C.K.1    Johnson, P.S.2    Moriwaki, A.3    Seidleck, B.K.4    Blaschak, C.J.5    Wang, J.B.6    Uhl, G.R.7
  • 30
    • 0029937609 scopus 로고    scopus 로고
    • Role of aromatic transmembrane residues of the δ-opioid receptor in ligand recognition
    • DOI 10.1074/jbc.271.17.10161
    • Befort, K.; Tabbara, L.; Kling, D.; Maigret, B.; Kieffer, B. L. Role of aromatic transmembrane residues of the delta-opioid receptor in ligand recognition J. Biol. Chem. 1996, 271, 10161-10168 (Pubitemid 26131579)
    • (1996) Journal of Biological Chemistry , vol.271 , Issue.17 , pp. 10161-10168
    • Befort, K.1    Tabbara, L.2    Kling, D.3    Maigret, B.4    Kieffer, B.L.5
  • 31
    • 0033603318 scopus 로고    scopus 로고
    • Constitutive activation of the delta opioid receptor by mutations in transmembrane domains III and VII
    • Befort, K.; Zilliox, C.; Filliol, D.; Yue, S. Y.; Kieffer, B. L. Constitutive activation of the delta opioid receptor by mutations in transmembrane domains III and VII J. Biol. Chem. 1999, 274, 18574-18581
    • (1999) J. Biol. Chem. , vol.274 , pp. 18574-18581
    • Befort, K.1    Zilliox, C.2    Filliol, D.3    Yue, S.Y.4    Kieffer, B.L.5
  • 32
    • 0033050225 scopus 로고    scopus 로고
    • Opioid peptide receptor studies, 11: Involvement of Tyr148, Trp318, and His319 of the rat μ-opioid receptor in binding of μ-selective ligands
    • DOI 10.1002/(SICI)1098-2396(199904)32:1<23::AID-SYN3>3.0.CO;2-N
    • Xu, H.; Lu, Y. F.; Partilla, J. S.; Zheng, Q. X.; Wang, J. B.; Brine, G. A.; Carroll, F. I.; Rice, K. C.; Chen, K. X.; Chi, Z. Q.; Rothman, R. B. Opioid peptide receptor studies, 11: Involvement of Tyr148, Trp318 and His319 of the rat mu-opioid receptor in binding of mu-selective ligands Synapse 1999, 32, 23-28 (Pubitemid 29124093)
    • (1999) Synapse , vol.32 , Issue.1 , pp. 23-28
    • Xu, H.1    Lu, Y.-F.2    Partilla, J.S.3    Zheng, Q.-X.4    Wang, J.-B.5    Brine, G.A.6    Carroll, F.I.7    Rice, K.C.8    Chen, K.-X.9    Chi, Z.-Q.10    Rothman, R.B.11
  • 34
    • 0034868637 scopus 로고    scopus 로고
    • Design in topographical space of peptide and peptidomimetic ligands that affect behavior. A chemist's glimpse at the mind-body problem
    • DOI 10.1021/ar990063q
    • Hruby, V. J. Design in topographical space and peptidomimetic ligands that affect behavior. A chemist's glipse at the mind-body problem Acc. Chem. Res. 2001, 34, 389-397 (Pubitemid 32816460)
    • (2001) Accounts of Chemical Research , vol.34 , Issue.5 , pp. 389-397
    • Hruby, V.J.1
  • 35
    • 73149121371 scopus 로고    scopus 로고
    • Organic chemistry and biology: Chemical biology through the eyes of collaboration
    • Hruby, V. J. Organic chemistry and biology: chemical biology through the eyes of collaboration J. Org. Chem. 2009, 74, 9245-9264
    • (2009) J. Org. Chem. , vol.74 , pp. 9245-9264
    • Hruby, V.J.1
  • 37
    • 59749089198 scopus 로고    scopus 로고
    • Influence of ring substitutions on the conformation and β-turn mimicry of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one peptide mimetics
    • De Wachter, R.; Brans, L.; Ballet, S.; Van den Eynde, I.; Urbanczyk-Lipkovska, Z.; Tourwe, D. Influence of ring substitutions on the conformation and β-turn mimicry of 4-amino-1,2,4,5-tetrahydro-2-benzazepin- 3-one peptide mimetics Tetrahedron 2009, 65, 2266-2278
    • (2009) Tetrahedron , vol.65 , pp. 2266-2278
    • De Wachter, R.1    Brans, L.2    Ballet, S.3    Van Den Eynde, I.4    Urbanczyk-Lipkovska, Z.5    Tourwe, D.6
  • 38
    • 2342586724 scopus 로고    scopus 로고
    • Conformational Analysis of Drug-Like Molecules Bound to Proteins: An Extensive Study of Ligand Reorganization upon Binding
    • DOI 10.1021/jm030563w
    • Perola, E.; Charifson, E. Conformational analysis of drug-like molecules bound to proteins: an extensive study of ligand reorganization upon binding J. Med. Chem. 2004, 47, 2499-510 (Pubitemid 38580088)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.10 , pp. 2499-2510
    • Perola, E.1    Charifson, P.S.2
  • 39
    • 0019605383 scopus 로고
    • Amino-acid-composition and sequence-analysis of sauvagine, a new active peptide from the skin of Phyllomedusa sauvagei
    • Montecucchi, P. C.; Henschen, A. Amino-acid-composition and sequence-analysis of sauvagine, a new active peptide from the skin of Phyllomedusa sauvagei Int. J. Pept. Protein Res. 1981, 18, 113-120
    • (1981) Int. J. Pept. Protein Res. , vol.18 , pp. 113-120
    • Montecucchi, P.C.1    Henschen, A.2
  • 40
    • 0024234671 scopus 로고
    • Characterization of the receptor-binding profile of (H-3) dermorphin in the rat-brain
    • Amiche, M.; Sagan, S.; Mor, A.; Delfour, A.; Nicolas, P. Characterization of the receptor-binding profile of (H-3) dermorphin in the rat-brain Int. J. Pept. Protein Res. 1988, 32, 506-511
    • (1988) Int. J. Pept. Protein Res. , vol.32 , pp. 506-511
    • Amiche, M.1    Sagan, S.2    Mor, A.3    Delfour, A.4    Nicolas, P.5
  • 41
    • 0019489204 scopus 로고
    • Pharmacological data on dermorphins, a new class of potent opioid peptides from amphibian skin
    • Broccardo, M.; Erspamer, V.; Falconierierspamer, G.; Improta, G.; Linari, G.; Melchiorri, P.; Montecucchi, P. C. Pharmacological data on dermorphins, a new class of potent opioid-peptides from amphibian skin Br. J. Pharmacol. 1981, 73, 625-631 (Pubitemid 11067899)
    • (1981) British Journal of Pharmacology , vol.73 , Issue.3 , pp. 625-631
    • Broccardo, M.1    Erspamer, V.2    Falconieri Erspamer, G.3
  • 42
    • 0030272919 scopus 로고    scopus 로고
    • The dermorphin peptide family
    • DOI 10.1016/0306-3623(95)02149-3
    • Melchiorri, P.; Negri, L. The dermorphin peptide family Gen. Pharmacol. 1996, 27, 1099-1107 (Pubitemid 26375421)
    • (1996) General Pharmacology , vol.27 , Issue.7 , pp. 1099-1107
    • Melchiorri, P.1    Negri, L.2
  • 44
    • 0026602250 scopus 로고
    • Preparation and opioid activity of analogs of the analgesic dipeptide 2,6-dimethyl- l -tyrosyl- N -(3-phenylpropyl)- d -alaninamide
    • Chandrakumar, N. S.; Yonan, P. K.; Stapelfeld, A.; Savage, M.; Rorbacher, E.; Contreras, P. C.; Hammond, D. Preparation and opioid activity of analogs of the analgesic dipeptide 2,6-dimethyl- l -tyrosyl- N -(3-phenylpropyl)- d -alaninamide J. Med. Chem. 1992, 35, 223-233
    • (1992) J. Med. Chem. , vol.35 , pp. 223-233
    • Chandrakumar, N.S.1    Yonan, P.K.2    Stapelfeld, A.3    Savage, M.4    Rorbacher, E.5    Contreras, P.C.6    Hammond, D.7
  • 45
    • 0005544241 scopus 로고    scopus 로고
    • Opioid Peptide Analogs with Novel Activity Profiles as Potential Therapeutic Agents for Use in Analgesia
    • In, Proceedings of the 1st International Peptide Symposium, Kyoto, Japan, Dec 1997; Shimonishi, Y. Kluwer Academic Publishers: Dordrecht, The Netherlands
    • Schiller, P. W.; Weltrowska, G.; Schmidt, R.; Nguyen, T. M. D.; Berezowska, I.; Chen, Y.; Lemieux, C.; Chung, N. N.; Wilkes, B. C.; Carpenter, K. A. Opioid Peptide Analogs with Novel Activity Profiles as Potential Therapeutic Agents for Use in Analgesia. In Peptide Science: Present and Future, Proceedings of the 1st International Peptide Symposium, Kyoto, Japan, Dec 1997; Shimonishi, Y., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; pp 665-669.
    • (1999) Peptide Science: Present and Future , pp. 665-669
    • Schiller, P.W.1    Weltrowska, G.2    Schmidt, R.3    Nguyen, T.M.D.4    Berezowska, I.5    Chen, Y.6    Lemieux, C.7    Chung, N.N.8    Wilkes, B.C.9    Carpenter, K.A.10
  • 47
    • 0343114238 scopus 로고    scopus 로고
    • Opioid Peptide Analogs Containing 2′-Hydroxy, 6′- Methyltyrosine in Place of Tyr1 Display Greatly Enhanced δ Agonist Potency but Unchanged μ Agonist Potency
    • In, Proceedings of the 25th European Peptide Symposium, Budapest, Hungary; Bajusz, S. Hudecz, F. Akadémiai Kiadó: Budapest, Hungary
    • Berezowska, I.; Lemieux, C.; Nguyen, T. M. D.; Chung, N. N.; Schiller, P. W. Opioid Peptide Analogs Containing 2′-Hydroxy, 6′-Methyltyrosine in Place of Tyr1 Display Greatly Enhanced δ Agonist Potency but Unchanged μ Agonist Potency. In Peptides 1998, Proceedings of the 25th European Peptide Symposium, Budapest, Hungary; Bajusz, S.; Hudecz, F., Eds.; Akadémiai Kiadó: Budapest, Hungary, 1998; pp 718-719.
    • (1998) Peptides 1998 , pp. 718-719
    • Berezowska, I.1    Lemieux, C.2    Nguyen, T.M.D.3    Chung, N.N.4    Schiller, P.W.5
  • 53
    • 43049097850 scopus 로고    scopus 로고
    • Blood-brain barrier penetration by two dermorphin tetrapeptide analogues: Role of lipophilicity vs structural flexibility
    • DOI 10.1021/jm701404s
    • Ballet, S.; Misicka, A.; Kosson, P.; Lemieux, C.; Chung, N. N.; Schiller, P. W.; Lipkowski, A. W.; Tourwe, D. Blood-brain barrier penetration by two dermorphin tetrapeptide analogues: role of lipophilicity vs structural flexibility J. Med. Chem. 2008, 51, 2571-2574 (Pubitemid 351628519)
    • (2008) Journal of Medicinal Chemistry , vol.51 , Issue.8 , pp. 2571-2574
    • Ballet, S.1    Misicka, A.2    Kosson, P.3    Lemieux, C.4    Chung, N.N.5    Schiller, P.W.6    Lipkowski, A.W.7    Tourwe, D.8
  • 54
    • 0017159096 scopus 로고
    • Studies of unusual amino-acids and their peptides. 6. Synthesis and optical resolutions of beta-methylphenylalanine and its dipeptide present in bottromycin
    • Kataoka, Y.; Seto, Y; Yamamoto, M. Studies of unusual amino-acids and their peptides. 6. Synthesis and optical resolutions of beta-methylphenylalanine and its dipeptide present in bottromycin Bull. Chem. Soc. Jpn. 1976, 46, 1081-1084
    • (1976) Bull. Chem. Soc. Jpn. , vol.46 , pp. 1081-1084
    • Kataoka, Y.1    Seto, Y.2    Yamamoto, M.3
  • 55
    • 51849181148 scopus 로고
    • Determination of d -amino acids. 2. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene
    • Marfey, P. Determination of d -amino acids. 2. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene Carlsberg Res. Commun. 1984, 49, 591-596
    • (1984) Carlsberg Res. Commun. , vol.49 , pp. 591-596
    • Marfey, P.1
  • 56
    • 0039117872 scopus 로고    scopus 로고
    • Separation of enantiomeric β-methyl amino acids and of β-methyl amino acid containing peptides
    • DOI 10.1016/0021-9673(95)01022-X
    • Péter, J.; Tóth, G.; Török, G.; Tourwé, D. Separation of enantiomeric β-methyl amino acids and of β-methyl amino acid containing peptides J. Chromatogr., A 1996, 728, 455-465 (Pubitemid 26143297)
    • (1996) Journal of Chromatography A , vol.728 , Issue.1-2 , pp. 455-465
    • Peter, A.1    Toth, G.2    Torok, G.3    Tourwe, D.4
  • 57
    • 33745808337 scopus 로고    scopus 로고
    • Improved Schöllkopf construction of quaternary α-amino acids: efficient enantioselective synthesis of integrin LFA-1 antagonist BIRT-377
    • DOI 10.1016/j.tetasy.2006.06.019, PII S0957416606004150
    • Vassiliou, S.; Magriotis, P. A. Improved Schöllkopf construction of quaternary alpha-amino acids: efficient enantioselective synthesis of integrin LFA-1 antagonist BIRT-377 Tetrahedron: Asymmetry 2006, 17, 1754-1757 (Pubitemid 44038369)
    • (2006) Tetrahedron Asymmetry , vol.17 , Issue.11 , pp. 1754-1757
    • Vassiliou, S.1    Magriotis, P.A.2
  • 58
    • 80053900461 scopus 로고    scopus 로고
    • Asymmetric synthesis and conformational analysis by NMR spectroscopy and MD of Aba- and α-MeAba-containing dermorphin analogues
    • [Online early access]. DOI: 10.1002/cmdc.201100314. Published Online: Aug 29.
    • Vandormael, B.; De Wachter, R.; Martins, J. C.; Hendrickx, P. M. S.; Keresztes, A.; Ballet, S.; Mallaredy, J. R.; Tóth, F.; Tóth, G.; Tourwé, D. Asymmetric synthesis and conformational analysis by NMR spectroscopy and MD of Aba- and α-MeAba-containing dermorphin analogues. ChemMedChem [Online early access]. DOI: 10.1002/cmdc.201100314. Published Online: Aug 29, 2011.
    • (2011) ChemMedChem
    • Vandormael, B.1    De Wachter, R.2    Martins, J.C.3    Hendrickx, P.M.S.4    Keresztes, A.5    Ballet, S.6    Mallaredy, J.R.7    Tóth, F.8    Tóth, G.9    Tourwé, D.10
  • 59
    • 0028986870 scopus 로고
    • Modulation by mu-opioid agonists of guanosine-5′- O -(3-[S-35]thio)triphosphate binding to membranes from human neuroblastoma Sh-Sy5y cells
    • Traynor, J. R.; Nahorski, S. R. Modulation by mu-opioid agonists of guanosine-5′- O -(3-[S-35]thio)triphosphate binding to membranes from human neuroblastoma Sh-Sy5y cells Mol. Pharmacol. 1995, 47, 848-854
    • (1995) Mol. Pharmacol. , vol.47 , pp. 848-854
    • Traynor, J.R.1    Nahorski, S.R.2
  • 60
    • 0021213731 scopus 로고
    • Structure-activity studies of dermorphin. The role of side chains of amino acid residues on the biological activity of dermorphin
    • DOI 10.1016/0196-9781(84)90007-X
    • Darlak, K.; Grzonka, Z.; Krascik, P.; Janicki, P.; Gumulka, S. W. Structure-activity studies of dermorphin. The role of side chains of amino acid residues on the biological activity of dermorphin Peptides 1984, 5, 687-689 (Pubitemid 14058544)
    • (1984) Peptides , vol.5 , Issue.4 , pp. 687-689
    • Darlak, K.1    Grzonka, Z.2
  • 65
    • 10144241052 scopus 로고    scopus 로고
    • Involvement of Trp-284, Val-296, and Val-297 of the human δ-opioid receptor in binding of δ-selective ligands
    • DOI 10.1074/jbc.271.31.18789
    • Valiquette, M.; Vu, H. K.; Yue, S. Y.; Wahlestedt, C.; Walker, P. Involvement of Trp-284, Val-296, and Val-297 of the human delta-opioid receptor in binding of delta-selective ligands J. Biol. Chem. 1996, 271, 18789-18796 (Pubitemid 26322748)
    • (1996) Journal of Biological Chemistry , vol.271 , Issue.31 , pp. 18789-18796
    • Valiquette, M.1    Vu, H.K.2    Yue, S.Y.3    Wahlestedt, C.4    Walker, P.5
  • 66
    • 34247343346 scopus 로고    scopus 로고
    • Surflex-Dock 2.1: Robust performance from ligand energetic modeling, ring flexibility, and knowledge-based search
    • DOI 10.1007/s10822-007-9114-2
    • Jain, A. N. Surflex-Dock 2.1: robust performance from ligand energetic modeling, ring flexibility, and knowledge-based search J. Comput.-Aided Mol. Des. 2007, 21, 281-306 (Pubitemid 46630055)
    • (2007) Journal of Computer-Aided Molecular Design , vol.21 , Issue.5 , pp. 281-306
    • Jain, A.N.1
  • 67
    • 0034284055 scopus 로고    scopus 로고
    • Selectivity of mu-opioid receptor determined by interfacial residues near third extracellular loop
    • Bonner, G.; Meng, F.; Akil, H. Selectivity of mu-opioid receptor determined by interfacial residues near third extracellular loop Eur. J. Pharmacol. 2000, 403, 37-44
    • (2000) Eur. J. Pharmacol. , vol.403 , pp. 37-44
    • Bonner, G.1    Meng, F.2    Akil, H.3
  • 68
    • 33846933784 scopus 로고    scopus 로고
    • Optimizing fragment and scaffold docking by use of molecular interaction fingerprints
    • DOI 10.1021/ci600342e
    • Marcou, G.; Rognan, D. Optimizing fragment and scaffold docking by use of molecular interaction fingerprints J. Chem. Inf. Model. 2007, 47, 195-207 (Pubitemid 46237537)
    • (2007) Journal of Chemical Information and Modeling , vol.47 , Issue.1 , pp. 195-207
    • Marcou, G.1    Rognan, D.2
  • 69
    • 41149156578 scopus 로고    scopus 로고
    • Molecular modeling of the second extracellular loop of G-protein coupled receptors and its implication on structure-based virtual screening
    • DOI 10.1002/prot.21724
    • de Graaf, C.; Foata, N.; Engkvist, O.; Rognan, D. Molecular modeling of the second extracellular loop of G-protein coupled receptors and its implication on structure-based virtual screening Proteins 2008, 71, 599-620 (Pubitemid 351430001)
    • (2008) Proteins: Structure, Function and Genetics , vol.71 , Issue.2 , pp. 599-620
    • De Graaf, C.1    Foata, N.2    Engkvist, O.3    Rognan, D.4
  • 70
    • 0036176035 scopus 로고    scopus 로고
    • Determinants of ligand selectivity at the κ-receptor based on the structure of the orphanin FQ receptor
    • DOI 10.1124/jpet.300.3.992
    • Owens, C. E.; Akil, H. Determinants of ligand selectivity at the κ-receptor based on the structure of the orphanin FQ receptor J. Pharmacol. Exp. Ther. 2002, 300, 992-999 (Pubitemid 34165006)
    • (2002) Journal of Pharmacology and Experimental Therapeutics , vol.300 , Issue.3 , pp. 992-999
    • Owens, C.E.1    Akil, H.2
  • 71
    • 84857139805 scopus 로고    scopus 로고
    • version 2.3.1; OpenEye Scientific Software: Santa Fe, NM.
    • ROCS, version 2.3.1; OpenEye Scientific Software: Santa Fe, NM; www.eyesopen.com.
    • ROCS
  • 72
    • 0030803817 scopus 로고    scopus 로고
    • Synthesis and opioid binding activity of dermorphin analogues containing cyclic β-amino acids
    • DOI 10.1016/S0143-4179(97)90073-1
    • Bozü, B.; Fülöp, F.; Toth, G. K.; Toth, G.; Szücs, M. Synthesis and opioid binding activity of dermorphin analogues containing cyclic beta-amino acids Neuropeptides 1997, 31, 367-372 (Pubitemid 27394784)
    • (1997) Neuropeptides , vol.31 , Issue.4 , pp. 367-372
    • Bozu, B.1    Fulop, F.2    Toth, G.K.3    Toth, G.4    Szucs, M.5
  • 73
    • 0017184389 scopus 로고    scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 2008, 72, 248-254
    • (2008) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 74
    • 2942722780 scopus 로고    scopus 로고
    • High-throughput modeling of human G-protein coupled receptors: Amino acid sequence alignment, three-dimensional model building, and receptor library screening
    • Bissantz, C.; Logean, A.; Rognan, D. High-throughput modeling of human G-protein coupled receptors: amino acid sequence alignment, three-dimensional model building, and receptor library screening J. Chem. Inf. Comput. Sci. 2004, 44, 1162-1176
    • (2004) J. Chem. Inf. Comput. Sci. , vol.44 , pp. 1162-1176
    • Bissantz, C.1    Logean, A.2    Rognan, D.3
  • 75
    • 0036945574 scopus 로고    scopus 로고
    • Development and validation of opioid ligand-receptor interaction models: The structural basis of mu vs. delta selectivity
    • DOI 10.1034/j.1399-3011.2002.21061.x
    • Mosberg, H. I.; Fowler, C. B. Development and validation of opioid ligand-receptor interaction models: the structural basis of mu vs. delta selectivity J. Pept. Res. 2002, 60, 329-335 (Pubitemid 36071896)
    • (2002) Journal of Peptide Research , vol.60 , Issue.6 , pp. 329-335
    • Mosberg, H.I.1    Fowler, C.B.2
  • 77
    • 0027136282 scopus 로고
    • Comparative protein modelling by satisfaction of spatial restraints
    • DOI 10.1006/jmbi.1993.1626
    • Sali, A.; Blundell, T. L. Comparative protein modeling by satisfaction of spatial restraints J. Mol. Biol. 1993, 234, 779-815 (Pubitemid 24007801)
    • (1993) Journal of Molecular Biology , vol.234 , Issue.3 , pp. 779-815
    • Sali, A.1    Blundell, T.L.2
  • 78
    • 20444478293 scopus 로고    scopus 로고
    • An activation switch in the rhodopsin family of G protein-coupled receptors: The thyrotropin receptor
    • DOI 10.1074/jbc.M414678200
    • Urizar, E.; Claeysen, S.; Deupi, X.; Govaerts, C.; Costagliola, S.; Vassart, G.; Pardo, L. An activation switch in the rhodopsin family of G protein-coupled receptors. The thyrotropin receptor J. Biol. Chem. 2005, 280, 17135-17141 (Pubitemid 41389178)
    • (2005) Journal of Biological Chemistry , vol.280 , Issue.17 , pp. 17135-17141
    • Urizar, E.1    Claeysen, S.2    Deupi, X.3    Govaerts, C.4    Costagliola, S.5    Vassart, G.6    Pardo, L.7
  • 79
    • 84857141460 scopus 로고    scopus 로고
    • version 2.2.1; OpenEye Scientific Software: Santa Fe, NM.
    • OMEGA, version 2.2.1; OpenEye Scientific Software: Santa Fe, NM; www.eyesopen.com.
    • OMEGA


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