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Volumn 40, Issue 17, 1997, Pages 2740-2749

β-methylation of the Phe7 and Trp9 melanotropin side chain pharmacophores affects ligand-receptor interactions and prolonged biological activity

Author keywords

[No Author keywords available]

Indexed keywords

DRUG CARRIER; INTERMEDIN; N METHYLTRYPTOPHAN; PHENYLALANINE; TRYPTOPHAN; HORMONE RECEPTOR; INTERMEDIN RECEPTOR; LIGAND;

EID: 0030610607     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970018t     Document Type: Article
Times cited : (67)

References (45)
  • 1
    • 0020157524 scopus 로고
    • Neuropeptides Derived from Pro-Opiocortin: Behavioral, Physiological, and Neurochemical Effects
    • De Wied, D.; Jolles, J. Neuropeptides Derived from Pro-Opiocortin: Behavioral, Physiological, and Neurochemical Effects. Physiol. Rev. 1982, 62, 976-1059.
    • (1982) Physiol. Rev. , vol.62 , pp. 976-1059
    • De Wied, D.1    Jolles, J.2
  • 3
    • 0002293913 scopus 로고
    • Melanotropins: Structural, Conformational and Biological Considerations in the Development of Superpotent and Superprolonged Analogs
    • Hruby, V. J.; Wilkes, B. C.; Cody, W. L.; Sawyer, T. K.; Hadley, M. E. Melanotropins: Structural, Conformational and Biological Considerations in the Development of Superpotent and Superprolonged Analogs. Pept. Protein Rev. 1984, 3, 1-64.
    • (1984) Pept. Protein Rev. , vol.3 , pp. 1-64
    • Hruby, V.J.1    Wilkes, B.C.2    Cody, W.L.3    Sawyer, T.K.4    Hadley, M.E.5
  • 7
  • 8
    • 0000448866 scopus 로고
    • 4-Norleucine, 7-D- Phenylalanine-α-Melanocyte-Stimulating Hormone: A Highly Potent α-Melanotropin with Ultra Long Biological Activity
    • Sawyer, T. K.; Sanfillippo, P. J.; Hruby, V. J.; Engel, M. H.; Heward, C. B.; Burnett, J. B.; Hadley, M. E. 4-Norleucine, 7-D-Phenylalanine-α-Melanocyte-Stimulating Hormone: A Highly Potent α-Melanotropin with Ultra Long Biological Activity. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 5754-5758.
    • (1980) Proc. Natl. Acad. Sci. U.S.A. , vol.77 , pp. 5754-5758
    • Sawyer, T.K.1    Sanfillippo, P.J.2    Hruby, V.J.3    Engel, M.H.4    Heward, C.B.5    Burnett, J.B.6    Hadley, M.E.7
  • 9
    • 0019890250 scopus 로고
    • Calcium-Dependent Prolonged Effects on Melanophores of [4-Norleucine, 7-D-Phenylalanine]-α-Melanotropin
    • Hadley, M. E.; Anderson, B.; Heward, C. B.; Sawyer, T. K.; Hruby, V. J. Calcium-Dependent Prolonged Effects on Melanophores of [4-Norleucine, 7-D-Phenylalanine]-α-Melanotropin. Science 1981, 213, 1025-1027.
    • (1981) Science , vol.213 , pp. 1025-1027
    • Hadley, M.E.1    Anderson, B.2    Heward, C.B.3    Sawyer, T.K.4    Hruby, V.J.5
  • 10
    • 0024551431 scopus 로고
    • Design of a New Class of Superpotent Cyclic α-Melanotropins Based on Quenched Dynamic Stimulations
    • Al-Obeidi, F.; Hadley, M. E.; Pettitt, B. M.; Hruby, V. J. Design of a New Class of Superpotent Cyclic α-Melanotropins Based on Quenched Dynamic Stimulations. J. Am. Chem. Soc. 1989, 111, 3413-3416.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3413-3416
    • Al-Obeidi, F.1    Hadley, M.E.2    Pettitt, B.M.3    Hruby, V.J.4
  • 11
    • 0024310869 scopus 로고
    • Potent and Prolonged Acting Cyclic Lactam Analogues of α-Melanotropin: Design Based on Molecular Dynamics
    • Al-Obeidi, F.; Castrucci, A. M.; Hadley, M. E.; Hruby, V. J. Potent and Prolonged Acting Cyclic Lactam Analogues of α-Melanotropin: Design Based on Molecular Dynamics. J. Med. Chem. 1989, 32, 2555-2561.
    • (1989) J. Med. Chem. , vol.32 , pp. 2555-2561
    • Al-Obeidi, F.1    Castrucci, A.M.2    Hadley, M.E.3    Hruby, V.J.4
  • 15
    • 0028799933 scopus 로고
    • Topographical Modifications of Melanotropin Peptide Analogues with β-Methyltryptophan Isomers at Position 9 Leads to Differential Potencies and Prolonged Biological Activities
    • Haskell-Luevano, C.; Boteju, L. W.; Miwa, H.; Dickinson, C.; Gantz, I.; Yamada, T.; Hadley, M. E.; Hruby, V. J. Topographical Modifications of Melanotropin Peptide Analogues with β-Methyltryptophan Isomers at Position 9 Leads to Differential Potencies and Prolonged Biological Activities. J. Med. Chem. 1995, 38, 4720-4729.
    • (1995) J. Med. Chem. , vol.38 , pp. 4720-4729
    • Haskell-Luevano, C.1    Boteju, L.W.2    Miwa, H.3    Dickinson, C.4    Gantz, I.5    Yamada, T.6    Hadley, M.E.7    Hruby, V.J.8
  • 16
    • 0001924921 scopus 로고    scopus 로고
    • Use of Topographical Modifications of Peptides to Examine Biological Mechanisms Such as Prolongation
    • Kaumaya, P. T. P., Hodges, R. S., Eds.; Mayflower Scientific Ltd: Kingswinford, England
    • Haskell-Luevano, C.; Boteju, L. W.; Miwa, H.; Job, C.; Al-Obeidi, F.; Gantz, I.; Hadley, M. E.; Hruby, V. J. Use of Topographical Modifications of Peptides to Examine Biological Mechanisms Such as Prolongation. In Peptides, Chemistry, Structure and Biology; Kaumaya, P. T. P., Hodges, R. S., Eds.; Mayflower Scientific Ltd: Kingswinford, England, 1996; pp 831-832.
    • (1996) Peptides, Chemistry, Structure and Biology , pp. 831-832
    • Haskell-Luevano, C.1    Boteju, L.W.2    Miwa, H.3    Job, C.4    Al-Obeidi, F.5    Gantz, I.6    Hadley, M.E.7    Hruby, V.J.8
  • 17
    • 15144342235 scopus 로고
    • Ph.D. Thesis, University of Arizona
    • Haskell-Luevano, C. Ph.D. Thesis, University of Arizona, 1995.
    • (1995)
    • Haskell-Luevano, C.1
  • 18
    • 0000545418 scopus 로고
    • Peptidomimetics for Drug Design
    • Wolff, M. E., Eds.; Wiley: New York, Principles and Practice
    • Goodman, M.; Ro, S. Peptidomimetics for Drug Design. In Burger's Medicinal Chemistry and Drug Discovery; Wolff, M. E., Eds.; Wiley: New York, 1995; Vol. 1: Principles and Practice, pp 803-861.
    • (1995) Burger's Medicinal Chemistry and Drug Discovery , vol.1 , pp. 803-861
    • Goodman, M.1    Ro, S.2
  • 19
    • 0025336463 scopus 로고
    • Emerging Approaches in the Molecular Design of Receptor-Selective Peptide Ligands - Conformational, Topographical and Dynamic Considerations
    • Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Emerging Approaches In The Molecular Design of Receptor-Selective Peptide Ligands - Conformational, Topographical And Dynamic Considerations. Biochem. J. 1990, 268, 249-262.
    • (1990) Biochem. J. , vol.268 , pp. 249-262
    • Hruby, V.J.1    Al-Obeidi, F.2    Kazmierski, W.3
  • 20
    • 0027626855 scopus 로고
    • Conformational and Topographical Considerations in the Design of Biologically Active Peptides
    • Hruby, V. J. Conformational and Topographical Considerations in the Design of Biologically Active Peptides. Biopolymers 1993, 33, 1073-1082.
    • (1993) Biopolymers , vol.33 , pp. 1073-1082
    • Hruby, V.J.1
  • 23
    • 0026647625 scopus 로고
    • Ring Substituted and Other Conformationally Constrained Tyrosine Analogues of [D-Pen2,D-Pen5]enkephalin with δ Opiod Receptor Selectivity
    • Toth, G.; Russell, K. C.; Landis, G.; Kramer, T. H.; Fang, L.; Knapp, R.; Davis, P.; Burks, T. F.; Yamamura, H. I.; Hruby, V. J. Ring Substituted and Other Conformationally Constrained Tyrosine Analogues of [D-Pen2,D-Pen5]enkephalin with δ Opiod Receptor Selectivity. J. Med. Chem. 1992, 35, 2384-2391.
    • (1992) J. Med. Chem. , vol.35 , pp. 2384-2391
    • Toth, G.1    Russell, K.C.2    Landis, G.3    Kramer, T.H.4    Fang, L.5    Knapp, R.6    Davis, P.7    Burks, T.F.8    Yamamura, H.I.9    Hruby, V.J.10
  • 27
    • 0029993270 scopus 로고    scopus 로고
    • Topographical Amino Acid Substitution in Position 10 of Glucagon Leads to Antagonists/Partial Agonists with Greater Binding Differences
    • Azizeh, B. Y.; Shenderovich, M. D.; Trivedi, D.; Li, G.; Sturm, N. S.; Hruby, V. J. Topographical Amino Acid Substitution in Position 10 of Glucagon Leads to Antagonists/Partial Agonists with Greater Binding Differences. J. Med. Chem. 1996, 39, 2449-2455.
    • (1996) J. Med. Chem. , vol.39 , pp. 2449-2455
    • Azizeh, B.Y.1    Shenderovich, M.D.2    Trivedi, D.3    Li, G.4    Sturm, N.S.5    Hruby, V.J.6
  • 29
    • 0001534216 scopus 로고
    • Conformational Analysis of Four β-Methylphenylalanine Stereoisomers in a Bioactive Peptide by z-Filtered Relay NMR Spectroscopy
    • Köver, K. E.; Jiao, D.; Fang, S.; Hruby, V. J. Conformational Analysis of Four β-Methylphenylalanine Stereoisomers in a Bioactive Peptide by z-Filtered Relay NMR Spectroscopy. Magn. Reson. Chem. 1993, 31, 1072-1076.
    • (1993) Magn. Reson. Chem. , vol.31 , pp. 1072-1076
    • Köver, K.E.1    Jiao, D.2    Fang, S.3    Hruby, V.J.4
  • 30
    • 0027085885 scopus 로고
    • Main Chain and Side Chain Chiral Methylated Somatostatin Analogs: Syntheses and Conformation Analyses
    • Huang, Z.; He, Y.; Raynor, K.; Tallent, M.; Reisine, T.; Goodman, M. Main Chain and Side Chain Chiral Methylated Somatostatin Analogs: Syntheses and Conformation Analyses. J. Am. Chem. Soc. 1992, 114, 9390-9401.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9390-9401
    • Huang, Z.1    He, Y.2    Raynor, K.3    Tallent, M.4    Reisine, T.5    Goodman, M.6
  • 31
    • 0026480590 scopus 로고
    • Constrained Phenylalanine Analogues Preferred Conformation of the 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid (Tic) Residue
    • Valle, G.; Kazmierski, W. M.; Crisma, M.; Bonora, G. M.; Toniolo, C.; Hruby, V. J. Constrained Phenylalanine Analogues Preferred Conformation of the 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid (Tic) Residue. Int. J. Pept. Protein Res. 1992, 40, 222-232.
    • (1992) Int. J. Pept. Protein Res. , vol.40 , pp. 222-232
    • Valle, G.1    Kazmierski, W.M.2    Crisma, M.3    Bonora, G.M.4    Toniolo, C.5    Hruby, V.J.6
  • 32
    • 84924830720 scopus 로고
    • In Vitro Bioassay for the Melanocyte Stimulating Hormone
    • Shizume, K.; Lerner, A. B.; Fitzpatrick, T. B. In Vitro Bioassay for the Melanocyte Stimulating Hormone. Endocrinology 1954, 54, 533-560.
    • (1954) Endocrinology , vol.54 , pp. 533-560
    • Shizume, K.1    Lerner, A.B.2    Fitzpatrick, T.B.3
  • 33
    • 0014788807 scopus 로고
    • Evidence for Separate Receptors for Melanophore Stimulating Hormone and Catecholamine Regulation of Cyclic AMP in the Control of Melanophore Responses
    • Goldman, J. M.; Hadley, M. E. Evidence for Separate Receptors for Melanophore Stimulating Hormone and Catecholamine Regulation of Cyclic AMP in the Control of Melanophore Responses. Br. J. Pharmacol. 1970, 39, 160-166.
    • (1970) Br. J. Pharmacol. , vol.39 , pp. 160-166
    • Goldman, J.M.1    Hadley, M.E.2
  • 34
    • 84909526988 scopus 로고
    • Receptor-Specific Calcium Requirement for Melanophore-Stimulating Hormone
    • Riley, V., Eds.; S. Karger: Basel
    • Vesely, D. L.; Hadley, M. E. Receptor-Specific Calcium Requirement for Melanophore-Stimulating Hormone. In Pigment Cell: Unique Properties of Melanocytes; Riley, V., Eds.; S. Karger: Basel, 1976; Vol. 3, 265-274.
    • (1976) Pigment Cell: Unique Properties of Melanocytes , vol.3 , pp. 265-274
    • Vesely, D.L.1    Hadley, M.E.2
  • 35
    • 34249762127 scopus 로고
    • Removal of the N-Indole-(Mesitylenesulfonyl) Protecting Group Using HF Cleavage Conditions
    • Haskell-Luevano, C.; Boteju, L. W.; Hruby, V. J. Removal of the N-Indole-(Mesitylenesulfonyl) Protecting Group Using HF Cleavage Conditions. Lett. Pept. Sci. 1995, 1, 163-170.
    • (1995) Lett. Pept. Sci. , vol.1 , pp. 163-170
    • Haskell-Luevano, C.1    Boteju, L.W.2    Hruby, V.J.3
  • 36
    • 0027958406 scopus 로고
    • Asymmetric Synthesis of Unusual Amino Acids: Synthesis of Optically Pure Isomers of N-Indole-(2-mesitylenesulfonyl)-β-methyltrypotphan
    • Boteju, L. W.; Wegner, K.; Qian, X.; Hruby, V. J. Asymmetric Synthesis of Unusual Amino Acids: Synthesis of Optically Pure Isomers of N-Indole-(2-mesitylenesulfonyl)-β-methyltrypotphan. Tetrahedron 1994, 50, 2391-2404.
    • (1994) Tetrahedron , vol.50 , pp. 2391-2404
    • Boteju, L.W.1    Wegner, K.2    Qian, X.3    Hruby, V.J.4
  • 37
    • 0029740203 scopus 로고    scopus 로고
    • Probing the Stereochemical Requirement for Receptor Recognition at δ Opiod Agonists Through Topographical Modifications at Posisiton 1
    • Qian, X.; Shenderovich, M. D.; Köver, K. E.; Davis, P.; Horwath, R.; Zalseska, T.; Yamamura, H. I.; Porreca, F.; Hruby, V. J. Probing the Stereochemical Requirement for Receptor Recognition at δ Opiod Agonists Through Topographical Modifications at Posisiton 1. J. Am. Chem. Soc. 1996, 118, 7280-7290.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7280-7290
    • Qian, X.1    Shenderovich, M.D.2    Köver, K.E.3    Davis, P.4    Horwath, R.5    Zalseska, T.6    Yamamura, H.I.7    Porreca, F.8    Hruby, V.J.9
  • 39
    • 0020544444 scopus 로고
    • Differentiation of the Structural Features of Melanotropins Important for Biological Potency and Prolonged Activity in Vitro
    • Wilkes, B. C.; Sawyer, T. K.; Hruby, V. J.; Hadley, M. E. Differentiation of the Structural Features of Melanotropins Important for Biological Potency and Prolonged Activity in Vitro. Int. J. Pept. Protein Res. 1983, 22, 313-324.
    • (1983) Int. J. Pept. Protein Res. , vol.22 , pp. 313-324
    • Wilkes, B.C.1    Sawyer, T.K.2    Hruby, V.J.3    Hadley, M.E.4
  • 41
    • 0029863304 scopus 로고    scopus 로고
    • Binding of Melanotropic Hormones to the Melanocortin Receptor MC1R on Human Melanocytes Stimulates Proliferation and Melanogenesis
    • Suzuki, I.; Cone, R. D.; Im, S.; Nordlund, J.; Abdel-Malek, Z. A. Binding of Melanotropic Hormones to the Melanocortin Receptor MC1R on Human Melanocytes Stimulates Proliferation and Melanogenesis. Endocrinology 1996, 137, 1627-1633.
    • (1996) Endocrinology , vol.137 , pp. 1627-1633
    • Suzuki, I.1    Cone, R.D.2    Im, S.3    Nordlund, J.4    Abdel-Malek, Z.A.5
  • 42
    • 0028080970 scopus 로고
    • Binding and cAMP Studies of Melanotropin Peptides with the Cloned Human Peripheral Melanocortin Receptor, hMC1R
    • Haskell-Luevano, C.; Miwa, H.; Dickinson, C.; Hruby, V. J.; Yamada, T.; Gantz, I. Binding and cAMP Studies of Melanotropin Peptides with the Cloned Human Peripheral Melanocortin Receptor, hMC1R. Biochem. Biophys. Res. Commun. 1994, 204, 1137-1142.
    • (1994) Biochem. Biophys. Res. Commun. , vol.204 , pp. 1137-1142
    • Haskell-Luevano, C.1    Miwa, H.2    Dickinson, C.3    Hruby, V.J.4    Yamada, T.5    Gantz, I.6
  • 43
    • 0030069715 scopus 로고    scopus 로고
    • Characterizations of the Unusual Dissociation Properties of Melanotropin Peptides from the Melanocortin Receptor, hMC1R
    • Haskell-Luevano, C.; Miwa, H.; Dickinson, C.; Hadley, M. E.; Hruby, V. J.; Yamada, T.; Gantz, I. Characterizations of the Unusual Dissociation Properties of Melanotropin Peptides From the Melanocortin Receptor, hMC1R. J. Med. Chem. 1996, 39, 432-435.
    • (1996) J. Med. Chem. , vol.39 , pp. 432-435
    • Haskell-Luevano, C.1    Miwa, H.2    Dickinson, C.3    Hadley, M.E.4    Hruby, V.J.5    Yamada, T.6    Gantz, I.7
  • 44
    • 0014772602 scopus 로고
    • Color Test for Detection of Free Terminal Amino Groups in the Solid- Phase Synthesis of Peptides
    • Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color Test for Detection of Free Terminal Amino Groups in the Solid-Phase Synthesis of Peptides. Anal. Biochem. 1970, 34, 595-598.
    • (1970) Anal. Biochem. , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3    Cook, P.I.4
  • 45
    • 0002071468 scopus 로고
    • On the Movement of Pigment Granules in Frog Melanocytes
    • Wright, R. M.; Lerner, A. B. On the Movement of Pigment Granules in Frog Melanocytes. Endocrinology 1960, 66, 599-609.
    • (1960) Endocrinology , vol.66 , pp. 599-609
    • Wright, R.M.1    Lerner, A.B.2


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