Helix-inducing α-aminoisobutyric acid in opioid mimetic deltorphin C analogues

Journal of Medicinal Chemistry

Volumn 40, Issue 16, 1997, Pages 2579-2587

  Bryant, Sharon D ^a   Guerrini, Remo ^b   Salvadori, Severo ^b   Bianchi, Clementina ^b   Tomatis, Roberto ^b   Attila, Martti ^c   Lazarus, Lawrence H ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^b UNIVERSITY OF FERRARA   (Italy)

^c UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 2 METHYLPROPIONIC ACID; DELTORPHIN; PHENYLALANINE; SIGMA OPIATE RECEPTOR;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; BINDING AFFINITY; CHIRALITY; LIGAND BINDING; PROTEIN CONFORMATION; PROTEIN SECONDARY STRUCTURE; RECEPTOR AFFINITY; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANALGESICS, OPIOID; ANIMALS; BRAIN; GAMMA-AMINOBUTYRIC ACID; KINETICS; MICE; MODELS, CHEMICAL; MOLECULAR MIMICRY; MOLECULAR SEQUENCE DATA; OLIGOPEPTIDES; PROTEIN STRUCTURE, SECONDARY; RATS; SYNAPTOSOMES;

EID: 0030745579     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9700530     Document Type: Article

References (92)

1. 2,5]enkephalin, H-Tyr-[D-Pen-Gly-Phe-D-Pen]-OH; DSSP, dictionary of protein secondary structure; Ot-Bu, tert-butyl ester; Fmoc, 9-fluorenylmethyloxycarbonyl; GPI, guinea pig ileum; HOBt, 1-hydroxybenzotriazole; MD, molecular dynamics; Pen, β,β-dimethylcysteine; Tic, 1,2,3,4-tetrahydro-3-isoquinoline-3-carboxylic acid.
2. Toniolo, C.; Bonora, G. M.; Bavoso, A.; Benedetti, E.; di Blasio, B.; Pavone, V.; Pedone, C. Preferred Conformations of Peptides Containing α,α-Disubstituted α-Amino Acids. Biopolymers 1983, 22, 205-215.
3. Karle, I. L.; Balaram, P. Structural Characteristics of α-Helical Peptide Molecules Containing Aib Residues. Biochemistry 1990, 29, 6747-6756.
4. Marshall, G. R.; Hodgkin, E. E.; Langs, D. A.; Smith, G. D.; Zabrocki, J.; Leplawy, M. T. Factors Governing Helical Preference of Peptides Containing Multiple α,α-Dialkyl Amino Acids. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 487-491.
5. 10/α-Helical Transition Upon Sequence Permutation. Biopolymers 1991, 31, 1763-1774.
6. 10-Helices. Int. J. Pept. Protein Res. 1994, 44, 539-548.
7. 3c Homo-Oligopeptides. Biopolymers 1989, 28, 175-184.
8. (b) Karle, I. L. Flexibility in Peptide Molecules and Restraints Imposed by Hydrogen Bonds, the Aib Residue, and Core Inserts. Biopolymers 1996, 40, 157-180.
9. di Blasio, B.; Pavone, V.; Lombardi, A.; Pedone, C.; Benedetti, E. Noncoded Residues as Building Blocks in the Design of Specific Secondary Structures: Symmetrically Disubstituted Glycines and β-Alanine. Biopolymers 1993, 33, 1037-1049.
10. Cotton, R.; Giles, M. G.; Miller, L.; Shaw, J. S.; Timms, D. ICI 174864: A Highly Selective Antagonist for the Opioid δ-Receptor. Eur. J. Pharmacol. 1984, 97, 331-332.
11. 5]-Enkephalin (DPDPE). Int. J. Pept. Protein Res. 1990, 36, 139-146.
12. (a) Sudha, T. H.; Balaram, P. Conformational Flexibility in Enkephalins: Solvent Dependent Transitions in Peptides with Gly-Gly Segments Detected by Circular Dichroism. FEBS Lett. 1981, 134, 32-36.
13. 2-DMSO. A Fragment of a Biologically Active Enkephalin Analogue. J. Chem. Soc., Perkin Trans. 1983, I, 417-421.
14. (c) Sudha, T. S.; Balaram, P. Stabilization of β-Turn Conformations in Enkephalins. Int. J. Pept. Protein Res. 1983, 21, 381-383.
15. (d) Kimura, S.; Sasaki-Yagi, Y.; Imanishi, Y. Receptor Selectivity of Enkephalin Analogs Carrying Artificial Address Peptides. Int. J. Pept. Protein Res. 1990, 35, 550-556.
16. Olsen, G. A.; Olsen, R. D.; Kastin, A. J. Endogenous Opiates. Peptides 1996, 17, 1421-1466.
17. (a) Arakawa, K.; Akami, T.; Okamoto, M.; Akioka, K.; Nakai, I.; Oka, T.; Nagase, H. Immunosuppression by Delta Opioid Receptor Antagonist. Transplant. Proc. 1993, 25, 738-740.
18. 2]-Enkephalin). J. Thorac. Cadiovasc. Surg. 1994, 107, 964-967.
19. (c) Caroleo, M. C.; Arbitrio, M.; Melchiorri, D.; Nisticb, G. A Reappraisal of the Role of the Various Opioid Subtypes in Cell-Mediated Immunity. Neuroimmunodulation 1994, 1, 141 -147.
20. (a) Hammond, D. L. Pharmacological Mechanisms of Pain Modulation. An Update on δ Receptors. In Current and Emerging Issues in Cancer Pain: Research and Practice; Chapman, C. R., Foley, K. M., Eds.; Raven Press: New York, 1993; pp 175-183.
21. (b) Ziegler, D. K. Opiate and Opioid Use in Patients with Refractory Headache. Cephalagia 1995, 14, 5-10.
22. (c) Portenoy, R. K. Opioid Therapy for Chronic Nonmalignant Pain: A Review of the Critical Issues. J. Pain Sympt. Manag. 1996, 11, 203-217.
23. Abdelhamid, E. E.; Sultana, M.; Portoghese, P. S.; Takemori, A. E. Selective Blockage of Delta Opioid Receptors Prevents the Development of Morphine Tolerance and Dependence in Mice. J. Pharmacol. Exp. Ther. 1991, 258, 299-303.
24. (a) Froelich, J. C.; Li, T.-K. Opioid Peptides. In Recent Developments in Alcoholism, Volume II: Ten Years of Progress; Galanter, M., Ed.; Plenum Press: New York, 1995; pp 187-205.
25. (b) Terenius, L. Alcohol Addiction (Alcoholism) and the Opioid System. Alcohol 1996, 13, 31-34.
26. Gillberg, C. Endogenous Opioids and Opiate Antagonists in Autism: A Brief Review of Empirical Findings and Implications for Clinicians. Dev. Med. Child Neurol. 1995, 37, 239-245.
27. (a) Erspamer, V. The Opioid Peptides of the Amphibian Skin. Int. J. Dev. Neurosci. 1992, 10, 3-30.
28. (b) Lazarus, L. H.; Attila, M. The Toad, Ugly and Venomous, Wears Yet a Precious Jewel in His Skin. Prog. Neurobiol. 1993, 41, 473-507.
29. Hruby, V. J.; Gehrig, C. A. Recent Developments in the Design of Receptor Specific Opioid Peptides. Med. Res. Rev. 1989, 9, 343-401.
30. (a) Lazarus, L. H.; Salvadori, S.; Tomatis, R.; Wilson, W. E. Opioid Receptor Selectivity Reversal in Deltorphin Tetrapeptide Analogues. Biochem. Biophys. Res. Commun. 1991, 178, 110-115.
31. (b) Charpentier, S.; Sagan, S.; Delfour, A.; Nicolas, P. Dermenkephalin and Deltorphin I Reveal Similarities within Ligand-Binding Domains of μ- and δ-Opioid Receptors and an Additional Address Subsite on the δ-Receptor. Biochem. Biophys. Res. Commun. 1991, 179, 1161-1168.
32. Lazarus, L. H.; de Castiglione, R.; Guglietta, A.; Wilson, W. E. Highly Selective δ-Opioid Receptor Peptide from Preprodermorphin Gene Sequence. J. Biol. Chem. 1989, 264, 3047-3050.
33. Mor, A.; Delfour, A.; Sagan, S.; Amiche, M.; Pradelles, P.; Rossier, J.; Nicolas, P. Isolation of Dermenkephalin from Amphibian Skin, a High-Affinity δ-Selective Opioid Heptapeptide Containing a D-Amino Acid Residue. FEBS Lett. 1989, 255, 269-274.
34. Kreil, G.; Barra, D.; Simmaco, M.; Erspamer, V.; Falconieri Erspamer, G.; Negri, L.; Severini, C.; Corsi, R.; Melchiorri, P. Deltorphin, A Novel Amphibian Skin Peptide with High Selectivity and Affinity for d Opioid Receptors. Eur. J. Pharmacol. 1989, 162, 123-128.
35. Erspamer, V.; Melchiorri, P.; Faleonieri Erspamer, G.; Negri, L.; Corsi, R.; Severini, C.; Barra, D.; Simmaco, M.; Kreil, G. Deltorphins: A Family of Naturally Occurring Peptides with High Affinity and Selectivity for 2 Opioid Binding Sites. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 5188-5192.
36. 2]Deltorphin Precursors from Skin of Phyllomedusa Bicolor Also Contain Genetic Information for Three Dermorphin-Related Opioid Peptides. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 4836-4839.
37. Lazarus, L. H.; Salvadori, S.; Balboni, G.; Tomatis, R.; Wilson, W. E. Stereospecificity of Amino Acid Side Chains in Deltorphin Defines Binding to Opioid Receptors. J. Med. Chem. 1992, 35, 1222-1227.
38. Bryant, S. D.; Attila, M.; Salvadori, S.; Guerrini, R.; Lazarus, L. H. Molecular Dynamics Conformations of Deltorphin Analogues Advocated δ Opioid Binding Site Models. Peptide Res. 1994, 7, 175-184.
39. 3 Deltorphin Analogues: Enhanced Selectivity of Halogenated Derivatives for δ Opioid Receptor Sites. J. Med. Chem. 1992, 35, 4651-4657.
40. 2]Deltorphin I Analogs with Extraordinary Delta Receptor Selectivity. In New Leads in Opioid Research; van Ree, J. M., Mulder, A. H., Wiegant, V. M., van Wimersma Greidanus, T. B., Eds.; Excerpta Medica: Amsterdam, 1990; pp 288-290.
41. 3-Substituted Analogues of Deltorphin C. Spatial Conformation and Topography of the Aromatic Ring in Peptide Recognition by δ Opioid Receptors. J. Med. Chem. 1993, 36, 3748-3756.
42. 3 Residue in the δ-Selective Opioid Peptide Deltorphin I: Effects on Binding Affinity and Selectivity. Int. J. Pept. Protein Res. 1994, 44, 420-426.
43. 3 Replacement with Ring-Substituted and Heterocyclic Amino Acids. J. Med. Chem. 1995, 38, 1242-1246.
44. Breveglieri, A.; Guerrini, R.; Salvadori, S.; Bianchi, C.; Bryant, S. D.; Attila, M.; Lazarus, L. H. Design and Synthesis of 1-Aminocycloalkane-1-carboxylic Acid Substituted Deltorphin Analogues: Unique δ and μ Opioid Activity in Modified Peptides. J. Med. Chem. 1996, 39, 773-780.
45. Lazarus, L. H.; Bryant, S. D.; Salvadori, S.; Attila, M.; Jones, L. S. Opioid Infidelity: Novel Opioid Peptides with Dual High Affinity for δ- and μ-Receptors. Trends Neurosci. 1996, 19, 31-35.
46. Balboni, G.; Marastoni, M.; Picone, D.; Salvadori, S.; Tancredi, T.; Temussi, P. A.; Tomatis, R. New Features of the δ Opioid Receptor: Conformational Properties of Deltorphin I Analogues. Biochem. Biophys. Res. Commun. 1990, 169, 617-622.
47. Amodeo, P.; Motta, A.; Tancredi, T.; Salvadori, S.; Tomatis, R.; Picone, D.; Saviano, G.; Temussi, P. A. Solution Structure of Deltorphin I at 265 K: A Quantitative NMR Study. Peptide Res. 1992, 5, 48-55.
48. Bryant, S. D.; Salvadori, S.; Attila, M.; Lazarus, L. H. Topographical Conformations of the Deltorphins Predicate δ Opioid Receptor Affinity. J. Am. Chem. Soc. 1993, 115, 8503-8504.
49. (a) Temussi, P. A.; Picone, D.; Tancredi, T.; Tomatis, R.; Salvadori, S.; Marastoni, M.; Balboni, G. Conformational Properties of Deltorphin: New Features of the δ-Opioid Receptors. FEBS Lett. 1989, 247, 283-288.
50. (b) Tancredi, T.; Temussi, P. A.; Picone, D.; Amodeo, P.; Tomatis, R.; Salvadori, S.; Marastoni, M.; Santagada, V.; Balboni, G. New insights on μ/δ Selectivity of Opioid Peptides: Conformational Analysis of Deltorphin Analogues. Biopolymers 1991, 31, 751-760.
51. Duchnesne, D.; Naim, M.; Nicolas, P.; Baron, D. Folding Trends in a Flexible Peptide: Two Dimensional NMR* Study of Deltorphin-I, a δ Selective Opioid Heptapeptide. Biochem. Biophys. Res. Commun. 1993, 195, 630-636.
52. Balaji, V. N.; Ramnarayan, K.; Chan, M. F.; Rao, S. N. Conformational Studies on Model Peptides with 1-Aminocyclopropane-1-carboxylic Acid Residues. Peptide Res. 1994, 7, 60-71.
53. Kabsch, W.; Sander, C. Dictionary of Protein Secondary Structure: Pattern Recognition of Hydrogen-Bonded and Geometrical Features. Biopolymers 1983, 22, 2577-2637.
54. Schiller, P. W.; Nguyen, T. M.-D.; Chung, N. N.; Lemieux, C. Dermorphin Analogues Carrying an Increased Positive Net Charge in their "Message" Domain Display Extremely High μ Opioid Receptor Selectivity. J. Med. Chem. 1989, 32, 698-703.
55. Schiller, P. W.; Weltrowska, G.; Nguyen, T. M.-D.; Wilkes, B. C.; Chung, N. N.; Lemieux, C. Conformationally Restricted Deltorphin Analogues. J. Med. Chem. 1992, 35, 3956-3561.
56. 1 Analogues. Arch. Int. Pharmocodyn. 1995, 330, 361-369.
57. 2): A Potent and Fully Specific Agonist for the δ Opioid Receptor. Mol. Pharmacol. 1989, 35, 774-779.
58. (b) Sagan, S.; Amiche, M.; Delfour, A.; Camus, A.; Mor, A.; Nicolas, P. Differential Contribution of C-Terminal Regions of Dermorphin and Dermenkephalin to Opioid-Sites Selection and Binding Potency. Biochem. Biophys. Res. Commun. 1989, 163, 726-732.
59. (c) Melchiorri, P.; Negri, L.; Falconieri-Erspamer, G.; Severini, C.; Corsi, R.; Soaje, M.; Erspamer, V.; Barra, D. Structure-Activity Relationships of the δ-Opioid Selective Agonists, Deltorphins. Eur. J. Pharmacol. 1991, 195, 201-207.
60. 2-Substitution in Dermorphin, Deltorphin I and Dynorphin A Analogues: Effect on Opioid Receptor Binding and Opioid Activity In Vitro. Reg. Pept. 1994, 54, 259-260.
61. 4 in Deltorphin A for High δ Opioid Receptor Selectivity. Amino Acids 1994, 7, 291-304.
62. (a) Evans, C. J.; Keith, D. E., Jr.; Morrison, H.; Magendzo, K.; Edwards, R. H. Cloning of a Delta Opioid Receptor by Functional Expression. Science 1992, 258, 1952-1955.
63. (b) Kieffer, B. L.; Befort, K.; Gaveriaux-Ruff, C.; Hirth, C. G. The δ-Opioid Receptor: Isolation of a cDNA by Expression Cloning and Pharmacological Characterization. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 12048-12052.
64. (c) Chen, Y.; Mestek, A.; Liu, J.; Yu, L. Molecular Cloning and Functional Expression of Mu-Opioid Receptor from Rat Brain. Biochem. J. 1993, 95, 625-628.
65. (d) Fukuda, K.; Kato, S.; Mori, K.; Nishi, M.; Takashima, H. Primary Structures and Expression from cDNAs of Rat Opioid Receptor δ- and μ-Subtypes. FEBS Lett. 1993, 327, 311-314.
66. (e) Yasuda, K.; Raynor, K.; Kong, H.; Breder, C. D.; Takeda, J.; Resine, T.; Bell, G. I. Cloning and Functional Comparison of κ and δ Opioid Receptors from Mouse Brain. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6736-6740.
67. Lazarus, L. H.; Salvadori, S.; Santagada, V.; Tomatis, R.; Wilson, W. E. Function of Negative Charge in the "Address Domain" of Deltorphins. J. Med. Chem. 1991, 34, 1350-1359.
68. Sagan, S.; Charpentier, S.; Delfour, A.; Amiche, M.; Nicolas, P. The Aspartic Acid in Deltorphin I and Dermenkephalin Promotes Targeting to δ-Opioid Receptor Independently of Receptor Binding. Biochem. Biophys. Res. Commun. 1992, 187, 1203-1210.
69. (a) Schiller, P. W.; Nguyen, T. M.-D.; Weltrowska, G.; Wilkes, B. C.; Marsden, B. J.; Lemieux, C.; Chung, N. N. Differential Stereochemical Requirements of μ vs. δ Opioid Receptors for Ligand Binding and Signal Transduction: Development of a Class of Potent and Highly δ-Selective Peptide Antagonists. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 11871-11875.
70. (b) Schiller, P. W.; Weltroska, G.; Nguyen, T. M.-D.; Wilkes, B. C.; Chung, N. N.; Lemieux, C. TIPP [Ψ]: a Highly Potent and Stable Pseudopeptide δ Opioid Receptor Antagonist with Extraordinary δ Selectivity. J. Med. Chem. 1993, 36, 3182-3187.
71. (c) Mosberg, H. L; Omnass, J. R.; Sobczyk-Kojiro, K.; Dua, R.; Ho, J. C.; Ma, W.; Bush, R.; Mousigian, C.; Lomize, A. Pharmacophore Elements of the TIPP Class of Delta Opioid Receptor Antagonists. Lett. Pept. Sci. 1994, 1, 69-72.
72. Temussi, P. A.; Salvadori, S.; Amodeo, P.; Bianchi, C.; Guerrini, R.; Tomatis, R.; Lazarus, L. H.; Picone, D.; Tancredi, T. Selective Opioid Dipeptides. Biochem. Biophys. Res. Commun. 1994, 198, 933-939.
73. Salvadori, S.; Attila, M.; Balboni, G.; Bianchi, C.; Bryant, S. D.; Crescenzi, O.; Guerrini, R.; Picone, D.; Tancredi, T.; Temussi, P. A.; Lazarus, L. H. δ Opioidmimetic Antagonists: Prototypes for Designing a New Generation of Ultraselective Opioid Peptides. Mol. Med. 1995, 1, 678-689.
74. Vaughn, L. K.; Wire, W. S.; Davis, P.; Shimohigashi, Y.; Tóth, G.; Knapp, R. J.; Hruby, V. J.; Burks, T. F.; Yamamura, H. I. Differentiation Between Rat Brain and Mouse Vas Deferens δ Opioid Receptors. Eur. J. Pharmacol. 1990, 177, 99-101.
75. Marraud, M.; Aubry, A. Crystal Structures of Peptides and Modified Peptides. Biopolymers 1996, 40, 45-83.
76. Flippen-Anderson, J. L.; George, C.; Deschamps, J. R.; Reddy, P. A.; Lewin, A.; Brine, G. A. X-ray Structures of the δ Opioid Antagonist TIPP and a Protected Derivative of the δ Opioid Antagonist ICI 174,864. Lett. Pept. Sci. 1994, 1, 107-115.
77. Befort, K.; Tabbara, L.; Kling, D.; Maigret, B.; Kieffer, B. Role of Aromatic Transmembrane Residues of the δ-Opioid Receptor in Ligand Recognition. J. Biol. Chem. 1996, 271, 10161-10168.
78. Valiquette, M.; Vu, H. K.; Yue, S. Y.; Wahlestedt, C.; Walker, P. Involvement of Trp-284, Val-296, and Val-297 of the Human δ-Opioid Receptor in Binding of δ-Selective Ligands. J. Biol. Chem. 1996, 271, 18789-18796.
79. (a) Surratt, C. K.; Johnson, P. S.; Moriwaki, A.; Seidleck, B. K.; Blaschak, C. J.; Wang, J. B.; Uhl, G. R. μ Opiate Receptor. Charged Transmembrane Domain Amino Acids for Agonist Recognition and Intrinsic Activity. J. Biol. Chem. 1994, 269, 20548-20553.
80. (b) Kong, H.; Raynor, K.; Yasuda, K.; Moe, S. T.; Portoghese, P.; Bell, G. I.; Reisine, T. A Single Residue, Aspartic Acid 95, in the δ Opioid Receptor Specifies Selective High Affinity Agonist Binding. J. Biol. Chem. 1993, 268, 23055-23058.
81. Befort, K.; Tabbara, L.; Bausch, S.; Chavkin, C.; Evans, C.; Kieffer, B. The Conserved Aspartate Residue in the Third Putative Transmembrane Domain of the δ-Opioid Receptor is not the Anionic Counterpart for Cationic Opiate Binding but is a Constituent of the Receptor Binding Site. Mol. Pharmacol. 1996, 49, 216-223.
82. Schwyzer, R. ACTH: A Short Introductory Review. Ann. N. Y. Acad. Sci. 1977, 297, 3-26.
83. Schwyzer, R. Molecular Mechanism of Opioid Receptor Selection. Biochemistry 1986, 25, 6335-6342.
84. (a) Balboni, G.; Guerrini, R.; Salvadori, S.; Tomatis, R.; Bianchi, C.; Attila, M.; Bryant, S. D.; Lazarus, L. H. Opioid Diketopiperazines: Synthesis and Activity of a Prototypic Class of Unique Opioid Antagonists. Biol. Chem. 1997, 378, 19-22.
85. (b) Bryant, S. D.; Balboni, G.; Guerrini, R.; Salvadori, S.; Tomatis, R.; Lazarus, L. H. Opioid Diketopiperazines: Refinement of the δ Opioid Antagonist Pharmacophore. Biol. Chem. 1997, 378, 107-114.
86. Dougherty, D. A. Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp. Science 1996, 271, 163-168.
87. Schmitt, H.; Jung, G. Total Synthesis of the α-Helical Eicosapeptide Antibiotic Alamethicin. Liebigs Ann. Chem. 1985, 321-344.
88. Leplawy, M. T.; Jones, D. S.; Kenner, G. W.; Shepard, R. C. Synthesis of Peptides Derived From α-Methylalanine. Tetrahedron 1960, 11, 39-51.
89. Singh, U. C.; Weiner, D. K.; Caldwell, J. W.; Kollman, P. A. AMBER (version 3.1); Department of Pharmaceutical Chemistry, University of California: San Francisco, CA, 1988.
90. Chou, P. Y.; Fasman, G. β-Turn in Proteins. J. Mol. Biol. 1977, 115, 135-175.
91. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
92. Attila, M.; Salvadori, S.; Balboni, G.; Bryant, S. D.; Lazarus, L. H. Synthesis and Receptor Binding Analysis of Dermorphin Hepta-, Hexa- and Pentapeptide Analogues. Evidence for One- and Two-Site Binding Models for the μ-Opioid Receptors. Int. J. Pept. Protein Res. 1993, 42, 550-559.