Opioid diketopiperazines: Refinement of the δ opioid antagonist pharmacophore

Biological Chemistry

Volumn 378, Issue 2, 1997, Pages 107-114

  Bryant, Sharon D ^a   Balboni, Gianfranco ^b   Guerrini, Remo ^b   Salvadori, Severo ^b   Tomatis, Roberto ^b   Lazarus, Lawrence H ^a  

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

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

Antagonist; Diketopiperazine; Monte Carlo; Opioid peptide; Pharmacophore

Indexed keywords

DELTA OPIATE RECEPTOR ANTAGONIST; NALTRINDOLE; OPIATE PEPTIDE; PIPERAZINEDIONE;

ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR MODEL; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RECEPTOR AFFINITY; RECEPTOR BINDING; X RAY CRYSTALLOGRAPHY;

EID: 0030897933     PISSN: 14316730     EISSN: None     Source Type: Journal    
DOI: 10.1515/bchm.1997.378.2.107     Document Type: Article

References (48)

1. Abdelhamid, E.E., Sultana, M., Portoghese, P.S., and Takemori, A.E. (1991). Selective blockage of delta opioid receptors prevents the development of morphine tolerance and dependence in mice. J. Pharmacol. Exp. Therap. 258, 299-303.
2. Amodeo, P., Balboni, G., Crescenzi, O., Guerrini, R., Picone, D., Salvadori, S., Tancredi, T., and Temussi, P.A. (1995). Conformational analysis of potent and very selective δ opioid dipeptide antagonists. FEBS Lett. 377, 363-367.
3. Attila M., Salvadori, S., Balboni, G., Bryant, S.D., and Lazarus, L.H. (1993). Synthesis and receptor binding analysis of dermorphin hepta-, hexa-, and pentapeptide analogues. Int. J. Peptide Protein Res. 42, 550-559.
4. Balboni, G., Guerrini, R., Salvadori, S., Tomatis, R., Bryant, S.D., Bianchi, C., Attila, M., and Lazarus, L.H. (1997). Opioid diketopiperazines: Synthesis and activity of a prototypic class of opioid antagonists. Biol. Chem. 378, 19-29.
5. Banks, W.A., Kastan, A.J., Akerstromy, and Jaspan, J.B. (1993). Radioactive iodinated cyclo(His-Pro) crosses the blood brain barrier and reverses ethanol-induced narcosis. Amer. J. Physiol. 264, E723-E729.
6. Befort, K., Tabbara, L., Kling, D., Maigret, B., and Kieffer, B. (1996). Role of aromatic transmembrane residues of the δ-opioid receptor in ligand recognition. J. Biol. Chem. 271, 10161-10168.
7. Benedetti, E., Corradini, P., and Pedone, C. (1969a). Crystal and molecular structure of L-cis-3,6-dimethyl-2,5-piperazinedione (L-alanyl-L-alanyl-2,5-diketopiperazine). Biopolymers 7, 751-764.
8. Benedetti, E., Corradini, P., and Pedone, C. (1969b). The crystal and molecular structure of trans-3,6-dimethyl-2,5-piperazinedione (L-alanyl-L-alanyl-2,5-diketopiperazine). J. Phys. Chem. 73, 2891-2895.
9. Breveglieri, A., Guerrini, R., Salvadori, S., Bianchi, C., Bryant, S.D., Attila, M., and Lazarus, L.H. (1996). Design and synthesis of 1-aminocycloalkane-1-carboxylic acid-substituted deltorphin analogues: unique δ and μ opioid activity in modified peptides. J. Med. Chem. 39, 773-780.
10. Bryant, S.D., Attila, M., Salvadori, S., Guerrini, R., and Lazarus, L.H. (1994). Molecular dynamics conformations of deltorphin analogues advocate δ opioid binding site models. Peptide Res. 7, 175-184.
11. Capasso, A., Guerrini, R., Balboni, G., Sorrentino, L., Temussi, P.A., Lazarus, L.H., Bryant, S.D., and Salvadori, S. (1996). Dmt-Tic-OH, a highly selective and potent δ opioidmimetic receptor antagonist after systemic administration in the mouse. Life Sci. 59, PL93-PL98.
12. Caroleo, M.C., Arbitrio, M., Melchiorri, D., and Nisticò, G. (1994). A reappraisal of the role of the various opioid receptor subtypes in cell-mediated immunity. Neuroimmunodulation 1, 141-147.
13. Carpenter, K.A., Schiller, P.W., Schmidt, R., and Wilkes, B.C. (1996). Distinct conformational preferences of three cyclic β-casomorphin-5 analogs determined using NMR spectroscopy and theoretical analysis. Int. J. Peptide Prot. Res. 48, 102-111.
14. Chao, T., Perez, J.J., and Loew, G.H. (1996). Characterization of the bioactive form of linear peptide antagonists at the δ-opioid receptor. Biopolymers. 38, 759-768.
15. Ciajolo, M.R., Balboni, G., Picone, D., Salvadori, S., Tancredi, T., Temussi, P.A., and Tuzi, A. (1995). Solution and solid-state structure of the diketopiperazine of tyrosyl-tetrahydroisoquinoline-3-carboxylic acid. Int. J. Pept. Prot. Res. 46, 134-138.
16. Degeilh, R., and Marsh, R.E. (1959). A refinement of the crystal structure of diketopiperazine (2,5-piperazinedione). Acta Cryst. 12, 1007-1014.
17. Dougherty, D.A. (1996). Cation-π interactions in chemistry and biology: a new view of benzene, Phe, Tyr, and Trp. Science. 271, 163-168.
18. Flippen-Anderson, J., George, C., Deschamps, J., Anantha Reddy, P., Lewin, A.H., and Brine, G.A. (1994a). X-ray structures of the δ opioid antagonist TIPP and a protected derivative of the δ opioid antagonist ICI 174,864. Lett. Peptide Science. 1, 107-115.
19. 5]enkephalin, a highly potent, δ opioid receptor-selective compound: comparisons with proposed solution conformations. J. Am. Chem. Soc. 116, 7523-7531.
20. Froelich, J.C., and Li, T-K. (1993). Opioid peptides. In: Recent Developments in Alcholism, Volume II: Ten Years of Progress, M. Galanter, ed. (New York: Plenum Press), pp. 187-205.
21. Gillberg, C. (1995). Endogenous opioids and opiate antagonists in autism: brief review of emperical findings and implications for clinicians. Dev. Med. Child Neurol. 37, 239-245.
22. Grebow, P.E., and Hooker, T.M., Jr. (1974). Conformation of histidine model peptides. I. Conformational energy calculations for L-alanyl-L-histidine diketopiperazine. Biopolymers 13, 2349-2366.
23. 1]deltorphin B. Eur. J. Pharm. 302, 37-42.
24. Hammond, D.L. (1993). Pharmacological mechanisms of pain modulation. An update of & opioid receptors. In: Current and Emerging Issues in Cancer Pain: Research and Practice, C.R. Chapman and K.M. Foley, eds (New York: Raven Press), pp. 175-183.
25. Karle, I.L., Ottenhym, H.C.J., and Witkop, B. (1974). On the conformation and synthesis of diketopiperazines. 3,4-Dehydroproline anhydride. J. Amer. Chem. Soc. 96, 539-543.
26. Kong, H., Raynor, K., Yasuda, K., Moe, S.T., Portoghese, P.S., Bell, G.I., and Reisine, T. (1993). A single reside, aspartic acid 95, in the δ opioid receptor specifies selective high affinity agonist binding. J. Biol. Chem. 268, 23055-23058.
27. Lin, C.-F., and Webb, L.E. (1973). Crystal structures and conformation of the cyclic dipeptides cyclo-(glycyl-L-tyrosyl) and cyclo-(L-seryl-L-tyrosyl) monohydrate. J. Amer. Chem. Soc. 95, 6803-6811.
28. Lomize, A.L., Pogozheva, I.D., and Mosberg, H.I. (1996). Development of a model for the δ-opioid receptor pharmacophore: 3. Comparison of the cyclic tetrapeptide Tyr-C[D-CysPhe-D-Pen]OH with other conformationally constrained δ-receptor selective ligands. Biopolymers 38, 221-234.
29. Metzger, T.G., and Ferguson, D.M. (1995). On the role of extracellular loops of opioid receptors in conferring ligand selectivity. FEBS Lett. 375, 1-4.
30. Mohamadi, F., Richards, N.G.J., Guida, W.C., Liskamp, R., Lipton, M., Caufield, C., Chang, G., Hendrickson, T., and Still, W.C. (1990). MacroModel: An integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 11, 440-467.
31. Mosberg, H.I., Hurst, R., Hruby, V.J., Gee, K., Yamamura, H.I., Galligan, J.J., and Burks, T.F. (1983). Bis-penicillamine enkephalins possess highly improved specificity toward δ opioid receptors. Proc. Natl. Acad. Sci. USA 80, 5871-5874.
32. 1 replacements in the cyclic δ receptor selective tetrapeptide Tyr-C[D-Cys-Phe-D-Pen]OH (JOM-13). J. Med. Chem. 37, 4371-4383.
33. 3 replacements in the cyclic δ receptor selective tetrapeptide Tyr-C[D-Cys-Phe-D-Pen]OH (JOM-13). J. Med. Chem. 37, 4384-4391.
34. Mosberg, H.I., Dua, R.K., Pogozheva, I.D., and Lomize, A.L. (1996). Development of a model for the δ-opioid receptor pharmacophore: 4. Residue 3 dehydrophenylalanine analogues of Tyr-C[D-Cys-Phe-D-Pen]OH (JOM-13) confirm required gauche orientation of aromatic side chain. Biopolymers 39, 287-296.
35. Portenoy, R.K. (1996). Opioid therapy for chronic nonmalignant pain: a review of the critical issues. J. Pain Sympt. Manag. 11, 203-217.
36. Portoghese, P.S., Nagase, H., MaloneyHuss, K.E., Lin, C.-E., and Takemori, A.E. (1991). Role of spacer and address components in peptidomimetic δ opioid receptor antagonists related to naltrindole. J. Med. Chem. 34, 1715-1720.
37. Ramachandran, G.N., and Sasisekharan, V. (1968). Conformation of polypeptides and proteins. Adv. Prot. Chem. 23, 283-437.
38. Salvadori, S., Attila, M., Balboni, G., Bianchi, C., Bryant, S.D., Crescenzi, O., Guerrini, R., Picone, D., Tancredi, T., Temussi, P.A., and Lazarus, L.H. (1995). δ Opioidmimetic antagonists: prototypes for designing a new generation of ultraselective opioid peptides. Mol. Med. 1, 678-689.
39. Schiller, P.W., Nguyen, T.M.-D., Weltrowska, G., Wilkes, B.C., Marsden, B.J., Lemieux, C., and Chung, N.N. (1992). 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. USA 89, 11871-11875.
40. Schmidt, R., Vogel, D., Mrestani-Klaus, C., Brandt, W., Neubert, K., Chung, N.N., Lemieux, C., and Schiller, P.W. (1994). Cyclic β-casomorphin analogues with mixed μ agonist/δ antagonist properties: synthesis, pharmacological characterization, and conformational aspects. J. Med. Chem. 37, 1136-1144.
41. Takemori, A.E., Sultana, M., Nagase, H., and Portoghese, P.S. (1992). Agonist and antagonist activities of ligands derived from naltrexone and oxymorphone. Life Sci. 50, 1491-1495.
42. Tancredi, T., Salvadori, S., Amodeo, P., Picone, D., Lazarus, L.H., Bryant, S.D., Guerrini, R., Marzola, G., and Temussi, P.A. (1994). Conversion of enkephalin and dermorphin into δ-selective opioid antagonists by single-residue substitution. Eur. J. Biochem. 223, 241-247.
43. Temussi, P.A., Salvadori, S., Amodeo, P., Bianchi, C., Guerrini, R., Tomatis, R., Lazarus, L.H., Picone, D., and Tancredi, T. (1994). Selective opioid dipeptides. Biochem. Biophys. Res. Commun. 198, 933-939.
44. Terenius, L. (1996). Alcohol addiction (alcoholism) and the opioid system. Alcohol 13, 31-34.
45. Valiquette, M., Vu, H.K., Yue, S.Y., Wahlestedt, C., and Walker, P. (1996). Involvement of Trp-284, Val-296, and Val-297 of the human δ-opioid receptor in binding of δ-selective ligands. J. Biol. Chem. 271, 18789-18796.
46. Wilkes, B.C., and Schiller, P.W. (1995). Comparative analysis of various proposed models of the receptor bound conformation of H-Tyr-Tic-Phe-OH related δ-opioid antagonists. Biopolymers 37, 391-400.
47. Wilkes, B.C., Schmidt, R., and Schiller, P.W. (1996). Theoretical analysis of conformationally restricted cyclic β-casomorphin analogs. In: Peptides: Chemistry, Structure and Biology. P.T.P. Kaumaya and R.S. Hodges, eds. (West Midlands, UK: Mayflower Scientific), pp. 505-506.
48. Ziegler, D.K. (1994). Opiate and opioid use in patients with refractory headache. Cephalagia 14, 5-10.