Opioid peptides: Simultaneous δ agonism and μ antagonism in somatostatin analogues

Peptides

Volumn 18, Issue 1, 1997, Pages 93-100

  Bonner, G Gregg ^a   Davis, Peg ^b   Stropova, Dagmar ^b   Ferguson, Ron ^a   Yamamura, Henry I ^b   Porreca, Frank ^b   Hruby, Victor J ^a,c  

^a UNIVERSITY OF ARIZONA   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

^c University of Arizona   (United States)

Author keywords

MePhe; agonist; analgesia; antagonist; antinocic eption; convulsions; CTAP; GPI; MVD; opioid; somatostatin

Indexed keywords

DELTA OPIATE RECEPTOR AGONIST; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; ENKEPHALIN[2,5 DEXTRO PENICILLAMINE]; MU OPIATE RECEPTOR ANTAGONIST; OPIATE PEPTIDE; SOMATOSTATIN DERIVATIVE;

AMINO TERMINAL SEQUENCE; ANALGESIA; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINOCICEPTION; ARTICLE; BIOASSAY; BRAIN HOMOGENATE; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; GUINEA PIG; ILEUM; INTRACEREBROVENTRICULAR DRUG ADMINISTRATION; MALE; MOUSE; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; RAT; SIGNAL TRANSDUCTION; SMOOTH MUSCLE CONTRACTION; TAIL FLICK TEST; VAS DEFERENS;

ANALGESICS; ANIMALS; BINDING, COMPETITIVE; BRAIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; ENKEPHALIN, ALA(2)-MEPHE(4)-GLY(5)-; ENKEPHALIN, D-PENICILLAMINE (2,5)-; ENKEPHALINS; GUINEA PIGS; ILEUM; MALE; MICE; MOLECULAR STRUCTURE; OPIOID PEPTIDES; PEPTIDES; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, MU; SOMATOSTATIN; VAS DEFERENS;

EID: 0030890110     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0196-9781(96)00242-2     Document Type: Article

References (53)

1. Al Obeidi F., Hadley M. E., Pettitt B. M., Hruby V. J. Design of a new class of superpotent cyclic melanotropins based on quenched dynamics simulations. J. Am. Chem. Soc. 111:1989;3413-3416.
2. Comer S. D., Hoenicke E. M., Sable A. I., McNutt R. W., Chang K.-J., DeCosta B. R., Mosberg H. I., Woods J. H. Convulsive effects of systemic administration of the delta opioid agonist BW373U86 in mice. J. Pharmacol. Exp. Ther. 267:1993;888-895.
3. Damore A., Lorenzini P., Massotti M. Antinociceptive action of opiates and opioid peptides after unilateral microinjection into the area tempestas in rats. J. Pharmacol. Exp. Ther. 259:1991;1308-1315.
4. De Lean A., Munson P. J., Rodbard D. Simultaneous analysis of families of sigmoidal curves: Applications to bioassay, radioligand assay, and physiological dose-response curves. Am. J. Physiol. 235:1978;E97-E102.
5. De Sarro G., Ascioti C., Donato Di Paola E., Vidal M. J., De Sarro A. Effects of antiepeleptic drugs, calcium channel blockers and other compounds on seizures induced by activation of voltage-dependent L-calcium channel in DBA-2 mice. Gen. Pharmacol. 23:1992;1205-1216.
6. Dharanipragada R., Nicolás E., Tóth G., Hruby V. J. Asymmetric synthesis of unusual amino acids: Synthesis of optically pure isomers of beta-methylphenylalanine. Tetrahedron Lett. 30:1989;6841-6844.
7. Dharanipragada R., Nicolás E., Tóth G., Hruby V. J. Asymmetric synthesis of unusual amino acids: synthesis of optically pure isomers of β -methyltyrosine. Tetrahedron Lett. 30:1989;6845-6848.
8. Gehrig C. A., Tóth G., Prakash O., Hruby V. J. β -MePhe-containing enkephalin analogues with high selectivity for the delta opioid receptor. Shimonishi Y. Peptide Chemistry 1990. 1991;261-264 Protein Research Foundation, Osaka.
9. Haskell-Luevano C., Boteju L., Miwa H., Dickinson C., Gantz I., Yamada T., Hadley M., Hruby V. J. Topographical modification of melanotropin peptide analogues with beta-methyltryptophan isomers at position 9 leads to differential potencies and prolonged biological activities. J. Med. Chem. 38:1995;4720-4729.
10. Haskell-Luevano C., Boteju L. W., Miwa H., Job C., Al-Obeidi F., Gantz I., Hadley M. E., Hruby V. J. Topographical modifications of peptides can be used to examine biological mechanisms such as prolongation. Kaumaya P. T. P., Hodges R. S. Peptides: Chemistry, structure, and biology: Proceedings of the Fourteenth American Peptide Symposium. 1996;831-832 Mayflower Sa. Ltd, Kingswinford.
11. 1]CTAP: Potential for novel mechanism of action. Eur. J. Pharmacol. 233:1993;53-62.
12. Hruby V. J. Conformational restrictions of biologically active peptides via amino acid side chain groups. Life Sci. 31:1982;189-199.
13. Hruby V. J., Al-Obeidi F., Kazmierski W. K. Emerging approaches in the molecular design of receptor selective peptide ligands: Conformational, topographical and dynamic considerations. Biochem. J. 268:1990;249-262.
14. 4]-DPDPE possess extraordinary δ -opioid receptor selectivities. Jung G., Bayer E. Peptides 1988, Proceedings of the 20th European Peptide Symposium. 1989;616-618 W. de Gruyter & Co, Berlin.
15. 5]enkephalin. J. Med. Chem. 34:1991;1823-1830.
16. Hughes J., H. Kosterlitz W., Leslie F. M. Effect of morphine on adrenergic transmission in the mouse vas deferens: Assessment of agonist and antagonist potencies of narcotic analgesics. Br. J. Pharmacol. 53:1975;371-381.
17. Jackson H. C., McNutt D. J. Differential effects of selective mu opioid, kappa opioid, and delta opioid antagonists on electroshock seizure threshold in mice. Psychopharmacology (Berlin). 103:1991;380-383.
18. Kazmierski W. M., Hruby V. J. A new approach to receptor ligand design: Synthesis and conformation of a new class of potent and highly selective μ opioid antagonists utilizing tetrahydroisoquinoline carboxylic acid. Tetrahedron. 44:1988;697-710.
19. Kazmierski W. M., Yamamura H. I., Hruby V. J. Topographic design of peptide neurotransmitters and hormones on stable backbone templates: Relation of conformation and dynamics to bioactivity. J. Am. Chem. Soc. 113:1991;2275-2283.
20. Kazmierski W. M., Ferguson R. D., Lipkowski A. W., Hruby V. J. A topograghical model of mu-opioid and brain somatostatin receptor selective ligands. Int. J. Pept. Protein Res. 46:1995;265-278.
21. Kazmierski W. M., Wire W. S., Lui G. K, Knapp R. J., Shook J. E., Burks T. F., Yamamura H. I., Hruby V. J. Design and synthesis of somatostatin analogues with topographical properties that lead to highly potent and specific mu opioid receptor antagonists with greatly reduced binding at somatostatin receptors. J. Med. Chem. 31:1988;2170-2177.
22. Kazmierski, W. M. Personal communication.
23. Kosterlitz H. W., Lydon R. J., Watt A. J. The effects of adrenaline, noradrenaline, and isoprenaline on inhibitory alpha- and beta-adrenoceptors in the longitudinal muscle of the guinea-pig ileum. Br. J. Pharmacol. 39:1970;398-413.
24. Kramer T. H., Shook J. E., Kazmierski W. K., Ayres E. A., Wire W. S., Hruby V. J., Burks T. F. Novel peptidic mu opioid antagonists: Pharmacological characterization in vitro and in vivo. J. Pharmacol. Exp. Ther. 249:1989;544-551.
25. Kramer T. H., Davis P., Hruby V. J., Burks T. F., Porreca F. In vitro potency, affinity and agonist efficacy of highly selective delta opioid receptor ligands. J. Pharmacol. Exp. Ther. 266:1993;577-584.
26. Li G., Patel D., Hruby V. J. 1,2-Asymmetric cis induction and its application to the asymmetric syntheses of precursors of beta-branched unusual amino acids. Tetrahedron Lett. 35:1994;2301-2304.
27. Misicka A. S., Cavagnero R., Horvath P., Davis T. P., Kramer T. H., Yamamura H. I., Hruby V. J. Topographical requirements for delta opioid ligands: The synthesis and biological properties of β -MePhe-containing deltorphin I and dermenkephalin analogues. Yanaihara H. Peptide Chemistry 1992, Proceedings of the 2nd Japanese Symposium on Peptide Chemistry. 1993;378-380 ESCOM Sci. Publ, Leiden.
28. Mosberg H. I., Hurst R., Hruby V. J., Gee K., Yamamura H. I., Galligan J. J., Burks T. F. Bis-penicillamine enkephalins possess highly improved specificity toward delta opioid receptors. Proc. Natl. Acad. Sci. USA. 80:1983;5871-5874.
29. 3 replacements in the cyclic delta receptor selective tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13). J. Med. Chem. 37:1994;4384-4391.
30. Munson P. J., Rodbard D. Ligand: A versatile computerized approach for characterization of ligand-binding systems. Anal. Biochem. 107:1980;220-239.
31. Narita M., Takahashi Y., Suzuki T., Misawa M., Nagase H. An ATP-sensitive potassium channel blocker abolishes the potentiating effect of morphine on the bicuculline-induced convulsion in mice. Psychopharmacology (Berlin). 110:1993;500-502.
32. Pelton J. T., Gulya K., Hruby V. J., Duckles S. P., Yamamura H. I. Conformationally restricted analogues of somatostatin with high mu-opiate receptor specificity. Proc. Natl. Acad. Sci. USA. 82:1985;236-239.
33. Pelton J. T., Kazmierski W. M., Gulya K., Yamamura H. I., Hruby V. J. Design and synthesis of conformationally constrained somatostatin analogues with high potency and specificity for mu opioid receptors. J. Med. Chem. 29:1986;2370-2375.
34. Peter A., Toth G., Olajos E., Tourwe D. Chromatographic behaviour of opioid peptides containing beta-methylphenylalanine isomers. J. Chromatogr. A. 705:1995;267-273.
35. Porreca F., Nunan L., Kazmierski W. M., Hruby V. J. Effect of a novel opioid peptide antagonist on rat bladder motility in vivo. Peptides. 8:1987;625-632.
36. Qian X., Shenderovich M. D., Kövér K. E., Bilsky E. J., Horvath R., Davis P., Yamamura H. I., Porreca F., Hruby V. J. Probing the stereochemical requirements for receptor recognition of δ opioid agonists through topographical modifications in position. I. J. Am. Chem. Soc. 118:1996;7280-7290.
37. Qian X., Kövér K. E., Shenderovich M. D., Lou B.-S., Misicka A., Zalewska T., Horvath R., Davis P., Bilsky E. J., Porreca F., Yamamura H. I., Hruby V. J. Newly discovered stereochemical requirements in the side-chain conformation of delta opioid agonists for recognizing opioid delta receptors. J. Med. Chem. 37:1994;1746-1757.
38. 2]-dermorphin tripeptide analogues. J. Pharmacol. Exp. Ther. 263:1992;793-799.
39. Sasaki Y., Chiba T. Novel deltorphin heptapeptide analogues with potent delta agonist, delta antagonist, or mixed mu antagonist/delta agonist properties. J. Med. Chem. 38:1995;3995-3999.
40. Schmidt R., Vogel D., Mrestani-Klaus C., Brandt W., Neubert K., Chung N. N., Lemieux C., Schiller P. W. Cyclic beta-casomorphin analogues with mixed mu agonist/delta antagonist properties: Synthesis, pharmacological characterization, and conformational aspects. J. Med. Chem. 37:1994;1136-1144.
41. Schiller P. W., Nguyen T. M., Lemieux C., Maziak L. A. Synthesis and activity profiles of novel cyclic opioid peptide monomers and dimers. J. Med. Chem. 28:1985;1766-1771.
42. Shen K. F., Crain S. M. Antagonists at excitatory opioid receptors on sensory neurons in culture increase potency and specificity of opiate analgesics and attenuate development of tolerance/dependence. Brain Res. 636:1994;286-297.
43. Shook J. E., Pelton J. T., Wire W. S., Hirning L. D., Hruby V. J., Burks T. F. Pharmacologic evaluation of a cyclic somatostatin analogue with antagonist activity at mu opioid receptors in vitro. J. Pharmacol. Exp. Ther. 34:1987;772-777.
44. PCNOCIN and NONLIN84: Software for the statistical analysis of nonlinear models. Am. Statist. 40:1986;52-60.
45. Stewart J. M., Young J. D. Solid phase peptide synthesis. 1969;W. H. Freeman and Company, San Francisco.
46. Takeuchi K. Pharmacological study of endogenous opioid systems and seizures by electroconvulsive shock and neurotoxins. Acta Schol. Med. Univ. Gifu. 39:1991;76-93.
47. Tallarida R. J., Murray R. B. Manual of pharmacological calculations with computer programs. 2nd ed. 1987;26-31 Springer-Verlag, New York.
48. Thaisrivongs S., Pals D. T., Turner S. R., Kroll L. T. Renin inhibitory peptides: A study of structural modifications in the peptide backbone. J. Hypertens. Suppl. 7:1989;S21-S23.
49. 5]enkephalin with delta opioid receptor selectivity. J. Med. Chem. 26:1992;2384-2391.
50. 5] enkephalin after intraperitoneal, intravenous, oral and subcutaneous administration. J. Pharmacol. Exp. Ther. 263:1992;1308-1316.
51. Wynants C., Tourwe D., Kazmierski W. M., Hruby V. J., Van Binst G. Conformation of two somatostatin analogues in aqueous solution. Eur. J. Biochem. 185:1989;371-381.
52. Yamazaki T., Said-Nejad O. E., Schiller P. W., Goodman M. Conformational studies of stereoisomeric 14-membered cyclic enkephalin analogues containing 1-naphthylalanine at the fourth position: Chirality effect of leucine at the fifth position on biological activity and receptor selectivity. Biopolymers. 31:1991;877-898.
53. Yokoyama H., Onodera K., Suzuki T., Iinuma K., Watanabe T. Opioid mu-deficient CXBK mouse and the role of mu-1 receptors in electrically induced convulsions. Brain Res. 595:1992;137-140.