Dmt-Tic-NH-CH2-Bid (UFP-502), a potent DOP receptor agonist: In vitro and in vivo studies

Peptides

Volumn 27, Issue 12, 2006, Pages 3322-3330

  Vergura, Raffaella ^a   Valenti, Elena ^b   Hebbes, Christopher P ^c   Gavioli, Elaine C ^a   Spagnolo, Barbara ^a   McDonald, John ^c   Lambert, David G ^c   Balboni, Gianfranco ^d,e   Salvadori, Severo ^d   Regoli, Domenico ^a   Calo', Girolamo ^a  

^a Neuroscience Center   (Italy)

^b UFPeptides srl   (Italy)

^c UNIVERSITY OF LEICESTER   (United Kingdom)

^d UNIVERSITY OF FERRARA   (Italy)

^e UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Bioassay; Delta opioid peptide receptor; Forced swimming and tail withdrawal assays; Mice; Opioids; Receptor binding; UFP 502

Indexed keywords

DELTA OPIATE RECEPTOR; DELTA OPIATE RECEPTOR AGONIST; ENKEPHALIN[2,5 DEXTRO PENICILLAMINE]; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); NALOXONE; NALTRINDOLE; RADIOLIGAND; UFP 502; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINOCICEPTION; ARTICLE; BINDING AFFINITY; BIOASSAY; CONTROLLED STUDY; DRUG POTENCY; FORCED SWIMMING TEST; IMMOBILIZATION; MOUSE; NONHUMAN; PRIORITY JOURNAL; RECEPTOR BINDING; VAS DEFERENS;

ANIMALS; BENZIMIDAZOLES; CHO CELLS; CRICETINAE; CRICETULUS; DIPEPTIDES; HUMANS; MALE; MICE; RECEPTORS, OPIOID, DELTA;

RODENTIA;

EID: 33750952845     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2006.07.015     Document Type: Article

References (47)

1. Baamonde A., Dauge V., Ruiz-Gayo M., Fulga I.G., Turcaud S., Fournie-Zaluski M.C., et al. Antidepressant-type effects of endogenous enkephalins protected by systemic RB 101 are mediated by opioid delta and dopamine D1 receptor stimulation. Eur J Pharmacol 216 (1992) 157-166
2. Balboni G., Guerrini R., Salvadori S., Bianchi C., Rizzi D., Bryant S.D., et al. Evaluation of the Dmt-Tic pharmacophore: conversion of a potent delta-opioid receptor antagonist into a potent delta agonist and ligands with mixed properties. J Med Chem 45 (2002) 713-720
3. Balboni G., Guerrini R., Salvadori S., Tomatis R., Bryant S.D., Bianchi C., et al. Opioid diketopiperazines: synthesis and activity of a prototypic class of opioid antagonists. Biol Chem 378 (1997) 19-29
4. Berger H., Calo G., Albrecht E., Guerrini R., and Bienert M. [Nphe(1)]NC(1-13)NH(2) selectively antagonizes nociceptin/orphanin FQ-stimulated G-protein activation in rat brain. J Pharmacol Exp Ther 294 (2000) 428-433
5. Bigoni R., Giuliani S., Calo G., Rizzi A., Guerrini R., Salvadori S., et al. Characterization of nociceptin receptors in the periphery: in vitro and in vivo studies. Naunyn Schmiedebergs Arch Pharmacol 359 (1999) 160-167
6. Broom D.C., Jutkiewicz E.M., Rice K.C., Traynor J.R., and Woods J.H. Behavioral effects of delta-opioid receptor agonists: potential antidepressants?. Jpn J Pharmacol 90 (2002) 1-6
7. Broom D.C., Jutkiewicz E.M., Folk J.E., Traynor J.R., Rice K.C., and Woods J.H. Convulsant activity of a non-peptidic delta-opioid receptor agonist is not required for its antidepressant-like effects in Sprague-Dawley rats. Psychopharmacology (Berl) 164 (2002) 42-48
8. Broom D.C., Jutkiewicz E.M., Folk J.E., Traynor J.R., Rice K.C., and Woods J.H. Nonpeptidic delta-opioid receptor agonists reduce immobility in the forced swim assay in rats. Neuropsychopharmacology 26 (2002) 744-755
9. Broom D.C., Jutkiewicz E.M., Folk J.E., Traynor J.R., Rice K.C., and Woods J.H. Convulsant activity of a non-peptidic delta-opioid receptor agonist is not required for its antidepressant-like effects in Sprague-Dawley rats. Psychopharmacology (Berl) 164 (2002) 42-48
10. Calo G., Guerrini R., Rizzi A., Bigoni R., Varani K., Salvadori S., et al. Pharmacological characterization of the nociceptin receptor in the mouse: receptor binding, bioassay and behavioral studies. Naunyn Schmiedebergs Arch Pharmacol 358 Suppl 2 (1998) 16.7
11. Calo G., Guerrini R., Bigoni R., Rizzi A., Marzola G., Okawa H., et al. Characterization of [Nphe(1)]nociceptin(1-13)NH(2), a new selective nociceptin receptor antagonist. Br J Pharmacol 129 (2000) 1183-1193
12. Capasso S., Sica F., Mazzarella L., Balboni G., Guerrini R., and Salvadori S. Acid catalysis in the formation of dioxopiperazines from peptides containing tetrahydroisoquinoline-3-carboxylic acid at position 2. Int J Pept Protein Res 45 (1995) 567-573
13. Comer S.D., Hoenicke E.M., Sable A.I., McNutt R.W., Chang K.J., De Costa B.R., et al. Convulsive effects of systemic administration of the delta opioid agonist BW373U86 in mice. J Pharmacol Exp Ther 267 (1993) 888-895
14. Cox B.M., Chavkin C., Christie M.J., Civelli O., Evans C., Hamon M.D., et al. Opioid receptors. In: Girdlestone D. (Ed). The IUPHAR compendium of receptor characterization and classification (2000), IUPHAR Media Ltd., London 321-333
15. Cryan J.F., Markou A., and Lucki I. Assessing antidepressant activity in rodents: recent developments and future needs. Trends Pharmacol Sci 23 (2002) 238-245
16. Duman R.S. Role of neurotrophic factors in the etiology and treatment of mood disorders. Neuromolecular Med 5 (2004) 11-25
17. Emmerson P.J., Liu M.R., Woods J.H., and Medzihradsky F. Binding affinity and selectivity of opioids at mu, delta and kappa receptors in monkey brain membranes. J Pharmacol Exp Ther 271 (1994) 1630-1637
18. Fichna J., Janecka A., Piestrzeniewicz M., Costentin J., and do Rego J.C. Antidepressant-like effect of endomorphin-1 and endomorphin-2 in mice. Neuropsychopharmacology (2006)
19. Filliol D., Ghozland S., Chluba J., Martin M., Matthes H.W., Simonin F., et al. Mice deficient for delta- and mu-opioid receptors exhibit opposing alterations of emotional responses. Nat Genet 25 (2000) 195-200
20. Gavioli E.C., Marzola G., Guerrini R., Bertorelli R., Zucchini S., De Lima T.C., et al. Blockade of nociceptin/orphanin FQ-NOP receptor signalling produces antidepressant-like effects: pharmacological and genetic evidences from the mouse forced swimming test. Eur J Neurosci 17 (2003) 1987-1990
21. Hylden J.L., and Wilcox G.L. Intrathecal morphine in mice: a new technique. Eur J Pharmacol 67 (1980) 313-316
22. Jutkiewicz E.M. The antidepressant-like effects of delta-opioid receptor agonists. Mol Interv 6 (2006) 162-169
23. Jutkiewicz E.M., Rice K.C., Woods J.H., and Winsauer P.J. Effects of the delta-opioid receptor agonist SNC80 on learning relative to its antidepressant-like effects in rats. Behav Pharmacol 14 (2003) 509-516
24. Jutkiewicz E.M., Eller E.B., Folk J.E., Rice K.C., Traynor J.R., and Woods J.H. Delta-opioid agonists: differential efficacy and potency of SNC80, its 3-OH (SNC86) and 3-desoxy (SNC162) derivatives in Sprague-Dawley rats. J Pharmacol Exp Ther 309 (2004) 173-181
25. Jutkiewicz E.M., Walker N.P., Folk J.E., Rice K.C., Portoghese P.S., Woods J.H., et al. Comparison of peptidic and nonpeptidic delta-opioid agonists on guanosine 5′-O-(3-[35S]thio)triphosphate ([35S]GTPgammaS) binding in brain slices from Sprague-Dawley rats. J Pharmacol Exp Ther 312 (2005) 1314-1320
26. Kieffer B.L. Opioids: first lessons from knockout mice. Trends Pharmacol Sci 20 (1999) 19-26
27. Kieffer B.L., and Gaveriaux-Ruff C. Exploring the opioid system by gene knockout. Prog Neurobiol 66 (2002) 285-306
28. Kita A., Imano K., Seto Y., Yakuo I., Deguchi T., and Nakamura H. Antinociceptive and antidepressant-like profiles of BL-2401, a novel enkephalinase inhibitor, in mice and rats. Jpn J Pharmacol 75 (1997) 337-346
29. Kitayama M., Barnes T.A., Carra G., McDonald J., Calo G., Guerrini R., et al. Pharmacological profile of the cyclic nociceptin/orphanin FQ analogues c[Cys10,14]N/OFQ(1-14)NH2 and c[Nphe1,Cys10,14]N/OFQ(1-14)NH2. Naunyn Schmiedebergs Arch Pharmacol 368 (2003) 528-537
30. Konig M., Zimmer A.M., Steiner H., Holmes P.V., Crawley J.N., Brownstein M.J., et al. Pain responses, anxiety and aggression in mice deficient in pre-proenkephalin. Nature 383 (1996) 535-538
31. Labarre M., Butterworth J., St-Onge S., Payza K., Schmidhammer H., Salvadori S., et al. Inverse agonism by Dmt-Tic analogues and HS 378, a naltrindole analogue. Eur J Pharmacol 406 (2000) R1-R3
32. Laursen S.E., and Belknap J.K. Intracerebroventricular injections in mice. Some methodological refinements. J Pharmacol Meth 16 (1986) 355-357
33. Neubig R.R., Spedding M., Kenakin T., and Christopoulos A. International Union of Pharmacology Committee on Receptor Nomenclature and Drug Classification. XXXVIII. Update on terms and symbols in quantitative pharmacology. Pharmacol Rev 55 (2003) 597-606
34. Porsolt R.D., Le Pichon M., and Jalfre M. Depression: a new animal model sensitive to antidepressant treatments. Nature 266 (1977) 730-732
35. Portoghese P.S., Sultana M., and Takemori A.E. Design of peptidomimetic delta opioid receptor antagonists using the message-address concept. J Med Chem 33 (1990) 1714-1720
36. Ragnauth A., Schuller A., Morgan M., Chan J., Ogawa S., Pintar J., et al. Female preproenkephalin-knockout mice display altered emotional responses. Proc Natl Acad Sci USA 98 (2001) 1958-1963
37. Rizzi A., Bigoni R., Marzola G., Guerrini R., Salvadori S., Regoli D., et al. Characterization of the locomotor activity-inhibiting effect of nociceptin/orphanin FQ in mice. Naunyn Schmiedebergs Arch Pharmacol 363 (2001) 161-165
38. Rizzi A., Rizzi D., Marzola G., Regoli D., Larsen B.D., Petersen J.S., et al. Pharmacological characterization of the novel nociceptin/orphanin FQ receptor ligand, ZP120: in vitro and in vivo studies in mice. Br J Pharmacol 137 (2002) 369-374
39. Saitoh A., Kimura Y., Suzuki T., Kawai K., Nagase H., and Kamei J. Potential anxiolytic and antidepressant-like activities of SNC80, a selective delta-opioid agonist, in behavioral models in rodents. J Pharmacol Sci 95 (2004) 374-380
40. Salvadori S., Balboni G., Guerrini R., Tomatis R., Bianchi C., Bryant S.D., et al. Evolution of the Dmt-Tic pharmacophore: N-terminal methylated derivatives with extraordinary delta opioid antagonist activity. J Med Chem 40 (1997) 3100-3108
41. Salvadori S., Attila M., Balboni G., Bianchi C., Bryant S.D., Crescenzi O., et al. Delta opioidmimetic antagonists: prototypes for designing a new generation of ultraselective opioid peptides. Mol Med 1 (1995) 678-689
42. Tejedor-Real P., Mico J.A., Maldonado R., Roques B.P., and Gibert-Rahola J. Effect of mixed (RB 38A) and selective (RB 38B) inhibitors of enkephalin degrading enzymes on a model of depression in the rat. Biol Psychiatry 34 (1993) 100-107
43. Tejedor-Real P., Mico J.A., Maldonado R., Roques B.P., and Gibert-Rahola J. Implication of endogenous opioid system in the learned helplessness model of depression. Pharmacol Biochem Behav 52 (1995) 145-152
44. Tejedor-Real P., Mico J.A., Smadja C., Maldonado R., Roques B.P., and Gilbert-Rahola J. Involvement of delta-opioid receptors in the effects induced by endogenous enkephalins on learned helplessness model. Eur J Pharmacol 354 (1998) 1-7
45. Thomas J.B., Herault X.M., Rothman R.B., Atkinson R.N., Burgess J.P., Mascarella S.W., et al. Factors influencing agonist potency and selectivity for the opioid delta receptor are revealed in structure-activity relationship studies of the 4-[(N-substituted-4-piperidinyl)arylamino]-N,N-diethylbenzamides. J Med Chem 44 (2001) 972-987
46. Torregrossa M.M., Jutkiewicz E.M., Mosberg H.I., Balboni G., Watson S.J., and Woods J.H. Peptidic delta opioid receptor agonists produce antidepressant-like effects in the forced swim test and regulate BDNF mRNA expression in rats. Brain Res 1069 (2006) 172-181
47. Zomkowski A.D., Santos A.R., and Rodrigues A.L. Evidence for the involvement of the opioid system in the agmatine antidepressant-like effect in the forced swimming test. Neurosci Lett 381 (2005) 279-283