[Dmt1, d-1-Nal3]morphiceptin, a novel opioid peptide analog with high analgesic activity

Peptides

Volumn 29, Issue 4, 2008, Pages 633-638

  Fichna, Jakub ^a   do Rego, Jean Claude ^b   Chung, Nga N ^c   Costentin, Jean ^b   Schiller, Peter W ^c   Janecka, Anna ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

^b IFRMP 23   (France)

^c CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BETA FUNALTREXAMINE; ENDOMORPHIN 2; MORPHICEPTIN; MU OPIATE RECEPTOR; OPIATE PEPTIDE; TYROSINE; ENDORPHIN; MORPHICEPTIN, DMT(1) NAL(3); MORPHICEPTIN, DMT(1)-NAL(3)-; NARCOTIC ANALGESIC AGENT;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DOSE RESPONSE; DRUG DETERMINATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOT PLATE TEST; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN FOLDING; SPINAL ANESTHESIA; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; SYNTHESIS;

ANALGESICS, OPIOID; ANIMALS; ENDORPHINS; MICE; OPIOID PEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 40249111499     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2007.12.005     Document Type: Article

References (29)

1. Ambo A., Murase H., Niizuma H., Ouchi H., Yamamoto Y., and Sasaki Y. Dermorphin and deltorphin heptapeptide analogues: replacement of Phe residue by Dmp greatly improves opioid receptor affinity and selectivity. Bioorg Med Chem Lett 12 (2002) 879-881
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 δ-opioid receptor antagonist into a potent δ agonist and ligands with mixed properties. J Med Chem 45 (2002) 713-720
3. Cardillo G., Gentilucci L., Qasem A.R., Sgarzi F., and Spampinato S. Endomorphin-1 analogues containing beta-proline are mu-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance. J Med Chem 45 (2002) 2571-2578
4. Chang K.-J., Lillian A., Hazum E., Cuatrecasas P., and Chang J.-K. Morphiceptin (NH4-Tyr-Pro-Phe-Pro-CONH2): a potent and specific agonist for morphine (mu) receptors. Science 121 (1981) 75-77
5. 4]endomorphin-2 (Antanal-2). J Med Chem 50 (2007) 512-520
6. Fichna J., do-Rego J.-C., Costentin J., Chung N.N., Schiller P.W., Kosson P., et al. Opioid receptor binding and in vivo antinociceptive activity of position 3-substituted morphiceptin analogs. Biochem Biophys Res Commun 320 (2004) 531-536
7. Fichna J., do-Rego J.-C., Costentin J., and Janecka A. Characterization of antinociceptive activity of novel endomorphin-2 and morphiceptin analogs modified in the third position. Biochem Pharmacol 69 (2005) 179-185
8. Fichna J., Gach K., Piestrzeniewicz M., Burgeon E., Poels J., Vanden Broeck J., et al. Functional characterization of opioid receptor ligands by aequorin luminescence-based calcium assay. J Pharmacol Exp Ther 317 (2006) 1150-1154
9. Fichna J., Janecka A., Bailly L., Marsais F., Costentin J., and do-Rego J.-C. In vitro characterization of novel peptide inhibitors of endomorphin-degrading enzymes in the rat brain. Chem Biol Drug Des 68 (2006) 173-175
10. Fichna J., Janecka A., Costentin J., and do-Rego J.-C. The endomorphin system and its evolving neurophysiological role. Pharmacol Rev 59 (2007) 88-123
11. Fujita Y., Tsuda Y., Li T., Motoyama T., Takahashi M., Shimizu Y., et al. Development of potent bifunctional endomorphin-2 analogues with mixed mu-/delta-opioid agonist and delta-opioid antagonist properties. J Med Chem 47 (2004) 3591-3599
12. 5]enkephalin. J Med Chem 35 (1992) 684-687
13. Janecka A., Fichna J., Kruszynski R., Sasaki Y., Ambo A., Costentin J., et al. Synthesis and antinociceptive activity of cyclic endomorphin-2 and morphiceptin analogs. Biochem Pharmacol 71 (2005) 188-195
14. Jinsmaa Y., Marczak E., Fujita Y., Shiotani K., Miyazaki A., Li T., et al. Potent in vivo antinociception and opioid receptor preference of the novel analogue [Dmt1]endomorphin-1. Pharmacol Biochem Behav 84 (2006) 252-258
15. Kruszynski R., Fichna J., do-Rego J.-C., Chung N.N., Schiller P.W., Kosson P., et al. Novel endomorphin-2 analogs with μ-opioid receptor antagonist activity. J Pept Res 66 (2005) 125-131
16. Kruszynski R., Fichna J., do-Rego J.-C., Janecki T., Kosson P., Pakulska W., et al. Synthesis and biological activity of N-methylated analogs of endomorphin-2. Bioorg Med Chem 13 (2005) 6713-6717
17. Lengyel I., Orosz G., Biyashev D., Kocsis L., Al-Khrasani M., Ronai A., et al. Side chain modifications change the binding and agonist properties of endomorphin 2. Biochem Biophys Res Commun 290 (2002) 153-161
18. Li T., Shiotani K., Miyazaki A., Tsuda Y., Ambo A., Sasaki Y., et al. Bifunctional [2′,6′-dimethyl-l-tyrosine1]endomorphin-2 analogues substituted at position 3 with alkylated phenylalanine derivatives yield potent mixed mu-agonist/delta-antagonist and dual mu-agonist/delta-agonist opioid ligands. J Med Chem 50 (2007) 2753-2766
19. Okada Y., Fujita Y., Motoyama T., Tsuda Y., Yokoi T., Li T., et al. Structural studies of [2′,6′-dimethyl-l-tyrosine1]endomorphin-2 analogues: enhanced activity and cis orientation of the Dmt-Pro amide bond. Bioorg Med Chem 11 (2003) 1983-1994
20. Sasaki Y., Ambo A., Murase H., Hirabuki M., Ouchi H., and Yamamoto Y. In: Shioiri T. (Ed). Peptide Science 2000 (2001), The Japanese Peptide Society, Osaka 117-120
21. Sasaki Y., Sasaki A., Niizuma H., Goto H., and Ambo A. Endomorphin 2 analogues containing Dmp residue as an aromatic amino acid surrogate with high mu-opioid receptor affinity and selectivity. Bioorg Med Chem 11 (2003) 675-678
22. Sasaki Y., Suto T., Ambo A., Ouchi H., and Yamamoto Y. Biological properties of opioid peptides replacing Tyr at position 1 by 2,6-dimethyl-Tyr. Chem Pharm Bull (Tokyo) 47 (1999) 1506-1509
23. Schiller P.W., Fundytus M.E., Merovitz L., Weltrowska G., Nguyen T.M., Lemieux C., et al. The opioid mu agonist/delta antagonist DIPP-NH(2)[Psi] produces a potent analgesic effect, no physical dependence, and less tolerance than morphine in rats. J Med Chem 42 (1999) 3520-3526
24. Schiller P.W., Nguyen T.M.-D., Berezowska I., Dupuis S., Weltrowska G., Chung N.N., et al. Synthesis and in vitro opioid activity profiles of DALDA analogues. Eur J Med Chem 35 (2000) 895-901
25. Schiller P.W., Weltrowska G., Schmidt R., Nguyen T.M.-D., Berezowska I., Lemieux C., et al. Four different types of opioid peptides with mixed μ agonist/δ antagonist properties. Analgesia 1 (1995) 703-706
26. Szeto H.H., Lovelace J.L., Fridland G., Soong Y., Fasolo J., Wu D., et al. In vivo pharmacokinetics of selective μ-opioid peptide agonists. J Pharmacol Exp Ther 298 (2001) 57-61
27. Tömböly C., Kövér K.E., Péter A., Tourwé D., Biyashev D., Benyhe S., et al. Structure-activity study on the Phe side chain arrangement of endomorphins using conformationally constrained analogues. J Med Chem 47 (2004) 735-743
28. Zadina J.E., Hackler L., Ge L.-J., and Kastin A.J. A potent and selective endogenous agonist for the mu-opiate receptor. Nature 386 (1997) 499-502
29. Zhao Q.Y., Chen Q., Yang D.J., Feng Y., Long Y., Wang P., et al. Endomorphin 1[psi] and endomorphin 2[psi], endomorphins analogues containing a reduced (CH2NH) amide bond between Tyr1 and Pro2, display partial agonist potency but significant antinociception. Life Sci 77 (2005) 1155-1165