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Volumn 71, Issue 1-2, 2005, Pages 188-195

Synthesis and antinociceptive activity of cyclic endomorphin-2 and morphiceptin analogs

Author keywords

, and opioid receptors; Binding studies; Hot plate test; Locomotor activity; Solid phase peptide synthesis

Indexed keywords

DELTA OPIATE RECEPTOR; DYNORPHIN A; ENDOMORPHIN 2; KAPPA OPIATE RECEPTOR ANTAGONIST; MORPHICEPTIN; MORPHICEPTIN DERIVATIVE; MU OPIATE RECEPTOR; NALOXONE; TYROSYLCYCLO(ASPARTYLPHENYLALANYL DEXTRO PROLYLLYSINE)AMIDE; TYROSYLCYCLO(ASPARTYLPHENYLALANYLPHENYLALANYLLYSINE)AMIDE; TYROSYLCYCLO(LYSYLPHENYLALANYL DEXTRO PROLYLASPARTIC ACID)AMIDE; TYROSYLCYCLO(LYSYLPHENYLALANYLPHENYLALANYLASPARTIC ACID)AMIDE; UNCLASSIFIED DRUG;

EID: 28244494745     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2005.10.018     Document Type: Article
Times cited : (30)

References (26)
  • 1
    • 0016701344 scopus 로고
    • Identification of two related pentapeptides from the brain with potent opiate agonist activity
    • J. Hughes, T.W. Smith, H.W. Kosterlitz, L.A. Fothergill, B.A. Morgan, and H.R. Morris Identification of two related pentapeptides from the brain with potent opiate agonist activity Nature 258 1975 577 580
    • (1975) Nature , vol.258 , pp. 577-580
    • Hughes, J.1    Smith, T.W.2    Kosterlitz, H.W.3    Fothergill, L.A.4    Morgan, B.A.5    Morris, H.R.6
  • 2
    • 0030068392 scopus 로고    scopus 로고
    • Tissue distribution of opioid receptor gene expression in the rat
    • G. Wittert, P. Hope, and D. Pyle Tissue distribution of opioid receptor gene expression in the rat Biochem Biophys Res Commun 218 1996 877 881
    • (1996) Biochem Biophys Res Commun , vol.218 , pp. 877-881
    • Wittert, G.1    Hope, P.2    Pyle, D.3
  • 3
    • 0032428284 scopus 로고    scopus 로고
    • Opiate tolerance and dependence: Receptors, G-proteins, and anti-opiates
    • L.M. Harrison, A.J. Kastin, and J.E. Zadina Opiate tolerance and dependence: receptors, G-proteins, and anti-opiates Peptides 19 1998 1603 1630
    • (1998) Peptides , vol.19 , pp. 1603-1630
    • Harrison, L.M.1    Kastin, A.J.2    Zadina, J.E.3
  • 4
    • 0033013383 scopus 로고    scopus 로고
    • Opioids: First lessons from knockout mice
    • B.L. Kieffer Opioids: First lessons from knockout mice Trends Pharmacol Sci 20 1999 19 26
    • (1999) Trends Pharmacol Sci , vol.20 , pp. 19-26
    • Kieffer, B.L.1
  • 5
    • 0024331850 scopus 로고
    • Kappa opiate receptor multiplicity: Evidence for two U50 488-sensitive kappa 1 subtypes and a novel kappa 3 subtype
    • J.A. Clark, L. Riu, M. Prince, B. Hersh, M. Edelson, and G.W. Pasternak Kappa opiate receptor multiplicity: evidence for two U50 488-sensitive kappa 1 subtypes and a novel kappa 3 subtype J Pharmacol Exp Ther 251 1989 461 468
    • (1989) J Pharmacol Exp Ther , vol.251 , pp. 461-468
    • Clark, J.A.1    Riu, L.2    Prince, M.3    Hersh, B.4    Edelson, M.5    Pasternak, G.W.6
  • 6
    • 2142658722 scopus 로고    scopus 로고
    • New trends in the development of opioid peptide analogues as advanced remedies for pain relief
    • L. Gentilucci New trends in the development of opioid peptide analogues as advanced remedies for pain relief Curr Top Med Chem 4 2004 19 38
    • (2004) Curr Top Med Chem , vol.4 , pp. 19-38
    • Gentilucci, L.1
  • 7
    • 0019205723 scopus 로고
    • D-Tyr-Ser-Gly-Phe-Leu-Thr, a highly preferential ligand for delta opiate receptors
    • G. Gacel, M.C. Fournie-Zaluski, and B.P. Roques d-Tyr-Ser-Gly-Phe-Leu- Thr, a highly preferential ligand for delta opiate receptors FEBS Lett 118 1980 245 247
    • (1980) FEBS Lett , vol.118 , pp. 245-247
    • Gacel, G.1    Fournie-Zaluski, M.C.2    Roques, B.P.3
  • 8
    • 0020029345 scopus 로고
    • Dynorphin is a specific endogenous ligand of the kappa opioid receptor
    • C. Chavkin, I.F. James, and A. Goldstein Dynorphin is a specific endogenous ligand of the kappa opioid receptor Science 215 1982 413 415
    • (1982) Science , vol.215 , pp. 413-415
    • Chavkin, C.1    James, I.F.2    Goldstein, A.3
  • 9
    • 0030933655 scopus 로고    scopus 로고
    • A potent and selective endogenous agonist for the mu-opiate receptor
    • J.E. Zadina, L. Hackler, L.J. Ge, and A.J. Kastin A potent and selective endogenous agonist for the mu-opiate receptor Nature 386 1997 499 502
    • (1997) Nature , vol.386 , pp. 499-502
    • Zadina, J.E.1    Hackler, L.2    Ge, L.J.3    Kastin, A.J.4
  • 10
    • 0018687626 scopus 로고
    • Novel opioid peptides derived from casein (beta-casomorphins) I. Isolation from bovine casein peptone
    • V. Brantl, H. Teschemacher, J. Blasig, A. Henschen, and F. Lottspeich Novel opioid peptides derived from casein (beta-casomorphins) I. Isolation from bovine casein peptone Hoppe Seylers Z Physiol Chem 360 1979 1211 1216
    • (1979) Hoppe Seylers Z Physiol Chem , vol.360 , pp. 1211-1216
    • Brantl, V.1    Teschemacher, H.2    Blasig, J.3    Henschen, A.4    Lottspeich, F.5
  • 11
    • 0020395598 scopus 로고
    • Antinociceptive potencies of beta-casomorphin analogs as compared to their affinitie towards mu and delta opiate receptor sites in brain and periphery
    • V. Brantl, A. Pfeiffer, A. Herz, A. Henschen, and F. Lottspeich Antinociceptive potencies of beta-casomorphin analogs as compared to their affinitie towards mu and delta opiate receptor sites in brain and periphery Peptides 3 1982 793 797
    • (1982) Peptides , vol.3 , pp. 793-797
    • Brantl, V.1    Pfeiffer, A.2    Herz, A.3    Henschen, A.4    Lottspeich, F.5
  • 12
    • 0019394119 scopus 로고
    • Morphiceptin (NH4-Tyr-Pro-Phe-Pro-CONH2): A potent and specific agonist for morphine (mu) receptors
    • K.J. Chang, A. Lillian, E. Hazum, P. Cuatrecasas, and J.-K. Chang Morphiceptin (NH4-Tyr-Pro-Phe-Pro-CONH2): a potent and specific agonist for morphine (mu) receptors Science 212 1981 75 77
    • (1981) Science , vol.212 , pp. 75-77
    • Chang, K.J.1    Lillian, A.2    Hazum, E.3    Cuatrecasas, P.4    Chang, J.-K.5
  • 13
    • 0022261490 scopus 로고
    • Isolation of a specific mu-opiate receptor peptide, morphiceptin, from an enzymatic digest of milk proteins
    • K.J. Chang, Y.F. Su, D.A. Brent, and J.K. Chang Isolation of a specific mu-opiate receptor peptide, morphiceptin, from an enzymatic digest of milk proteins J Biol Chem 260 1985 9706 9712
    • (1985) J Biol Chem , vol.260 , pp. 9706-9712
    • Chang, K.J.1    Su, Y.F.2    Brent, D.A.3    Chang, J.K.4
  • 16
    • 0028801099 scopus 로고
    • Novel deltorphin heptapeptide analogs with potent delta agonist, delta antagonist, or mixed mu antagonist/delta agonist properties
    • Y. Sasaki, and T. Chiba Novel deltorphin heptapeptide analogs with potent delta agonist, delta antagonist, or mixed mu antagonist/delta agonist properties J Med Chem 38 1995 3995 3999
    • (1995) J Med Chem , vol.38 , pp. 3995-3999
    • Sasaki, Y.1    Chiba, T.2
  • 17
    • 0037170786 scopus 로고    scopus 로고
    • Dermorphin and deltorphin heptapeptide analogues: Replacement of Phe residue by Dmp greatly improves opioid receptor affinity and selectivity
    • A. Ambo, H. Murase, H. Niizuma, H. Ouchi, Y. Yamamoto, and Y. Sasaki Dermorphin and deltorphin heptapeptide analogues: replacement of Phe residue by Dmp greatly improves opioid receptor affinity and selectivity Bioorg Med Chem Lett 12 2002 879 882
    • (2002) Bioorg Med Chem Lett , vol.12 , pp. 879-882
    • Ambo, A.1    Murase, H.2    Niizuma, H.3    Ouchi, H.4    Yamamoto, Y.5    Sasaki, Y.6
  • 18
    • 0015861774 scopus 로고
    • Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction
    • Y. Cheng, and W.H. Prusoff Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction Biochem Pharmacol 22 1973 3099 3108
    • (1973) Biochem Pharmacol , vol.22 , pp. 3099-3108
    • Cheng, Y.1    Prusoff, W.H.2
  • 19
    • 70449139880 scopus 로고
    • Pharmacological effects produced by intracerebral injection of drugs in the conscious mouse
    • T.J. Haley, and W.G. McCormick Pharmacological effects produced by intracerebral injection of drugs in the conscious mouse Br J Pharmacol 12 1957 12 15
    • (1957) Br J Pharmacol , vol.12 , pp. 12-15
    • Haley, T.J.1    McCormick, W.G.2
  • 20
    • 84935383230 scopus 로고
    • Synthetic analgesics II. Dithienylbutenyl- and dithienylbutylamines
    • N.B. Eddy, and D. Leimbach Synthetic analgesics II. Dithienylbutenyl- and dithienylbutylamines J Pharmacol Exp Ther 107 1953 385 393
    • (1953) J Pharmacol Exp Ther , vol.107 , pp. 385-393
    • Eddy, N.B.1    Leimbach, D.2
  • 22
    • 0042261466 scopus 로고    scopus 로고
    • Structure-activity relationship, conformation and pharmacology studies of morphiceptin analogues - Selective μ-opioid receptor ligands
    • A. Janecka, J. Fichna, M. Mirowski, and T. Janecki Structure-activity relationship, conformation and pharmacology studies of morphiceptin analogues - selective μ-opioid receptor ligands Mini Rev Med Chem 2 2002 565 572
    • (2002) Mini Rev Med Chem , vol.2 , pp. 565-572
    • Janecka, A.1    Fichna, J.2    Mirowski, M.3    Janecki, T.4
  • 25
    • 0032860434 scopus 로고    scopus 로고
    • The mu-opioid receptor gene-dose dependent reductions in G-protein activation in the pons/medulla and antinociception induced by endomorphins in mu-opioid receptor knockout mice
    • H. Mizoguchi, M. Narita, D.E. Oji, C. Suganuma, H. Nagase, and I. Sora The mu-opioid receptor gene-dose dependent reductions in G-protein activation in the pons/medulla and antinociception induced by endomorphins in mu-opioid receptor knockout mice Neuroscience 94 1999 203 207
    • (1999) Neuroscience , vol.94 , pp. 203-207
    • Mizoguchi, H.1    Narita, M.2    Oji, D.E.3    Suganuma, C.4    Nagase, H.5    Sora, I.6
  • 26
    • 0036023897 scopus 로고    scopus 로고
    • The antinociceptive properties of endomorphin-1 and endomorphin-2 in the mouse
    • L.F. Tseng The antinociceptive properties of endomorphin-1 and endomorphin-2 in the mouse Jpn J Pharmacol 89 2002 216 220
    • (2002) Jpn J Pharmacol , vol.89 , pp. 216-220
    • Tseng, L.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.