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Volumn 50, Issue 12, 2007, Pages 2753-2766

Bifunctional [2′,6′-dimethyl-L-tyrosine1] endomorphin-2 analogues substituted at position 3 with alkylated phenylalanine derivatives yield potent mixed μ-agonist/δ-antagonist and dual μ-agonist/δ-agonist opioid ligands

Author keywords

[No Author keywords available]

Indexed keywords

2',6' DIMETHYLTYROSYLPROLYL 2' ETHYL 6' METHYLPHENYLALANYLPHENYLALANYLAMIDE; 2',6' DIMETHYLTYROSYLPROLYL 2' ISOPROPYL 6' METHYLPHENYLALANYLPHENYLALANYLAMIDE; 2',6' DIMETHYLTYROSYLPROLYL 2' METHYLPHENYLALANYLPHENYLALANYLAMIDE; 2',6' DIMETHYLTYROSYLPROLYL 2',4',6' TRIMETHYLPHENYLALANYLPHENYLALANYLAMIDE; 2',6' DIMETHYLTYROSYLPROLYL 2',6' DIMETHYLPHENYLALANYLPHENYLALANYLAMIDE; 2',6' DIMETHYLTYROSYLPROLYL 2',6' DIMETHYLTYROSYLPHENYLALANYLAMIDE; 2',6' DIMETHYLTYROSYLPROLYL 3',5' DIMETHYLPHENYLALANYLPHENYLALANYLAMIDE; DELTA OPIATE RECEPTOR AGONIST; DELTA OPIATE RECEPTOR ANTAGONIST; ENDOMORPHIN 2; ENDORPHIN DERIVATIVE; MU OPIATE RECEPTOR AGONIST; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE; TYROSYLPROLYL 2' ETHYL 6' METHYLPHENYLALANYLPHENYLALANYLAMIDE; TYROSYLPROLYL 2' ISOPROPYL 6' METHYLPHENYLALANYLPHENYLALANYLAMIDE; TYROSYLPROLYL 2' METHYLPHENYLALANYLPHENYLALANYLAMIDE; TYROSYLPROLYL 2',4',6' TRIMETHYLPHENYLALANYLPHENYLALANYLAMIDE; TYROSYLPROLYL 2',6' DIMETHYLPHENYLALANYLPHENYLALANYLAMIDE; TYROSYLPROLYL 2',6' DIMETHYLTYROSYLPHENYLALANYLAMIDE; TYROSYLPROLYL 3',5' DIMETHYLPHENYLALANYLPHENYLALANYLAMIDE; UNCLASSIFIED DRUG; DELTA OPIATE RECEPTOR; DRUG DERIVATIVE; LIGAND; MU OPIATE RECEPTOR; OLIGOPEPTIDE; TYROSINE;

EID: 34250891407     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061238m     Document Type: Article
Times cited : (40)

References (69)
  • 1
    • 0030933655 scopus 로고    scopus 로고
    • Zadina, J. E.; Hackler, L.; Ge, L. J.; Kastin, A. J. A Potent and selective endogenous agonist for the mu-opiate receptor. Nature 1997, 386, 499-502.
    • Zadina, J. E.; Hackler, L.; Ge, L. J.; Kastin, A. J. A Potent and selective endogenous agonist for the mu-opiate receptor. Nature 1997, 386, 499-502.
  • 3
    • 0033832518 scopus 로고    scopus 로고
    • Endomorphin-1 induces antinociception without immunomodulatory effects in the rat
    • Carrigan, K. A.; Nelson, C. J.; Lysle, D. T. Endomorphin-1 induces antinociception without immunomodulatory effects in the rat. Psychopharmacology 2000, 151, 299-305.
    • (2000) Psychopharmacology , vol.151 , pp. 299-305
    • Carrigan, K.A.1    Nelson, C.J.2    Lysle, D.T.3
  • 4
    • 0032051847 scopus 로고    scopus 로고
    • Differential effects of endomorphin-1, endomorphin-2, and Tyr-W-MIF-1 on activation of G-proteins in SH-SY5Y human neuroblastoma membranes
    • Harrison, L. M.; Kastin, A. J.; Zadina, J. E. Differential effects of endomorphin-1, endomorphin-2, and Tyr-W-MIF-1 on activation of G-proteins in SH-SY5Y human neuroblastoma membranes. Peptides 1998, 19, 749-753.
    • (1998) Peptides , vol.19 , pp. 749-753
    • Harrison, L.M.1    Kastin, A.J.2    Zadina, J.E.3
  • 6
    • 0034647838 scopus 로고    scopus 로고
    • Analgesic effects of endomorphin-1 and endomorphin-2 in the formalin test in mice
    • Soignier, R. D.; Vaccarino, A. L.; Brennan, A. M.; Kastin, A. J.; Zadina, J. E. Analgesic effects of endomorphin-1 and endomorphin-2 in the formalin test in mice. Life Sci. 2000, 67, 907-912.
    • (2000) Life Sci , vol.67 , pp. 907-912
    • Soignier, R.D.1    Vaccarino, A.L.2    Brennan, A.M.3    Kastin, A.J.4    Zadina, J.E.5
  • 7
    • 0038066385 scopus 로고    scopus 로고
    • Endomorphin-1 and -2 induced naloxone-precipitated withdrawal syndromes in rats
    • Chen.; J.-C.; Tao, P.-L.; Li, J.-Y.; Wong, C.-H.; Huang, E. Y.-K. Endomorphin-1 and -2 induced naloxone-precipitated withdrawal syndromes in rats. Peptides 2003, 24, 477-481.
    • (2003) Peptides , vol.24 , pp. 477-481
    • Chen, J.-C.1    Tao, P.-L.2    Li, J.-Y.3    Wong, C.-H.4    Huang, E.Y.-K.5
  • 8
    • 23844480802 scopus 로고    scopus 로고
    • Endomorphins interact with tachykinin receptors
    • Kosson, P.; Bonney, I.; Carr, D. B.; Lipkowski, A. W. Endomorphins interact with tachykinin receptors. Peptides 2005, 26, 1667-1669.
    • (2005) Peptides , vol.26 , pp. 1667-1669
    • Kosson, P.1    Bonney, I.2    Carr, D.B.3    Lipkowski, A.W.4
  • 10
    • 0141504412 scopus 로고    scopus 로고
    • Conformational analysis of endomorphin-1 by molecular dynamics methods
    • Leitgeb, B.; Szekeres, A.; Tóth, G. Conformational analysis of endomorphin-1 by molecular dynamics methods. J. Peptide Res. 2003, 62, 145-157.
    • (2003) J. Peptide Res , vol.62 , pp. 145-157
    • Leitgeb, B.1    Szekeres, A.2    Tóth, G.3
  • 11
    • 17144452429 scopus 로고    scopus 로고
    • Conformational analysis of the endogenous μ-opioid agonist endomorphin-1 using NMR spectroscopy and molecular modeling
    • Podlogar, B. L.; Paterlini, G.; Ferguson, D. M.; Leo, G. C.; Demeter, D. A.; Brown, F. K.; Reitz, A. B. Conformational analysis of the endogenous μ-opioid agonist endomorphin-1 using NMR spectroscopy and molecular modeling. FEBS Lett. 1998, 439, 13-20.
    • (1998) FEBS Lett , vol.439 , pp. 13-20
    • Podlogar, B.L.1    Paterlini, G.2    Ferguson, D.M.3    Leo, G.C.4    Demeter, D.A.5    Brown, F.K.6    Reitz, A.B.7
  • 12
    • 0344500751 scopus 로고    scopus 로고
    • Preferred conformation of endomorphin-1 in aqueous and membrane-mimetic environments
    • Fiori, S.; Renner, C.; Cramer, J.; Pegoraro, S.; Moroder, L. Preferred conformation of endomorphin-1 in aqueous and membrane-mimetic environments. J. Mol. Biol. 1999, 291, 163-175.
    • (1999) J. Mol. Biol , vol.291 , pp. 163-175
    • Fiori, S.1    Renner, C.2    Cramer, J.3    Pegoraro, S.4    Moroder, L.5
  • 13
    • 0035829437 scopus 로고    scopus 로고
    • Pseudoproline-containing analogues of morphiceptin and endomorphin-2: Evidence for a cis-Tyr-Pro amide bond in the bioactive conformation
    • Keller, M.; Boissard, C.; Patiny, L.; Chung, N. N.; Lemieux, C.; Mutter, M.; Schiller, P. W. Pseudoproline-containing analogues of morphiceptin and endomorphin-2: evidence for a cis-Tyr-Pro amide bond in the bioactive conformation. J. Med. Chem. 2001, 44, 3896-3903.
    • (2001) J. Med. Chem , vol.44 , pp. 3896-3903
    • Keller, M.1    Boissard, C.2    Patiny, L.3    Chung, N.N.4    Lemieux, C.5    Mutter, M.6    Schiller, P.W.7
  • 17
    • 4744353375 scopus 로고    scopus 로고
    • Synthesis and evaluation of the affinity toward μ-opioid receptors of atypical, lipophilic ligands based on the sequence c[-Tyr-Pro-Trp-Phe-Gly-]
    • Cadillo, G.; Gentilucci, L.; Tolomelli, A.; Spinosa, R.; Calienni, M.; Qasen, A.; Spampinato, S. Synthesis and evaluation of the affinity toward μ-opioid receptors of atypical, lipophilic ligands based on the sequence c[-Tyr-Pro-Trp-Phe-Gly-]. J. Med. Chem. 2004, 47, 5198-5203.
    • (2004) J. Med. Chem , vol.47 , pp. 5198-5203
    • Cadillo, G.1    Gentilucci, L.2    Tolomelli, A.3    Spinosa, R.4    Calienni, M.5    Qasen, A.6    Spampinato, S.7
  • 20
    • 0037030643 scopus 로고    scopus 로고
    • Endomorphin-1 analogues containing β-proline are μ-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance
    • Cardillo, G.; Gentilucci, L.; Qasem, A. R.; Sgarzi, F.; Spampinato, S. Endomorphin-1 analogues containing β-proline are μ-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance. J. Med. Chem. 2002, 45, 2571-2578.
    • (2002) J. Med. Chem , vol.45 , pp. 2571-2578
    • Cardillo, G.1    Gentilucci, L.2    Qasem, A.R.3    Sgarzi, F.4    Spampinato, S.5
  • 21
    • 19944408240 scopus 로고    scopus 로고
    • Structure-activity relationships of novel endomorphin-2 analogues with N-O turns induced by α-aminoxy acids
    • Wei, J.; Shao, X.; Gong, M.-Z.; Zhu, B.-B.; Cui, Y.-X.; Gao, Y.-F.; Wang, R. Structure-activity relationships of novel endomorphin-2 analogues with N-O turns induced by α-aminoxy acids. Bioorg. Med. Chem. Lett. 2005, 15, 2986-2989.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 2986-2989
    • Wei, J.1    Shao, X.2    Gong, M.-Z.3    Zhu, B.-B.4    Cui, Y.-X.5    Gao, Y.-F.6    Wang, R.7
  • 26
    • 15044364083 scopus 로고    scopus 로고
    • Structure-activity relationship of the novel bivalent and C-terminal modified analogues of endomorphin-2
    • Gao, Y.-F.; Liu, X.; Wei, J.; Zhu, B.-B.; Chen, Q.; Wang, R. Structure-activity relationship of the novel bivalent and C-terminal modified analogues of endomorphin-2. Bioorg. Med. Chem. Lett. 2005, 15, 1847-1850.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 1847-1850
    • Gao, Y.-F.1    Liu, X.2    Wei, J.3    Zhu, B.-B.4    Chen, Q.5    Wang, R.6
  • 27
    • 0024334804 scopus 로고
    • Recent development in the design of receptor specific opioid peptides
    • Hruby, V. J.; Gehrig, C. A. Recent development in the design of receptor specific opioid peptides. Med. Res. Rev. 1989, 9, 343-401.
    • (1989) Med. Res. Rev , vol.9 , pp. 343-401
    • Hruby, V.J.1    Gehrig, C.A.2
  • 30
    • 0030065629 scopus 로고    scopus 로고
    • Opioid infidelity. Novel opioid agonists with dual high affinities for δ and μ receptors
    • (a) Lazarus, L. H.; Bryant, S. D.; Salvadori, S.; Attila, M.; Jones, L. S. Opioid infidelity. Novel opioid agonists with dual high affinities for δ and μ receptors. Trends Neurosci. 1998, 19, 31-35.
    • (1998) Trends Neurosci , vol.19 , pp. 31-35
    • Lazarus, L.H.1    Bryant, S.D.2    Salvadori, S.3    Attila, M.4    Jones, L.S.5
  • 35
    • 32844464020 scopus 로고    scopus 로고
    • ORL1 and opioid receptor preferences of nociceptin and dynorphin A analogues with Dmp substituted for N-terminal aromatic residues
    • Sasaki, Y.; Kawano, S.; Kohara, H.; Watanabe, H.; Ambo, A. ORL1 and opioid receptor preferences of nociceptin and dynorphin A analogues with Dmp substituted for N-terminal aromatic residues. Bioorg. Med. Chem. 2006, 14, 2433-2437.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 2433-2437
    • Sasaki, Y.1    Kawano, S.2    Kohara, H.3    Watanabe, H.4    Ambo, A.5
  • 36
    • 0035847697 scopus 로고    scopus 로고
    • Enkephalin analogues with 2′,6′-dimethylphenylalanine replacing phenylalanine in position 4
    • Sasaki, Y.; Hirabuki, M.; Ambo, A.; Ouchi, H.; Yamamoto, Y. Enkephalin analogues with 2′,6′-dimethylphenylalanine replacing phenylalanine in position 4. Bioorg. Med. Chem. Lett. 2001, 11, 327-329.
    • (2001) Bioorg. Med. Chem. Lett , vol.11 , pp. 327-329
    • Sasaki, Y.1    Hirabuki, M.2    Ambo, A.3    Ouchi, H.4    Yamamoto, Y.5
  • 37
    • 0037170786 scopus 로고    scopus 로고
    • Dermorphin and deltorphin heptapeptide analogues: Replacement of Phe residue by Dmp greatly improves opioid receptor affinity and selectivity
    • Ambo, A.; Murase, H.; Niizuma, H.; Ouchi, H.; Yamamoto, Y.; Sasaki, Y. Dermorphin and deltorphin heptapeptide analogues: replacement of Phe residue by Dmp greatly improves opioid receptor affinity and selectivity. Bioorg. Med. Chem. Lett. 2002, 12, 879-881.
    • (2002) Bioorg. Med. Chem. Lett , vol.12 , pp. 879-881
    • Ambo, A.1    Murase, H.2    Niizuma, H.3    Ouchi, H.4    Yamamoto, Y.5    Sasaki, Y.6
  • 38
    • 0037424706 scopus 로고    scopus 로고
    • Dermorphin tetrapeptide analogues with 2′,6′-dimethylphenylalanine (Dmp) substituted for aromatic amino acids have high μ opioid receptor binding and biological activities
    • Ambo, A.; Niizuma, H.; Sasaki, A.; Kohara, H.; Sasaki, Y. Dermorphin tetrapeptide analogues with 2′,6′-dimethylphenylalanine (Dmp) substituted for aromatic amino acids have high μ opioid receptor binding and biological activities. Bioorg. Med. Chem. Lett. 2003, 13, 1269-1272.
    • (2003) Bioorg. Med. Chem. Lett , vol.13 , pp. 1269-1272
    • Ambo, A.1    Niizuma, H.2    Sasaki, A.3    Kohara, H.4    Sasaki, Y.5
  • 39
    • 0037356635 scopus 로고    scopus 로고
    • Endomorphin 2 analogues containing Dmp residues as an aromatic amino acid surrogate with high μ-opioid receptor affinity and selectivity
    • Sasaki, Y.; Sasaki, A.; Niizuma, H.; Goto, H.; Ambo, A. Endomorphin 2 analogues containing Dmp residues as an aromatic amino acid surrogate with high μ-opioid receptor affinity and selectivity. Bioorg. Med. Chem. 2003, 11, 675-678.
    • (2003) Bioorg. Med. Chem , vol.11 , pp. 675-678
    • Sasaki, Y.1    Sasaki, A.2    Niizuma, H.3    Goto, H.4    Ambo, A.5
  • 43
    • 0027055922 scopus 로고
    • Permeability of the blood-brain barrier to peptides: An approach to the development of therapeutically useful drugs
    • (a) Banks, W. A.; Audus, K. L.; Davis, T. P. Permeability of the blood-brain barrier to peptides: an approach to the development of therapeutically useful drugs. Peptides 1992, 13, 1289-1292.
    • (1992) Peptides , vol.13 , pp. 1289-1292
    • Banks, W.A.1    Audus, K.L.2    Davis, T.P.3
  • 44
    • 0030893316 scopus 로고    scopus 로고
    • Blood-brain barrier permeability and bioavailability of a highly potent and μ-selective opioid receptor antagonist, CTAP: Comparison with morphine
    • (b) Abbruscato, T.; Thomas, S.; Hruby, V.; Davis, T. Blood-brain barrier permeability and bioavailability of a highly potent and μ-selective opioid receptor antagonist, CTAP: comparison with morphine. J. Pharmacol. Exp. Ther. 1997, 280, 402-409.
    • (1997) J. Pharmacol. Exp. Ther , vol.280 , pp. 402-409
    • Abbruscato, T.1    Thomas, S.2    Hruby, V.3    Davis, T.4
  • 45
    • 0031763418 scopus 로고    scopus 로고
    • Transport of opioid peptides into the central nervous system
    • (c) Egleton, R. D.; Abbruscato, T. J.; Thomas, S. A.; Davis, T. P. Transport of opioid peptides into the central nervous system. J. Pharm. Sci. 1998, 87, 1433-1439.
    • (1998) J. Pharm. Sci , vol.87 , pp. 1433-1439
    • Egleton, R.D.1    Abbruscato, T.J.2    Thomas, S.A.3    Davis, T.P.4
  • 48
    • 0030880687 scopus 로고    scopus 로고
    • Evolution of the Dmt-Tic pharmacophore: N-terminal methylated derivatives with extraordinary δ opioid antagonist activity
    • (a) Salvadori, S.; Balboni, G.; Guerrini, R.; Tomatis, R.; Bianchi, C.; Bryant, S. D.; Cooper, P. S.; Lazarus, L. H. Evolution of the Dmt-Tic pharmacophore: N-terminal methylated derivatives with extraordinary δ opioid antagonist activity. J. Med. Chem. 1997, 40, 3100-3108.
    • (1997) J. Med. Chem , vol.40 , pp. 3100-3108
    • Salvadori, S.1    Balboni, G.2    Guerrini, R.3    Tomatis, R.4    Bianchi, C.5    Bryant, S.D.6    Cooper, P.S.7    Lazarus, L.H.8
  • 49
  • 51
    • 0028788399 scopus 로고
    • Attenuation of morphine tolerance and dependence with the highly selective δ-opioid receptor antagonist TTPP[Ψ]
    • Fundytus, M.; Schiller, P.; Shapiro, M.; Wetrowska, G.; Coderre, T. J. Attenuation of morphine tolerance and dependence with the highly selective δ-opioid receptor antagonist TTPP[Ψ]. Eur. J. Pharmacol. 1995, 286, 105-108.
    • (1995) Eur. J. Pharmacol , vol.286 , pp. 105-108
    • Fundytus, M.1    Schiller, P.2    Shapiro, M.3    Wetrowska, G.4    Coderre, T.J.5
  • 53
    • 33744761796 scopus 로고    scopus 로고
    • Enantioselective synthesis of a phenylalanine library containing alkyl groups on the aromatic moiety: Confirmation of stereostructure by X-ray analysis
    • Li, T.; Tsuda, Y.; Minoura, K.; In, Y.; Ishida, T.; Lazarus, L. H.; Okada, Y. Enantioselective synthesis of a phenylalanine library containing alkyl groups on the aromatic moiety: confirmation of stereostructure by X-ray analysis. Chem. Pharm. Bull. 2006, 54, 873-877.
    • (2006) Chem. Pharm. Bull , vol.54 , pp. 873-877
    • Li, T.1    Tsuda, Y.2    Minoura, K.3    In, Y.4    Ishida, T.5    Lazarus, L.H.6    Okada, Y.7
  • 54
    • 0025234616 scopus 로고
    • Opioid peptides: Synthesis and biological properties of dermorphin related hexapeptides
    • Salvadori, S.; Marastoni, M.; Balboni, G.; Borea, P.; Tomatis, R. Opioid peptides: synthesis and biological properties of dermorphin related hexapeptides. Eur. J. Med. Chem. 1990, 25, 171-177.
    • (1990) Eur. J. Med. Chem , vol.25 , pp. 171-177
    • Salvadori, S.1    Marastoni, M.2    Balboni, G.3    Borea, P.4    Tomatis, R.5
  • 56
    • 33746541095 scopus 로고    scopus 로고
    • Opioid receptor binding and antinociceptive activity of the analogues of endomorphin-2 and morphiceptin with phenylalanine mimics in the position 3 or 4
    • Gao, Y.-F.; Liu, X.; Liu, W.-X.; Qi, Y.-M.; Liu, X.-F.; Zhou, Y.-F.; Wang, R. Opioid receptor binding and antinociceptive activity of the analogues of endomorphin-2 and morphiceptin with phenylalanine mimics in the position 3 or 4. Bioorg. Med. Chem. Lett. 2006, 16, 3688-3692.
    • (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 3688-3692
    • Gao, Y.-F.1    Liu, X.2    Liu, W.-X.3    Qi, Y.-M.4    Liu, X.-F.5    Zhou, Y.-F.6    Wang, R.7
  • 57
    • 0037309774 scopus 로고    scopus 로고
    • Synthesis and evaluation of potential affinity labels derived from endomorphin-2
    • Chao, H.; Murray, T. F.; Aldrich, J. V. Synthesis and evaluation of potential affinity labels derived from endomorphin-2. J. Peptide Res. 2003, 61, 58-62.
    • (2003) J. Peptide Res , vol.61 , pp. 58-62
    • Chao, H.1    Murray, T.F.2    Aldrich, J.V.3
  • 58
    • 2542625998 scopus 로고    scopus 로고
    • 2 phenotypes. Selective targeting of δ-κ heterodimers. J. Med. Chem. 2004, 47, 2969-2972.
    • 2 phenotypes. Selective targeting of δ-κ heterodimers. J. Med. Chem. 2004, 47, 2969-2972.
  • 59
    • 15744401602 scopus 로고    scopus 로고
    • Heterodimerizaiton of μ- and δ-opioid receptors occurs at the cell surface only and requires receptor-G protein interaction
    • (b) Law, P.-Y.; Ericson-Herbandson, L. J.; Zha, Q. Q.; Solberg, J.; Chu, J.; Sarre, A.; Loh, H. H. Heterodimerizaiton of μ- and δ-opioid receptors occurs at the cell surface only and requires receptor-G protein interaction. J. Biol. Chem. 2005, 280, 11152-11164.
    • (2005) J. Biol. Chem , vol.280 , pp. 11152-11164
    • Law, P.-Y.1    Ericson-Herbandson, L.J.2    Zha, Q.Q.3    Solberg, J.4    Chu, J.5    Sarre, A.6    Loh, H.H.7
  • 60
    • 33745934035 scopus 로고    scopus 로고
    • μ-δ opioid receptor functional interaction: Insight using receptor-G protein fusions
    • (c) Snook, L. A.; Milligan, G.; Kieffer, B. L.; Massotte, D. μ-δ opioid receptor functional interaction: insight using receptor-G protein fusions. J. Pharmacol. Exp. Ther. 2006, 318, 683-690.
    • (2006) J. Pharmacol. Exp. Ther , vol.318 , pp. 683-690
    • Snook, L.A.1    Milligan, G.2    Kieffer, B.L.3    Massotte, D.4
  • 61
    • 1842687121 scopus 로고    scopus 로고
    • Gomes, I.; Gupta, A.; Filipovska, J.; Szeto, H. H.; Pintar, J. E.; Devi, L. A. A role of heterodimerization of μ and δ opiate receptors in enhancing morphine analgesia. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5135-5139.
    • Gomes, I.; Gupta, A.; Filipovska, J.; Szeto, H. H.; Pintar, J. E.; Devi, L. A. A role of heterodimerization of μ and δ opiate receptors in enhancing morphine analgesia. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5135-5139.
  • 62
    • 30044442319 scopus 로고    scopus 로고
    • Opioid-induced tolerance and dependence in mice is modulated by the distance between pharmacophores in a bivalent ligand series
    • Daniels, D. J.; Lenard, N. R.; Etienne, C. L.; Law, P.-Y.; Roerig, S. C.; Portoghese, P. S. Opioid-induced tolerance and dependence in mice is modulated by the distance between pharmacophores in a bivalent ligand series. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 19208-19213.
    • (2005) Proc. Natl. Acad. Sci. U.S.A , vol.102 , pp. 19208-19213
    • Daniels, D.J.1    Lenard, N.R.2    Etienne, C.L.3    Law, P.-Y.4    Roerig, S.C.5    Portoghese, P.S.6
  • 64
    • 0025827095 scopus 로고
    • Selective blockage of delta opioid receptors prevents the development of morphine tolerance and dependence in mice
    • Abdelhamid, E. E.; Sultana, M.; Portoghese, P. S.; Takemori, A. E. Selective blockage of delta opioid receptors prevents the development of morphine tolerance and dependence in mice. J. Pharmacol. Exp. Ther. 1991, 258, 299-303.
    • (1991) J. Pharmacol. Exp. Ther , vol.258 , pp. 299-303
    • Abdelhamid, E.E.1    Sultana, M.2    Portoghese, P.S.3    Takemori, A.E.4
  • 65
    • 34250902344 scopus 로고    scopus 로고
    • Bryant, S. D.; Salvadori, S.; Okada, Y.; Takahshi, M.; Sasaki, Y.; Lazarus, L. H. Computational Chemistry and Opioidmimetics: Receptor Ligand Interaction of Three Classes of Biologically Potent Peptides. In Peptide 2000; Martinez, J., Fehrentz, J.-A., Eds., Editions EDK: Paris, 2001; pp 407-408.
    • Bryant, S. D.; Salvadori, S.; Okada, Y.; Takahshi, M.; Sasaki, Y.; Lazarus, L. H. Computational Chemistry and Opioidmimetics: Receptor Ligand Interaction of Three Classes of Biologically Potent Peptides. In Peptide 2000; Martinez, J., Fehrentz, J.-A., Eds., Editions EDK: Paris, 2001; pp 407-408.
  • 69
    • 0009644628 scopus 로고
    • Some quantitative uses of drug antagonists
    • Arunlakshana, O.; Schild, H. O. Some quantitative uses of drug antagonists. Br. J. Pharmacol. 1959, 14, 48-58.
    • (1959) Br. J. Pharmacol , vol.14 , pp. 48-58
    • Arunlakshana, O.1    Schild, H.O.2


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