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Volumn 49, Issue 18, 2006, Pages 5610-5617

Effect of lysine at C-terminus of the Dmt-Tic opioid pharmacophore

Author keywords

[No Author keywords available]

Indexed keywords

2',6' DIMETHYLTYROSYL 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXYLIC ACID DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; DELTA OPIATE RECEPTOR AGONIST; DELTA OPIATE RECEPTOR ANTAGONIST; GLYCINE; LYSINE; MU OPIATE RECEPTOR AGONIST; PEPTIDE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33748545633     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060741w     Document Type: Article
Times cited : (25)

References (48)
  • 1
    • 0003177483 scopus 로고
    • Abbreviations. In addition to the IUPAC-IUB Commission on Biochemical Nomenclature (J. Biol. Chem. 1985, 260, 14-42), this paper uses additional symbols and abbreviations, which are listed in Abbreviations.
    • (1985) J. Biol. Chem. , vol.260 , pp. 14-42
  • 3
    • 0033518261 scopus 로고    scopus 로고
    • Further studies on the Dmt-Tic pharmacophore: Hydrophobic substituents at the C-terminus endow δ antagonists to manifest μ agonism or δ antagonism
    • Salvadori, S.; Guerrini, R.; Balboni, G.; Bianchi, C.; Bryant, S. D.; Cooper, P. S.; Lazarus, L. H. Further studies on the Dmt-Tic pharmacophore: hydrophobic substituents at the C-terminus endow δ antagonists to manifest μ agonism or δ antagonism. J. Med. Chem. 1999, 42, 5010-5019.
    • (1999) J. Med. Chem. , vol.42 , pp. 5010-5019
    • Salvadori, S.1    Guerrini, R.2    Balboni, G.3    Bianchi, C.4    Bryant, S.D.5    Cooper, P.S.6    Lazarus, L.H.7
  • 5
    • 0027049066 scopus 로고
    • Differential stereochemical requirements of μ vs δ opioid receptors for ligand binding and signal transduction: Development of a class of potent and highly δ-selective peptide antagonists
    • Schiller, P. W.; Nguyen, T. M.-D.; Weltrowska, G.; Wilkes, B. C.; Marsden, B. J.; Lemieux, C.; Chung, N. N. Differential stereochemical requirements of μ vs δ opioid receptors for ligand binding and signal transduction: development of a class of potent and highly δ-selective peptide antagonists. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 11871-11875.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 11871-11875
    • Schiller, P.W.1    Nguyen, T.M.-D.2    Weltrowska, G.3    Wilkes, B.C.4    Marsden, B.J.5    Lemieux, C.6    Chung, N.N.7
  • 8
    • 0030880687 scopus 로고    scopus 로고
    • Evolution of the Dmt-Tic pharmacophore: N-Terminal methylated derivatives with extraordinary δ opioid antagonist activity
    • 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
  • 11
    • 0037204052 scopus 로고    scopus 로고
    • Evaluation of the Dmt-Tic pharmacophore: Conversion of a potent δ-opioid receptor antagonist into a potent δ-agonist and ligands with mixed properties
    • Balboni, G.; Guerrini, R.; Salvadori, S.; Bianchi, C.; Rizzi, D.; Bryant, S. D.; Lazarus, L. H. 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. 2002, 45, 713-720.
    • (2002) J. Med. Chem. , vol.45 , pp. 713-720
    • Balboni, G.1    Guerrini, R.2    Salvadori, S.3    Bianchi, C.4    Rizzi, D.5    Bryant, S.D.6    Lazarus, L.H.7
  • 18
    • 33644805964 scopus 로고    scopus 로고
    • Opioid peptide-derived analgesics
    • Schiller, P. W. Opioid peptide-derived analgesics. AAPS Journal 2005, 7, E560-E565.
    • (2005) AAPS Journal , vol.7
    • Schiller, P.W.1
  • 19
    • 3242811223 scopus 로고    scopus 로고
    • Direct influence of the C-terminally substituted amino acids in the Dmt-Tic pharmacophore on δ-opioid receptor selectivity and antagonism
    • Balboni, G.; Salvadori, S.; Guerrini, R.; Negri, L.; Giannini, E.; Bryant, S. D.; Jinsmaa, Y.; Lazarus, L. H. Direct influence of the C-terminally substituted amino acids in the Dmt-Tic pharmacophore on δ-opioid receptor selectivity and antagonism. J. Med. Chem. 2004, 47, 4066-4071.
    • (2004) J. Med. Chem. , vol.47 , pp. 4066-4071
    • Balboni, G.1    Salvadori, S.2    Guerrini, R.3    Negri, L.4    Giannini, E.5    Bryant, S.D.6    Jinsmaa, Y.7    Lazarus, L.H.8
  • 23
    • 12144289451 scopus 로고    scopus 로고
    • Identification of opioid ligands possessing mixed μ agonist/δ antagonist activity among pyridomorphinans derived from naloxone, oxymorphone and hydromorphone
    • Ananthan, S.; Khare, N. K.; Saini, S. K.; Seitz, L. E.; Bartlett, J. L.; Davis, P.; Dersch, C. M.; Porreca, F.; Rothman, R. B.; Bilsky, E. J. Identification of opioid ligands possessing mixed μ agonist/δ antagonist activity among pyridomorphinans derived from naloxone, oxymorphone and hydromorphone. J. Med. Chem. 2004, 47, 1400-1412.
    • (2004) J. Med. Chem. , vol.47 , pp. 1400-1412
    • Ananthan, S.1    Khare, N.K.2    Saini, S.K.3    Seitz, L.E.4    Bartlett, J.L.5    Davis, P.6    Dersch, C.M.7    Porreca, F.8    Rothman, R.B.9    Bilsky, E.J.10
  • 25
    • 31344460390 scopus 로고    scopus 로고
    • Peptidic delta opioid receptor agonists produce antidepressant-like effects in the forced swim test and regulate BDNF mRNA expression in rats
    • and references herein
    • Torregrossa, M. M.; Jutkiewicz, E. M.; Mosberg, H. I.; Balboni, G.; Watson, S. J.; 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. 2006, 1069, 172-181 and references herein.
    • (2006) Brain Res. , vol.1069 , pp. 172-181
    • Torregrossa, M.M.1    Jutkiewicz, E.M.2    Mosberg, H.I.3    Balboni, G.4    Watson, S.J.5    Woods, J.H.6
  • 26
    • 3843124281 scopus 로고    scopus 로고
    • Potential anxiolytic and antidepressant-like activities of SNC80, a selective delta-opioid agonist, in behavioral models in rodents
    • Saitoh, A.; Kimura, Y.; Suzuki, T.; Kawai, K.; Nagase, H.; Kamei, J. Potential anxiolytic and antidepressant-like activities of SNC80, a selective delta-opioid agonist, in behavioral models in rodents. J. Pharmacol. Sci. 2004, 95, 374-380.
    • (2004) J. Pharmacol. Sci. , vol.95 , pp. 374-380
    • Saitoh, A.1    Kimura, Y.2    Suzuki, T.3    Kawai, K.4    Nagase, H.5    Kamei, J.6
  • 27
    • 30044451754 scopus 로고    scopus 로고
    • The immunomodulator glatiramer acetate augments the expression of neurotrophic factors in brains of experimental autoimmune encephalomyelitis mice
    • Aharoni, R.; Eilam, R.; Domev, H.; Labunskay, G.; Sela, M.; Arnon, R. The immunomodulator glatiramer acetate augments the expression of neurotrophic factors in brains of experimental autoimmune encephalomyelitis mice. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 19045-19050.
    • (2005) Proc. Natl. Acad. Sci. U.S.A. , vol.102 , pp. 19045-19050
    • Aharoni, R.1    Eilam, R.2    Domev, H.3    Labunskay, G.4    Sela, M.5    Arnon, R.6
  • 28
    • 0036080357 scopus 로고    scopus 로고
    • Neuroprotective role of delta-opioid receptors in cortical neurons
    • Zhang, J.; Gibney, G. T.; Zhao, P.; Xia, Y. Neuroprotective role of delta-opioid receptors in cortical neurons. Am. J. Physiol. 2002, 282, C1225-C1234.
    • (2002) Am. J. Physiol. , vol.282
    • Zhang, J.1    Gibney, G.T.2    Zhao, P.3    Xia, Y.4
  • 29
    • 19444382560 scopus 로고    scopus 로고
    • 5) enkephalin: Linking hibernation and neuroprotection
    • 5) enkephalin: linking hibernation and neuroprotection. Front. Biosci. 2004, 9, 3392-3398.
    • (2004) Front. Biosci. , vol.9 , pp. 3392-3398
    • Borlongan, C.V.1    Wang, Y.2    Su, T.P.3
  • 31
    • 0346368469 scopus 로고    scopus 로고
    • Exogenous activation of delta- and kappa-opioid receptors affords cardioprotection in isolated murine heart
    • Peart, J. N.; Gross, G. J. Exogenous activation of delta- and kappa-opioid receptors affords cardioprotection in isolated murine heart. Basic Res. Cardiol. 2004, 99, 29-37.
    • (2004) Basic Res. Cardiol. , vol.99 , pp. 29-37
    • Peart, J.N.1    Gross, G.J.2
  • 33
    • 0030933655 scopus 로고    scopus 로고
    • A potent and selective endogenous agonist for the mu opiate receptor
    • 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.
    • (1997) Nature , vol.386 , pp. 499-502
    • Zadina, J.E.1    Hackler, L.2    Ge, L.J.3    Kastin, A.J.4
  • 35
    • 20444428364 scopus 로고    scopus 로고
    • NPY-induced feeding: Pharmacological characterization using selective opioid antagonists and antisense probes in rats
    • Israel, Y.; Kandov, Y.; Khaimova, E.; Kest, A.; Lewis, S. R.; Pasternak, G. W.; Pan, Y. X.; Rossi, G. C.; Bodnar, R. J. NPY-induced feeding: pharmacological characterization using selective opioid antagonists and antisense probes in rats. Peptides 2005, 26, 1167-1175.
    • (2005) Peptides , vol.26 , pp. 1167-1175
    • Israel, Y.1    Kandov, Y.2    Khaimova, E.3    Kest, A.4    Lewis, S.R.5    Pasternak, G.W.6    Pan, Y.X.7    Rossi, G.C.8    Bodnar, R.J.9
  • 38
    • 0035111309 scopus 로고    scopus 로고
    • Ethanol consumption and reward are decreased in μ-opiate receptor knockout mice
    • (c) Hall, F. S.; Sora, I.; Uhl, G. R. Ethanol consumption and reward are decreased in μ-opiate receptor knockout mice. Psychopharmacology 2001, 154, 43-49.
    • (2001) Psychopharmacology , vol.154 , pp. 43-49
    • Hall, F.S.1    Sora, I.2    Uhl, G.R.3
  • 40
    • 2442658861 scopus 로고    scopus 로고
    • Opioids and alcoholism
    • (e) Oswald, L. H.; Wand, G. S. Opioids and alcoholism. Physiol. Behav. 2004, 81, 339-358.
    • (2004) Physiol. Behav. , vol.81 , pp. 339-358
    • Oswald, L.H.1    Wand, G.S.2
  • 42
    • 0027511496 scopus 로고
    • Interaction of deltorphin with opioid receptors: Molecular determinants for affinity and selectivity
    • Lazarus, L. H.; Salvadori, S.; Attila, M.; Grieco, P.; Bundy, D. M.; Wilson, W. E.; Tomatis, R. Interaction of deltorphin with opioid receptors: Molecular determinants for affinity and selectivity. Peptides 1993, 14, 21-28.
    • (1993) Peptides , vol.14 , pp. 21-28
    • Lazarus, L.H.1    Salvadori, S.2    Attila, M.3    Grieco, P.4    Bundy, D.M.5    Wilson, W.E.6    Tomatis, R.7
  • 43
    • 0024519402 scopus 로고
    • Dermorphin gene sequence peptide with high affinity and selectivity for δ-opioid receptors
    • Lazarus, L. H.; Wilson, W. E.; de Castglione, R.; Guglietta, A. Dermorphin gene sequence peptide with high affinity and selectivity for δ-opioid receptors. J. Biol. Chem. 1989, 264, 3047-3050.
    • (1989) J. Biol. Chem. , vol.264 , pp. 3047-3050
    • Lazarus, L.H.1    Wilson, W.E.2    De Castglione, R.3    Guglietta, A.4
  • 45
    • 0037356635 scopus 로고    scopus 로고
    • Endomorphin 2 analogues containing Dmp residue 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 residue 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
  • 46
    • 0009644628 scopus 로고
    • Some quantitative uses of drug antagonists
    • Arunlakshana, Q.; 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, Q.1    Schild, H.O.2
  • 47
    • 0033551723 scopus 로고    scopus 로고
    • Synthesis of novel proline and γ-lactam derivatives as non-peptide mimics of somatostatin/sandostatin
    • Damour, D.; Herman, F.; Labaudiniere, R.; Pantel, G.; Vuilhorgne, M.; Mignani, S. Synthesis of novel proline and γ-lactam derivatives as non-peptide mimics of somatostatin/sandostatin. Tetrahedron 1999, 55, 10135-10154.
    • (1999) Tetrahedron , vol.55 , pp. 10135-10154
    • Damour, D.1    Herman, F.2    Labaudiniere, R.3    Pantel, G.4    Vuilhorgne, M.5    Mignani, S.6
  • 48
    • 0017092001 scopus 로고
    • Synthese von 2-(1′-amino-1′-substituiertem alkyl)-benzimidazol aus aminosäuren und ihre biologische aktivität
    • Maekawa, K.; Ohtani, J. Synthese von 2-(1′-amino-1′- substituiertem alkyl)-benzimidazol aus aminosäuren und ihre biologische aktivität. Agric. Biol. Chem. 1976, 40, 791-799.
    • (1976) Agric. Biol. Chem. , vol.40 , pp. 791-799
    • Maekawa, K.1    Ohtani, J.2


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