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Volumn 45, Issue 25, 2002, Pages 5556-5563

Potent δ-opioid receptor agonists containing the Dmt-Tic pharmacophore

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 1H BENZIMIDAZOL 2 YL; 2',6' DIMETHYLTYROSINE; AMIDE; AMINO ACID; AROMATIC COMPOUND; ASPARAGINE; ASPARTIC ACID; ASPARTIC ACID DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DELTA OPIATE RECEPTOR; DELTA OPIATE RECEPTOR AGONIST; DELTA OPIATE RECEPTOR ANTAGONIST; LINK PROTEIN; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037028032     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020336e     Document Type: Article
Times cited : (86)

References (46)
  • 1
    • 0003177483 scopus 로고
    • 3CN, sodium cyanoborohydride; NMM, 4-methylmorpholine; NTI, naltrindole; NH-tBut, tert-butylamine; OMe, methyl ester; Pe, petroleum ether; Ph, phenyl; TEA, triethylamine; TFA, trifluoroacetic acid; Tic, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; TIP(P), H-Tyr-Tic-Phe-(Phe)-OH; TLC, thin-layer chromatography; WSC, 1-ethyl-3-[(3′-dimethyl)aminopropyl]carbodiimide hydrochloride; Z, benzyloxycarbonyl.
    • (1985) J. Biol. Chem. , vol.260 , pp. 14-42
  • 2
    • 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
  • 3
    • 0033518261 scopus 로고    scopus 로고
    • Further studies on the Dmt-Tic pharmacophore: Hydrophobic substituents at the C-terminus endows δ antagonists to manifest μ agonism or μ 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 endows δ antagonists to manifest μ agonism or μ 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
  • 4
    • 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
  • 5
    • 0035913055 scopus 로고    scopus 로고
    • Novel C-terminus modifications of the Dmt-Tic motif: A new class of dipeptide analogues showing altered pharmacological profiles toward the opioid receptors
    • 2661
    • Pagé, D.; Naismith, A.; Schmidt, R.; Coupal, M.; Labarre, M.; Gosselin, M.; Bellemare, D.; Payza, K.; Brown, W. Novel C-terminus modifications of the Dmt-Tic motif: A new class of dipeptide analogues showing altered pharmacological profiles toward the opioid receptors. J. Med. Chem. 2661, 44, 2387-2390.
    • J. Med. Chem. , vol.44 , pp. 2387-2390
    • Pagé, D.1    Naismith, A.2    Schmidt, R.3    Coupal, M.4    Labarre, M.5    Gosselin, M.6    Bellemare, D.7    Payza, K.8    Brown, W.9
  • 12
    • 0032713301 scopus 로고    scopus 로고
    • Biological properties of opioid peptides replacing Tyr at position 1 by 2,6-dimethyl-Tyr
    • Sasaki, Y.; Suto, T.; Ambo, A.; Ouchi, H.; Yamamoto, Y. Biological properties of opioid peptides replacing Tyr at position 1 by 2,6-dimethyl-Tyr. Chem. Pharm. Bull. 1999, 47, 1506-1507.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 1506-1507
    • Sasaki, Y.1    Suto, T.2    Ambo, A.3    Ouchi, H.4    Yamamoto, Y.5
  • 18
    • 0012003413 scopus 로고    scopus 로고
    • Development of endomorphin derivatives with dual functions and studies on their three-dimensional structure
    • Lebl, M., Houghten, R. A.; Eds.; American Peptide Society: San Diego, CA
    • Fujita, Y.; Takahashi, M.; Yokoi, T.; Tsuda, Y.; Lazarus, L. H.; Bryant, S. D.; Anbo, A.; Sasaki, Y.; Okada, Y. Development of endomorphin derivatives with dual functions and studies on their three-dimensional structure. In American Peptide Symposium; Lebl, M., Houghten, R. A.; Eds.; American Peptide Society: San Diego, CA, 2001.
    • (2001) American Peptide Symposium
    • Fujita, Y.1    Takahashi, M.2    Yokoi, T.3    Tsuda, Y.4    Lazarus, L.H.5    Bryant, S.D.6    Anbo, A.7    Sasaki, Y.8    Okada, Y.9
  • 22
    • 0344069680 scopus 로고    scopus 로고
    • Endomorphin-1 and endomorphin-2 show differences in their activation of μ opioid receptor-regulated G proteins in supraspinal antinociception in mice
    • Sanchez-Blazquez, P.; Rodriguez-Diaz, M.; deAntonio, I.; Garzon, J. Endomorphin-1 and endomorphin-2 show differences in their activation of μ opioid receptor-regulated G proteins in supraspinal antinociception in mice. J. Pharmacol. Exp. Ther. 1999, 291, 12-19.
    • (1999) J. Pharmacol. Exp. Ther. , vol.291 , pp. 12-19
    • Sanchez-Blazquez, P.1    Rodriguez-Diaz, M.2    DeAntonio, I.3    Garzon, J.4
  • 23
    • 18844476070 scopus 로고    scopus 로고
    • On the spatial disposition of the fifth transmembrane helix and the structural integrity of the transmembrane binding site in the opioid and ORL G protein-coupled receptor family
    • Topham, C. M.; Mouledous, L.; Meunier, J.-C. On the spatial disposition of the fifth transmembrane helix and the structural integrity of the transmembrane binding site in the opioid and ORL G protein-coupled receptor family. Protein Eng. 2000, 13, 477-490.
    • (2000) Protein Eng. , vol.13 , pp. 477-490
    • Topham, C.M.1    Mouledous, L.2    Meunier, J.-C.3
  • 28
    • 0029850452 scopus 로고    scopus 로고
    • Synthesis and activity of pseudotripeptides inhibitors of HIV-1 protease containing D(-)-O-(benzyl)tartaric acid
    • Marastoni, M.; Fantin, G.; Bortolotti, F.; Tomatis, R. Synthesis and activity of pseudotripeptides inhibitors of HIV-1 protease containing D(-)-O-(benzyl)tartaric acid. Arzneim.-Forsch. 1996, 46, 1099-1101.
    • (1996) Arzneim.-Forsch. , vol.46 , pp. 1099-1101
    • Marastoni, M.1    Fantin, G.2    Bortolotti, F.3    Tomatis, R.4
  • 31
    • 0011947794 scopus 로고    scopus 로고
    • Computational chemistry and opioidmimetics: Receptor ligand interaction of three classes of biologically potent peptides
    • Martinez, J., Fehrentz, J.-A., Eds.; Editions EDK: Paris
    • (c) Bryant, S. D.; Salvadori, S.; Okada, Y.; Takahashi, M.; Sasaki, Y.; Lazarus, L. H. Computational chemistry and opioidmimetics: Receptor ligand interaction of three classes of biologically potent peptides. In Peptides 2000; Martinez, J., Fehrentz, J.-A., Eds.; Editions EDK: Paris, 2000; pp 407-408.
    • (2000) Peptides 2000 , pp. 407-408
    • Bryant, S.D.1    Salvadori, S.2    Okada, Y.3    Takahashi, M.4    Sasaki, Y.5    Lazarus, L.H.6
  • 32
    • 0024334804 scopus 로고
    • Recent developments in the design of receptor specific opioid peptides
    • Hruby, V. J.; Gehrig, C. Recent developments 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.2
  • 35
    • 0030070839 scopus 로고    scopus 로고
    • Development of a model for the δ-opioid receptor pharmacophore: 3. Comparison of the cyclic tetrapeptide Try-C[D-Cys-Phe-D-Pen]OH with other conformationally constrained δ-receptor selective ligands
    • Lomize, A. I.; Pogozheva, I.; Mosberg, H. I. Development of a model for the δ-opioid receptor pharmacophore: 3. Comparison of the cyclic tetrapeptide Try-C[D-Cys-Phe-D-Pen]OH with other conformationally constrained δ-receptor selective ligands. Biopolymers 1996, 38, 221-234.
    • (1996) Biopolymers , vol.38 , pp. 221-234
    • Lomize, A.I.1    Pogozheva, I.2    Mosberg, H.I.3
  • 39
    • 0033508973 scopus 로고    scopus 로고
    • The TIPP opioid peptide family: Development of δ antagonists, δ agonists, and mixed μ agonists/δ antagonists
    • Schiller, P. W.; Weltroska, G.; Berezowska, I.; Nguyen, T. M.-D.; Wilkes, B. C.; Lemieux, C.; Chung, N. N. The TIPP opioid peptide family: Development of δ antagonists, δ agonists, and mixed μ agonists/δ antagonists. Biopolymers 1999, 51, 411-425.
    • (1999) Biopolymers , vol.51 , pp. 411-425
    • Schiller, P.W.1    Weltroska, G.2    Berezowska, I.3    Nguyen, T.M.-D.4    Wilkes, B.C.5    Lemieux, C.6    Chung, N.N.7
  • 41
    • 0001292815 scopus 로고
    • Preparation of some benzimidazolyl-amino acids. Reactions of amino acids with o-phenylenediamines
    • Cescon, L. A.; Day, A. R. Preparation of some benzimidazolyl-amino acids. Reactions of amino acids with o-phenylenediamines. J. Org. Chem. 1962, 27, 581-586.
    • (1962) J. Org. Chem. , vol.27 , pp. 581-586
    • Cescon, L.A.1    Day, A.R.2
  • 42
    • 0030272919 scopus 로고    scopus 로고
    • The dermorphin peptide family
    • Melchiorri, P.; Negri, L. The dermorphin peptide family. Gen. Pharmacol. 1996, 27, 1099-1107.
    • (1996) Gen. Pharmacol. , vol.27 , pp. 1099-1107
    • Melchiorri, P.1    Negri, L.2
  • 43
    • 0024494134 scopus 로고
    • Dimeric dermorphin analogues as μ-receptor probes on rat brain membranes. Correlation between central μ-receptor potency and suppression of gastric acid secretion
    • Lazarus, L. H.; Guglietta, A.; Wilson, W. E.; Irons, B. J.; de Castiglione, R. Dimeric dermorphin analogues as μ-receptor probes on rat brain membranes. Correlation between central μ-receptor potency and suppression of gastric acid secretion. J. Biol. Chem. 1989, 264, 354-362.
    • (1989) J. Biol. Chem. , vol.264 , pp. 354-362
    • Lazarus, L.H.1    Guglietta, A.2    Wilson, W.E.3    Irons, B.J.4    De Castiglione, R.5
  • 45
    • 0017121082 scopus 로고
    • Opiate receptor affinities and behavioral effects of enkephalin: Structure-activity relationship of 10 synthetic peptide analogues
    • Chang, J.; Fong, B. Opiate receptor affinities and behavioral effects of enkephalin: Structure-activity relationship of 10 synthetic peptide analogues. Life Sci. 1976, 18, 1473-1482.
    • (1976) Life Sci. , vol.18 , pp. 1473-1482
    • Chang, J.1    Fong, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.