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Volumn 46, Issue 15, 2003, Pages 3201-3209

Unique high-affinity synthetic μ-opioid receptor agonists with central- and systemic-mediated analgesia

Author keywords

[No Author keywords available]

Indexed keywords

ANALGESIC AGENT; AROMATIC COMPOUND; ETHYLENE DERIVATIVE; MORPHINE; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR AGONIST; NALOXONE; TYROSINE DERIVATIVE;

EID: 0038155285     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020459z     Document Type: Article
Times cited : (42)

References (41)
  • 1
    • 0003177483 scopus 로고
    • 2, negative log of the molar concentration required to double the agonist concentration to achieve the original response; Ph, phenyl; PyBOP, benzoltriazol-1-yloxy-trispyrrolidinophosphonium hexafluorphosphate; TEA, triethylamine; TFA, trifluoroacetic acid; TLC, thin-layer chromatography; Z, benzyloxycarbonyl.
    • (1985) J. Biol. Chem. , vol.260 , pp. 14-42
  • 2
    • 0034534528 scopus 로고    scopus 로고
    • Endogenous opiates: 1999
    • Vaccarino, A. L.; Kastin, A. J. Endogenous opiates: 1999. Peptides 2000, 21, 1975-2034.
    • (2000) Peptides , vol.21 , pp. 1975-2034
    • Vaccarino, A.L.1    Kastin, A.J.2
  • 3
    • 0027328548 scopus 로고
    • The toad, ugly and venomous, wears yet a precious jewel in his skin
    • Lazarus, L. H.; Attila, M. The toad, ugly and venomous, wears yet a precious jewel in his skin. Prog. Neurobiol. 1993, 41, 473-507.
    • (1993) Prog. Neurobiol. , vol.41 , pp. 473-507
    • Lazarus, L.H.1    Attila, M.2
  • 5
    • 0026602250 scopus 로고
    • Preparation and opioid activity of analogues of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide
    • Chandrakumar, N. S.; Yonan, P. K.; Stapelfeld, A.; Savage, M.; Rorbacher, E.; Contreras, P. C.; Hammond, D. Preparation and opioid activity of analogues of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide. J. Med. Chem. 1992, 35, 223-233.
    • (1992) J. Med. Chem. , vol.35 , pp. 223-233
    • Chandrakumar, N.S.1    Yonan, P.K.2    Stapelfeld, A.3    Savage, M.4    Rorbacher, E.5    Contreras, P.C.6    Hammond, D.7
  • 9
    • 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
  • 11
    • 0038693669 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 Peptides: The Wave of the Future; Lebl, M., Houghten, R. A., Eds.; American Peptide Society: San Diego, CA, 2001; pp 616-617.
    • (2001) Peptides: The Wave of the Future , pp. 616-617
    • 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
  • 12
    • 0027049066 scopus 로고
    • Differential stereo-chemical 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, J.; Lemieux, C.; Chung, N. N. Differential stereo-chemical 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, J.5    Lemieux, C.6    Chung, N.N.7
  • 13
    • 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
  • 14
    • 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
  • 16
    • 0017620408 scopus 로고
    • ACTH A short introductory review
    • Schwyzer, R. ACTH: A short introductory review. Ann. N. Y. Acad. Sci. 1977, 297, 3-26.
    • (1977) Ann. N. Y. Acad. Sci. , vol.297 , pp. 3-26
    • Schwyzer, R.1
  • 17
    • 0023024852 scopus 로고
    • Molecular mechanism of opioid selection
    • Schwyzer, R. Molecular mechanism of opioid selection. Biochemistry 1986, 25, 6335-6342.
    • (1986) Biochemistry , vol.25 , pp. 6335-6342
    • Schwyzer, R.1
  • 18
    • 0024405504 scopus 로고
    • Bivalent ligands and the message-address concept in the design of selective opioid receptor antagonists
    • Portoghese, P. S. Bivalent ligands and the message-address concept in the design of selective opioid receptor antagonists. Trends Pharmacol. Sci. 1989, 10, 230-235.
    • (1989) Trends Pharmacol. Sci. , vol.10 , pp. 230-235
    • Portoghese, P.S.1
  • 19
    • 0025314942 scopus 로고
    • Design of peptidomimetic δ opioid receptor antagonists using the message-address concept
    • Portoghese, P.; Takemori, A. E.; Sultana, M. Design of peptidomimetic δ opioid receptor antagonists using the message-address concept. J. Med. Chem. 1990, 33, 1714-1720.
    • (1990) J. Med. Chem. , vol.33 , pp. 1714-1720
    • Portoghese, P.1    Takemori, A.E.2    Sultana, M.3
  • 20
    • 0025895073 scopus 로고
    • Role of spacer and address components in peptidomimetic δ opioid receptor antagonist related to naltrindole
    • Portoghese, P. S.; Nagase, H.; MaloneyHuss, K. E.; Lin, C.-E.; Takemori, A. Role of spacer and address components in peptidomimetic δ opioid receptor antagonist related to naltrindole. J. Med. Chem. 1991, 34, 1715-1720.
    • (1991) J. Med. Chem. , vol.34 , pp. 1715-1720
    • Portoghese, P.S.1    Nagase, H.2    MaloneyHuss, K.E.3    Lin, C.-E.4    Takemori, A.5
  • 21
    • 0030933655 scopus 로고    scopus 로고
    • A potent and selective endogenous agonist for the μ-opiate receptor
    • Zadina, J. E.; Hackler, L.; Ge, L.-J.; Kastin, A. J. A potent and selective endogenous agonist for the μ-opiate receptor. Nature 1996, 386, 499-501.
    • (1996) Nature , vol.386 , pp. 499-501
    • Zadina, J.E.1    Hackler, L.2    Ge, L.-J.3    Kastin, A.J.4
  • 23
    • 0033544785 scopus 로고    scopus 로고
    • Amino acids and peptides. LVI. Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor binding activity
    • Okada, Y.; Fukumizu, A.; Takahasi, M.; Yamazaki, J.; Yokoi, T.; Tsuda, Y.; Bryant, S. D.; Lazarus, L. H. Amino acids and peptides. LVI. Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor binding activity. Tetrahedron 1999, 55, 14391-14406.
    • (1999) Tetrahedron , vol.55 , pp. 14391-14406
    • Okada, Y.1    Fukumizu, A.2    Takahasi, M.3    Yamazaki, J.4    Yokoi, T.5    Tsuda, Y.6    Bryant, S.D.7    Lazarus, L.H.8
  • 24
    • 0032869694 scopus 로고    scopus 로고
    • Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor-binding activity
    • Okada, Y.; Fukumizu, A.; Takahashi, M.; Yokoi, T.; Tsuda, Y.; Bryant, S. D.; Lazarus, L. H. Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor-binding activity. Chem. Pharm. Bull. 1999, 47, 1193-1195.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 1193-1195
    • Okada, Y.1    Fukumizu, A.2    Takahashi, M.3    Yokoi, T.4    Tsuda, Y.5    Bryant, S.D.6    Lazarus, L.H.7
  • 26
    • 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
  • 28
    • 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
  • 29
    • 0016701344 scopus 로고
    • Identification of two related pentapeptides from the brain with potent opiate agonist activity
    • Hughes, J.; Smith, T. W.; Kosterlitz, H. W.; Fothergill, L. A.; Morgan, B. A.; Morris, H. R. Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature 1975, 258, 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
  • 30
    • 0018570746 scopus 로고
    • Demonstration of the crucial role of the phenyl-alanine moiety in enkephalin analogues for differential recognition of the μ- and δ-receptors
    • Roques, B. P.; Gacel, G.; Fournie-Zaluski, M.-C.; Senault, B.; Lecomte, J.-M. Demonstration of the crucial role of the phenyl-alanine moiety in enkephalin analogues for differential recognition of the μ- and δ-receptors. Eur. J. Pharmacol. 1979, 60, 109-110.
    • (1979) Eur. J. Pharmacol. , vol.60 , pp. 109-110
    • Roques, B.P.1    Gacel, G.2    Fournie-Zaluski, M.-C.3    Senault, B.4    Lecomte, J.-M.5
  • 31
    • 0037679246 scopus 로고    scopus 로고
    • Design and synthesis of opioid mimetics containing pyrazinone ring and examination of their opioid receptor binding activity
    • Tam, J. P., Kaumaya, P. T. P., Eds.; Kluwer Academic: Dodrecht, The Netherlands
    • Okada, Y.; Tsukatani, M.; Taguchi, H.; Yokoi, T.; Bryant, S. D.; Lazarus, L. H. Design and synthesis of opioid mimetics containing pyrazinone ring and examination of their opioid receptor binding activity. In Peptides: Frontiers of Peptide Science; Tam, J. P., Kaumaya, P. T. P., Eds.; Kluwer Academic: Dodrecht, The Netherlands, 1997; pp 660-661.
    • (1997) Peptides: Frontiers of Peptide Science , pp. 660-661
    • Okada, Y.1    Tsukatani, M.2    Taguchi, H.3    Yokoi, T.4    Bryant, S.D.5    Lazarus, L.H.6
  • 32
    • 0027786962 scopus 로고
    • The molecular basis of opioid potency and selectivity: Morphiceptins, dermorphins, deltorphins, and enkephalins
    • Goodman, M.; Ro, S.; Osapay, G.; Yamazaki, T.; Polinsky, A. The molecular basis of opioid potency and selectivity: morphiceptins, dermorphins, deltorphins, and enkephalins. NIDA Res. Monogr. 1993, 143, 195-209.
    • (1993) NIDA Res. Monogr. , vol.143 , pp. 195-209
    • Goodman, M.1    Ro, S.2    Osapay, G.3    Yamazaki, T.4    Polinsky, A.5
  • 33
    • 0027379723 scopus 로고
    • Topographical conformations of the deltorphins predicate δ opioid receptor affinity
    • (a) Bryant, S. D.; Salvadori, S.; Attila, M.; Lazarus, L. H. Topographical conformations of the deltorphins predicate δ opioid receptor affinity. J. Am. Chem. Soc. 1993, 115, 8503-8504.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 8503-8504
    • Bryant, S.D.1    Salvadori, S.2    Attila, M.3    Lazarus, L.H.4
  • 35
    • 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.; Takahshi, 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, 2001; pp 407-408.
    • (2001) Peptides 2000 , pp. 407-408
    • Bryant, S.D.1    Salvadori, S.2    Okada, Y.3    Takahshi, M.4    Sasaki, Y.5    Lazarus, L.H.6
  • 38
    • 0020078940 scopus 로고
    • Dimeric enkephalins display enhanced affinity and selectivity for the delta opioid receptor
    • Shimohigashi, Y.; Costa, T.; Mastuura, S.; Chen, H.-C.; Rodbard, D. Dimeric enkephalins display enhanced affinity and selectivity for the delta opioid receptor. Mol. Pharmacol. 1982, 21, 558-563.
    • (1982) Mol. Pharmacol. , vol.21 , pp. 558-563
    • Shimohigashi, Y.1    Costa, T.2    Mastuura, S.3    Chen, H.-C.4    Rodbard, D.5
  • 39
    • 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


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