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Volumn 46, Issue 24, 2003, Pages 5162-5170

Design and Synthesis of Novel Dimeric Morphinan Ligands for κ and μ Opioid Receptors

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE; CYCLORPHAN; ETHYLKETAZOCINE; GUANINE NUCLEOTIDE BINDING PROTEIN; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); KAPPA OPIATE RECEPTOR; LEVORPHANOL; MORPHINAN DERIVATIVE; MU OPIATE RECEPTOR; PARTIAL AGONIST; SULFUR 35;

EID: 0242522896     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030139v     Document Type: Article
Times cited : (76)

References (35)
  • 1
    • 0012047617 scopus 로고    scopus 로고
    • Narcotic Analgesics
    • Abraham, D., Ed.; John Wiley & Sons: New York, Chapter 7
    • Aldrich, J. V.; Vigil-Cruz, S. C. Narcotic Analgesics. In Burger's Medicinal Chemistry and Drug Discovery; Abraham, D., Ed.; John Wiley & Sons: New York, 2003; Vol. 6, Chapter 7, pp 329-481.
    • (2003) Burger's Medicinal Chemistry and Drug Discovery , vol.6 , pp. 329-481
    • Aldrich, J.V.1    Vigil-Cruz, S.C.2
  • 2
    • 0017735536 scopus 로고
    • Endogenous Opioid Peptides: Multiple Agonists and Receptors
    • Lord, J. A. H.; Waterfield, A. A.; Hughes, J.; Kosterlitz, H. W. Endogenous Opioid Peptides: Multiple Agonists and Receptors, Nature 1977, 267, 495-499.
    • (1977) Nature , vol.267 , pp. 495-499
    • Lord, J.A.H.1    Waterfield, A.A.2    Hughes, J.3    Kosterlitz, H.W.4
  • 4
    • 0030759112 scopus 로고    scopus 로고
    • Effects of Kappa Opioids on Cocaine Self-administration by Rhesus Monkeys
    • (a) Negus, S. S.; Mello, N. K.; Portoghese, P. S.; Lin, C.-E. Effects of Kappa Opioids on Cocaine Self-administration by Rhesus Monkeys. J. Pharmacol. Exp. Ther. 1997, 282, 44-55.
    • (1997) J. Pharmacol. Exp. Ther. , vol.282 , pp. 44-55
    • Negus, S.S.1    Mello, N.K.2    Portoghese, P.S.3    Lin, C.-E.4
  • 5
    • 0032437428 scopus 로고    scopus 로고
    • Effects of Kappa Opioids Agonists on Schedule-Controlled Behavior and Cocaine Self-Administration by Rhesus Monkeys
    • (b) Mello, N. K.; Negus, S. S. Effects of Kappa Opioids Agonists on Schedule-Controlled Behavior and Cocaine Self-Administration by Rhesus Monkeys. J. Pharmacol. Exp. Ther. 1998, 286, 812-824.
    • (1998) J. Pharmacol. Exp. Ther. , vol.286 , pp. 812-824
    • Mello, N.K.1    Negus, S.S.2
  • 6
    • 0041342088 scopus 로고    scopus 로고
    • Effects of Mixed-Action Kappa/Mu Opioids on Cocaine Self-Administration and Cocaine Discrimination by Rhesus Monkeys
    • (c) Bowen, C. A.; Negus, S. S.; Zong, R.; Neumeyer, J. L.; Bidlack, J. M.; Mello, N. K. Effects of Mixed-Action Kappa/Mu Opioids on Cocaine Self-Administration and Cocaine Discrimination by Rhesus Monkeys. Neuropsychopharmacology 2003, 28, 1125-1139.
    • (2003) Neuropsychopharmacology , vol.28 , pp. 1125-1139
    • Bowen, C.A.1    Negus, S.S.2    Zong, R.3    Neumeyer, J.L.4    Bidlack, J.M.5    Mello, N.K.6
  • 7
    • 0034642516 scopus 로고    scopus 로고
    • Synthesis and Opioid Receptor Affinity of Morphinan and Benzomorphan Derivatives: Mixed κ Agonists and μ Agonists/Antagonists as Potential Pharmacotherapeutics for Cocaine Dependence
    • (a) Neumeyer, J. L.; Bidlack, J. M.; Zong, R.; Bakthavachalam, V.; Gao, P.; Cohen, D. J.; Negus, S. S.; Mello, N. K. Synthesis and Opioid Receptor Affinity of Morphinan and Benzomorphan Derivatives: Mixed κ Agonists and μ Agonists/Antagonists as Potential Pharmacotherapeutics for Cocaine Dependence. J. Med. Chem. 2000, 43, 114-122.
    • (2000) J. Med. Chem. , vol.43 , pp. 114-122
    • Neumeyer, J.L.1    Bidlack, J.M.2    Zong, R.3    Bakthavachalam, V.4    Gao, P.5    Cohen, D.J.6    Negus, S.S.7    Mello, N.K.8
  • 9
    • 0035935189 scopus 로고    scopus 로고
    • Mixed κ Agonists and μ Agonists/Antagonists as Potential Pharmacotherapeutics for Cocaine Abuse: Synthesis and Opioid Receptor Binding Affinity of N-Substituted Derivatives of Morphinan
    • Neumeyer, J. L.; Gu, X.-H.; van Vliet, L. A.; DeNunzio, N. J.; Rusovici, D. E.; Cohen, D. J.; Negus, S. S.; Mello, N. K.; Bidlack, J. M. Mixed κ Agonists and μ Agonists/Antagonists as Potential Pharmacotherapeutics for Cocaine Abuse: Synthesis and Opioid Receptor Binding Affinity of N-Substituted Derivatives of Morphinan. Bioorg. Med. Chem. Lett. 2001, 11, 2735-2740.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2735-2740
    • Neumeyer, J.L.1    Gu, X.-H.2    Van Vliet, L.A.3    DeNunzio, N.J.4    Rusovici, D.E.5    Cohen, D.J.6    Negus, S.S.7    Mello, N.K.8    Bidlack, J.M.9
  • 10
    • 0030760634 scopus 로고    scopus 로고
    • Dimerization of the δ opioid Receptor: Implication for a Role in Receptor Internalization
    • (a) Cvejic, S.; Devi, L. Dimerization of the δ opioid Receptor: Implication for a Role in Receptor Internalization. J. Biol. Chem. 1997, 272, 26959-26964.
    • (1997) J. Biol. Chem. , vol.272 , pp. 26959-26964
    • Cvejic, S.1    Devi, L.2
  • 12
    • 0024405504 scopus 로고
    • Bivalent Ligands and the Message-Address Concept in the Design of Selective Opioid Receptor Antagonists
    • (c) Portoghese, P. 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.1
  • 13
    • 0242719134 scopus 로고    scopus 로고
    • Design and Synthesis of κ-δ Opioid Bivalent Ligands as Probes to Study Opioid Receptor Dimerization
    • Division of Medicinal Chemistry, Boston, MA, August 18-22, 2002; American Chemical Society: Washington, DC; No. 242
    • (d) Bhushan, R. G.; Sharma, S. K.; Portoghese, P. S. Design and Synthesis of κ-δ Opioid Bivalent Ligands as Probes To Study Opioid Receptor Dimerization. Abstracts of Papers, 224th National Meeting of the American Chemical Society, Division of Medicinal Chemistry, Boston, MA, August 18-22, 2002; American Chemical Society: Washington, DC, 2002; No. 242.
    • (2002) Abstracts of Papers, 224th National Meeting of the American Chemical Society
    • Bhushan, R.G.1    Sharma, S.K.2    Portoghese, P.S.3
  • 14
    • 0034714335 scopus 로고    scopus 로고
    • Oligomerization of μ- and δ-Opioid Receptors: Generation of Novel Functional Properties
    • (e) George, S. R.; Fan, T.; Xie, Z.; Tse, R.; Tamni, V.; Varghese, G.; O'Dowd, B. F. Oligomerization of μ- and δ-Opioid Receptors: Generation of Novel Functional Properties. J. Biol. Chem. 2000, 275 (34), 26128-26135.
    • (2000) J. Biol. Chem. , vol.275 , Issue.34 , pp. 26128-26135
    • George, S.R.1    Fan, T.2    Xie, Z.3    Tse, R.4    Tamni, V.5    Varghese, G.6    O'Dowd, B.F.7
  • 16
    • 0037169345 scopus 로고    scopus 로고
    • Regulation of Opioid Receptor Trafficking and Morphine Tolerance by Receptor Oligomerization
    • (g) He, L.; Fong, J.; von Zastrow, M.; Whistler, J. L. Regulation of Opioid Receptor Trafficking and Morphine Tolerance by Receptor Oligomerization. Cell 2002, 108, 271-282.
    • (2002) Cell , vol.108 , pp. 271-282
    • He, L.1    Fong, J.2    Von Zastrow, M.3    Whistler, J.L.4
  • 17
    • 0019990819 scopus 로고
    • Narcotic Antagonistic Potency of Bivalent Ligands Which Contain β-Naltrexamine. Evidence for Bridging between Proximal Recognition Sites
    • Erez, M.; Takemori, A. E.; Portoghese, P. S. Narcotic Antagonistic Potency of Bivalent Ligands Which Contain β-Naltrexamine. Evidence for Bridging between Proximal Recognition Sites. J. Med. Chem. 1982, 25, 847-849,
    • (1982) J. Med. Chem. , vol.25 , pp. 847-849
    • Erez, M.1    Takemori, A.E.2    Portoghese, P.S.3
  • 18
    • 0022922731 scopus 로고
    • Synthesis and Opioid Antagonist Potencies of Naltrexamine Bivalent Ligands with Conformationally Restricted Spacers
    • Portoghese, P. S.; Ronsisvalle, G.; Larson, D. L.; Takemori, A. E. Synthesis and Opioid Antagonist Potencies of Naltrexamine Bivalent Ligands with Conformationally Restricted Spacers. J. Med. Chem. 1986, 29, 1650-1653.
    • (1986) J. Med. Chem. , vol.29 , pp. 1650-1653
    • Portoghese, P.S.1    Ronsisvalle, G.2    Larson, D.L.3    Takemori, A.E.4
  • 19
    • 0022902748 scopus 로고
    • Opioid Agonist and Antagonist Bivalent Ligands. The Relationship between Spacer Length and Selectivity at Multiple Opioid Receptors
    • Portoghese, P. S.; Larson, D. L.; Sayre, L. M.; Yim, C. B.; Ronsisvalle, G.; Tam, S. W.; Takemori, A. E. Opioid Agonist and Antagonist Bivalent Ligands. The Relationship between Spacer Length and Selectivity at Multiple Opioid Receptors. J. Med. Chem. 1986, 29, 1855-1861.
    • (1986) J. Med. Chem. , vol.29 , pp. 1855-1861
    • Portoghese, P.S.1    Larson, D.L.2    Sayre, L.M.3    Yim, C.B.4    Ronsisvalle, G.5    Tam, S.W.6    Takemori, A.E.7
  • 20
    • 0022251438 scopus 로고
    • Stereostructure-Activity Relationship of Opioid Agonist and Antagonist Bivalent Ligands. Evidence for Bridging between Vicinal Opioid Receptors
    • Portoghese, P. S.; Larson, D. L.; Yim, C. B.; Sayre, L. M.; Ronsisvalle, G.; Lipkowski, A. W.; Takemori, A. E.; Rice, K. C.; Tam, S. W. Stereostructure-Activity Relationship of Opioid Agonist and Antagonist Bivalent Ligands. Evidence for Bridging Between Vicinal Opioid Receptors. J. Med. Chem. 1985, 28, 1140-1141.
    • (1985) J. Med. Chem. , vol.28 , pp. 1140-1141
    • Portoghese, P.S.1    Larson, D.L.2    Yim, C.B.3    Sayre, L.M.4    Ronsisvalle, G.5    Lipkowski, A.W.6    Takemori, A.E.7    Rice, K.C.8    Tam, S.W.9
  • 21
    • 0023765567 scopus 로고
    • Only One Pharmacophore Is Required for the κ Opioid Antagonist Selectivity of Norbinaltorphimine
    • Portoghese, P. S.; Nagase, H.; Takemori, A. E. Only One Pharmacophore Is Required for the κ Opioid Antagonist Selectivity of Norbinaltorphimine. J. Med. Chem. 1988, 31, 1344-1347.
    • (1988) J. Med. Chem. , vol.31 , pp. 1344-1347
    • Portoghese, P.S.1    Nagase, H.2    Takemori, A.E.3
  • 22
    • 0035811447 scopus 로고    scopus 로고
    • From Models to Molecules: Opioid Receptor Dimers, Bivalent Ligands, and Selective Opioid Receptor Probes
    • Portoghese, P. S. From Models to Molecules: Opioid Receptor Dimers, Bivalent Ligands, and Selective Opioid Receptor Probes. J. Med Chem. 2001, 44, 2259-2269.
    • (2001) J. Med Chem. , vol.44 , pp. 2259-2269
    • Portoghese, P.S.1
  • 23
    • 0000105892 scopus 로고
    • Some Potent Morphine Antagonists Possessing High Analgesic Activity
    • Gates, M.; Montzka, T. A. Some Potent Morphine Antagonists Possessing High Analgesic Activity. J. Med. Chem. 1964, 7, 127-131.
    • (1964) J. Med. Chem. , vol.7 , pp. 127-131
    • Gates, M.1    Montzka, T.A.2
  • 24
    • 0242634802 scopus 로고    scopus 로고
    • N-Cyclopropylmethyl- and -cyclobutylmethylmorphinans. U.S. 3,285,922, 1966; CAN 66:28955, AN 1967:28955
    • Gates, M. N-Cyclopropylmethyl- and -cyclobutylmethylmorphinans. U.S. 3,285,922, 1966; CAN 66:28955, AN 1967:28955.
    • Gates, M.1
  • 25
    • 0021260262 scopus 로고
    • A New Reagent for the Selective, High Yield N-Dealkylation of Tertiary Amines: Improved Synthesis of Naltrexone and Nalbuphine
    • Olfoson, R. A.; Marts, J. T.; Seret, J. P.; Piteau, M.; Malfroot, T. A. A New Reagent for the Selective, High Yield N-Dealkylation of Tertiary Amines: Improved Synthesis of Naltrexone and Nalbuphine. J. Org. Chem. 1984, 49, 2081-2082.
    • (1984) J. Org. Chem. , vol.49 , pp. 2081-2082
    • Olfoson, R.A.1    Marts, J.T.2    Seret, J.P.3    Piteau, M.4    Malfroot, T.A.5
  • 30
    • 0034699499 scopus 로고    scopus 로고
    • Selective Protection and Functionalization of Morphine: Synthesis and Opioid Receptor Binding Properties of 3-Amino-3-desoxymorphine Derivatives
    • (c) Wentland, M. P.; Duan, W.; Cohen, D. J.; Bidlack, J. M. Selective Protection and Functionalization of Morphine: Synthesis and Opioid Receptor Binding Properties of 3-Amino-3-desoxymorphine Derivatives. J. Med. Chem. 2000, 43, 3558-3565.
    • (2000) J. Med. Chem. , vol.43 , pp. 3558-3565
    • Wentland, M.P.1    Duan, W.2    Cohen, D.J.3    Bidlack, J.M.4
  • 31
    • 0035848380 scopus 로고    scopus 로고
    • 8-Carboxamidocyclazocine Analogues: Redefining the Structure-Activity Relationships of 2,6-Methano-3-benzazocines
    • (d) Wentland, M. P.; Lou, R.; Ye, Y.; Cohen, D. J.; Richardson, G. P.; Bidlack, J. M. 8-Carboxamidocyclazocine Analogues: Redefining the Structure-Activity Relationships of 2,6-Methano-3-benzazocines. Bioorg. Med. Chem. Lett. 2001, 11, 623-626.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 623-626
    • Wentland, M.P.1    Lou, R.2    Ye, Y.3    Cohen, D.J.4    Richardson, G.P.5    Bidlack, J.M.6
  • 32
    • 0035833120 scopus 로고    scopus 로고
    • 3-Carboxamido Analogues of Morphine and Naltrexone: Synthesis and Opioid Receptor Binding Properties
    • (e) Wentland, M. P.; Lou, R.; Dehnhardt, C. M.; Duan, W.; Cohen, D. J.; Bidlack, J. M. 3-Carboxamido Analogues of Morphine and Naltrexone: Synthesis and Opioid Receptor Binding Properties. Bioorg. Med. Chem. Lett. 2001, 11, 1717.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 1717
    • Wentland, M.P.1    Lou, R.2    Dehnhardt, C.M.3    Duan, W.4    Cohen, D.J.5    Bidlack, J.M.6
  • 33
    • 0034710723 scopus 로고    scopus 로고
    • 3-Deoxyclocinnamox: The First High-Affinity, Nonpeptide μ-Opioid Antagonist Lacking a Phenolic Hydroxyl Group
    • Derrick, I.; Neilan, C. L.; Andes, J.; Husbands, S. M.; Woods, J. H.; Traynor, J. R.; Lewis, J. W. 3-Deoxyclocinnamox: The First High-Affinity, Nonpeptide μ-Opioid Antagonist Lacking a Phenolic Hydroxyl Group. J. Med. Chem. 2000, 43, 3348-3350.
    • (2000) J. Med. Chem. , vol.43 , pp. 3348-3350
    • Derrick, I.1    Neilan, C.L.2    Andes, J.3    Husbands, S.M.4    Woods, J.H.5    Traynor, J.R.6    Lewis, J.W.7
  • 35
    • 0017184389 scopus 로고
    • A Rapid Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding
    • Bradford, M. M. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding. Anal. Biochem. 1976, 72, 248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1


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