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Volumn 28, Issue 2, 1998, Pages 117-124

Opioid peptide receptor studies. 7. The methylfentanyl congener RTI- 4614-4 and its four enantiomers bind to different domains of the rat μ opioid receptor

Author keywords

receptor; (+) 3 methylfentanyl; RTI 4614 4

Indexed keywords

FENTANYL DERIVATIVE; OPIATE PEPTIDE; OPIATE RECEPTOR;

EID: 6844254562     PISSN: 08874476     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2396(199802)28:2<117::AID-SYN2>3.0.CO;2-E     Document Type: Article
Times cited : (13)

References (41)
  • 1
    • 0029130047 scopus 로고
    • Phosphorylation and agonist-specific intracellular trafficking of an epitope-tagged mu-opioid receptor expressed in HEK 293 cells
    • Arden, J.R., Segredo, V., Wang, Z., Lameh, J., and Sadee, W. (1995) Phosphorylation and agonist-specific intracellular trafficking of an epitope-tagged mu-opioid receptor expressed in HEK 293 cells. J. Neurochem., 65:1636-1645.
    • (1995) J. Neurochem. , vol.65 , pp. 1636-1645
    • Arden, J.R.1    Segredo, V.2    Wang, Z.3    Lameh, J.4    Sadee, W.5
  • 2
    • 0025695025 scopus 로고
    • The potent opiate agonist, (+)-cis-3-methylfentanyl binds pseudoirreversibly to the opioid receptor complex in vitro and in vivo: Evidence for a novel mechanism of action
    • Band, L., Xu, H., Bykov, V., Greig, N., Kim, C.-H., Newman, A., Jacobson, A.E., Rice, K.C., and Rothman, R.B. (1990) The potent opiate agonist, (+)-cis-3-methylfentanyl binds pseudoirreversibly to the opioid receptor complex in vitro and in vivo: Evidence for a novel mechanism of action. Life Sci., 47:2231-2240.
    • (1990) Life Sci. , vol.47 , pp. 2231-2240
    • Band, L.1    Xu, H.2    Bykov, V.3    Greig, N.4    Kim, C.-H.5    Newman, A.6    Jacobson, A.E.7    Rice, K.C.8    Rothman, R.B.9
  • 3
    • 0342267076 scopus 로고
    • Enantiomers of (±)-cis-N-[1-(2-hydroxy-2-phenylethyl)-3-methyl-4-piperidyl]-N- phenylpropanamide: Influence of the hydroxyl group
    • Brine, G.A., Stark, P.A., Carroll, F.I., Xu, H., and Rothman, R.B. (1992) Enantiomers of (±)-cis-N-[1-(2-hydroxy-2-phenylethyl)-3-methyl-4-piperidyl]-N- phenylpropanamide: Influence of the hydroxyl group. Med. Chem. Res., 2:34-40.
    • (1992) Med. Chem. Res. , vol.2 , pp. 34-40
    • Brine, G.A.1    Stark, P.A.2    Carroll, F.I.3    Xu, H.4    Rothman, R.B.5
  • 4
    • 0028923802 scopus 로고
    • Enantiomers of diastereomeric cis-N-[1-(2-hydroxy-2-phenylethyl)-3-methyl-4-piperidyl]-N-phenyl propanamide: Synthesis, x-ray analysis, and biological activities
    • Brine, G.A., Stark, P.A., Liu, Y., Carroll, F.I., Singh, P., Xu, H., and Rothman, R.B. (1995) Enantiomers of diastereomeric cis-N-[1-(2-hydroxy-2-phenylethyl)-3-methyl-4-piperidyl]-N-phenyl propanamide: Synthesis, x-ray analysis, and biological activities. J. Med. Chem., 38:1547-1557.
    • (1995) J. Med. Chem. , vol.38 , pp. 1547-1557
    • Brine, G.A.1    Stark, P.A.2    Liu, Y.3    Carroll, F.I.4    Singh, P.5    Xu, H.6    Rothman, R.B.7
  • 5
    • 0003925387 scopus 로고
    • Fentanyl and the 4-anilinopiperidine group of analgesics
    • Plenum Press, New York
    • Casy, A.F., and Parfitt, R.T. (1986) Fentanyl and the 4-anilinopiperidine group of analgesics. In: Opioid analgesics. Chemistry and Receptors. Plenum Press, New York, pp. 287-301.
    • (1986) Opioid Analgesics. Chemistry and Receptors , pp. 287-301
    • Casy, A.F.1    Parfitt, R.T.2
  • 10
    • 0019569826 scopus 로고
    • Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives
    • Jin, W.Q., Xu, H., Zhu, Y.C., Fang, S.N., Xia, X.L., Huang, Z.M., Ge, B.L., and Chi, Z.Q. (1981) Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives. Sci. Sin., 24:710-720.
    • (1981) Sci. Sin. , vol.24 , pp. 710-720
    • Jin, W.Q.1    Xu, H.2    Zhu, Y.C.3    Fang, S.N.4    Xia, X.L.5    Huang, Z.M.6    Ge, B.L.7    Chi, Z.Q.8
  • 11
    • 0026634655 scopus 로고
    • Site-directed mutagenesis of a single residue changes the binding properties of the serotonin 5-HT2 receptor from a human to a rat pharmacology
    • Kao, H.T., Adham, N., Olsen, M.A., Weinshank, R.L., Branchek, T.A., and Hartig, P.R. (1992) Site-directed mutagenesis of a single residue changes the binding properties of the serotonin 5-HT2 receptor from a human to a rat pharmacology. FEBS Lett., 307:324-328.
    • (1992) FEBS Lett. , vol.307 , pp. 324-328
    • Kao, H.T.1    Adham, N.2    Olsen, M.A.3    Weinshank, R.L.4    Branchek, T.A.5    Hartig, P.R.6
  • 14
    • 0027249759 scopus 로고
    • Mutation of an aspartate at residue 89 in somatostatin receptor subtype 2 prevents Na+ regulation of agonist binding but does not alter receptor-G protein association
    • Kong, H., Raynor, K., Yasuda, K., Bell, G.I., and Reisine, T. (1993a) Mutation of an aspartate at residue 89 in somatostatin receptor subtype 2 prevents Na+ regulation of agonist binding but does not alter receptor-G protein association. Mol. Pharmacol., 44:380-384.
    • (1993) Mol. Pharmacol. , vol.44 , pp. 380-384
    • Kong, H.1    Raynor, K.2    Yasuda, K.3    Bell, G.I.4    Reisine, T.5
  • 15
    • 0027444691 scopus 로고
    • Asingle residue, aspartic acid 95, in the delta opioid receptor specifies selective high affinity agonist binding
    • Kong, H., Raynor, K., Yasuda, K, Moe, S.T., Portoghese, P.S., Bell, G.I., and Reisine, T. (1993b) Asingle residue, aspartic acid 95, in the delta opioid receptor specifies selective high affinity agonist binding. J. Biol. Chem., 268:23055-23058.
    • (1993) J. Biol. Chem. , vol.268 , pp. 23055-23058
    • Kong, H.1    Raynor, K.2    Yasuda, K.3    Moe, S.T.4    Portoghese, P.S.5    Bell, G.I.6    Reisine, T.7
  • 16
    • 0027988826 scopus 로고
    • Pharmacological characterization of the cloned kappa opioid receptor as a kappa 1b subtype
    • Lai, J., Ma, S.W., Zhu, R.H., Rothman, R.B., Lentes, K.U., and Porreca, F. (1994) Pharmacological characterization of the cloned kappa opioid receptor as a kappa 1b subtype. Neuroreport, 5:2161-2164.
    • (1994) Neuroreport , vol.5 , pp. 2161-2164
    • Lai, J.1    Ma, S.W.2    Zhu, R.H.3    Rothman, R.B.4    Lentes, K.U.5    Porreca, F.6
  • 17
    • 0017738595 scopus 로고
    • Differentiation of opiate and neuroleptic receptor binding in rat brain
    • Leysen, J., Tollenaere, J.P., Koch, M.H., and Laduron, P. (1977) Differentiation of opiate and neuroleptic receptor binding in rat brain. Eur. J. Pharmacol., 43:253-267.
    • (1977) Eur. J. Pharmacol. , vol.43 , pp. 253-267
    • Leysen, J.1    Tollenaere, J.P.2    Koch, M.H.3    Laduron, P.4
  • 20
    • 0029017044 scopus 로고
    • A chimeric study of the molecular basis of affinity and selectivity of the kappa and the delta opioid receptors. Potential role of extracellular domains
    • Meng, F., Hoversten, M.T., Thompson, R.C., Taylor, L., Watson, S.J., and Akil, H. (1995) A chimeric study of the molecular basis of affinity and selectivity of the kappa and the delta opioid receptors. Potential role of extracellular domains. J. Biol. Chem., 270:12730-12736.
    • (1995) J. Biol. Chem. , vol.270 , pp. 12730-12736
    • Meng, F.1    Hoversten, M.T.2    Thompson, R.C.3    Taylor, L.4    Watson, S.J.5    Akil, H.6
  • 21
    • 0028986733 scopus 로고
    • DAMGO, a mu-opioid receptor selective ligand, distinguishes between mu- and kappa-opioid receptors at a different region from that for the distinction between mu- and delta-opioid receptors
    • Minami, M., Onogi, T., Nakagawa, T., Katao, Y., Aoki, Y., Katsumata, S., and Satoh, M. (1995) DAMGO, a mu-opioid receptor selective ligand, distinguishes between mu- and kappa-opioid receptors at a different region from that for the distinction between mu- and delta-opioid receptors. FEBS Lett., 364:23-27.
    • (1995) FEBS Lett. , vol.364 , pp. 23-27
    • Minami, M.1    Onogi, T.2    Nakagawa, T.3    Katao, Y.4    Aoki, Y.5    Katsumata, S.6    Satoh, M.7
  • 22
    • 0025863465 scopus 로고
    • Pivotal role for aspartate-80 in the regulation of dopamine D2 receptor affinity for drugs and inhibition of adenyl cyclase
    • Neve, K.A., Cox, B.A., Henningsen, R.A., Spanoyannis, A., and Neve, R.L. (1991) Pivotal role for aspartate-80 in the regulation of dopamine D2 receptor affinity for drugs and inhibition of adenyl cyclase. Mol. Pharmacol., 39:733-739.
    • (1991) Mol. Pharmacol. , vol.39 , pp. 733-739
    • Neve, K.A.1    Cox, B.A.2    Henningsen, R.A.3    Spanoyannis, A.4    Neve, R.L.5
  • 24
    • 0027368964 scopus 로고
    • Stereochemical requirements for pseudoirreversible inhibition of opioid mu receptor binding by the 3-methylfentanyl congeners, RTI-4614-4 and its enantiomers: Evidence for different binding domains
    • Ni, Q., Xu, H., Partilla, J.S., Stark, P.A., Carroll, F.I., Brine, G.A., and Rothman, R.B. (1993b) Stereochemical requirements for pseudoirreversible inhibition of opioid mu receptor binding by the 3-methylfentanyl congeners, RTI-4614-4 and its enantiomers: Evidence for different binding domains. Synapse, 15:296-306.
    • (1993) Synapse , vol.15 , pp. 296-306
    • Ni, Q.1    Xu, H.2    Partilla, J.S.3    Stark, P.A.4    Carroll, F.I.5    Brine, G.A.6    Rothman, R.B.7
  • 25
    • 0023815680 scopus 로고
    • Site-directed mutagenesis of the cytoplasmic domains of the human beta-2-adrenergic receptor localization of regions involved in G protein-receptor coupling
    • O'Dowd, B.F., Hantowich, M., Regan, J.W., Leader, W.M., and Caron, M.G. (1988) Site-directed mutagenesis of the cytoplasmic domains of the human beta-2-adrenergic receptor localization of regions involved in G protein-receptor coupling. J. Biol. Chem., 263:15985-15992.
    • (1988) J. Biol. Chem. , vol.263 , pp. 15985-15992
    • O'Dowd, B.F.1    Hantowich, M.2    Regan, J.W.3    Leader, W.M.4    Caron, M.G.5
  • 26
    • 0028978424 scopus 로고
    • DAMGO, a mu-opioid receptor selective agonist, distinguishes between mu- and delta-opioid receptors around their first extracellular loops
    • Onogi, T., Minami, M., Katao, Y., Nakagawa, T., Aoki, Y., Toya, T., Katsumata, S., and Satoh, M. (1995) DAMGO, a mu-opioid receptor selective agonist, distinguishes between mu- and delta-opioid receptors around their first extracellular loops. FEBS Lett., 357:93-97.
    • (1995) FEBS Lett. , vol.357 , pp. 93-97
    • Onogi, T.1    Minami, M.2    Katao, Y.3    Nakagawa, T.4    Aoki, Y.5    Toya, T.6    Katsumata, S.7    Satoh, M.8
  • 27
    • 0017250843 scopus 로고
    • Statistical characterization of the random errors in the radioimmunoassay dose-response variable
    • Rodbard, D., Lenox, R.H., Wray, H.L., and Ramseth, D. (1976) Statistical characterization of the random errors in the radioimmunoassay dose-response variable. Clin. Chem., 22:350-358.
    • (1976) Clin. Chem. , vol.22 , pp. 350-358
    • Rodbard, D.1    Lenox, R.H.2    Wray, H.L.3    Ramseth, D.4
  • 28
    • 0021334921 scopus 로고
    • Opiate receptor binding-effect relationship: Sufentanil and etorphine produce analgesia at the mu-site with low fractional receptor occupancy
    • Rosenbaum, J.S., Holford, N.H., and Sadee, W. (1984) Opiate receptor binding-effect relationship: Sufentanil and etorphine produce analgesia at the mu-site with low fractional receptor occupancy. Brain Res., 291:317-324.
    • (1984) Brain Res. , vol.291 , pp. 317-324
    • Rosenbaum, J.S.1    Holford, N.H.2    Sadee, W.3
  • 29
    • 0023830870 scopus 로고
    • 3H]cycloFOXY: An opiate antagonist suitable for positron emission tomography
    • 3H]cycloFOXY: An opiate antagonist suitable for positron emission tomography. Biol. Psychol., 23:435-458.
    • (1988) Biol. Psychol. , vol.23 , pp. 435-458
    • Rothman, R.B.1    McLean, S.2
  • 30
    • 0025256967 scopus 로고
    • Interaction of endogenous opioid peptides and other drugs with four kappa opioid binding sites in guinea pig brain
    • Rothman, R.B., Bykov, V., de Costa, B.R., Jacobson, A.E., Rice, K.C., and Brady, L.S. (1990) Interaction of endogenous opioid peptides and other drugs with four kappa opioid binding sites in guinea pig brain. Peptides, 11:311-331.
    • (1990) Peptides , vol.11 , pp. 311-331
    • Rothman, R.B.1    Bykov, V.2    De Costa, B.R.3    Jacobson, A.E.4    Rice, K.C.5    Brady, L.S.6
  • 31
    • 0025729102 scopus 로고
    • RTI-4614-4: An analog of (+)-cis-3-methylfentanyl with a 27,000-fold binding selectivity for mu versus delta opioid binding sites
    • Rothman, R.B., Xu, H., Seggel, M., Jacobson, A.E., Rice, K.C., Brine, G.A., and Carroll, F.I. (1991) RTI-4614-4: An analog of (+)-cis-3-methylfentanyl with a 27,000-fold binding selectivity for mu versus delta opioid binding sites. Life Sci., 48:PL111-PL116.
    • (1991) Life Sci. , vol.48
    • Rothman, R.B.1    Xu, H.2    Seggel, M.3    Jacobson, A.E.4    Rice, K.C.5    Brine, G.A.6    Carroll, F.I.7
  • 33
    • 0016245082 scopus 로고
    • Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-[3-Methyl- 1-(2-phenylethyl)-4-piperidyl]-N-phenylpropanamide and N-[3-Methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl]-N-phenylpropa namide
    • Van Bever, W.F.M., Niemegeers, C.J.E., and Janssen, P.A.J. (1974) Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-[3-Methyl- 1-(2-phenylethyl)-4-piperidyl]-N-phenylpropanamide and N-[3-Methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl]-N-phenylpropa namide. J. Med. Chem., 17:1047-1051.
    • (1974) J. Med. Chem. , vol.17 , pp. 1047-1051
    • Van Bever, W.F.M.1    Niemegeers, C.J.E.2    Janssen, P.A.J.3
  • 35
    • 0029101452 scopus 로고
    • Stereoisomers of N-[1(2-hydroxy-2-phenylethyl)-3-methyl-4-piperidyl]-N-phenylpropa namide: Synthesis, stereochemistry, analgesic activity, and opioid receptor binding characteristics
    • Wang, Z.-X., Zhu, Y.-C., Jin, W.-Q., Chen, X.-J., Chen, J., Ji, R.-Y., and Chi, Z.-Q. (1995) Stereoisomers of N-[1(2-hydroxy-2-phenylethyl)-3-methyl-4-piperidyl]-N-phenylpropa namide: Synthesis, stereochemistry, analgesic activity, and opioid receptor binding characteristics. J. Med. Chem., 38:3652-3659.
    • (1995) J. Med. Chem. , vol.38 , pp. 3652-3659
    • Wang, Z.-X.1    Zhu, Y.-C.2    Jin, W.-Q.3    Chen, X.-J.4    Chen, J.5    Ji, R.-Y.6    Chi, Z.-Q.7
  • 36
    • 0016668483 scopus 로고
    • Homologous N-alkylnorketobemidones. Correlation of receptor binding with analgesic potency
    • Wilson, R.S., Rogers, M.E., Pert, C.B., and Snyder, S.H. (1975) Homologous N-alkylnorketobemidones. Correlation of receptor binding with analgesic potency. J. Med. Chem., 18:240-242.
    • (1975) J. Med. Chem. , vol.18 , pp. 240-242
    • Wilson, R.S.1    Rogers, M.E.2    Pert, C.B.3    Snyder, S.H.4
  • 37
    • 0023228877 scopus 로고
    • Potent 3-methylfentanyl analogs: Morphine-like catalepsy and receptor binding characteristics
    • Xu, H., Yao, Y.H., Zhu, Y.C., Chen, J., and Chi, Z.Q. (1987) Potent 3-methylfentanyl analogs: Morphine-like catalepsy and receptor binding characteristics. Chung Kuo Yao Li Hsueh Pao, 8:289-292.
    • (1987) Chung Kuo Yao Li Hsueh Pao , vol.8 , pp. 289-292
    • Xu, H.1    Yao, Y.H.2    Zhu, Y.C.3    Chen, J.4    Chi, Z.Q.5
  • 38
    • 0025858946 scopus 로고
    • (+)-cis-methylfentanyl and its analogs bind pseudoirreversibly to the mu opioid binding site: Evidence for pseudoallosteric modulation
    • Xu, H., Kim, C.-H., Zhu, Y.C., Weber, R.J., Rice, K.C., and Rothman, R.B. (1991) (+)-cis-methylfentanyl and its analogs bind pseudoirreversibly to the mu opioid binding site: Evidence for pseudoallosteric modulation. Neuropharmacology, 30:455-462.
    • (1991) Neuropharmacology , vol.30 , pp. 455-462
    • Xu, H.1    Kim, C.-H.2    Zhu, Y.C.3    Weber, R.J.4    Rice, K.C.5    Rothman, R.B.6
  • 39
    • 0028104682 scopus 로고
    • Differential binding domains of peptide and non-peptide ligands in the cloned rat kappa opioid receptor
    • Xue, J.C., Chen, C., Zhu, J., Kunapuli, S., DeRiel, J.K., Yu, L., and Liu-Chen, L.Y. (1994) Differential binding domains of peptide and non-peptide ligands in the cloned rat kappa opioid receptor. J. Biol. Chem., 269:30195-30199.
    • (1994) J. Biol. Chem. , vol.269 , pp. 30195-30199
    • Xue, J.C.1    Chen, C.2    Zhu, J.3    Kunapuli, S.4    DeRiel, J.K.5    Yu, L.6    Liu-Chen, L.Y.7
  • 40
    • 0029045917 scopus 로고
    • The third extracellular loop of the mu opioid receptor is important for agonist selectivity
    • Xue, J.C., Chen, C., Zhu, J., Kunapuli, S.P., de Riel, J.K., Yu, L., and Liu-Chen, L.Y. (1995) The third extracellular loop of the mu opioid receptor is important for agonist selectivity. J. Biol. Chem., 270: 12977-12979.
    • (1995) J. Biol. Chem. , vol.270 , pp. 12977-12979
    • Xue, J.C.1    Chen, C.2    Zhu, J.3    Kunapuli, S.P.4    De Riel, J.K.5    Yu, L.6    Liu-Chen, L.Y.7
  • 41
    • 0026656356 scopus 로고
    • Replacement of lysine-181 by aspartic acid in the third transmembrane region of endothelin type b receptor reduces its affinity to endothelin peptides and sarafotoxin 6c without affecting G protein coupling
    • Zhu, G., Wu, L.H., Mauzy, C., Egloff, A.M., Mirzadegan, T., and Chung, F.Z. (1992) Replacement of lysine-181 by aspartic acid in the third transmembrane region of endothelin type b receptor reduces its affinity to endothelin peptides and sarafotoxin 6c without affecting G protein coupling. J. Cell. Biochem., 50:159-164.
    • (1992) J. Cell. Biochem. , vol.50 , pp. 159-164
    • Zhu, G.1    Wu, L.H.2    Mauzy, C.3    Egloff, A.M.4    Mirzadegan, T.5    Chung, F.Z.6


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