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Volumn 7, Issue 3, 2016, Pages 297-304

17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(4′-pyridylcarboxamido)morphinan (NAP) Modulating the Mu Opioid Receptor in a Biased Fashion

Author keywords

biased signaling; functional selectivity; Mu opioid receptor; nalbuphine; NAP; arrestin2

Indexed keywords

17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6BETA (4' PYRIDYLCARBOXAMIDO)MORPHINAN; BETA ARRESTIN 2; CALCIUM ION; GAG PROTEIN; MORPHINE; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR AGONIST; NALTREXAMINE DERIVATIVE; UNCLASSIFIED DRUG; MORPHINAN DERIVATIVE; NARCOTIC ANALGESIC AGENT;

EID: 84962224127     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/acschemneuro.5b00245     Document Type: Article
Times cited : (15)

References (31)
  • 1
    • 0038024615 scopus 로고    scopus 로고
    • The G-protein-coupled receptors in the human genome form five main families. Phylogenetic analysis, paralogon groups, and fingerprints
    • Fredriksson, R., Lagerstrom, M. C., Lundin, L. G., and Schioth, H. B. (2003) The G-protein-coupled receptors in the human genome form five main families. Phylogenetic analysis, paralogon groups, and fingerprints Mol. Pharmacol. 63, 1256-1272 10.1124/mol.63.6.1256
    • (2003) Mol. Pharmacol. , vol.63 , pp. 1256-1272
    • Fredriksson, R.1    Lagerstrom, M.C.2    Lundin, L.G.3    Schioth, H.B.4
  • 3
    • 0028950255 scopus 로고
    • The two-state model of receptor activation
    • Leff, P. (1995) The two-state model of receptor activation Trends Pharmacol. Sci. 16, 89-97 10.1016/S0165-6147(00)88989-0
    • (1995) Trends Pharmacol. Sci. , vol.16 , pp. 89-97
    • Leff, P.1
  • 4
    • 84856470106 scopus 로고    scopus 로고
    • The plasticity of the 7TMR signaling machinery and the search for pharmacological selectivity
    • Flordellis, C. S. (2012) The plasticity of the 7TMR signaling machinery and the search for pharmacological selectivity Curr. Pharm. Des. 18, 145-160 10.2174/138161212799040556
    • (2012) Curr. Pharm. Des. , vol.18 , pp. 145-160
    • Flordellis, C.S.1
  • 5
    • 0029054965 scopus 로고
    • Agonist-receptor efficacy. II. Agonist trafficking of receptor signals
    • Kenakin, T. (1995) Agonist-receptor efficacy. II. Agonist trafficking of receptor signals Trends Pharmacol. Sci. 16, 232-238 10.1016/S0165-6147(00)89032-X
    • (1995) Trends Pharmacol. Sci. , vol.16 , pp. 232-238
    • Kenakin, T.1
  • 6
    • 77951844975 scopus 로고    scopus 로고
    • Teaching old receptors new tricks: Biasing seven-transmembrane receptors
    • Rajagopal, S., Rajagopal, K., and Lefkowitz, R. J. (2010) Teaching old receptors new tricks: Biasing seven-transmembrane receptors Nat. Rev. Drug Discovery 9, 373-386 10.1038/nrd3024
    • (2010) Nat. Rev. Drug Discovery , vol.9 , pp. 373-386
    • Rajagopal, S.1    Rajagopal, K.2    Lefkowitz, R.J.3
  • 9
    • 84930278822 scopus 로고    scopus 로고
    • Beta-arrestins: Regulatory role and therapeutic potential in opioid and cannabinoid receptor-mediated analgesia
    • Raehal, K. M. and Bohn, L. M. (2014) beta-arrestins: Regulatory role and therapeutic potential in opioid and cannabinoid receptor-mediated analgesia Handb. Exp. Pharmacol. 219, 427-443 10.1007/978-3-642-41199-1-22
    • (2014) Handb. Exp. Pharmacol. , vol.219 , pp. 427-443
    • Raehal, K.M.1    Bohn, L.M.2
  • 10
    • 0037707295 scopus 로고    scopus 로고
    • Management of opioid side effects in cancer-related and chronic noncancer pain: A systematic review
    • McNicol, E., Horowicz-Mehler, N., Fisk, R. A., Bennett, K., Gialeli-Goudas, M., Chew, P. W., Lau, J., and Carr, D. (2003) Management of opioid side effects in cancer-related and chronic noncancer pain: A systematic review J. Pain 4, 231-256 10.1016/S1526-5900(03)00556-X
    • (2003) J. Pain , vol.4 , pp. 231-256
    • McNicol, E.1    Horowicz-Mehler, N.2    Fisk, R.A.3    Bennett, K.4    Gialeli-Goudas, M.5    Chew, P.W.6    Lau, J.7    Carr, D.8
  • 13
    • 64349119538 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of 6alpha- A nd 6beta-N-heterocyclic substituted naltrexamine derivatives as mu opioid receptor selective antagonists
    • Li, G., Aschenbach, L. C., Chen, J., Cassidy, M. P., Stevens, D. L., Gabra, B. H., Selley, D. E., Dewey, W. L., Westkaemper, R. B., and Zhang, Y. (2009) Design, synthesis, and biological evaluation of 6alpha- A nd 6beta-N-heterocyclic substituted naltrexamine derivatives as mu opioid receptor selective antagonists J. Med. Chem. 52, 1416-1427 10.1021/jm801272c
    • (2009) J. Med. Chem. , vol.52 , pp. 1416-1427
    • Li, G.1    Aschenbach, L.C.2    Chen, J.3    Cassidy, M.P.4    Stevens, D.L.5    Gabra, B.H.6    Selley, D.E.7    Dewey, W.L.8    Westkaemper, R.B.9    Zhang, Y.10
  • 14
    • 80051995849 scopus 로고    scopus 로고
    • Preclinical disposition (in vitro) of novel mu-opioid receptor selective antagonists
    • Mitra, P., Venitz, J., Yuan, Y., Zhang, Y., and Gerk, P. M. (2011) Preclinical disposition (in vitro) of novel mu-opioid receptor selective antagonists Drug Metab. Dispos. 39, 1589-1596 10.1124/dmd.111.038588
    • (2011) Drug Metab. Dispos. , vol.39 , pp. 1589-1596
    • Mitra, P.1    Venitz, J.2    Yuan, Y.3    Zhang, Y.4    Gerk, P.M.5
  • 15
    • 79960720063 scopus 로고    scopus 로고
    • Characterization of 6alpha- A nd 6beta-N-heterocyclic substituted naltrexamine derivatives as novel leads to development of mu opioid receptor selective antagonists
    • Yuan, Y., Li, G., He, H., Stevens, D. L., Kozak, P., Scoggins, K. L., Mitra, P., Gerk, P. M., Selley, D. E., Dewey, W. L., and Zhang, Y. (2011) Characterization of 6alpha- A nd 6beta-N-heterocyclic substituted naltrexamine derivatives as novel leads to development of mu opioid receptor selective antagonists ACS Chem. Neurosci. 2, 346-351 10.1021/cn2000348
    • (2011) ACS Chem. Neurosci. , vol.2 , pp. 346-351
    • Yuan, Y.1    Li, G.2    He, H.3    Stevens, D.L.4    Kozak, P.5    Scoggins, K.L.6    Mitra, P.7    Gerk, P.M.8    Selley, D.E.9    Dewey, W.L.10    Zhang, Y.11
  • 16
    • 84863480944 scopus 로고    scopus 로고
    • 6beta-N-heterocyclic substituted naltrexamine derivative NAP as a potential lead to develop peripheral mu opioid receptor selective antagonists
    • Yuan, Y., Stevens, D. L., Braithwaite, A., Scoggins, K. L., Bilsky, E. J., Akbarali, H. I., Dewey, W. L., and Zhang, Y. (2012) 6beta-N-heterocyclic substituted naltrexamine derivative NAP as a potential lead to develop peripheral mu opioid receptor selective antagonists Bioorg. Med. Chem. Lett. 22, 4731-4734 10.1016/j.bmcl.2012.05.075
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 4731-4734
    • Yuan, Y.1    Stevens, D.L.2    Braithwaite, A.3    Scoggins, K.L.4    Bilsky, E.J.5    Akbarali, H.I.6    Dewey, W.L.7    Zhang, Y.8
  • 17
    • 0041932084 scopus 로고    scopus 로고
    • Relative efficacy of buprenorphine, nalbuphine and morphine in opioid-treated rhesus monkeys discriminating naltrexone
    • Sell, S. L., McMahon, L. R., and France, C. P. (2003) Relative efficacy of buprenorphine, nalbuphine and morphine in opioid-treated rhesus monkeys discriminating naltrexone J. Pharmacol. Exp. Ther. 306, 1167-1173 10.1124/jpet.103.051425
    • (2003) J. Pharmacol. Exp. Ther. , vol.306 , pp. 1167-1173
    • Sell, S.L.1    McMahon, L.R.2    France, C.P.3
  • 18
    • 84858121231 scopus 로고    scopus 로고
    • Tools for GPCR drug discovery
    • Zhang, R. and Xie, X. (2012) Tools for GPCR drug discovery Acta Pharmacol. Sin. 33, 372-384 10.1038/aps.2011.173
    • (2012) Acta Pharmacol. Sin. , vol.33 , pp. 372-384
    • Zhang, R.1    Xie, X.2
  • 19
    • 84925668837 scopus 로고    scopus 로고
    • Design, Syntheses, and Pharmacological Characterization of 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3-carboxamido)morphinan Analogues as Opioid Receptor Ligands
    • Yuan, Y., Zaidi, S. A., Stevens, D. L., Scoggins, K. L., Mosier, P. D., Kellogg, G. E., Dewey, W. L., Selley, D. E., and Zhang, Y. (2015) Design, Syntheses, and Pharmacological Characterization of 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3-carboxamido)morphinan Analogues as Opioid Receptor Ligands Bioorg. Med. Chem. 23, 1701-15 10.1016/j.bmc.2015.02.055
    • (2015) Bioorg. Med. Chem. , vol.23 , pp. 1701-1715
    • Yuan, Y.1    Zaidi, S.A.2    Stevens, D.L.3    Scoggins, K.L.4    Mosier, P.D.5    Kellogg, G.E.6    Dewey, W.L.7    Selley, D.E.8    Zhang, Y.9
  • 20
    • 27144434813 scopus 로고    scopus 로고
    • Techniques: Promiscuous Galpha proteins in basic research and drug discovery
    • Kostenis, E., Waelbroeck, M., and Milligan, G. (2005) Techniques: Promiscuous Galpha proteins in basic research and drug discovery Trends Pharmacol. Sci. 26, 595-602 10.1016/j.tips.2005.09.007
    • (2005) Trends Pharmacol. Sci. , vol.26 , pp. 595-602
    • Kostenis, E.1    Waelbroeck, M.2    Milligan, G.3
  • 22
    • 84908866820 scopus 로고    scopus 로고
    • Identification of selective agonists and positive allosteric modulators for micro- A nd delta-opioid receptors from a single high-throughput screen
    • Burford, N. T., Wehrman, T., Bassoni, D., O'Connell, J., Banks, M., Zhang, L., and Alt, A. (2014) Identification of selective agonists and positive allosteric modulators for micro- A nd delta-opioid receptors from a single high-throughput screen J. Biomol. Screening 19, 1255-1265 10.1177/1087057114542975
    • (2014) J. Biomol. Screening , vol.19 , pp. 1255-1265
    • Burford, N.T.1    Wehrman, T.2    Bassoni, D.3    O'Connell, J.4    Banks, M.5    Zhang, L.6    Alt, A.7
  • 23
    • 84900677861 scopus 로고    scopus 로고
    • Behavioral and cellular pharmacology characterization of 17-cyclopropylmethyl-3,14beta-dihydroxy-4,5alpha-epoxy-6alpha-(isoquinoline-3′-ca rboxamido)morphinan (NAQ) as a mu opioid receptor selective ligand
    • Zhang, Y., Braithwaite, A., Yuan, Y., Streicher, J. M., and Bilsky, E. J. (2014) Behavioral and cellular pharmacology characterization of 17-cyclopropylmethyl-3,14beta-dihydroxy-4,5alpha-epoxy-6alpha-(isoquinoline-3′-ca rboxamido)morphinan (NAQ) as a mu opioid receptor selective ligand Eur. J. Pharmacol. 736, 124-130 10.1016/j.ejphar.2014.04.041
    • (2014) Eur. J. Pharmacol. , vol.736 , pp. 124-130
    • Zhang, Y.1    Braithwaite, A.2    Yuan, Y.3    Streicher, J.M.4    Bilsky, E.J.5
  • 24
    • 84857349362 scopus 로고    scopus 로고
    • The role of beta-arrestin2 in the mechanism of morphine tolerance in the mouse and Guinea pig gastrointestinal tract
    • Kang, M., Maguma, H. T., Smith, T. H., Ross, G. R., Dewey, W. L., and Akbarali, H. I. (2012) The role of beta-arrestin2 in the mechanism of morphine tolerance in the mouse and guinea pig gastrointestinal tract J. Pharmacol. Exp. Ther. 340, 567-576 10.1124/jpet.111.186320
    • (2012) J. Pharmacol. Exp. Ther. , vol.340 , pp. 567-576
    • Kang, M.1    Maguma, H.T.2    Smith, T.H.3    Ross, G.R.4    Dewey, W.L.5    Akbarali, H.I.6
  • 25
    • 33947395692 scopus 로고    scopus 로고
    • In vitro characterization of the effects of endomorphin 1 and 2, endogenous ligands for mu-opioid receptors, on mouse colonic motility
    • Yu, Y., Cui, Y., Wang, X., Lai, L. H., Wang, C. L., Fan, Y. Z., Liu, J., and Wang, R. (2007) In vitro characterization of the effects of endomorphin 1 and 2, endogenous ligands for mu-opioid receptors, on mouse colonic motility Biochem. Pharmacol. 73, 1384-1393 10.1016/j.bcp.2007.01.011
    • (2007) Biochem. Pharmacol. , vol.73 , pp. 1384-1393
    • Yu, Y.1    Cui, Y.2    Wang, X.3    Lai, L.H.4    Wang, C.L.5    Fan, Y.Z.6    Liu, J.7    Wang, R.8
  • 26
    • 0030953721 scopus 로고    scopus 로고
    • Opioid receptor expression in the rat gastrointestinal tract: A quantitative study with comparison to the brain
    • Fickel, J., Bagnol, D., Watson, S. J., and Akil, H. (1997) Opioid receptor expression in the rat gastrointestinal tract: A quantitative study with comparison to the brain Mol. Brain Res. 46, 1-8 10.1016/S0169-328X(96)00266-5
    • (1997) Mol. Brain Res. , vol.46 , pp. 1-8
    • Fickel, J.1    Bagnol, D.2    Watson, S.J.3    Akil, H.4
  • 27
    • 28444479463 scopus 로고    scopus 로고
    • Diversity and complexity of the mu opioid receptor gene: Alternative pre-mRNA splicing and promoters
    • Pan, Y. X. (2005) Diversity and complexity of the mu opioid receptor gene: Alternative pre-mRNA splicing and promoters DNA Cell Biol. 24, 736-750 10.1089/dna.2005.24.736
    • (2005) DNA Cell Biol. , vol.24 , pp. 736-750
    • Pan, Y.X.1
  • 30
    • 84885186318 scopus 로고    scopus 로고
    • Binding mode characterization of 6alpha- A nd 6beta-N-heterocyclic substituted naltrexamine derivatives via docking in opioid receptor crystal structures and site-directed mutagenesis studies: Application of the 'message-address' concept in development of mu opioid receptor selective antagonists
    • Zaidi, S. A., Arnatt, C. K., He, H., Selley, D. E., Mosier, P. D., Kellogg, G. E., and Zhang, Y. (2013) Binding mode characterization of 6alpha- A nd 6beta-N-heterocyclic substituted naltrexamine derivatives via docking in opioid receptor crystal structures and site-directed mutagenesis studies: Application of the 'message-address' concept in development of mu opioid receptor selective antagonists Bioorg. Med. Chem. 21, 6405-6413 10.1016/j.bmc.2013.08.042
    • (2013) Bioorg. Med. Chem. , vol.21 , pp. 6405-6413
    • Zaidi, S.A.1    Arnatt, C.K.2    He, H.3    Selley, D.E.4    Mosier, P.D.5    Kellogg, G.E.6    Zhang, Y.7


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