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Volumn 27, Issue 2, 2008, Pages 131-139

Chemical function-based pharmacophore development for novel, selective kappa opioid receptor agonists

Author keywords

Agonist; Analgesics; G protein coupled receptor (GPCR); Kappa opioid receptor; New chemical entities (NCEs); Peripherally restricted; Pharmacophore

Indexed keywords

ARSENIC COMPOUNDS; CHLORINE COMPOUNDS;

EID: 52049125021     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmgm.2008.03.007     Document Type: Article
Times cited : (17)

References (50)
  • 1
    • 0029102878 scopus 로고
    • Molecular biology of the opioid receptors: structures, functions and distributions
    • Minami M., and Satoh M. Molecular biology of the opioid receptors: structures, functions and distributions. Neurosci. Res. 23 (1995) 121-145
    • (1995) Neurosci. Res. , vol.23 , pp. 121-145
    • Minami, M.1    Satoh, M.2
  • 2
    • 0029609445 scopus 로고
    • Molecular pharmacology of the opioid receptors
    • Satoh M., and Minami M. Molecular pharmacology of the opioid receptors. Pharmacol. Ther. 68 (1995) 343-364
    • (1995) Pharmacol. Ther. , vol.68 , pp. 343-364
    • Satoh, M.1    Minami, M.2
  • 3
    • 0022886435 scopus 로고
    • Multiple opioid systems and pain
    • Millan M.J. Multiple opioid systems and pain. Pain 27 (1986) 303-347
    • (1986) Pain , vol.27 , pp. 303-347
    • Millan, M.J.1
  • 4
    • 0021049819 scopus 로고
    • Pharmacology of opioids
    • Martin W.R. Pharmacology of opioids. Pharmacol. Rev. 35 (1983) 283-323
    • (1983) Pharmacol. Rev. , vol.35 , pp. 283-323
    • Martin, W.R.1
  • 5
    • 0017064976 scopus 로고
    • The effects of morphine- and nalorphine-like drugs in the nondependent and morphine-dependent chronic spinal dog
    • Martin W.R., Eades C.G., Thompson J.A., Huppler R.E., and Gilbert P.E. The effects of morphine- and nalorphine-like drugs in the nondependent and morphine-dependent chronic spinal dog. J. Pharmacol. Exp. Ther. 197 (1976) 517-532
    • (1976) J. Pharmacol. Exp. Ther. , vol.197 , pp. 517-532
    • Martin, W.R.1    Eades, C.G.2    Thompson, J.A.3    Huppler, R.E.4    Gilbert, P.E.5
  • 8
    • 0034694363 scopus 로고    scopus 로고
    • Arylacetamides as peripherally restricted kappa opioid receptor agonists
    • Kumar V., Marella M.A., Cortes-Burgos L., et al. Arylacetamides as peripherally restricted kappa opioid receptor agonists. Bioorg. Med. Chem. Lett. 10 (2000) 2567-2570
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 2567-2570
    • Kumar, V.1    Marella, M.A.2    Cortes-Burgos, L.3
  • 9
    • 0344589372 scopus 로고    scopus 로고
    • Effects of neurotoxins and hindpaw inflammation on opioid receptor immunoreactivities in dorsal root ganglia
    • Zhang Q., Schaffer M., Elde R., and Stein C. Effects of neurotoxins and hindpaw inflammation on opioid receptor immunoreactivities in dorsal root ganglia. Neuroscience 85 (1998) 281-291
    • (1998) Neuroscience , vol.85 , pp. 281-291
    • Zhang, Q.1    Schaffer, M.2    Elde, R.3    Stein, C.4
  • 10
    • 2442472275 scopus 로고    scopus 로고
    • Peripheral kappa-opioid agonists for visceral pain
    • Riviere P.J. Peripheral kappa-opioid agonists for visceral pain. Br. J. Pharmacol. 141 (2004) 1331-1334
    • (2004) Br. J. Pharmacol. , vol.141 , pp. 1331-1334
    • Riviere, P.J.1
  • 11
    • 0024506654 scopus 로고
    • ICI 204448: a kappa-opioid agonist with limited access to the CNS
    • Shaw J., Carroll J.A., Alcock P., and Main B.G. ICI 204448: a kappa-opioid agonist with limited access to the CNS. Br. J. Pharmacol. 96 (1989) 986-992
    • (1989) Br. J. Pharmacol. , vol.96 , pp. 986-992
    • Shaw, J.1    Carroll, J.A.2    Alcock, P.3    Main, B.G.4
  • 12
    • 0032102772 scopus 로고    scopus 로고
    • Effects of antihyperalgesic drugs on experimentally induced hyperalgesia in man
    • Bickel A., Dorfs S., Schmelz M., Forster C., Uhl W., and Handwerker H.O. Effects of antihyperalgesic drugs on experimentally induced hyperalgesia in man. Pain 76 (1998) 317-325
    • (1998) Pain , vol.76 , pp. 317-325
    • Bickel, A.1    Dorfs, S.2    Schmelz, M.3    Forster, C.4    Uhl, W.5    Handwerker, H.O.6
  • 13
    • 0033813577 scopus 로고    scopus 로고
    • Influence of asimadoline, a new κ-opioid receptor agonist, on tubular water absorption and vasopressin secretion in man
    • Kramer H., Uhl W., Ladstetter B., and Backer A. Influence of asimadoline, a new κ-opioid receptor agonist, on tubular water absorption and vasopressin secretion in man. Br. J. Pharmacol. 50 (2000) 227-235
    • (2000) Br. J. Pharmacol. , vol.50 , pp. 227-235
    • Kramer, H.1    Uhl, W.2    Ladstetter, B.3    Backer, A.4
  • 14
    • 0344731442 scopus 로고    scopus 로고
    • Peripheral effects of the κ-opioid agonist EMD 61753 on pain and inflammation in rats and humans
    • Machelska H., Pfluger M., Weber W., et al. Peripheral effects of the κ-opioid agonist EMD 61753 on pain and inflammation in rats and humans. J. Pharmacol. Exp. Ther. 290 (1999) 354-361
    • (1999) J. Pharmacol. Exp. Ther. , vol.290 , pp. 354-361
    • Machelska, H.1    Pfluger, M.2    Weber, W.3
  • 15
    • 0030003322 scopus 로고    scopus 로고
    • Aspartic acid conjugates of 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1(3-aminophenyl)-2-(1-pyrrolidinyl) ethyl]acetamide: kappa opioid receptor agonists with limited access to the central nervous system
    • Chang A.C., Cowan A., Takemori A.E., and Portoghese P.S. Aspartic acid conjugates of 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1(3-aminophenyl)-2-(1-pyrrolidinyl) ethyl]acetamide: kappa opioid receptor agonists with limited access to the central nervous system. J. Med. Chem. 39 (1996) 4478-4482
    • (1996) J. Med. Chem. , vol.39 , pp. 4478-4482
    • Chang, A.C.1    Cowan, A.2    Takemori, A.E.3    Portoghese, P.S.4
  • 16
    • 1442276958 scopus 로고    scopus 로고
    • Peripherally restricted opioid agonists as novel analgesic agents
    • DeHaven-Hudkins D.L., and Dolle R.E. Peripherally restricted opioid agonists as novel analgesic agents. Curr. Pharm. Des. 10 (2004) 743-757
    • (2004) Curr. Pharm. Des. , vol.10 , pp. 743-757
    • DeHaven-Hudkins, D.L.1    Dolle, R.E.2
  • 17
    • 20144388985 scopus 로고    scopus 로고
    • Synthesis and evaluation of novel peripherally restricted kappa-opioid receptor agonists
    • Kumar V., Guo D., Cassel J.A., et al. Synthesis and evaluation of novel peripherally restricted kappa-opioid receptor agonists. Bioorg. Med. Chem. Lett. 15 (2005) 1091-1095
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1091-1095
    • Kumar, V.1    Guo, D.2    Cassel, J.A.3
  • 18
    • 52049100980 scopus 로고    scopus 로고
    • Catalyst, version 4.8, Burlington, Accelrys Inc., 2003.
    • Catalyst, version 4.8, Burlington, Accelrys Inc., 2003.
  • 19
    • 26844490394 scopus 로고    scopus 로고
    • Potent and highly selective kappa opioid receptor agonists incorporating chroman- and 2,3-dihydrobenzofuran-based constraints
    • Chu G.H., Gu M., Cassel J.A., et al. Potent and highly selective kappa opioid receptor agonists incorporating chroman- and 2,3-dihydrobenzofuran-based constraints. Bioorg. Med. Chem. Lett. 15 (2005) 5114-5119
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 5114-5119
    • Chu, G.H.1    Gu, M.2    Cassel, J.A.3
  • 20
    • 20944445103 scopus 로고    scopus 로고
    • Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity
    • Le Bourdonnec B., Ajello C.W., Seida P.R., et al. Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity. Bioorg. Med. Chem. Lett. 15 (2005) 2647-2652
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 2647-2652
    • Le Bourdonnec, B.1    Ajello, C.W.2    Seida, P.R.3
  • 21
    • 0028827113 scopus 로고
    • CCB, a novel specific kappa opioid agonist, which discriminates between opioid and sigma 1 recognition sites
    • Ronsisvalle G., Prezzavento O., Pasquinucci L., et al. CCB, a novel specific kappa opioid agonist, which discriminates between opioid and sigma 1 recognition sites. Life Sci. 57 (1995) 1487-1495
    • (1995) Life Sci. , vol.57 , pp. 1487-1495
    • Ronsisvalle, G.1    Prezzavento, O.2    Pasquinucci, L.3
  • 22
    • 5144224991 scopus 로고    scopus 로고
    • Azepinone as a conformational constraint in the design of kappa-opioid receptor agonists
    • Tuthill P.A., Seida P.R., Barker W., et al. Azepinone as a conformational constraint in the design of kappa-opioid receptor agonists. Bioorg. Med. Chem. Lett. 14 (2004) 5693-5697
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 5693-5697
    • Tuthill, P.A.1    Seida, P.R.2    Barker, W.3
  • 23
    • 52049087656 scopus 로고    scopus 로고
    • Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans
    • Walsh S.L., Strain E.C., Abreu M.E., and Bigelow G.E. Enadoline, a selective kappa opioid agonist: comparison with butorphanol and hydromorphone in humans. Psychopharmacology (Berl.) 160 (2001) 170-181
    • (2001) Psychopharmacology (Berl.) , vol.160 , pp. 170-181
    • Walsh, S.L.1    Strain, E.C.2    Abreu, M.E.3    Bigelow, G.E.4
  • 24
    • 0025106267 scopus 로고
    • CI-977, a novel and selective agonist for the kappa-opioid receptor
    • Hunter J.C., Leighton G.E., Meecham K.G., et al. CI-977, a novel and selective agonist for the kappa-opioid receptor. Br. J. Pharmacol. 101 (1990) 183-189
    • (1990) Br. J. Pharmacol. , vol.101 , pp. 183-189
    • Hunter, J.C.1    Leighton, G.E.2    Meecham, K.G.3
  • 25
    • 0023929950 scopus 로고
    • Highly selective kappa opioid analgesics. Synthesis and structure-activity relationships of novel N-[2-aminocyclohexylaryl]acetamide and N-[2-aminocyclohexylaryloxy]acetamide derivatives
    • Clark C.R., Halfpenny P.R., Hill R.G., et al. Highly selective kappa opioid analgesics. Synthesis and structure-activity relationships of novel N-[2-aminocyclohexylaryl]acetamide and N-[2-aminocyclohexylaryloxy]acetamide derivatives. J. Med. Chem. 31 (1988) 831-836
    • (1988) J. Med. Chem. , vol.31 , pp. 831-836
    • Clark, C.R.1    Halfpenny, P.R.2    Hill, R.G.3
  • 26
    • 0034609861 scopus 로고    scopus 로고
    • Synthesis and opioid receptor affinity of a series of 2, 4-diaryl-substituted 3,7-diazabicylononanones
    • Siener T., Cambareri A., Kuhl U., et al. Synthesis and opioid receptor affinity of a series of 2, 4-diaryl-substituted 3,7-diazabicylononanones. J. Med. Chem. 43 (2000) 3746-3751
    • (2000) J. Med. Chem. , vol.43 , pp. 3746-3751
    • Siener, T.1    Cambareri, A.2    Kuhl, U.3
  • 27
    • 0030028469 scopus 로고    scopus 로고
    • Synthesis, biological evaluation, and quantitative receptor docking simulations of 2-[(acylamino)ethyl]-1,4-benzodiazepines as novel tifluadom-like ligands with high affinity and selectivity for kappa-opioid receptors
    • Cappelli A., Anzini M., Vomero S., et al. Synthesis, biological evaluation, and quantitative receptor docking simulations of 2-[(acylamino)ethyl]-1,4-benzodiazepines as novel tifluadom-like ligands with high affinity and selectivity for kappa-opioid receptors. J. Med. Chem. 39 (1996) 860-872
    • (1996) J. Med. Chem. , vol.39 , pp. 860-872
    • Cappelli, A.1    Anzini, M.2    Vomero, S.3
  • 28
    • 0027998232 scopus 로고
    • Selective kappa-opioid agonists: synthesis and structure-activity relationships of piperidines incorporating on oxo-containing acyl group
    • Giardina G., Clarke G.D., Dondio G., Petrone G., Sbacchi M., and Vecchietti V. Selective kappa-opioid agonists: synthesis and structure-activity relationships of piperidines incorporating on oxo-containing acyl group. J. Med. Chem. 37 (1994) 3482-3491
    • (1994) J. Med. Chem. , vol.37 , pp. 3482-3491
    • Giardina, G.1    Clarke, G.D.2    Dondio, G.3    Petrone, G.4    Sbacchi, M.5    Vecchietti, V.6
  • 30
    • 0026056624 scopus 로고
    • (1S)-1-(Aminomethyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinoline and heterocycle-condensed tetrahydropyridine derivatives: members of a novel class of very potent kappa opioid analgesics
    • Vecchietti V., Clarke G.D., Colle R., Giardina G., Petrone G., and Sbacchi M. (1S)-1-(Aminomethyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinoline and heterocycle-condensed tetrahydropyridine derivatives: members of a novel class of very potent kappa opioid analgesics. J. Med. Chem. 34 (1991) 2624-2633
    • (1991) J. Med. Chem. , vol.34 , pp. 2624-2633
    • Vecchietti, V.1    Clarke, G.D.2    Colle, R.3    Giardina, G.4    Petrone, G.5    Sbacchi, M.6
  • 31
    • 0024307659 scopus 로고
    • Highly selective kappa-opioid analgesics. Part 2. Synthesis and structure-activity relationships of novel N-[(2-aminocyclohexyl)aryl]acetamide derivatives
    • Halfpenny P.R., Hill R.G., Horwell D.C., et al. Highly selective kappa-opioid analgesics. Part 2. Synthesis and structure-activity relationships of novel N-[(2-aminocyclohexyl)aryl]acetamide derivatives. J. Med. Chem. 32 (1989) 1620-1626
    • (1989) J. Med. Chem. , vol.32 , pp. 1620-1626
    • Halfpenny, P.R.1    Hill, R.G.2    Horwell, D.C.3
  • 32
    • 13944261906 scopus 로고    scopus 로고
    • Amino acid conjugates as kappa opioid receptor agonists
    • Kumar V., Guo D., Daubert J.D., et al. Amino acid conjugates as kappa opioid receptor agonists. Bioorg. Med. Chem. Lett. 15 (2005) 1279-1282
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1279-1282
    • Kumar, V.1    Guo, D.2    Daubert, J.D.3
  • 33
    • 0035899195 scopus 로고    scopus 로고
    • Methylated analogues of methyl (R)-4-(3,4-dichlorophenylacetyl)-3-(pyrrolidin-1-ylmethyl)piperazine-1-carboxylate (GR-89,696) as highly potent kappa-receptor agonists: stereoselective synthesis, opioid-receptor affinity, receptor selectivity, and functional studies
    • Soukara S., Maier C.A., Predoiu U., Ehret A., Jackisch R., and Wunsch B. Methylated analogues of methyl (R)-4-(3,4-dichlorophenylacetyl)-3-(pyrrolidin-1-ylmethyl)piperazine-1-carboxylate (GR-89,696) as highly potent kappa-receptor agonists: stereoselective synthesis, opioid-receptor affinity, receptor selectivity, and functional studies. J. Med. Chem. 44 (2001) 2814-2826
    • (2001) J. Med. Chem. , vol.44 , pp. 2814-2826
    • Soukara, S.1    Maier, C.A.2    Predoiu, U.3    Ehret, A.4    Jackisch, R.5    Wunsch, B.6
  • 34
    • 0020450977 scopus 로고
    • Benzeneacetamide amines: structurally novel non-mu opioids
    • Szmuszkovicz J., and Von Voigtlander P.F. Benzeneacetamide amines: structurally novel non-mu opioids. J. Med. Chem. 25 (1982) 1125-1126
    • (1982) J. Med. Chem. , vol.25 , pp. 1125-1126
    • Szmuszkovicz, J.1    Von Voigtlander, P.F.2
  • 35
    • 5644236834 scopus 로고    scopus 로고
    • Pharmacophore modeling and three dimensional database searching for drug design using Catalyst: recent advances
    • Guner O., Clement O., and Kurogi Y. Pharmacophore modeling and three dimensional database searching for drug design using Catalyst: recent advances. Curr. Med. Chem. 11 (2004) 2991-3005
    • (2004) Curr. Med. Chem. , vol.11 , pp. 2991-3005
    • Guner, O.1    Clement, O.2    Kurogi, Y.3
  • 38
    • 84986522856 scopus 로고
    • Poling: promoting conformational variation
    • Smellie A., Teig S.L., and Towbin P. Poling: promoting conformational variation. J. Comput. Chem. 16 (1995) 171-187
    • (1995) J. Comput. Chem. , vol.16 , pp. 171-187
    • Smellie, A.1    Teig, S.L.2    Towbin, P.3
  • 39
    • 52049103176 scopus 로고    scopus 로고
    • English Philosopher and Franciscan Monk, William of Ockham, p. 1285.
    • English Philosopher and Franciscan Monk, William of Ockham, p. 1285.
  • 42
    • 0034214399 scopus 로고    scopus 로고
    • Modeling of kappa-opioid receptor/agonists interactions using pharmacophore-based and docking simulations
    • Lavecchia A., Greco G., Novellino E., Vittorio F., and Ronsisvalle G. Modeling of kappa-opioid receptor/agonists interactions using pharmacophore-based and docking simulations. J. Med. Chem. 43 (2000) 2124-2134
    • (2000) J. Med. Chem. , vol.43 , pp. 2124-2134
    • Lavecchia, A.1    Greco, G.2    Novellino, E.3    Vittorio, F.4    Ronsisvalle, G.5
  • 43
    • 0029994263 scopus 로고    scopus 로고
    • Application of the message-address concept to the docking of naltrexone and selective naltrexone-derived opioid antagonists into opioid receptor models
    • Metzger T.G., Paterlini M.G., Portoghese P.S., and Ferguson D.M. Application of the message-address concept to the docking of naltrexone and selective naltrexone-derived opioid antagonists into opioid receptor models. Neurochem. Res. 21 (1996) 1287-1294
    • (1996) Neurochem. Res. , vol.21 , pp. 1287-1294
    • Metzger, T.G.1    Paterlini, M.G.2    Portoghese, P.S.3    Ferguson, D.M.4
  • 44
    • 0037168078 scopus 로고    scopus 로고
    • Kappa-opioid receptor model in a phospholipid bilayer: molecular dynamics simulation
    • Iadanza M., Holtje M., Ronsisvalle G., and Holtje H.D. Kappa-opioid receptor model in a phospholipid bilayer: molecular dynamics simulation. J. Med. Chem. 45 (2002) 4838-4846
    • (2002) J. Med. Chem. , vol.45 , pp. 4838-4846
    • Iadanza, M.1    Holtje, M.2    Ronsisvalle, G.3    Holtje, H.D.4
  • 45
    • 7844249248 scopus 로고    scopus 로고
    • Conformational analysis and automated receptor docking of selective arylacetamide-based kappa-opioid agonists
    • Subramanian G., Paterlini M.G., Larson D.L., Portoghese P.S., and Ferguson D.M. Conformational analysis and automated receptor docking of selective arylacetamide-based kappa-opioid agonists. J. Med. Chem. 41 (1998) 4777-4789
    • (1998) J. Med. Chem. , vol.41 , pp. 4777-4789
    • Subramanian, G.1    Paterlini, M.G.2    Larson, D.L.3    Portoghese, P.S.4    Ferguson, D.M.5
  • 46
    • 0033896835 scopus 로고    scopus 로고
    • Building 3D-structural model of kappa opioid receptor and studying its interaction mechanism with dynorphin A(1-8)
    • Wan X.H., Huang X.Q., Zhou D.H., Jiang H.L., Chen K.X., and Chi Z.Q. Building 3D-structural model of kappa opioid receptor and studying its interaction mechanism with dynorphin A(1-8). Acta Pharmacol. Sin. 21 (2000) 701-708
    • (2000) Acta Pharmacol. Sin. , vol.21 , pp. 701-708
    • Wan, X.H.1    Huang, X.Q.2    Zhou, D.H.3    Jiang, H.L.4    Chen, K.X.5    Chi, Z.Q.6
  • 47
    • 0037431393 scopus 로고    scopus 로고
    • Mechanism of action of the diazabicyclononanone-type kappa-agonists
    • Holzgrabe U., and Brandt W. Mechanism of action of the diazabicyclononanone-type kappa-agonists. J. Med. Chem. 46 (2003) 1383-1389
    • (2003) J. Med. Chem. , vol.46 , pp. 1383-1389
    • Holzgrabe, U.1    Brandt, W.2
  • 48
    • 0035061847 scopus 로고    scopus 로고
    • Differentiation of delta, mu, and kappa opioid receptor agonists based on pharmacophore development and computed physicochemical properties
    • Filizola M., Villar H.O., and Loew G.H. Differentiation of delta, mu, and kappa opioid receptor agonists based on pharmacophore development and computed physicochemical properties. J. Comput. Mol. Des. 15 (2001) 297-307
    • (2001) J. Comput. Mol. Des. , vol.15 , pp. 297-307
    • Filizola, M.1    Villar, H.O.2    Loew, G.H.3
  • 49
    • 34249277652 scopus 로고    scopus 로고
    • A combined ligand-based and target-based drug design approach for G-protein coupled receptors: application to salvinorin A, a selective kappa opioid receptor agonist
    • Singh N., Chevé G., Ferguson D.M., and McCurdy C.R. A combined ligand-based and target-based drug design approach for G-protein coupled receptors: application to salvinorin A, a selective kappa opioid receptor agonist. J. Comput. Mol. Des. 20 (2006) 471-493
    • (2006) J. Comput. Mol. Des. , vol.20 , pp. 471-493
    • Singh, N.1    Chevé, G.2    Ferguson, D.M.3    McCurdy, C.R.4
  • 50
    • 33646271609 scopus 로고    scopus 로고
    • A unique binding epitope for salvinorin A, a non-nitrogenous kappa opioid receptor agonist
    • Kane B., Nieto M., McCurdy C., and Ferguson D. A unique binding epitope for salvinorin A, a non-nitrogenous kappa opioid receptor agonist. FEBS J. 273 (2006) 1966-1974
    • (2006) FEBS J. , vol.273 , pp. 1966-1974
    • Kane, B.1    Nieto, M.2    McCurdy, C.3    Ferguson, D.4


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