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Volumn 58, Issue 12, 2015, Pages 5038-5052

Structure-Activity Relationships of (+)-Naltrexone-Inspired Toll-like Receptor 4 (TLR4) Antagonists

Author keywords

[No Author keywords available]

Indexed keywords

11 (CYCLOPROPYLMETHYL) 3 METHOXY 4 PHENOXY 6,7,8,8A,9,10 HEXAHYDRO 5H 9,4B (EPIMINOETHANO) PHENANTHREN 8A OL; 11 (CYCLOPROPYLMETHYL) 3,8A DIHYDROXY 8,8A,9,10 TETRAHYDRO 5H 9,4B (EPIMINOETHANOL)PHENANTHREN 6(7H) ONE; 11 (CYCLOPROPYLMETHYL) 6,7,8,8A,9,10 HEXAHYDRO 5H 9,4B (EPIMINOETHANOL)PHENANTHRENE 3,8A DIOL; 11 HEXYL 3 METHOXY 8,8A,9,10 TETRAHYDRO 7H 9,4B (EPINIMOETHANO)PHENANTHREN 8A OL; 11 HEXYL 6,7,8,8A,9,10 HEXAHYDRO 5H 9,4B (EPIMINOETHANO)PHENANTHRENE 3,8A DIOL; 11 HEXYL 8,8A,9,10 TETRAHYDRO 7H 9,4B (EPIMINOETHANOL)PHENANTHRENE 3,8A DIOL; 3 (2 FLUOROPHENETHYL) 4A,9 DIHYDROXY 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN 7(7AH) ONE; 3 (CYCLOPROPYLMETHYL) 2,3,4,4A,5,6,7,7A OCTAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLINE 4A,7,9 TRIOL; 3 BUTYL 4A,9 DIHYDROXY 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN(7AH); 3 HEPTYL 4A,9 DIHYDROXY 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN 7 (7AH) ONE; 3 HEXYL 4A HYDROXY 9 METHOXY 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E] ISOQUINOLIN 7(7AH) ONE; 3 HEXYL 4A,9 DIHYDROXY 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN 7(7AH) ONE; 4A HYDROXY 9 METHOXY 3 PHENETHYL 2,3,4,4A,5,6, HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E] ISOQUINOLIN 7(7AH) ONE; 4A,9 DIHYDROXY 3 (3 PHENYLPROPYL) 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN 7(7AH) ONE; 4A,9 DIHYDROXY 3 (4 PHENYLBUTYL) 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN 7(7AH) ONE; 4A,9 DIHYDROXY 3 (5 PHENYLPENTYL) 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN 7(7AH) ONE; 4A,9 DIHYDROXY 3 OCTYL 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN 7(7AH) ONE; 4A,9 DIHYDROXY 3 PENTYL 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN 7 (7AH) ONE; 4A,9 DIHYDROXY 3 PHENETHYL 2,3,4,4A,5,6 HEXAHYDRO 1H 4,12 METHANOBENZOFURO[3,2 E]ISOQUINOLIN 7(7AH) ONE; LIPOPOLYSACCHARIDE; MORPHINE; NALTREXOL; NALTREXONE; NITRIC OXIDE; NOROXYMORPHONE; TOLL LIKE RECEPTOR 4; TOLL LIKE RECEPTOR AFFECTING AGENT; UNCLASSIFIED DRUG; MORPHINAN DERIVATIVE; NARCOTIC ANALGESIC AGENT;

EID: 84933036292     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b00426     Document Type: Article
Times cited : (78)

References (40)
  • 1
    • 77950343791 scopus 로고    scopus 로고
    • Pattern recognition receptors and inflammation
    • Takeuchi, O.; Akira, S. Pattern recognition receptors and inflammation Cell 2010, 140, 805-820
    • (2010) Cell , vol.140 , pp. 805-820
    • Takeuchi, O.1    Akira, S.2
  • 3
    • 84878652464 scopus 로고    scopus 로고
    • Targeting Toll-like receptors with small molecule agents
    • Wang, X.; Smith, C.; Yin, H. Targeting Toll-like receptors with small molecule agents Chem. Soc. Rev. 2013, 42, 4859-4866
    • (2013) Chem. Soc. Rev. , vol.42 , pp. 4859-4866
    • Wang, X.1    Smith, C.2    Yin, H.3
  • 6
    • 84879643635 scopus 로고    scopus 로고
    • Rifampin inhibits Toll-like receptor 4 signaling by targeting myeloid differentiation protein 2 and attenuates neuropathic pain
    • Wang, X.; Grace, P. M.; Pham, M. N.; Cheng, K.; Strand, K. A.; Smith, C.; Li, J.; Watkins, L. R.; Yin, H. Rifampin inhibits Toll-like receptor 4 signaling by targeting myeloid differentiation protein 2 and attenuates neuropathic pain FASEB J. 2013, 27, 2713-2722
    • (2013) FASEB J. , vol.27 , pp. 2713-2722
    • Wang, X.1    Grace, P.M.2    Pham, M.N.3    Cheng, K.4    Strand, K.A.5    Smith, C.6    Li, J.7    Watkins, L.R.8    Yin, H.9
  • 7
    • 84903814786 scopus 로고    scopus 로고
    • Emerging targets in neuroinflammation-driven chronic pain
    • Ji, R.-R.; Xu, Z.-Z.; Gao, Y.-J. Emerging targets in neuroinflammation-driven chronic pain Nat. Rev. Drug Discovery 2014, 13, 533-548
    • (2014) Nat. Rev. Drug Discovery , vol.13 , pp. 533-548
    • Ji, R.-R.1    Xu, Z.-Z.2    Gao, Y.-J.3
  • 9
    • 84859164991 scopus 로고    scopus 로고
    • Implications of central immune signaling caused by drugs of abuse: Mechanisms, mediators and new therapeutic approaches for prediction and treatment of drug dependence
    • Coller, J. K.; Hutchinson, M. R. Implications of central immune signaling caused by drugs of abuse: Mechanisms, mediators and new therapeutic approaches for prediction and treatment of drug dependence Pharmacol. Ther. 2012, 134, 219-245
    • (2012) Pharmacol. Ther. , vol.134 , pp. 219-245
    • Coller, J.K.1    Hutchinson, M.R.2
  • 10
    • 79960687433 scopus 로고    scopus 로고
    • Exploring the neuroimmunopharmacology of opioids: An integrative review of mechanisms of central immune signaling and their implications for opioid analgesia
    • Hutchinson, M. R.; Shavit, Y.; Grace, P. M.; Rice, K. C.; Maier, S. F.; Watkins, L. R. Exploring the neuroimmunopharmacology of opioids: An integrative review of mechanisms of central immune signaling and their implications for opioid analgesia Pharmacol. Rev. 2011, 63, 772-810
    • (2011) Pharmacol. Rev. , vol.63 , pp. 772-810
    • Hutchinson, M.R.1    Shavit, Y.2    Grace, P.M.3    Rice, K.C.4    Maier, S.F.5    Watkins, L.R.6
  • 11
    • 37349118058 scopus 로고    scopus 로고
    • Opioid-induced glial activation: Mechanisms of activation and implications for opioid analgesia, dependence, and reward
    • Hutchinson, M. R.; Bland, S. T.; Johnson, K. W.; Rice, K. C.; Maier, S. F.; Watkins, L. R. Opioid-induced glial activation: Mechanisms of activation and implications for opioid analgesia, dependence, and reward Sci. World J. 2007, 7, 98-111
    • (2007) Sci. World J. , vol.7 , pp. 98-111
    • Hutchinson, M.R.1    Bland, S.T.2    Johnson, K.W.3    Rice, K.C.4    Maier, S.F.5    Watkins, L.R.6
  • 12
    • 84933071385 scopus 로고    scopus 로고
    • Targeting the toll of drug abuse: The translational potential of toll-like receptor 4
    • [Online early access]. Published Online: May 29
    • Bachtell, R. K.; Hutchinson, M. R.; Wang, X.; Rice, K.; Maier, S. F.; Watkins, L. R. Targeting the toll of drug abuse: The translational potential of toll-like receptor 4. CNS Neurol. Disord.: Drug Targets [Online early access]. Published Online: May 29, 2015.
    • (2015) CNS Neurol. Disord.: Drug Targets
    • Bachtell, R.K.1    Hutchinson, M.R.2    Wang, X.3    Rice, K.4    Maier, S.F.5    Watkins, L.R.6
  • 13
    • 84933071386 scopus 로고    scopus 로고
    • Pharmacological characterization of the opioid inactive isomers (+)-naltrexone and (+)-naloxone as Toll-like receptor 4 antagonists
    • submitted
    • Wang, X.; Zhang, Y.; Hutchinson, M. R.; Rice, K. C.; Yin, H.; Watkins, L. R. Pharmacological characterization of the opioid inactive isomers (+)-naltrexone and (+)-naloxone as Toll-like receptor 4 antagonists. Br. J. Pharmacol., submitted.
    • Br. J. Pharmacol.
    • Wang, X.1    Zhang, Y.2    Hutchinson, M.R.3    Rice, K.C.4    Yin, H.5    Watkins, L.R.6
  • 16
    • 0018246347 scopus 로고
    • Synthesis and antinociceptive activity of 7-methoxycodeine
    • Iijima, I.; Minamikawa, J.; Rice, K. C.; Jacobson, A. E. Synthesis and antinociceptive activity of 7-methoxycodeine J. Med. Chem. 1978, 21, 1320-1322
    • (1978) J. Med. Chem. , vol.21 , pp. 1320-1322
    • Iijima, I.1    Minamikawa, J.2    Rice, K.C.3    Jacobson, A.E.4
  • 19
    • 84902097181 scopus 로고    scopus 로고
    • Synthesis of enantiopure 10-nornaltrexones in the search for Toll-like receptor 4 antagonists and opioid ligands
    • Selfridge, B.; Deschamps, J.; Jacobson, A.; Rice, K. Synthesis of enantiopure 10-nornaltrexones in the search for Toll-like receptor 4 antagonists and opioid ligands J. Org. Chem. 2014, 79, 5007-18
    • (2014) J. Org. Chem. , vol.79 , pp. 5007-5018
    • Selfridge, B.1    Deschamps, J.2    Jacobson, A.3    Rice, K.4
  • 20
    • 0014200764 scopus 로고
    • The synthesis of thebaine and northebaine from codeinone dimethyl ketal
    • Rapoport, H.; Lovell, C. H.; Reist, H. R.; Warren, M. E. The synthesis of thebaine and northebaine from codeinone dimethyl ketal J. Am. Chem. Soc. 1967, 89, 1942-1947
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1942-1947
    • Rapoport, H.1    Lovell, C.H.2    Reist, H.R.3    Warren, M.E.4
  • 21
    • 0018178770 scopus 로고
    • Studies in the (+)-morphinan series. 5. Synthesis and biological properties of (+)-naloxone
    • Iijima, I.; Minamikawa, J.; Jacobson, A. E.; Brossi, A.; Rice, K. C. Studies in the (+)-morphinan series. 5. Synthesis and biological properties of (+)-naloxone J. Med. Chem. 1978, 21, 398-400
    • (1978) J. Med. Chem. , vol.21 , pp. 398-400
    • Iijima, I.1    Minamikawa, J.2    Jacobson, A.E.3    Brossi, A.4    Rice, K.C.5
  • 22
    • 0026718415 scopus 로고
    • Probes for narcotic receptor mediated phenomena. 18
    • Epimeric 6α-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinans and 6β-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinans as potential ligands for opioid receptor single photon emission computed tomography-synthesis evaluation, and radiochemistry of 125I-6β-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan
    • de Costa, B. R.; Iadarola, M. J.; Rothman, R. B.; Berman, K. F.; George, C.; Newman, A. H.; Mahboubi, A.; Jacobson, A. E.; Rice, K. C. Probes for narcotic receptor mediated phenomena. 18. Epimeric 6α-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinans and 6β-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinans as potential ligands for opioid receptor single photon emission computed tomography-synthesis, evaluation, and radiochemistry of 125I-6β-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan J. Med. Chem. 1992, 35, 2826-2835
    • (1992) J. Med. Chem. , vol.35 , pp. 2826-2835
    • De Costa, B.R.1    Iadarola, M.J.2    Rothman, R.B.3    Berman, K.F.4    George, C.5    Newman, A.H.6    Mahboubi, A.7    Jacobson, A.E.8    Rice, K.C.9
  • 23
    • 84875897593 scopus 로고    scopus 로고
    • Brain microglia: Watchdogs with pedigree
    • Neumann, H.; Wekerle, H. Brain microglia: Watchdogs with pedigree Nat. Neurosci. 2013, 16, 253-255
    • (2013) Nat. Neurosci. , vol.16 , pp. 253-255
    • Neumann, H.1    Wekerle, H.2
  • 24
    • 84887121400 scopus 로고    scopus 로고
    • Why is neuroimmunopharmacology crucial for the future of addiction research?
    • Hutchinson, M. R.; Watkins, L. R. Why is neuroimmunopharmacology crucial for the future of addiction research? Neuropharmacology 2014, 76 (Part B) 218-227
    • (2014) Neuropharmacology , vol.76 , Issue.PART B , pp. 218-227
    • Hutchinson, M.R.1    Watkins, L.R.2
  • 25
    • 69949140066 scopus 로고    scopus 로고
    • The suitability of BV2 cells as alternative model system for primary microglia cultures or for animal experiments examining brain inflammation
    • Henn, A.; Lund, S.; Hedtjärn, M.; Schrattenholz, A.; Pörzgen, P.; Leist, M. The suitability of BV2 cells as alternative model system for primary microglia cultures or for animal experiments examining brain inflammation ALTEX 2009, 26, 83-94
    • (2009) ALTEX , vol.26 , pp. 83-94
    • Henn, A.1    Lund, S.2    Hedtjärn, M.3    Schrattenholz, A.4    Pörzgen, P.5    Leist, M.6
  • 26
    • 66249111509 scopus 로고    scopus 로고
    • No NO, no pain? the role of nitric oxide and cGMP in spinal pain processing
    • Schmidtko, A.; Tegeder, I.; Geisslinger, G. No NO, no pain? The role of nitric oxide and cGMP in spinal pain processing Trends Neurosci. 2009, 32, 339-346
    • (2009) Trends Neurosci. , vol.32 , pp. 339-346
    • Schmidtko, A.1    Tegeder, I.2    Geisslinger, G.3
  • 28
    • 58749107193 scopus 로고    scopus 로고
    • Modulation of opioid actions by nitric oxide signaling
    • Toda, N.; Kishioka, S.; Hatano, Y.; Toda, H. Modulation of opioid actions by nitric oxide signaling Anesthesiology 2009, 110, 166-181
    • (2009) Anesthesiology , vol.110 , pp. 166-181
    • Toda, N.1    Kishioka, S.2    Hatano, Y.3    Toda, H.4
  • 32
    • 29844457991 scopus 로고    scopus 로고
    • Position of coordination of the lithium ion determines the regioselectivity of demethylations of 3,4-dimethoxymorphinans with L-selectride
    • Wu, H.; Thatcher, L. N.; Bernard, D.; Parrish, D. A.; Deschamps, J. R.; Rice, K. C.; MacKerell, A. D.; Coop, A. Position of coordination of the lithium ion determines the regioselectivity of demethylations of 3,4-dimethoxymorphinans with L-selectride Org. Lett. 2005, 7, 2531-2534
    • (2005) Org. Lett. , vol.7 , pp. 2531-2534
    • Wu, H.1    Thatcher, L.N.2    Bernard, D.3    Parrish, D.A.4    Deschamps, J.R.5    Rice, K.C.6    Mackerell, A.D.7    Coop, A.8
  • 33
    • 67349182481 scopus 로고    scopus 로고
    • The structural basis of lipopolysaccharide recognition by the TLR4-MD-2 complex
    • Park, B. S.; Song, D. H.; Kim, H. M.; Choi, B.-S.; Lee, H.; Lee, J.-O. The structural basis of lipopolysaccharide recognition by the TLR4-MD-2 complex Nature 2009, 458, 1191-1195
    • (2009) Nature , vol.458 , pp. 1191-1195
    • Park, B.S.1    Song, D.H.2    Kim, H.M.3    Choi, B.-S.4    Lee, H.5    Lee, J.-O.6
  • 34
    • 2342460927 scopus 로고    scopus 로고
    • Practical procedures for the preparation of N - Tert -butyldimethylsilylhydrazones and their use in modified Wolff-Kishner reductions and in the synthesis of vinyl halides and gem-dihalides
    • Furrow, M. E.; Myers, A. G. Practical procedures for the preparation of N-tert -butyldimethylsilylhydrazones and their use in modified Wolff-Kishner reductions and in the synthesis of vinyl halides and gem-dihalides J. Am. Chem. Soc. 2004, 126, 5436-5445
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5436-5445
    • Furrow, M.E.1    Myers, A.G.2
  • 35
    • 0023924046 scopus 로고
    • A new and sensitive method for measuring thermal nociception in cutaneous hyperalgesia
    • Hargreaves, K.; Dubner, R.; Brown, F.; Flores, C.; Joris, J. A new and sensitive method for measuring thermal nociception in cutaneous hyperalgesia Pain 1988, 32, 77-88
    • (1988) Pain , vol.32 , pp. 77-88
    • Hargreaves, K.1    Dubner, R.2    Brown, F.3    Flores, C.4    Joris, J.5
  • 37
    • 85027936718 scopus 로고    scopus 로고
    • In vivo veritas: (+)-Naltrexone's actions define translational importance: A letter in response to Skolnick et al. "Translational potential of naloxone and naltrexone as TLR4 antagonists"
    • Watkins, L. R.; Wang, X.; Mustafa, S.; Hutchinson, M. R. In vivo veritas: (+)-Naltrexone's actions define translational importance: A letter in response to Skolnick et al. "Translational potential of naloxone and naltrexone as TLR4 antagonists" Trends Pharmacol. Sci. 2014, 35, 432-433
    • (2014) Trends Pharmacol. Sci. , vol.35 , pp. 432-433
    • Watkins, L.R.1    Wang, X.2    Mustafa, S.3    Hutchinson, M.R.4
  • 38
    • 85027934270 scopus 로고    scopus 로고
    • Translational potential of naloxone and naltrexone as TLR4 antagonists
    • Skolnick, P.; Davis, H.; Arnelle, D.; Deaver, D. Translational potential of naloxone and naltrexone as TLR4 antagonists Trends Pharmacol. Sci. 2014, 35, 431-432
    • (2014) Trends Pharmacol. Sci. , vol.35 , pp. 431-432
    • Skolnick, P.1    Davis, H.2    Arnelle, D.3    Deaver, D.4
  • 39
    • 0032771125 scopus 로고    scopus 로고
    • A method for increasing the viability of the external portion of lumbar catheters placed in the spinal subarachnoid space of rats
    • Milligan, E. D.; Hinde, J. L.; Mehmert, K. K.; Maier, S. F.; Watkins, L. R. A method for increasing the viability of the external portion of lumbar catheters placed in the spinal subarachnoid space of rats J. Neurosci. Methods 1999, 90, 81-86
    • (1999) J. Neurosci. Methods , vol.90 , pp. 81-86
    • Milligan, E.D.1    Hinde, J.L.2    Mehmert, K.K.3    Maier, S.F.4    Watkins, L.R.5
  • 40
    • 14544284026 scopus 로고    scopus 로고
    • Functionalization of the 6,14-bridge of the orvinols. 2. Preparation of 18- and 19-hydroxyl-substituted thevinols and their treatment with benzyl bromide
    • Wu, H. F.; Bernard, D.; Chen, W. B.; Strahan, G. D.; Deschamps, J. R.; Parrish, D. A.; Lewis, J. W.; MacKerell, A. D.; Coop, A. Functionalization of the 6,14-bridge of the orvinols. 2. Preparation of 18- and 19-hydroxyl-substituted thevinols and their treatment with benzyl bromide J. Org. Chem. 2005, 70, 1907-1910
    • (2005) J. Org. Chem. , vol.70 , pp. 1907-1910
    • Wu, H.F.1    Bernard, D.2    Chen, W.B.3    Strahan, G.D.4    Deschamps, J.R.5    Parrish, D.A.6    Lewis, J.W.7    Mackerell, A.D.8    Coop, A.9


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