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Volumn 3, Issue 12, 2012, Pages 1037-1049

Identification of the benzyloxyphenyl pharmacophore: A structural unit that promotes sodium channel slow inactivation

Author keywords

anticonvulsant activity; Benzyloxyphenyl pharmacophore; epilepsy; hyperexcitable neurons; slow inactivation; voltage gated sodium channels

Indexed keywords

BENZENE DERIVATIVE; CATECHOLAMINE DERIVATIVE; SODIUM CHANNEL; SODIUM CHANNEL NAV1.1; SODIUM CHANNEL NAV1.3; SODIUM CHANNEL NAV1.7; VOLTAGE GATED SODIUM CHANNEL;

EID: 84871318530     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn300129d     Document Type: Article
Times cited : (10)

References (35)
  • 1
    • 33746474680 scopus 로고    scopus 로고
    • Epilepsy: A review of selected clinical syndromes and advances in basic science
    • DOI 10.1038/sj.jcbfm.9600265, PII 9600265
    • Stafstrom, C. E. (2006) Epilepsy: A review of selected clinical syndromes and advances in basic science J. Cereb. Blood Flow Metab. 26, 983-1004 (Pubitemid 44134073)
    • (2006) Journal of Cerebral Blood Flow and Metabolism , vol.26 , Issue.8 , pp. 983-1004
    • Stafstrom, C.E.1
  • 2
    • 16344387731 scopus 로고    scopus 로고
    • Epileptic seizures and epilepsy: Definitions proposed by the International League Against Epilepsy (ILAE) and the International Bureau for Epilepsy (IBE)
    • DOI 10.1111/j.0013-9580.2005.66104.x
    • Fisher, R. S., Boas, W. v. E., Blume, W., Elger, C., Genton, P., Lee, P., and Engel, J., Jr. (2005) Epileptic seizures and epilepsy: Definitions proposed by the International League Against Epilepsy (ILAE) and the International Bureau for Epilepsy (IBE) Epilepsia 46, 470-472 (Pubitemid 40470667)
    • (2005) Epilepsia , vol.46 , Issue.4 , pp. 470-472
    • Fisher, R.S.1    Van Emde Boas, W.2    Blume, W.3    Elger, C.4    Genton, P.5    Lee, P.6    Engel Jr., J.7
  • 3
    • 47249105094 scopus 로고    scopus 로고
    • The prevalence of epilepsy and pharmacoresistant epilepsy in adults: A population-based study in a Western European country
    • DOI 10.1111/j.1528-1167.2008.01579.x
    • Picot, M. C., Baldy-Moulinier, M., Daurs, J. P., Dujols, P., and Crespel, A. (2008) The prevalence of epilepsy and pharmacoresistant epilepsy in adults: A population-based study in a western European country Epilepsia 49, 1230-1238 (Pubitemid 351991393)
    • (2008) Epilepsia , vol.49 , Issue.7 , pp. 1230-1238
    • Picot, M.-C.1    Baldy-Moulinier, M.2    Daures, J.-P.3    Dujols, P.4    Crespel, A.5
  • 4
    • 0026014156 scopus 로고
    • A rational guide to monitoring in patients receiving anticonvulsants
    • Pellock, J. M. and Willmore, L. J. (1991) A rational guide to monitoring in patients receiving anticonvulsants Neurology 41, 961-964
    • (1991) Neurology , vol.41 , pp. 961-964
    • Pellock, J.M.1    Willmore, L.J.2
  • 6
    • 0029898015 scopus 로고    scopus 로고
    • Synthesis and anticonvulsant activities of N -benzyl-2- acetamidopropionamide derivatives
    • Choi, D., Stables, J. P., and Kohn, H. (1996) Synthesis and anticonvulsant activities of N -benzyl-2-acetamidopropionamide derivatives J. Med. Chem. 39, 1907-1916
    • (1996) J. Med. Chem. , vol.39 , pp. 1907-1916
    • Choi, D.1    Stables, J.P.2    Kohn, H.3
  • 7
    • 0032491552 scopus 로고    scopus 로고
    • Synthesis and anticonvulsant activities of (R)-(O)-methylserine derivatives
    • PII S0957416698004030
    • Andurkar, S. V., Stables, J. P., and Kohn, H. (1998) Synthesis and anticonvulsant activities of (R)-(O)-methylserine derivatives Tetrahedron: Asymmetry 9, 3841-3854 (Pubitemid 28551602)
    • (1998) Tetrahedron Asymmetry , vol.9 , Issue.21 , pp. 3841-3854
    • Andurkar, S.V.1    Stables, J.P.2    Kohn, H.3
  • 8
    • 18244431460 scopus 로고    scopus 로고
    • N-Substituted amino acid N′-benzylamides: Synthesis, anticonvulsant, and metabolic activities
    • DOI 10.1016/j.bmc.2004.02.043, PII S0968089604002172
    • Béguin, C., LeTiran, A., Stables, J. P., Voyksner, R. D., and Kohn, H. (2004) N -Substituted amino acid N ′-benzylamides: Synthesis, anticonvulsant, and metabolic activities Bioorg. Med. Chem. 12, 3079-3096 (Pubitemid 38622142)
    • (2004) Bioorganic and Medicinal Chemistry , vol.12 , Issue.11 , pp. 3079-3096
    • Beguin, C.1    LeTiran, A.2    Stables, J.P.3    Voyksner, R.D.4    Kohn, H.5
  • 10
    • 77952052973 scopus 로고    scopus 로고
    • Merging the structural motifs of functionalized amino acids and α-aminoamides: Compounds with significant anticonvulsant activities
    • Salomé, C., Salomé-Grosjean, E., Stables, J. P., and Kohn, H. (2010) Merging the structural motifs of functionalized amino acids and α-aminoamides: Compounds with significant anticonvulsant activities J. Med. Chem. 53, 3756-3771
    • (2010) J. Med. Chem. , vol.53 , pp. 3756-3771
    • Salomé, C.1    Salomé-Grosjean, E.2    Stables, J.P.3    Kohn, H.4
  • 12
    • 80053914898 scopus 로고    scopus 로고
    • Primary amino acid derivatives: Substitution of the 4′- N ′-benzylamide site in (R)- N ′-benzyl 2-amino-3-methylbutanamide, (R)- N ′-benzyl 2-amino-3,3-dimethylbutanamide, and (R)- N ′-benzyl 2-amino-3-methoxypropionamide provides potent anticonvulsants with pain attenuating properties
    • King, A. M., Salomé, C., Salomé-Grosjean, E., De Ryck, M., Kaminski, R., Valade, A., Stables, J. P., and Kohn, H. (2011) Primary amino acid derivatives: Substitution of the 4′- N ′-benzylamide site in (R)- N ′-benzyl 2-amino-3-methylbutanamide, (R)- N ′-benzyl 2-amino-3,3-dimethylbutanamide, and (R)- N ′-benzyl 2-amino-3- methoxypropionamide provides potent anticonvulsants with pain attenuating properties J. Med. Chem. 54, 6417-6431
    • (2011) J. Med. Chem. , vol.54 , pp. 6417-6431
    • King, A.M.1    Salomé, C.2    Salomé-Grosjean, E.3    De Ryck, M.4    Kaminski, R.5    Valade, A.6    Stables, J.P.7    Kohn, H.8
  • 13
    • 0021611548 scopus 로고
    • Antiepileptic drug development program
    • Porter, R. J., Cereghino, J. J., Gladding, G. D., Hessie, B. J., Kupferberg, H. J., Scoville, B., and White, B. G. (1984) Antiepileptic Drug Development Program Cleveland Clin. Q. 51, 293-305 (Pubitemid 14038030)
    • (1984) Cleveland Clinic Quarterly , vol.51 , Issue.2 , pp. 293-305
    • Porter, R.J.1    Cereghino, J.J.2    Gladding, G.D.3
  • 15
    • 37349071555 scopus 로고    scopus 로고
    • The investigational anticonvulsant lacosamide selectively enhances slow inactivation of voltage-gated sodium channels
    • DOI 10.1124/mol.107.039867
    • Errington, A. C., Stöhr, T., Heers, C., and Lees, G. (2008) The investigational anticonvulsant lacosamide selectively enhances slow inactivation of voltage-gated sodium channels Mol. Pharmacol. 73, 157-169 (Pubitemid 350294207)
    • (2008) Molecular Pharmacology , vol.73 , Issue.1 , pp. 157-169
    • Errington, A.C.1    Stohr, T.2    Heers, C.3    Lees, G.4
  • 16
    • 45749155596 scopus 로고    scopus 로고
    • Differential block of sensory neuronal voltage-gated sodium channels by lacosamide [(2R)-2-(acetylamino)-N-benzyl-3-methoxypropanamide], lidocaine, and carbamazepine
    • DOI 10.1124/jpet.107.133413
    • Sheets, P. L., Heers, C., Stöhr, T., and Cummins, T. R. (2008) Differential block of sensory neuronal voltage-gated sodium channels by lacosamide [(2 R)-2-(acetylamino)- N -benzyl-3-methoxypropanamide], lidocaine, and carbamazepine J. Pharmacol. Exp. Ther. 326, 89-99 (Pubitemid 351872141)
    • (2008) Journal of Pharmacology and Experimental Therapeutics , vol.326 , Issue.1 , pp. 89-99
    • Sheets, P.L.1    Heers, C.2    Stoehr, T.3    Cummins, T.R.4
  • 17
    • 77955474694 scopus 로고    scopus 로고
    • In silico docking and electrophysiological characterization of lacosamide binding sites on collapsin response mediator protein-2 identifies a pocket important in modulating sodium channel slow inactivation
    • Wang, Y., Brittain, J. M., Jarecki, B. W., Park, K. D., Wilson, S. M., Wang, B., Hale, R., Meroueh, S. O., Cummins, T. R., and Khanna, R. (2010) In silico docking and electrophysiological characterization of lacosamide binding sites on collapsin response mediator protein-2 identifies a pocket important in modulating sodium channel slow inactivation J. Biol. Chem. 285, 25296-25307
    • (2010) J. Biol. Chem. , vol.285 , pp. 25296-25307
    • Wang, Y.1    Brittain, J.M.2    Jarecki, B.W.3    Park, K.D.4    Wilson, S.M.5    Wang, B.6    Hale, R.7    Meroueh, S.O.8    Cummins, T.R.9    Khanna, R.10
  • 18
    • 67651048942 scopus 로고    scopus 로고
    • Neuropathic pain: A maladaptive response of the nervous system to damage
    • Costigan, M., Scholz, J., and Woolf, C. (2009) Neuropathic pain: a maladaptive response of the nervous system to damage Annu. Rev. Neurosci. 32, 1-32
    • (2009) Annu. Rev. Neurosci. , vol.32 , pp. 1-32
    • Costigan, M.1    Scholz, J.2    Woolf, C.3
  • 20
    • 0242289522 scopus 로고    scopus 로고
    • Leading the charge - Pioneering treatments in the fight against neuropathic pain
    • DOI 10.1016/j.tips.2003.09.013
    • Dickinson, T., Lee, K., Spanswick, D., and Munro, F. E. (2003) Leading the charge-pioneering treatments in the fight against neuropathic pain Trends Pharmacol. Sci. 24, 555-557 (Pubitemid 37357136)
    • (2003) Trends in Pharmacological Sciences , vol.24 , Issue.11 , pp. 555-557
    • Dickinson, T.1    Lee, K.2    Spanswick, D.3    Munro, F.E.4
  • 21
    • 0036359609 scopus 로고    scopus 로고
    • Neurobiology of neuropathic pain: Mode of action of anticonvulsants
    • DOI 10.1053/eujp.2001.0323
    • Dickenson, A. H., Matthews, E. A., and Suzuki, R. (2002) Neurobiology of neuropathic pain: Mode of action of anticonvulsants Eur. J. Pain 6 (Suppl. A) 51-60 (Pubitemid 40023570)
    • (2002) European Journal of Pain , vol.6 , Issue.SUPPL. 1 , pp. 51-60
    • Dickenson, A.H.1    Matthews, E.A.2    Suzuki, R.3
  • 22
    • 79959205997 scopus 로고    scopus 로고
    • Merging structural motifs of functionalized amino acids and α-aminoamides results in novel anticonvulsant compounds with significant effects on slow and fast inactivation of voltage-gated sodium channels and in the treatment of neuropathic pain
    • Wang, Y., Wilson, S. M., Brittain, J. M., Ripsch, M. S., Salomé, C., Park, K. D., White, F. A., Khanna, R., and Kohn, H. (2011) Merging structural motifs of functionalized amino acids and α-aminoamides results in novel anticonvulsant compounds with significant effects on slow and fast inactivation of voltage-gated sodium channels and in the treatment of neuropathic pain ACS Chem. Neurosci. 2, 317-332
    • (2011) ACS Chem. Neurosci. , vol.2 , pp. 317-332
    • Wang, Y.1    Wilson, S.M.2    Brittain, J.M.3    Ripsch, M.S.4    Salomé, C.5    Park, K.D.6    White, F.A.7    Khanna, R.8    Kohn, H.9
  • 23
    • 79951845626 scopus 로고    scopus 로고
    • Development and characterization of novel derivatives of the antiepileptic drug lacosamide that exhibit far greater enhancement in slow inactivation of voltage-gated sodium channels
    • Wang, Y., Park, K. D., Salomé, C., Wilson, S. M., Stables, J. P., Liu, R., Khanna, R., and Kohn, H. (2010) Development and characterization of novel derivatives of the antiepileptic drug lacosamide that exhibit far greater enhancement in slow inactivation of voltage-gated sodium channels ACS Chem. Neurosci. 2, 90-106
    • (2010) ACS Chem. Neurosci. , vol.2 , pp. 90-106
    • Wang, Y.1    Park, K.D.2    Salomé, C.3    Wilson, S.M.4    Stables, J.P.5    Liu, R.6    Khanna, R.7    Kohn, H.8
  • 24
    • 77956677051 scopus 로고
    • The dual effect of membrane potential on sodium conductance in the giant axon of Loligo
    • Hodgkin, A. L. and Huxley, A. F. (1952) The dual effect of membrane potential on sodium conductance in the giant axon of Loligo J. Physiol. 116, 497-506
    • (1952) J. Physiol. , vol.116 , pp. 497-506
    • Hodgkin, A.L.1    Huxley, A.F.2
  • 25
    • 0018196425 scopus 로고
    • Slow inactivation of the sodium conductance in squid giant axons. Pronase resistance
    • Rudy, B. (1978) Slow inactivation of the sodium conductance in squid giant axons. Pronase resistance J. Physiol. 283, 1-21 (Pubitemid 9048094)
    • (1978) Journal of Physiology , vol.283 , pp. 1-21
    • Rudy, B.1
  • 26
    • 34248995257 scopus 로고    scopus 로고
    • The action potential in mammalian central neurons
    • DOI 10.1038/nrn2148, PII NRN2148
    • Bean, B. P. (2007) The action potential in mammalian central neurons Nat. Rev. Neurosci. 8, 451-465 (Pubitemid 46789230)
    • (2007) Nature Reviews Neuroscience , vol.8 , Issue.6 , pp. 451-465
    • Bean, B.P.1
  • 27
    • 0037561112 scopus 로고    scopus 로고
    • Subthreshold sodium currents and pacemaking of subthalamic neurons: Modulation by slow inactivation
    • DOI 10.1016/S0896-6273(03)00360-X
    • Do, M. T. H. and Bean, B. P. (2003) Subthreshold sodium currents and pacemaking of subthalamic neurons: Modulation by slow inactivation Neuron 39, 109-120 (Pubitemid 36830952)
    • (2003) Neuron , vol.39 , Issue.1 , pp. 109-120
    • Do, M.T.H.1    Bean, B.P.2
  • 28
    • 0035754168 scopus 로고    scopus 로고
    • Slow inactivation in voltage-gated sodium channels: Molecular substrates and contributions to channelopathies
    • DOI 10.1385/CBB:35:2:171
    • Vilin, Y. Y. and Ruben, P. C. (2001) Slow inactivation in voltage-gated sodium channels: molecular substrates and contributions to channelopathies Cell Biochem. Biophys. 35, 171-190 (Pubitemid 33622686)
    • (2001) Cell Biochemistry and Biophysics , vol.35 , Issue.2 , pp. 171-190
    • Vilin, Y.Y.1    Ruben, P.C.2
  • 29
    • 13444291643 scopus 로고    scopus 로고
    • Voltage gated ion channels: Targets for anticonvulsant drugs
    • DOI 10.2174/1568026053386872
    • Errington, A. C., Stohr, T., and Lees, G. (2005) Voltage gated ion channels: Targets for anticonvulsant drugs Curr. Top. Med. Chem. 5, 15-30 (Pubitemid 40202107)
    • (2005) Current Topics in Medicinal Chemistry , vol.5 , Issue.1 , pp. 15-30
    • Errington, A.C.1    Stohr, T.2    Lees, G.3
  • 32
    • 80053906575 scopus 로고    scopus 로고
    • Defining the structural parameters that confer anticonvulsant activity by the site-by-site modification of (R)- N ′-benzyl 2-amino-3- methylbutanamide
    • King, A. M., De Ryck, M., Kaminski, R., Valade, A., Stables, J. P., and Kohn, H. (2011) Defining the structural parameters that confer anticonvulsant activity by the site-by-site modification of (R)- N ′-benzyl 2-amino-3-methylbutanamide J. Med. Chem. 54, 6432-6442
    • (2011) J. Med. Chem. , vol.54 , pp. 6432-6442
    • King, A.M.1    De Ryck, M.2    Kaminski, R.3    Valade, A.4    Stables, J.P.5    Kohn, H.6
  • 33
    • 58149326824 scopus 로고    scopus 로고
    • Inherited neuronal ion channelopathies: New windows on complex neurological diseases
    • Catterall, W. A., Dib-Hajj, S., Meisler, M. H., and Pietrobon, D. (2008) Inherited neuronal ion channelopathies: new windows on complex neurological diseases J. Neurosci. 28, 11768-11777
    • (2008) J. Neurosci. , vol.28 , pp. 11768-11777
    • Catterall, W.A.1    Dib-Hajj, S.2    Meisler, M.H.3    Pietrobon, D.4
  • 34
    • 84861616705 scopus 로고    scopus 로고
    • Regulation of CREB signaling through L-type Ca(2+) channels by Nipsnap-2
    • Brittain, J. M., Wang, Y., Wilson, S. M., and Khanna, R. (2012) Regulation of CREB signaling through L-type Ca(2+) channels by Nipsnap-2 Channels (Austin) 6, 94-102
    • (2012) Channels (Austin) , vol.6 , pp. 94-102
    • Brittain, J.M.1    Wang, Y.2    Wilson, S.M.3    Khanna, R.4
  • 35
    • 11144325707 scopus 로고    scopus 로고
    • Enhanced excitability of dissociated primary sensory neurons after chronic compression of the dorsal root ganglion in the rat
    • DOI 10.1016/j.pain.2004.10.001, PII S0304395904004798
    • Ma, C. and LaMotte, R. H. (2005) Enhanced excitability of dissociated primary sensory neurons after chronic comprehension of the dorsal root ganglion in the rat Pain 113, 106-112 (Pubitemid 40038451)
    • (2005) Pain , vol.113 , Issue.1-2 , pp. 106-112
    • Ma, C.1    LaMotte, R.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.