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Volumn 54, Issue 11, 2011, Pages 3977-3981

Anticonvulsant 4-aminobenzenesulfonamide derivatives with branched-alkylamide moieties: X-ray crystallography and inhibition studies of human carbonic anhydrase isoforms I, II, VII, and XIV

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC CARBOXYLIC ACID; ANTICONVULSIVE AGENT; AROMATIC AMIDE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; ISOENZYME; SULFANILAMIDE; SULFONAMIDE;

EID: 79958174646     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200209n     Document Type: Article
Times cited : (68)

References (35)
  • 1
    • 78650178478 scopus 로고    scopus 로고
    • Progress report on new antiepileptic drugs: A summary of the tenth eilat conference (EILAT X)
    • Bialer, M.; Johannessen, S. I.; Levy, R. H.; Perucca, E.; Tomson, T.; White, H. S. Progress report on new antiepileptic drugs: A summary of the Tenth Eilat Conference (EILAT X). Epilepsy Res. 2010, 92, 89-124.
    • (2010) Epilepsy Res. , vol.92 , pp. 89-124
    • Bialer, M.1    Johannessen, S.I.2    Levy, R.H.3    Perucca, E.4    Tomson, T.5    White, H.S.6
  • 2
    • 0030053466 scopus 로고    scopus 로고
    • During afterdischarges in the young rat in vivo extracellular potassium is not elevated above adult levels
    • DOI 10.1016/0165-3806(95)00165-4
    • Stringer, J. L.; Lothman, E. W. During afterdischarges in the young rat in vivo extracellular potassium is not elevated above adult levels. Dev. Brain Res. 1996, 91, 136-139. (Pubitemid 26041746)
    • (1996) Developmental Brain Research , vol.91 , Issue.1 , pp. 136-139
    • Stringer, J.L.1    Lothman, E.W.2
  • 3
    • 0034652229 scopus 로고    scopus 로고
    • Activity-dependent intracellular acidification correlates with the duration of seizure activity
    • Xiong, Z. Q.; Saggau, P.; Stringer, J. L. Activity-dependent intracellular acidification correlates with the duration of seizure activity. J. Neurosci. 2000, 20, 1290-1296. (Pubitemid 30220407)
    • (2000) Journal of Neuroscience , vol.20 , Issue.4 , pp. 1290-1296
    • Xiong, Z.-Q.1    Saggau, P.2    Stringer, J.L.3
  • 4
    • 0032525343 scopus 로고    scopus 로고
    • --withdrawal from the bath medium of hippocampal slices: Biphasic effect on intracellular pH and bioelectric activity of CA3-neurons
    • DOI 10.1016/S0006-8993(98)00341-2, PII S0006899398003412
    • - - withdrawal from the bath medium of hippocampal slices: Biphasic effect on intracellular pH and bioelectric activity of CA3-neurons. Brain Res. 1998, 796, 161-170. (Pubitemid 28343245)
    • (1998) Brain Research , vol.796 , Issue.1-2 , pp. 161-170
    • Bonnet, U.1    Wiemann, M.2    Bingmann, D.3
  • 5
    • 0036278511 scopus 로고    scopus 로고
    • Effects of antiepileptic drugs on extracellular pH regulation in the hippocampal CA1 region in vivo
    • DOI 10.1016/S0920-1211(02)00019-0, PII S0920121102000190
    • Aribi, A. M.; Stringer, J. L. Effects of antiepileptic drugs on extracellular pH regulation in the hippocampal CA1 region in vivo. Epilepsy Res. 2002, 49, 143-151. (Pubitemid 34607362)
    • (2002) Epilepsy Research , vol.49 , Issue.2 , pp. 143-151
    • Aribi, A.M.1    Stringer, J.L.2
  • 6
    • 38849143765 scopus 로고    scopus 로고
    • Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators
    • DOI 10.1038/nrd2467, PII NRD2467
    • Supuran, C. T. Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators. Nat. Rev. Drug Discovery 2008, 7, 168-181. (Pubitemid 351194064)
    • (2008) Nature Reviews Drug Discovery , vol.7 , Issue.2 , pp. 168-181
    • Supuran, C.T.1
  • 7
    • 77954218410 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors
    • Supuran, C. T. Carbonic anhydrase inhibitors. Bioorg. Med. Chem. Lett. 2010, 20, 3467-3474.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 3467-3474
    • Supuran, C.T.1
  • 9
    • 0029965708 scopus 로고    scopus 로고
    • Acetazolamide in the treatment of seizures
    • Reiss, W. G.; Oles, K. S. Acetazolamide in the treatment of seizures. Ann. Pharmacother. 1996, 30, 514-519. (Pubitemid 26139249)
    • (1996) Annals of Pharmacotherapy , vol.30 , Issue.5 , pp. 514-519
    • Reiss, W.G.1    Oles, K.S.2
  • 10
    • 7044271164 scopus 로고    scopus 로고
    • Zonisamide: Chemistry, mechanism of action, and pharmacokinetics
    • DOI 10.1016/j.seizure.2004.04.016, PII S1059131104000950
    • Leppik, I. E. Zonisamide: Chemistry, mechanism of action, and pharmacokinetics. Seizure 2004, 13 (Suppl. 1), S5-S9. (Pubitemid 39420012)
    • (2004) Seizure , vol.13 , Issue.SUPPL. 1
    • Leppik, I.E.1
  • 11
    • 0343673858 scopus 로고    scopus 로고
    • Topiramate as an inhibitor of carbonic anhydrase isoenzymes
    • Dodgson, S. J.; Shank, R. P.; Maryanoff, B. E. Topiramate as an inhibitor of carbonic anhydrase isoenzymes. Epilepsia 2000, 41, S35-S39.
    • (2000) Epilepsia , vol.41
    • Dodgson, S.J.1    Shank, R.P.2    Maryanoff, B.E.3
  • 12
    • 0003150278 scopus 로고    scopus 로고
    • An overview of the preclinical aspects of topiramate: Pharmacology, pharmacokinetics, and mechanism of action
    • Shank, R. P.; Gardocki, J. F.; Streeter, A. J.; Maryanoff, B. E. An overview of the preclinical aspects of topiramate: Pharmacology, pharmacokinetics, and mechanism of action. Epilepsia 2000, 41, S3-S9.
    • (2000) Epilepsia , vol.41
    • Shank, R.P.1    Gardocki, J.F.2    Streeter, A.J.3    Maryanoff, B.E.4
  • 14
    • 0344193512 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV
    • DOI 10.1016/S0960-894X(03)00029-5
    • Casini, A.; Antel, J.; Abbate, F.; Scozzafava, A.; David, S.; Waldeck, H.; Schafer, S.; Supuran, C. T. Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. Bioorg. Med. Chem. Lett. 2003, 13, 841-845. (Pubitemid 36255550)
    • (2003) Bioorganic and Medicinal Chemistry Letters , vol.13 , Issue.5 , pp. 841-845
    • Casini, A.1    Antel, J.2    Abbate, F.3    Scozzafava, A.4    David, S.5    Waldeck, H.6    Schafer, S.7    Supuran, C.T.8
  • 15
    • 17144375722 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: Solution and X-ray crystallographic studies
    • DOI 10.1016/j.bmcl.2005.03.032
    • De Simone, G.; Di Fiore, A.; Menchise, V.; Pedone, C.; Antel, J.; Casini, A.; Scozzafava, A.; Wurl, M.; Supuran, C. T. Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: Solution and X-ray crystallographic studies. Bioorg. Med. Chem. Lett. 2005, 15, 2315-2320. (Pubitemid 40523093)
    • (2005) Bioorganic and Medicinal Chemistry Letters , vol.15 , Issue.9 , pp. 2315-2320
    • De Simone, G.1    Di Fiore, A.2    Menchise, V.3    Pedone, C.4    Antel, J.5    Casini, A.6    Scozzafava, A.7    Wurl, M.8    Supuran, C.T.9
  • 16
    • 77249175356 scopus 로고    scopus 로고
    • The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: The antiepileptic lacosamide as an example
    • Temperini, C.; Innocenti, A.; Scozzafava, A.; Parkkila, S.; Supuran, C. T. The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: The antiepileptic lacosamide as an example. J. Med. Chem. 2010, 53, 850-854.
    • (2010) J. Med. Chem. , vol.53 , pp. 850-854
    • Temperini, C.1    Innocenti, A.2    Scozzafava, A.3    Parkkila, S.4    Supuran, C.T.5
  • 17
    • 28844487465 scopus 로고    scopus 로고
    • Expression of carbonic anhydrases II, IV, VII, VIII and XII in rat brain after kainic acid induced status epilepticus
    • DOI 10.1016/j.neuint.2005.08.007, PII S0197018605002123
    • Halmi, P.; Parkkila, S.; Honkaniemi, J. Expression of carbonic anhydrases II, IV, VII, VIII and XII in rat brain after kainic acid induced status epilepticus. Neurochem. Int. 2006, 48, 24-30. (Pubitemid 41774276)
    • (2006) Neurochemistry International , vol.48 , Issue.1 , pp. 24-30
    • Halmi, P.1    Parkkila, S.2    Honkaniemi, J.3
  • 18
    • 0026650593 scopus 로고
    • Carbonic anhydrase IV on brain capillary endothelial cells: A marker associated with the blood-brain barrier
    • Ghandour, M. S.; Langley, O. K.; Zhu, X. L.; Waheed, A.; Sly, W. S. Carbonic anhydrase IV on brain capillary endothelial cells: A marker associated with the blood-brain barrier. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 6823-6827.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 6823-6827
    • Ghandour, M.S.1    Langley, O.K.2    Zhu, X.L.3    Waheed, A.4    Sly, W.S.5
  • 19
    • 1642412500 scopus 로고    scopus 로고
    • Carbonic Anhydrase Isoform VII Acts As A Molecular Switch in the Development of Synchronous Gamma-Frequency Firing of Hippocampal CA1 Pyramidal Cells
    • DOI 10.1523/JNEUROSCI.5176-03.2004
    • Ruusuvuori, E.; Li, H.; Huttu, K.; Palva, J. M.; Smirnov, S.; Rivera, C.; Kaila, K.; Voipio, J. Carbonic anhydrase isoform VII acts as a molecular switch in the development of synchronous gamma-frequency firing of hippocampal CA1 pyramidal cells. J. Neurosci. 2004, 24, 2699-2707. (Pubitemid 38380946)
    • (2004) Journal of Neuroscience , vol.24 , Issue.11 , pp. 2699-2707
    • Ruusuvuori, E.1    Li, H.2    Huttu, K.3    Palva, J.M.4    Smirnov, S.5    Rivera, C.6    Kaila, K.7    Voipio, J.8
  • 20
    • 14844356668 scopus 로고    scopus 로고
    • Acatalytic CAs: Carbonic anhydrase-related proteins
    • Supuran C. T., Scozzafava, A., Conway, J., Eds.; CRC Press: Boca Raton, Fl
    • Nishimori, I. Acatalytic CAs: Carbonic Anhydrase-Related Proteins. In Carbonic Anhydrase: Its Inhibitors and Activators; Supuran, C. T., Scozzafava, A., Conway, J., Eds.; CRC Press: Boca Raton, Fl, 2004; pp 25-43.
    • (2004) Carbonic Anhydrase: Its Inhibitors and Activators , pp. 25-43
    • Nishimori, I.1
  • 21
    • 0037122779 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties
    • DOI 10.1021/jm0109199
    • Masereel, B.; Rolin, S.; Abbate, F.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: Anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties. J. Med. Chem. 2002, 45, 312-320. (Pubitemid 34073450)
    • (2002) Journal of Medicinal Chemistry , vol.45 , Issue.2 , pp. 312-320
    • Masereel, B.1    Rolin, S.2    Abbate, F.3    Scozzafava, A.4    Supuran, C.T.5
  • 22
    • 2142808112 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity
    • DOI 10.1016/j.bmc.2004.03.008, PII S096808960400183X
    • Ilies, M. A.; Masereel, B.; Rolin, S.; Scozzafava, A.; Campeanu, G.; Cimpeanu, V.; Supuran, C. T. Carbonic anhydrase inhibitors: Aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity. Bioorg. Med. Chem. Lett. 2004, 12, 2717-2726. (Pubitemid 38548837)
    • (2004) Bioorganic and Medicinal Chemistry , vol.12 , Issue.10 , pp. 2717-2726
    • Ilies, M.A.1    Masereel, B.2    Rolin, S.3    Scozzafava, A.4    Campeanu, G.5    Cimpeanu, V.6    Supuran, C.T.7
  • 23
    • 41949096743 scopus 로고    scopus 로고
    • Exploration of the binding mode of indanesulfonamides as selective inhibitors of human carbonic anhydrase type VII by targeting Lys 91
    • Thiry, A.; Masereel, B.; Dogné, J. M.; Supuran, C. T.; Wouters, J.; Michaux, C. Exploration of the binding mode of indanesulfonamides as selective inhibitors of human carbonic anhydrase type VII by targeting Lys 91. ChemMedChem 2007, 2, 1273-1280.
    • (2007) Chem Med Chem , vol.2 , pp. 1273-1280
    • Thiry, A.1    Masereel, B.2    Dogné, J.M.3    Supuran, C.T.4    Wouters, J.5    Michaux, C.6
  • 24
    • 34247485893 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of isoforms I, II, IV, VA, VII, IX, and XIV with sulfonamides incorporating fructopyranose-thioureido tails
    • DOI 10.1016/j.bmcl.2007.03.008, PII S0960894X07003022
    • Winum, J. Y.; Thiry, A.; Cheikh, K. E.; Dogné, J. M.; Montero, J. L.; Vullo, D.; Scozzafava, A.; Masereel, B.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of isoforms I, II, IV, VA, VII, IX, and XIV with sulfonamides incorporating fructopyranose-thioureido tails. Bioorg. Med. Chem. Lett. 2007, 17, 2685-2691. (Pubitemid 46656456)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.10 , pp. 2685-2691
    • Winum, J.-Y.1    Thiry, A.2    Cheikh, K.E.3    Dogne, J.-M.4    Montero, J.-L.5    Vullo, D.6    Scozzafava, A.7    Masereel, B.8    Supuran, C.T.9
  • 25
    • 0033429351 scopus 로고    scopus 로고
    • Anticonvulsant activity of analogues of acetazolamide
    • DOI 10.1016/S0014-827X(99)00096-8, PII S0014827X99000968
    • Chufan, E. E.; Pedregosa, J. C.; Baldini, O. N.; Bruno-Blanch, L. Anticonvulsant activity of analogues of acetazolamide. Farmaco 1999, 54, 838-841. (Pubitemid 30009678)
    • (1999) Farmaco , vol.54 , Issue.11-12 , pp. 838-841
    • Chufan, E.E.1    Pedregosa, J.C.2    Baldini, O.N.3    Bruno-Blanch, L.4
  • 26
    • 34547585390 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Interaction of the antiepileptic drug sulthiame with twelve mammalian isoforms: Kinetic and X-ray crystallographic studies
    • DOI 10.1016/j.bmcl.2007.06.044, PII S0960894X0700724X
    • Temperini, C.; Innocenti, A.; Mastrolorenzo, A.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Interaction of the antiepileptic drug sulthiame with twelve mammalian isoforms: Kinetic and X-ray crystallographic studies. Bioorg. Med. Chem. Lett. 2007, 17, 4866-4872. (Pubitemid 47189737)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.17 , pp. 4866-4872
    • Temperini, C.1    Innocenti, A.2    Mastrolorenzo, A.3    Scozzafava, A.4    Supuran, C.T.5
  • 28
    • 68949199660 scopus 로고    scopus 로고
    • Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates?
    • De Simone, G.; Scozzafava, A.; Supuran, C. T. Which carbonic anhydrases are targeted by the antiepileptic sulfonamides and sulfamates?. Chem. Biol. Drug. Des. 2009, 74, 317-321.
    • (2009) Chem. Biol. Drug. Des. , vol.74 , pp. 317-321
    • De Simone, G.1    Scozzafava, A.2    Supuran, C.T.3
  • 29
    • 77952708293 scopus 로고    scopus 로고
    • Syntheses and evaluation of anticonvulsant profile and teratogenicity of novel amide derivatives of branched aliphatic carboxylic acids with 4-aminobenzensulfonamide
    • Hen, N.; Bialer, M.; Wlodarczyk, B.; Finnell, R. H.; Yagen, B. Syntheses and evaluation of anticonvulsant profile and teratogenicity of novel amide derivatives of branched aliphatic carboxylic acids with 4- aminobenzensulfonamide. J. Med. Chem. 2010, 53, 4177-4186.
    • (2010) J. Med. Chem. , vol.53 , pp. 4177-4186
    • Hen, N.1    Bialer, M.2    Wlodarczyk, B.3    Finnell, R.H.4    Yagen, B.5
  • 31
    • 78049375982 scopus 로고    scopus 로고
    • Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido- benzenesulfonamides and correlate to inhibitor potency
    • Cambridge, U. K
    • Pacchiano, F.; Aggarwal, M.; Avvaru, B. S.; Robbins, A. H.; Scozzafava, A.; McKenna, R.; Supuran, C. T. Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency. Chem. Commun. (Cambridge, U. K.) 2010, 46, 8371-8373.
    • (2010) Chem. Commun. , vol.46 , pp. 8371-8373
    • Pacchiano, F.1    Aggarwal, M.2    Avvaru, B.S.3    Robbins, A.H.4    Scozzafava, A.5    McKenna, R.6    Supuran, C.T.7
  • 32
    • 0010009818 scopus 로고    scopus 로고
    • Discovery and preclinical development of antiepileptic drugs
    • 5th ed.; Levy, R. H., Mattson, R. H, Meldrum, B. S, Perucca, E., Eds.; Lippincott Williams & Wilkins: New York
    • White, H. S.; Woodhead, J. H.; Wilcox, K. S.; Stables, J. P.; Kupferberg, H. J.; Wolf, H. H. Discovery and Preclinical Development of Antiepileptic Drugs. In Antiepileptic Drugs, 5th ed.; Levy, R. H., Mattson, R. H, Meldrum, B. S, Perucca, E., Eds.; Lippincott Williams & Wilkins: New York, 2002; pp 36-48.
    • (2002) Antiepileptic Drugs , pp. 36-48
    • White, H.S.1    Woodhead, J.H.2    Wilcox, K.S.3    Stables, J.P.4    Kupferberg, H.J.5    Wolf, H.H.6
  • 33
    • 0015239422 scopus 로고
    • The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C
    • Khalifah, R. G. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J. Biol. Chem. 1971, 246, 2561-2573.
    • (1971) J. Biol. Chem. , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 34
    • 77954653752 scopus 로고    scopus 로고
    • The first example of a significant active site conformational rearrangement in a carbonic anhydrase-inhibitor adduct: The carbonic anhydrase I-topiramate complex
    • Alterio, V.; Monti, S. M.; Truppo, E.; Pedone, C.; Supuran, C. T.; De Simone, G. The first example of a significant active site conformational rearrangement in a carbonic anhydrase-inhibitor adduct: The carbonic anhydrase I-topiramate complex. Org. Biomol. Chem. 2010, 8, 3528-3533.
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 3528-3533
    • Alterio, V.1    Monti, S.M.2    Truppo, E.3    Pedone, C.4    Supuran, C.T.5    De Simone, G.6
  • 35
    • 1342304082 scopus 로고    scopus 로고
    • Expression, assay, and structure of the extracellular domain of murine carbonic anhydrase XIV: Implications for selective inhibition of membrane-associated isozymes
    • DOI 10.1074/jbc.M310809200
    • Whittington, D. A.; Grubb, J. H.; Waheed, A.; Shah, G. N.; Sly, W. S.; Christianson, D. W. Expression, assay, and structure of the extracellular domain of murine carbonic anhydrase XIV: Implications for selective inhibition of membrane-associated isozymes. J. Biol. Chem. 2004, 279, 7223-7228. (Pubitemid 38248870)
    • (2004) Journal of Biological Chemistry , vol.279 , Issue.8 , pp. 7223-7228
    • Whittington, D.A.1    Grubb, J.H.2    Waheed, A.3    Shah, G.N.4    Sly, W.S.5    Christianson, D.W.6


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