The Acrylamide (S)-2 as a positive and negative modulator of Kv7 channels expressed in Xenopus laevis oocytes

PLoS ONE

Volumn 4, Issue 12, 2009, Pages

  Blom, Sigrid Marie ^a,b   Schmitt, Nicole ^b   Jensen, Henrik Sindal ^a  

^a H LUNDBECK A S   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

3 (5 CHLORO 2 METHOXYPHENYL) 3 FLUORO 2,3 DIHYDRO 6 TRIFLUOROMETHYL 1H INDOL 2 ONE; ACRYLAMIDE DERIVATIVE; N [1 (4 CYCLOPROPYLMETHYL 3,4 DIHYDRO 2H BENZO[1,4]OXACIN 6 YL)ETHYL] 3 (2 FLUOROPHENYL)ACRYLAMIDE; POTASSIUM CHANNEL KCNQ1; POTASSIUM CHANNEL KCNQ2; POTASSIUM CHANNEL KCNQ3; POTASSIUM CHANNEL KCNQ4; POTASSIUM CHANNEL KCNQ5; RETIGABINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; FEMALE; HYPERPOLARIZATION; NONHUMAN; OOCYTE; PROTEIN EXPRESSION; XENOPUS LAEVIS;

ACRYLAMIDE; ACRYLAMIDES; ANIMALS; BINDING SITES; CARBAMATES; HUMANS; ION CHANNEL GATING; KCNQ POTASSIUM CHANNELS; KINETICS; MEMBRANE POTENTIALS; MUTANT PROTEINS; OOCYTES; OXAZINES; PHENYLENEDIAMINES; TRYPTOPHAN; XENOPUS LAEVIS;

XENOPUS LAEVIS;

EID: 77953969319     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0008251     Document Type: Article

References (34)

1. Barhanin J, Lesage F, Guillemare E, Fink M, Lazdunski M, et al. (1996) KvLQT1 and IsK (minK) proteins associate to form the IKS cardiac potassium current. Nature 384: 78-80.
2. Sanguinetti MC, Curran ME, Zou A, Shen J, Specter PS, et al. (1996) Coassembly of KVLQT1 and minK (IsK) proteins to form cardiac IKS potassium channel. Nature 384: 80-83.
3. Robbins J (2001) KCNQ potassium channels: physiology, pathophysiology, and pharmacology. Pharmacol Therapeut 90: 1-19.
4. Mackie AR, Byron KL (2008) Cardiovascular KCNQ (Kv7) Potassium Channels: Physiological Regulators and New Targets for Therapeutic Intervention. Mol Pharmacol 74: 1171-1179.
5. Wang HS, Pan Z, Shi W, Brown BS, Wymore RS, et al. (1998) KCNQ2 and KCNQ3 Potassium Channel Subunits: Molecular Correlates of the M-Channel. Science 282: 1890-1893.
6. Jentsch TJ (2000) Neuronal KCNQ potassium channels:physislogy and role in disease. Nat Rev Neurosci 1: 21-30.
7. Wang HS, Pan Z, Shi W, Brown BS, Wymore RS, et al. (1998) KCNQ2 and KCNQ3 Potassium Channel Subunits: Molecular Correlates of the M-Channel. Science 282: 1890-1893.
8. Kubisch C, Schroeder BC, Friedrich T, Lütjohann B, El-Amraoui A, et al. (1999) KCNQ4, a Novel Potassium Channel Expressed in Sensory Outer Hair Cells, Is Mutated in Dominant Deafness. Cell 96: 437-446.
9. Selyanko AA, Hadley JK, Wood IC, Abogadie FC, Jentsch TJ, et al. (2000) Inhibition of KCNQ1-4 potassium channels expressed in mammalian cells via M1 muscarinic acetylcholine receptors. J Physiol 522 Pt 3: 349-355.
10. Schroeder BC, Hechenberger M, Weinreich F, Kubisch C, Jentsch TJ (2000) KCNQ5, a Novel Potassium Channel Broadly Expressed in Brain, Mediates Mtype Currents. J Biol Chem 275: 24089-24095.
11. Lerche C, Scherer CR, Seebohm G, Derst C, Wei AD, et al. (2000) Molecular cloning and functional expression of KCNQ5, a potassium channel subunit that may contribute to neuronal M-current diversity. J Biol Chem 275: 22395-22400.
12. Cooper EC, Harrington E, Jan YN, Jan LY (2001) M Channel KCNQ2 Subunits Are Localized to Key Sites for Control of Neuronal Network Oscillations and Synchronization in Mouse Brain. J Neurosci 21: 9529-9540.
13. Kharkovets T, Hardelin JP, Safieddine S, Schweizer M, El-Amraoui A, et al. (2000) From the Cover: KCNQ4, a K+ channel mutated in a form of dominant deafness, is expressed in the inner ear and the central auditory pathway. Proc Natl Acad Sci U S A 97: 4333-4338.
14. Martire M, D'Amico M, Panza E, Miceli F, Viggiano D, et al. (2007) Involvement of KCNQ2 subunits in [3H]dopamine release triggered by depolarization and pre-synaptic muscarinic receptor activation from rat striatal synaptosomes. J Neurochem 102: 179-193.
15. Hansen HH, Ebbesen C, Mathiesen C, Weikop P, Ronn LC, et al. (2006) The KCNQ Channel Opener Retigabine Inhibits the Activity of Mesencephalic Dopaminergic Systems of the Rat. J Pharmacol Exp Ther 318: 1006-1019.
16. Wickenden AD, Yu W, Zou A, Jegla T, Wagoner PK (2000) Retigabine, A Novel Anti-Convulsant, Enhances Activation of KCNQ2/Q3 Potassium Channels. Mol Pharmacol 58: 591-600.
17. Main MJ, Cryan JE, Dupere JRB, Cox B, Clare JJ, et al. (2000) Modulation of KCNQ2/3 Potassium Channels by the Novel Anticonvulsant Retigabine. Mol Pharmacol 58: 253-262.
18. Tatulian L, Delmas P, Abogadie FC, Brown DA (2001) Activation of Expressed KCNQ Potassium Currents and Native Neuronal M-Type Potassium Currents by the Anti-Convulsant Drug Retigabine. J Neurosci 21: 5535-5545.
19. Wu YJ, Boissard CG, Chen J, Fitzpatrick W, Gao Q, et al. (2004) (S)-N-[1-(4- Cyclopropylmethyl-3,4-dihydro-2H-benzo[ and ]oxazin-6-yl)-ethyl]-3-(2-fluorophenyl)- acrylamide is a potent and efficacious KCNQ2 opener which inhibits induced hyperexcitability of rat hippocampal neurons. Bioorg Med Chem Lett 14: 1991-1995.
20. Bentzen BH, Schmitt N, Calloe K, Dalby-Brown W, Grunnet M, et al. (2006) The acrylamide (S)-1 differentially affects Kv7 (KCNQ) potassium channels. Neuropharmacology 51: 1068-1077.
21. Jensen HS, Grunnet M, Olesen SP (2007) Inactivation as a New Regulatory Mechanism for Neuronal Kv7 Channels. Biophys J 92: 2747-2756.
22. Seebohm G, Strutz-Seebohm N, Baltaev R, Korniychuk G, Knirsch M, et al. (2005) Regulation of KCNQ4 Potassium Channel Prepulse Dependence and Current Amplitude by SGK1 in Xenopus oocytes. Cell Physiol Biochem 16: 255-262.
23. Wuttke TV, Seebohm G, Bail S, Maljevic S, Lerche H (2005) The New Anticonvulsant Retigabine Favors Voltage-Dependent Opening of the Kv7.2 (KCNQ2) Channel by Binding to Its Activation Gate. Mol Pharmacol 67: 1009-1017.
24. Schenzer A, Friedrich T, Pusch M, Saftig P, Jentsch TJ, et al. (2005) Molecular Determinants of KCNQ (Kv7) K+ Channel Sensitivity to the Anticonvulsant Retigabine. J Neurosci 25: 5051-5060.
25. Towart R, Linders JTM, Hermans AN, Rohrbacher J, van der Linde HJ, et al. (2009) Blockade of the IKs potassium channel: An overlooked cardiovascular liability in drug safety screening? Journal of Pharmacological and Toxicological Methods 60: 1-10.
26. Gao Z, Xiong Q, Sun H, Li M (2008) Desensitization of chemical activation by auxiliary subunits: convergence of molecular determinants critical for augmenting KCNQ1 potassium channels. J Biol Chem 283: 22649-22658.
27. Wang HS, Brown BS, McKinnon D, Cohen IS (2000) Molecular basis for differential sensitivity of KCNQ and I(Ks) channels to the cognitive enhancer XE991. Mol Pharmacol 57: 1218-1223.
28. Peretz A, Degani N, Nachman R, Uziyel Y, Gibor G, et al. (2005) Meclofenamic Acid and Diclofenac, Novel Templates of KCNQ2/Q3 Potassium Channel Openers, Depress Cortical Neuron Activity and Exhibit Anticonvulsant Properties. Mol Pharmacol 67: 1053-1066.
29. Schrøder RL, Jespersen T, Christophersen P, Strøbæk D, Jensen BS, et al. (2001) KCNQ4 channel activation by BMS-204352 and retigabine. Neuropharmacology 40: 888-898.
30. Selyanko AA, Hadley JK, Brown DA (2001) Properties of single M-type KCNQ2/KCNQ3 potassium channels expressed in mammalian cells. J Physiol 534: 15-24.
31. Tatulian L, Brown DA (2003) Effect of the KCNQ potassium channel opener retigabine on single KCNQ2/3 channels expressed in CHO cells. J Physiol 549: 57-63.
32. Li Y, Gamper N, Shapiro MS (2004) Single-Channel Analysis of KCNQ K+ Channels Reveals the Mechanism of Augmentation by a Cysteine-Modifying Reagent. J Neurosci 24: 5079-5090.
33. Xiong Q, Sun H, Li M (2007) Zinc pyrithione-mediated activation of voltagegated KCNQ potassium channels rescues epileptogenic mutants. Nat Chem Biol 3: 287-296.
34. Miceli F, Soldovieri MV, Martire M, Taglialatela M (2008) Molecular pharmacology and therapeutic potential of neuronal Kv7-modulating drugs. Curr Opin Pharmacol 8: 65-74.