Molecular determinants of stereoselective bupivacaine block of hKv1.5 channels

Circulation Research

Volumn 81, Issue 6, 1997, Pages 1053-1064

  Franqueza, Laura ^a   Longobardo, Mónica ^a   Vicente, Javier ^a   Delpon, Eva ^a   Tamkun, Michael M ^b   Tamargo, Juan ^a   Snyders, Dirk J ^b   Valenzuela, Carmen ^a,c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c SCHOOL OF MEDICINE   (Spain)

Author keywords

Bupivacaine; Drug binding site; Enantiomer; K+ channel; Local anesthetic

Indexed keywords

BUPIVACAINE;

ANIMAL CELL; ARTICLE; BINDING SITE; CARDIOTOXICITY; CHIRALITY; DRUG BINDING; ENANTIOMER; LOCAL ANESTHESIA; NONHUMAN; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; RECEPTOR AFFINITY; RECEPTOR BLOCKING; STEREOCHEMISTRY;

EID: 0030819261     PISSN: 00097330     EISSN: None     Source Type: Journal    
DOI: 10.1161/01.RES.81.6.1053     Document Type: Article

References (52)

1. Ariëns E. Nonchiral, homochiral and composite chiral drugs, Trends Pharmacol Sci. 1993;14:68-75.
2. Franks N, Lieb W. Stereospeeific effects of inhalational general anesthetic optical isomers on nerve ion channels. Science, 1994;254:427-430.
3. Valenzuela C, Snyders D, Bennett P, Tamargo J, Hondeghem L. Stereoselective block of cardiac sodium channels by bupivacaine in guinea pig ventricular myocytes. Circulation. 1995;92:3014-3024.
4. Valenzuela C, Delpón E, Tamkun M, Tamargo J, Snyders D. Stereoselective block of a human cardiac potassium channel (Kv1.5) by bupivacaine enantiomers, Biophys J. 1995;69:418-427.
5. A°berg G. Toxicological and local anaesthetic effects of optically active isomers of two local anaesthetic compounds. Acta Pharmacol Toxicol. 1972;31:273-286.
6. Stricbartz G, Ritchie J. The action of local anesthetics on ion channels of excitable tissues. In: Strichartz G, ed. Local Anesthetics Handbook of Experimental Pharmacology. Heidelberg, Germany; Springer-Vertag; 1987;81:21-52.
7. Covino B. Toxicity and systemic effects of local anesthetic agents. In: Strichartz G, ed. Local Anesthetics Handbook of Experimental Pharmacolog: Heidelberg, Germany: Springer-Verlag; 1987;81:187-212.
8. Luduena F, Bogado E. Tullar B, Optical isomers of mepivacaine and bupivacaine. Arch Int Phamacodyn. 1972;200:359-369.
9. Aps C, Reynolds F. An intradermal study of the local anaesthetic and vascular effects of the isomers of bupivacaine, Br J Clin Pharmacol. 1978;6:63-68.
10. Avery P, Redon D, Schaenzer G, Rusy B. The influence of serum potassium on the cerebral and cardiac toxicity of bupivacaine and lidocaine. Anesthesiology. 1984;61:134-138.
11. Wheeler D, Bradley E, Woods W. The electrophysiologic actions of lidocaine and bupivacaine in the isolated, perfused canine heart. Anesthesiology: 1988;68:201-212.
12. Solomon D, Bunegin L, Albin M. The effect of magnesium sulfate administration on cerebral and cardiac toxicity of bupivacaine in dogs, Anesthesiology. 1990;72:341-346.
13. Scott B, Lee A, Pagan D, Bowler G, Bloomfield P, Lundh R, Acute toxicity of ropivacaine compared with that of bupivacaine, Anesth Analg. 1989;69:563-569.
14. Kasten G, Martin S. Bupivacaine cardiovascular toxicity; comparison of treatment with bretylium and lidocaine, Anesth Analg. 1985;64:911-916.
15. Courtney K, Kendig J, Bupivacaine is an effective potassium channel blocker in heart. Biochim Biophys Acta. 1988;939:163-166.
16. Sanchez-Chapula J. Effects of bupivacaine on membrane currents of guinea-pig ventricular myocytes. Ear J Pharmacol. 1988;156:303-308.
17. + current but not the inward rectifier in rat ventricular myocytes. J Pharmacol Exp Ther. 1990;255:1038-1046.
18. Guo X, Castle N, Chernoff D, Strichartz G, Comparative inhibition of voltage-gated cation channels by local anesthetics, Ann NY Acad Sci. 1991;625:181-199.
19. Snyders D, Tamkun M, Bennett P. A rapidly activating and slowly inactivating potassium channel cloned from human heart. J Gen Physiol. 1993;101:513-543.
20. + current similar to Kvl.5 cloned channel currents. Circ Res. 1993;73:1061-1076.
21. Deal K, England S, Tamkun M. Molecular physiology of cardiac potassium channels. Physiol Rev. 1996;76:49-67.
22. + current in cultured adult human atrial myocytes, Circ Res. 1997;80:572-579.
23. + channel from vascular and visceral smooth muscles. Am J Physiol. 1994;267:C1231-C1238.
24. 3 clonal pituitary cells. Biochim Biophys Acta. 1995;1265:22-28.
25. García-Guzmán M, Sala F, Criado M, Sala S, A delayed rectifier potassium channel cloned from bovine adrenal medulla: functional analysis after expression in Xenopus oocytes and in a neuroblastoma cell line, FEBS Lett. 1994;354:173-176.
26. Mi H, Deerinck T, Ellisman M, Schwarz T. Differential distribution of closely related potassium channels in rat Schwarm cells. J Neurosci. 1995;15:3761-3774.
27. + channel polypeptides in rat hippocampal neurons developing in situ and in vitro. J Neurosci, 1995;15:3840-3851.
28. + channel comprises part of the pore. Nature, 1994; 367:179-182.
29. Aiyar J, Nguyen A, Chandy K, Grissmer S, The P-region and S6 of Kv3.1 contribute to the formation of the ton conduction pathway. Biophys J. 1994;67:2261-2264.
30. Choi K, Mossman C, Aubé J, Yellen G. The internal quaternary ammonium receptor site of Shaker potassium channels. Neuron. 1993;10:533-541.
31. Rampe D, Wible B, Brown A, Dage R. Effects of terfenadine and its metabolites on a delayed rectifier K channel cloned from human heart. Mol Phamacol. 1993;44:1240-1245.
32. Malayev A, Nelson D, Philipson L. Mechanism of cloftlium block of the human Kvl.5 delayed rectifier potassium channel. Mol Pharmacol. 1995;47:198-205
33. + channel: role of S6 in antiarrhythmic drug binding. Circ Res. 1996;78:1105-1114.
34. Snyders D, Yeola S. Determinants of antiarrhythmic drug action: electrostatic and Hydrophobic components of block of the human cardiac hKv1.5 channel. Circ Res. 1995;77:575-583.
35. + channel. Science. 1991;251:939-942.
36. Franqueza L, Delpóa E, Gay P, Snyders D, Tamargo J, Valenzuela C. Molecular determinants for stereoselective bupivacaine binding in hKv1, 5 channels. Biophys J. 1996;70:A400. Abstract.
37. Vicente J, Franqueza L, Delpón E, Tamkun M, Tamargo J, Snyders D, Valenzuela C. Threonine 505 determines the stercoselective bupivacaine block of hKvl.5 channels. Biophys J. 1997;72:A141. Abstract.
38. Snyders D, Knoth K, Roberds S, Tamkun M. Time-, state- and voltage-dependent block by quinidine of a cloned human cardiac channel. Mol Pharmacol. 1992;41:332-339.
39. Hamill O, Marty A, Neher E, Sakmann B, Sigworth F. Improved patch-clamp techniques for high resolution current recording from cells and cell-free membrane patches. Pflugers Arch. 1981;391:85-100.
40. + channels: ionic and gating current studies. J Gen Physiol, 1985;85:539-554.
41. + current activation in guinea pig ventricular myocytes. Cire Res. 1994;74:687-699.
42. + channels, Science. 1990;250: 276-279.
43. Pongs O. Molecular biology of voltage-dependent potassium channels. Physiol Rev. 1992;72:S69-S88.
44. Snyders D, Rich T, Mays D, Tamkun M, Yeola S, Involvement of S6 in voltage-dependent deactivation gating of hKvl.5 potassium channels. Biophys J. 1996;70:A144, Abstract.
45. Woodhull A, Ionic blockade of sodium channels in nerve. J Gen Physiol. 1973;61:687-708.
46. + channels. Proc Natl Acad Sci U S A. 1996;93:13357-13361.
47. Uebele V, England S, Chaundary A, Tamkun M, Snyders D. Functional differences in Kvl.5 currents expressed in mammalian cell lines are due to the presence of endogenous Kvβ2.l subunits, J Biol Chem. 1996;271:2406-2412.
48. Rich T. Getting of the hKv1.5 Delayed Rectifier: The Implications of Multiple Conducting States, Vanderbilt University, UMI, Ann Arbor, Mich (Microfilm #9714424). 1996:161. PhD thesis.
49. Yang J, Nung Y. Jan L. Determination of the subunit stoichiometry of an inwardly rectifying potassium channel, Neuron. 1995;15:1441-1447.
50. + channels by a quaternary ammonium ion: catalysis by a transitionintermediate state? J Physiol (Lond). 1993;471:319-341.
51. Singh B, Courtney K. The classification of antiarrhythmic mechanisms of drug action; experimental and clinical considerations. In: Zipes D, Jalife J, eds. Cardiac Electrophysiology: From Cell to Bedside. Philadelphia, Pa: WB Saunders; 1990:882-897.
52. Valenzuela C, Delpon E, Franqueza L, Gay P, Snyders DJ, Tamargo J. Effects of ropivacaine on a cardiac potassium channel (hKvl.5) cloned from human ventricle, Anesthesiology 1997;86:718-728.