SCOPUS 정보 검색 플랫폼

Volumn 46, Issue 8, 2011, Pages 3486-3498

Block of the hERG channel by bupivacaine: Electrophysiological and modeling insights towards stereochemical optimization

(4) Sintra Grilo, Liliana a,b Carrupt, Pierre Alain a Abriel, Hugues b Daina, Antoine a

a UNIVERSITY OF GENEVA (Switzerland)

b UNIVERSITY OF BERN (Switzerland)

Author keywords

Bupivacaine; Cardiotoxicity; Electrophysiology; hERG channel; Molecular docking; Stereoselectivity

Indexed keywords

BUPIVACAINE; POTASSIUM CHANNEL HERG; TERFENADINE;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG BINDING; ELECTROPHYSIOLOGY; ENANTIOMER; HUMAN; HUMAN CELL; HYDROGEN BOND; LIGAND BINDING; MOLECULAR DOCKING; MOLECULAR MECHANICS; MOLECULAR MODEL; MUTAGENESIS; PATCH CLAMP; PROTEIN INTERACTION; SIMULATION; STEREOCHEMISTRY; WILD TYPE;

ACTION POTENTIALS; ANESTHETICS, LOCAL; ANTI-ALLERGIC AGENTS; ARRHYTHMIAS, CARDIAC; BINDING SITES; BUPIVACAINE; ETHER-A-GO-GO POTASSIUM CHANNELS; HEART; HEK293 CELLS; HUMANS; MOLECULAR DYNAMICS SIMULATION; MUTATION; PLASMIDS; POTASSIUM CHANNEL BLOCKERS; PROTEIN BINDING; RECOMBINANT PROTEINS; STEREOISOMERISM; TERFENADINE; THERMODYNAMICS; TRANSFECTION;

EID: 79958255867 PISSN: 02235234 EISSN: 17683254 Source Type: Journal
DOI: 10.1016/j.ejmech.2011.05.015 Document Type: Article

Times cited : (12)

References (51)

1
- 0029002969
- M.C. Sanguinetti, C.G. Jiang, M.E. Curran, and M.T. Keating Cell 81 1995 299 307
- (1995) Cell , vol.81 , pp. 299-307
- Sanguinetti, M.C.¹ Jiang, C.G.² Curran, M.E.³ Keating, M.T.⁴

2
- 0028914969
- M.E. Curran, I. Splawski, K.W. Timothy, G.M. Vincent, E.D. Green, and M.T. Keating Cell 80 1995 795 803
- (1995) Cell , vol.80 , pp. 795-803
- Curran, M.E.¹ Splawski, I.² Timothy, K.W.³ Vincent, G.M.⁴ Green, E.D.⁵ Keating, M.T.⁶

3
- 33645317063
- M.C. Sanguinetti, and M. Tristani-Firouzi Nature 440 2006 463 469
- (2006) Nature , vol.440 , pp. 463-469
- Sanguinetti, M.C.¹ Tristani-Firouzi, M.²

4
- 0032411213
- R. Dumaine, M.L. Roy, and A.M. Brown J. Pharmacol. Exp. Ther. 286 1998 727 735
- (1998) J. Pharmacol. Exp. Ther. , vol.286 , pp. 727-735
- Dumaine, R.¹ Roy, M.L.² Brown, A.M.³

5
- 0038678580
- D. Thomas, K. Wu, S. Kathöfer, H.A. Katus, W. Schoels, J. Kiehn, and C.A. Karle Brit. J. Pharmacol. 139 2003 567 574
- (2003) Brit. J. Pharmacol. , vol.139 , pp. 567-574
- Thomas, D.¹ Wu, K.² Kathöfer, S.³ Katus, H.A.⁴ Schoels, W.⁵ Kiehn, J.⁶ Karle, C.A.⁷

6
- 0030693690
- S. Mohammad, Z.F. Zhou, Q.M. Gong, and C.T. January Am. J. Physio. Heart Circ. Physiol. 273 1997 H2534 H2538
- (1997) Am. J. Physio. Heart Circ. Physiol. , vol.273
- Mohammad, S.¹ Zhou, Z.F.² Gong, Q.M.³ January, C.T.⁴

7
- 1442306232
- D.M. Roden N. Engl. J. Med. 350 2004 1013 1022
- (2004) N. Engl. J. Med. , vol.350 , pp. 1013-1022
- Roden, D.M.¹

8
- 23844542866
- R.R. Shah Novartis. Found. Symp. 266 2005 251 280
- (2005) Novartis. Found. Symp. , vol.266 , pp. 251-280
- Shah, R.R.¹

9
- 41549099967
- E. Raschi, V. Vasina, E. Poluzzi, and P.F. De Pharmacol. Res. 57 2008 181 195
- (2008) Pharmacol. Res. , vol.57 , pp. 181-195
- Raschi, E.¹ Vasina, V.² Poluzzi, E.³ De, P.F.⁴

10
- 0034710933
- J.S. Mitcheson, J. Chen, M. Lin, C. Culberson, and M.C. Sanguinetti Proc. Natl. Acad. Sci. USA 97 2000 12329 12333
- (2000) Proc. Natl. Acad. Sci. USA , vol.97 , pp. 12329-12333
- Mitcheson, J.S.¹ Chen, J.² Lin, M.³ Culberson, C.⁴ Sanguinetti, M.C.⁵

11
- 0038298482
- J.S. Mitcheson Brit. J. Pharmacol. 139 2003 883 884
- (2003) Brit. J. Pharmacol. , vol.139 , pp. 883-884
- Mitcheson, J.S.¹

12
- 14644412444
- M.C. Sanguinetti, and J.S. Mitcheson Trends Pharmacol. Sci. 26 2005 119 124
- (2005) Trends Pharmacol. Sci. , vol.26 , pp. 119-124
- Sanguinetti, M.C.¹ Mitcheson, J.S.²

13
- 34250836484
- P.J. Stansfeld, P. Gedeck, M. Gosling, B. Cox, J.S. Mitcheson, and M.J. Sutcliffe Proteins: Struct. Funct. Bioinf. 68 2007 568 580
- (2007) Proteins: Struct. Funct. Bioinf. , vol.68 , pp. 568-580
- Stansfeld, P.J.¹ Gedeck, P.² Gosling, M.³ Cox, B.⁴ Mitcheson, J.S.⁵ Sutcliffe, M.J.⁶

14
- 34247210196
- C.B. Eap, S. Crettol, J.S. Rougier, J. Schläpfer, L. Sintra Grilo, J.J. Déglon, J. Besson, M. Croquette-Krokar, P.A. Carrupt, and H. Abriel Clin. Pharmacol. Ther. 81 2007 719 728
- (2007) Clin. Pharmacol. Ther. , vol.81 , pp. 719-728
- Eap, C.B.¹ Crettol, S.² Rougier, J.S.³ Schläpfer, J.⁴ Sintra Grilo, L.⁵ Déglon, J.J.⁶ Besson, J.⁷ Croquette-Krokar, M.⁸ Carrupt, P.A.⁹ Abriel, H.¹⁰

15
- 0036944998
- T. Gonzalez, C. Arias, R. Caballero, I. Moreno, E. Delpon, J. Tamargo, and C. Valenzuela Brit. J. Pharmacol. 137 2002 1269 1279
- (2002) Brit. J. Pharmacol. , vol.137 , pp. 1269-1279
- Gonzalez, T.¹ Arias, C.² Caballero, R.³ Moreno, I.⁴ Delpon, E.⁵ Tamargo, J.⁶ Valenzuela, C.⁷

16
- 21744445104
- C.C. Siebrands, N. Schmitt, and P. Friederich Anesthesiology 103 2005 102 112
- (2005) Anesthesiology , vol.103 , pp. 102-112
- Siebrands, C.C.¹ Schmitt, N.² Friederich, P.³

17
- 0348227676
- P. Friederich, A. Solth, S. Schillemeit, and D. Isbrandt Brit. J. Anaesth. 92 2004 93 101
- (2004) Brit. J. Anaesth. , vol.92 , pp. 93-101
- Friederich, P.¹ Solth, A.² Schillemeit, S.³ Isbrandt, D.⁴

18
- 0032773157
- S. Waldegger, G. Niemeyer, K. Mörike, C.A. Wagner, H. Suessbrich, A.E. Busch, F. Lang, and M. Eichelbaum Cell. Physiol. Biochem. 9 1999 81 89
- (1999) Cell. Physiol. Biochem. , vol.9 , pp. 81-89
- Waldegger, S.¹ Niemeyer, G.² Mörike, K.³ Wagner, C.A.⁴ Suessbrich, H.⁵ Busch, A.E.⁶ Lang, F.⁷ Eichelbaum, M.⁸

19
- 0029776056
- K. Hartigan-Go, D.N. Bateman, A.K. Daly, and S.H.L. Thomas Clin. Pharmacol. Ther. 1996 89 98
- (1996) Clin. Pharmacol. Ther. , pp. 89-98
- Hartigan-Go, K.¹ Bateman, D.N.² Daly, A.K.³ Thomas, S.H.L.⁴

20
- 84865972249
- L. Sintra Grilo, P. Carrupt, and H. Abriel Front. Pharmacol. 1 2010 137
- (2010) Front. Pharmacol. , vol.1 , pp. 137
- Sintra Grilo, L.¹ Carrupt, P.² Abriel, H.³

21
- 0038407463
- J.A. Sanchez-Chapula, T. Ferrer, R.A. Navarro-Polanco, and M.C. Sanguinetti Mol. Pharmacol. 63 2003 1051 1058
- (2003) Mol. Pharmacol. , vol.63 , pp. 1051-1058
- Sanchez-Chapula, J.A.¹ Ferrer, T.² Navarro-Polanco, R.A.³ Sanguinetti, M.C.⁴

22
- 0036039326
- R.R. Shah Br. J. Clin. Pharmacol. 54 2002 188 202
- (2002) Br. J. Clin. Pharmacol. , vol.54 , pp. 188-202
- Shah, R.R.¹

23
- 0030704669
- D. Rampe, M.L. Roy, A. Dennis, and A.M. Brown FEBS Lett. 417 1997 28 32
- (1997) FEBS Lett. , vol.417 , pp. 28-32
- Rampe, D.¹ Roy, M.L.² Dennis, A.³ Brown, A.M.⁴

24
- 0343485099
- W.J. Crumb, and J. Pharmacol Exp. Ther. 292 2000 261 264
- (2000) Exp. Ther. , vol.292 , pp. 261-264
- Crumb, W.J.¹ Pharmacol, J.²

25
- 0029761822
- M.L. Roy, R. Dumaine, and A.M. Brown Circulation 94 1996 817 823
- (1996) Circulation , vol.94 , pp. 817-823
- Roy, M.L.¹ Dumaine, R.² Brown, A.M.³

26
- 0028868256
- S.P. Pinney, B.S. Koller, M.R. Franz, R.L. Woosley, and J. Cardiovasc Pharmacol. 25 1995 30 34
- (1995) Pharmacol. , vol.25 , pp. 30-34
- Pinney, S.P.¹ Koller, B.S.² Franz, M.R.³ Woosley, R.L.⁴ Cardiovasc, J.⁵

27
- 34247473376
- C.C. Siebrands, and P. Friederich Anesthesiology 106 2007 523 531
- (2007) Anesthesiology , vol.106 , pp. 523-531
- Siebrands, C.C.¹ Friederich, P.²

28
- 33750092224
- J.T. Limberis, Z. Su, B.F. Cox, G.A. Gintant, and R.L. Martin Clin. Exp. Pharmacol. Physiol. 33 2006 1059 1065
- (2006) Clin. Exp. Pharmacol. Physiol. , vol.33 , pp. 1059-1065
- Limberis, J.T.¹ Su, Z.² Cox, B.F.³ Gintant, G.A.⁴ Martin, R.L.⁵

29
- 31044447745
- M. Perry, P.J. Stansfeld, J. Leaney, C. Wood, M.J. de Groot, D. Leishman, M.J. Sutcliffe, and J.S. Mitcheson Mol. Pharmacol. 69 2006 509 519
- (2006) Mol. Pharmacol. , vol.69 , pp. 509-519
- Perry, M.¹ Stansfeld, P.J.² Leaney, J.³ Wood, C.⁴ De Groot, M.J.⁵ Leishman, D.⁶ Sutcliffe, M.J.⁷ Mitcheson, J.S.⁸

30
- 36148997249
- R.M. Hardman, P.J. Stansfeld, S. Dalibalta, M.J. Sutcliffe, and J.S. Mitcheson J. Biol. Chem. 282 2007 31972 31981
- (2007) J. Biol. Chem. , vol.282 , pp. 31972-31981
- Hardman, R.M.¹ Stansfeld, P.J.² Dalibalta, S.³ Sutcliffe, M.J.⁴ Mitcheson, J.S.⁵

31
- 33644967111
- R. Farid, T. Day, R.A. Friesner, and R.A. Pearlstein Bioorg. Med. Chem. 14 2006 3160 3173
- (2006) Bioorg. Med. Chem. , vol.14 , pp. 3160-3173
- Farid, R.¹ Day, T.² Friesner, R.A.³ Pearlstein, R.A.⁴

32
- 0027025790
- An overview of class III electrophysiological agents: A new generation of antiarrhythmic therapy
- J.T.K. Morgan, and M.E. Sullivan An overview of class III electrophysiological agents: a new generation of antiarrhythmic therapy G.P. Ellis, D.K. Luscomb, Prog. Med. Chem. 1992 Elsevier Science Publishers Amsterdam 65 108
- (1992) Prog. Med. Chem. , pp. 65-108
- Morgan, J.T.K.¹ Sullivan, M.E.²

33
- 0038743107
- R.A. Pearlstein, R.J. Vaz, J. Kang, X.L. Chen, M. Preobrazhenskaya, A.E. Shchekotikhin, A.M. Korolev, L.N. Lysenkova, O.V. Miroshnikova, J. Hendrix, and D. Rampe Bioorg. Med. Chem. Lett. 13 2003 1829 1835
- (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 1829-1835
- Pearlstein, R.A.¹ Vaz, R.J.² Kang, J.³ Chen, X.L.⁴ Preobrazhenskaya, M.⁵ Shchekotikhin, A.E.⁶ Korolev, A.M.⁷ Lysenkova, L.N.⁸ Miroshnikova, O.V.⁹ Hendrix, J.¹⁰ Rampe, D.¹¹

34
- 0037194634
- A. Cavalli, E. Poluzzi, F. De Ponti, and M. Recanatini J. Med. Chem. 45 2002 3844 3853
- (2002) J. Med. Chem. , vol.45 , pp. 3844-3853
- Cavalli, A.¹ Poluzzi, E.² De Ponti, F.³ Recanatini, M.⁴

35
- 0031718230
- H. Bardsley, R. Gristwood, H. Baker, N. Watson, and W. Nimmo Br. J. Clin. Pharmacol. 46 1998 245 249
- (1998) Br. J. Clin. Pharmacol. , vol.46 , pp. 245-249
- Bardsley, H.¹ Gristwood, R.² Baker, H.³ Watson, N.⁴ Nimmo, W.⁵

36
- 56649106666
- K. Kamiya, R. Niwa, M. Morishima, H. Honjo, and M.C. Sanguinetti J. Pharmacol. Sci. 108 2008 301 307
- (2008) J. Pharmacol. Sci. , vol.108 , pp. 301-307
- Kamiya, K.¹ Niwa, R.² Morishima, M.³ Honjo, H.⁴ Sanguinetti, M.C.⁵

37
- 14644392097
- R. Rajamani, B.A. Tounge, J. Li, and C.H. Reynolds Bioorg. Med. Chem. Lett. 15 2005 1737 1741
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1737-1741
- Rajamani, R.¹ Tounge, B.A.² Li, J.³ Reynolds, C.H.⁴

38
- 0346118860
- A.J. Labro, A.L. Raes, I. Bellens, N. Ottschytsch, and D.J. Snyders J. Biol. Chem. 278 2003 50724 50731
- (2003) J. Biol. Chem. , vol.278 , pp. 50724-50731
- Labro, A.J.¹ Raes, A.L.² Bellens, I.³ Ottschytsch, N.⁴ Snyders, D.J.⁵

39
- 0033818157
- J.S. Mitcheson, J. Chen, and M.C. Sanguinetti J. Gen. Physiol. 115 2000 229 239
- (2000) J. Gen. Physiol. , vol.115 , pp. 229-239
- Mitcheson, J.S.¹ Chen, J.² Sanguinetti, M.C.³

40
- 1642370447
- D. Fernandez, A. Ghanta, G.W. Kauffman, and M.C. Sanguinetti J. Biol. Chem. 279 2004 10120 10127
- (2004) J. Biol. Chem. , vol.279 , pp. 10120-10127
- Fernandez, D.¹ Ghanta, A.² Kauffman, G.W.³ Sanguinetti, M.C.⁴

41
- 67650759939
- U. Zachariae, F. Giordanetto, and A.G. Leach J. Med. Chem. 52 2009 4266 4276
- (2009) J. Med. Chem. , vol.52 , pp. 4266-4276
- Zachariae, U.¹ Giordanetto, F.² Leach, A.G.³

42
- 33747505446
- C. Jamieson, E.M. Moir, Z. Rankovic, and G. Wishart J. Med. Chem. 49 2006 5029 5046
- (2006) J. Med. Chem. , vol.49 , pp. 5029-5046
- Jamieson, C.¹ Moir, E.M.² Rankovic, Z.³ Wishart, G.⁴

43
- 31544450787
- W. Sherman, T. Day, M.P. Jacobson, R.A. Friesner, and R. Farid J. Med. Chem. 49 2006 534 553
- (2006) J. Med. Chem. , vol.49 , pp. 534-553
- Sherman, W.¹ Day, T.² Jacobson, M.P.³ Friesner, R.A.⁴ Farid, R.⁵

44
- 58049201323
- University of California San Francisco
- D.A. Case, T.A. Darden, T.E. Cheatham, C.L. Simmerling, J. Wang, R.E. Duke, R. Luo, M. Crowley, R.C. Walker, W. Zhang, M. Merz, B. Wang, S. Hayik, G. Roitberg, G. Seabra, I. Kolossváry, K.F. Wong, F. Paesani, J. Vanicek, X. Wu, S.R. Brozell, T. Steinbrecher, H. Gohlke, L. Yang, C. Tan, J. Mongan, V. Hornak, G. Cui, D.H. Mathews, M.G. Seetin, C. Sagui, V. Babin, and P.A. Kollman AMBER 10 2008 University of California San Francisco
- (2008) AMBER 10
- Case, D.A.¹ Darden, T.A.² Cheatham, T.E.³ Simmerling, C.L.⁴ Wang, J.⁵ Duke, R.E.⁶ Luo, R.⁷ Crowley, M.⁸ Walker, R.C.⁹ Zhang, W.¹⁰ Merz, M.¹¹ Wang, B.¹² Hayik, S.¹³ Roitberg, G.¹⁴ Seabra, G.¹⁵ Kolossváry, I.¹⁶ Wong, K.F.¹⁷ Paesani, F.¹⁸ Vanicek, J.¹⁹ Wu, X.²⁰ more..

45
- 1842479952
- A. Onufriev, D. Bashford, and D.A. Case Proteins. Struct. Funct. Bioinf. 55 2004 383 394
- (2004) Proteins. Struct. Funct. Bioinf. , vol.55 , pp. 383-394
- Onufriev, A.¹ Bashford, D.² Case, D.A.³

46
- 49149147973
- J. Gasteiger, and M. Marsili Tetrahedron 36 1980 3219 3222
- (1980) Tetrahedron , vol.36 , pp. 3219-3222
- Gasteiger, J.¹ Marsili, M.²

47
- 40649101151
- A.P. Graves, D.M. Shivakumar, S.E. Boyce, M.P. Jacobson, D.A. Case, and B.K. Shoichet J. Mol. Biol. 377 2008 914 934
- (2008) J. Mol. Biol. , vol.377 , pp. 914-934
- Graves, A.P.¹ Shivakumar, D.M.² Boyce, S.E.³ Jacobson, M.P.⁴ Case, D.A.⁵ Shoichet, B.K.⁶

48
- 0000408363
- J. Weiser, P.S. Shenkin, and W.C. Still J. Comput. Chem. 20 1999 217 230
- (1999) J. Comput. Chem. , vol.20 , pp. 217-230
- Weiser, J.¹ Shenkin, P.S.² Still, W.C.³

49
- 0034851801
- S. Rey, G. Caron, G. Ermondi, P. Gaillard, A. Pagliara, P.A. Carrupt, and B. Testa J. Mol. Graphics Model. 19 2001 521 535
- (2001) J. Mol. Graphics Model. , vol.19 , pp. 521-535
- Rey, S.¹ Caron, G.² Ermondi, G.³ Gaillard, P.⁴ Pagliara, A.⁵ Carrupt, P.A.⁶ Testa, B.⁷

50
- 0036863260
- S. Rey, P.A. Carrupt, and B. Testa Ann. Pharm. Fr. 60 2002 386 396
- (2002) Ann. Pharm. Fr. , vol.60 , pp. 386-396
- Rey, S.¹ Carrupt, P.A.² Testa, B.³

51
- 77951556566
- L.S. Grilo, P.A. Carrupt, and A. Daina Chimia 64 2010 165 169
- (2010) Chimia , vol.64 , pp. 165-169
- Grilo, L.S.¹ Carrupt, P.A.² Daina, A.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.