Predicting the potency of hERG K + channel inhibition by combining 3D-QSAR pharmacophore and 2D-QSAR models

Journal of Molecular Modeling

Volumn 18, Issue 3, 2012, Pages 1023-1036

  Tan, Yayu ^a   Chen, Yadong ^a   You, Qidong ^a   Sun, Haopeng ^a   Li, Manhua ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

2D QSAR model; 3D QSAR pharmacophore model; Cardiac risk; HERG channel inhibitory potency

Indexed keywords

AMIODARONE; AMSACRINE; ASTEMIZOLE; BEPRIDIL; CHLORBUTOL; CISAPRIDE; CLEMASTINE; CLOMIFENE; CYAMEMAZINE; DOMPERIDONE; DOXAZOSIN; DRONEDARONE; DROPERIDOL; FLUNARIZINE; HALOFANTRINE; HALOPERIDOL; KETANSERIN; LIDOFLAZINE; MESORIDAZINE; NORASTEMIZOLE; PERGOLIDE; PIMOZIDE; POTASSIUM CHANNEL HERG; RISPERIDONE; SERTINDOLE; TERFENADINE; THIORIDAZINE; UNINDEXED DRUG; VERAPAMIL; ZIPRASIDONE;

ARTICLE; DRUG BINDING; DRUG RECEPTOR BINDING; HYDROPHOBICITY; IC 50; MACHINE LEARNING; MODEL; PHARMACOPHORE; PHYSICAL CHEMISTRY; PREDICTIVE VALUE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; THREE DIMENSIONAL QUANTITATIVE STRUCTURE ACTIVITY RELATION; TWO DIMENSIONAL QUANTITATIVE STRUCTURE ACTIVITY RELATION;

DRUG DESIGN; ETHER-A-GO-GO POTASSIUM CHANNELS; HUMANS; MODELS, MOLECULAR; POTASSIUM CHANNEL BLOCKERS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861334270     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-011-1136-y     Document Type: Article

References (100)

1. Wysowski DK, Corken A, Gallo-Torres H, Talarico L, Rodriguez EM (2001) Am J Gastroenterol 96:1698-1703
2. Woosley RL, Chen Y, Freiman JP, Gillis RA (1993) JAMA 269:1532-1536
3. Killeen MJ (2009) Drug Discov Today 14:589-597
4. ICH (2005) ICH Official web site. http://www.ich.org/fileadmin/Public- Web-Site/ICH-Products/Guidelines/Safety/S7B/Step4/S7B-Guideline.pdf
5. Sanguinetti MC, Jiang C, Curran ME, Keating MT (1995) Cell 81:299-307
6. Trudeau MC, Warmke JW, Ganetzky B, Robertson GA (1995) Science 269:92-95
7. Mitcheson JS, Chen J, Lin M, Culberson C, Sanguinetti MC (2000) Proc Natl Acad Sci USA 97:12329-12333
8. Sanchez-Chapula JA, Navarro-Polanco RA, Culberson C, Chen J, Sanguinetti MC (2002) J Biol Chem 277:23587-23595
9. Sanguinetti MC, Chen J, Fernandez D, Kamiya K, Mitcheson J, Sanchez-Chapula JA (2005) Novartis Found Symp 266:159-166
10. Perrin MJ, Subbiah RN, Vandenberg JI, Hill AP (2008) Prog Biophys Mol Biol 98:137-148
11. Myokai T, Ryu S, Shimizu H, Oiki S (2008) Mol Pharmacol 73:1643-1651
12. Zachariae U, Giordanetto F, Leach AG (2009) J Med Chem 52:4266-4276
13. Neher E, Sakmann B (1992) Sci Am 266:44-51
14. Kramer C, Beck B, Kriegl JM, Clark T (2008) Chem Med Chem 3:254-265
15. Leong MK (2007) Chem Res Toxicol 20:217-226
16. Aronov AM, Goldman BB (2004) BioorgMed Chem 12:2307-2315
17. Coi A, Massarelli I, Saraceno M, Carli N, Testai L, Calderone V, Bianucci AM (2009) Chem Biol Drug Des 74:416-433
18. Thai KM, Ecker GF (2009) Mol Divers 13:321-336
19. Nisius B, Goller AH, Bajorath J (2009) Chem Biol Drug Des 73:17-25
20. Ermondi G, Visentin S, Caron G (2009) Eur J Med Chem 44:1926-1932
21. Imai YN, Ryu S, Oiki S (2009) J Med Chem 52:1630-1638
22. Du L, Li M, You Q, Xia L (2007) Biochem Biophys Res Commun 355:889-894
23. Wang X, Yang Q, Yin D, Cheng Y, You Q (2008) Chin J Chem 26:2125-2132
24. Evans DA, Doman TN, Thorner DA, Bodkin MJ (2007) J Chem Inf Model 47:1248-1257
25. Schrödinger, LLC (2009) PHASE v.3.1. Schrödinger, LLC, New York
26. Dixon SL, Smondyrev AM, Rao SN (2006) Chem Biol Drug Des 67:370-372
27. Dixon SL, Smondyrev AM, Knoll EH, Rao SN, Shaw DE, Friesner RA (2006) J Comput Aided Mol Des 20:647-671
28. Hansen K, Rathke F, Schroeter T, Rast G, Fox T, Kriegl JM, Mika S (2009) J Chem Inf Model 49:1486-1496
29. Katritzky AR, Kulshyn OV, Stoyanova-Slavova I, Dobchev DA, Kuanar M, Fara DC, Karelson M (2006) Bioorg Med Chem 14:2333-2357
30. Coi A, Massarelli I, Murgia L, Saraceno M, Calderone V, Bianucci AM (2006) Bioorg Med Chem 14:3153-3159
31. Polak S, Wisniowska B, Brandys J (2009) J Appl Toxicol 29:183-206
32. Zhou Z, Vorperian VR, Gong Q, Zhang S, January CT (1999) J Cardiovasc Electrophysiol 10:836-843
33. Ridley JM, Milnes JT, Hancox JC, Witchel HJ (2006) J Mol Cell Cardiol 40:107-118
34. Kirsch GE, Trepakova ES, Brimecombe JC, Sidach SS, Erickson HD, Kochan MC, Shyjka LM, Lacerda AE, Brown AM (2004) J Pharmacol Toxicol Methods 50:93-101
35. Kornick CA, Kilborn MJ, Santiago-Palma J, Schulman G, Thaler HT, Keefe DL, Katchman AN, Pezzullo JC, Ebert SN, Woosley RL, Payne R, Manfredi PL (2003) Pain 105:499-506
36. Trepakova ES, Dech SJ, Salata JJ (2006) J Cardiovasc Pharmacol 47:211-220
37. Drolet B, Zhang S, Deschenes D, Rail J, Nadeau S, Zhou Z, January CT, Turgeon J (1999) J Cardiovasc Electrophysiol 10:1597-1604
38. Katchman AN, Koerner J, Tosaka T, Woosley RL, Ebert SN (2006) J Pharmacol Exp Ther 316:1098-1106
39. Traebert M, Dumotier B, Meister L, Hoffmann P, Dominguez- Estevez M, Suter W (2004) Eur J Pharmacol 484:41-48
40. Ridley JM, Milnes JT, Witchel HJ, Hancox JC (2004) Biochem Biophys Res Commun 325:883-891
41. Mbai M, Rajamani S, January CT (2002) Cardiovasc Res 55:799-805
42. Hurst RS, Higdon NR, Lawson JA, Clark MA, Rutherford-Root KL, McDonald WG, Haas JV, McGrath JP, Meglasson MD (2003) Eur J Pharmacol 482:31-37
43. Davie C, Pierre-Valentin J, Pollard C, Standen N, Mitcheson J, Alexander P, Thong B (2004) J Cardiovasc Electrophysiol 15:1302-1309
44. Kongsamut S, Kang J, Chen XL, Roehr J, Rampe D (2002) Eur J Pharmacol 450:37-41
45. Yuill KH, Borg JJ, Ridley JM, Milnes JT, Witchel HJ, Paul AA, Kozlowski RZ, Hancox JC (2004) Biochem Biophys Res Commun 318:556-561
46. Thomas D, Hammerling BC, Wu K, Wimmer AB, Ficker EK, Kirsch GE, Kochan MC, Wible BA, Scholz EP, Zitron E, Kathofer S, Kreye VA, Katus HA, Schoels W, Karle CA, Kiehn J (2004) Br J Pharmacol 142:485-494
47. Ducroq J, Printemps R, Le Grand M (2005) J Pharmacol Toxicol Methods 52:115-122
48. Thomas D, Bloehs R, Koschny R, Ficker E, Sykora J, Kiehn J, Schlomer K, Gierten J, Kathofer S, Zitron E, Scholz EP, Kiesecker C, Katus HA, Karle CA (2008) Eur J Pharmacol 579:98-103
49. Crumb W, Llorca PM, Lancon C, Thomas GP, Garay RP, Hameg A (2006) Eur J Pharmacol 532:270-278
50. Su Z, Martin R, Cox BF, Gintant G (2004) J Mol Cell Cardiol 36:151-160
51. Walker BD, Singleton CB, Tie H, Bursill JA, Wyse KR, Valenzuela SM, Breit SN, Campbell TJ (2000) Cardiovasc Res 48:44-58
52. Kim KS, Shin WH, Park SJ, Kim EJ (2007) Int J Toxicol 26:25-31
53. Scholz E, Konrad F, Weiss D, Zitron E, Kiesecker C, Bloehs R, Kulzer M, Thomas D, Kathöfer S, Bauer A, Maurer M, Seemann G, Katus H, Karle C (2007) Naunyn Schmiedebergs Arch Pharmacol 376:275-284
54. Shin WH, Kim KS, Kim EJ (2006) Pharmacol Res 54:414-420
55. Kim KS, Kim EJ (2005) Drug Chem Toxicol 28:303-313
56. Kiesecker C, Zitron E, Luck S, Bloehs R, Scholz EP, Kathofer S, Thomas D, Kreye VA, Katus HA, Schoels W, Karle CA, Kiehn J (2004) Naunyn Schmiedebergs Arch Pharmacol 370:423-435
57. Katayama Y, Fujita A, Ohe T, Findlay I, Kurachi Y (2000) J Pharmacol Exp Ther 294:339-346
58. Ferreira S, Crumb WJ Jr, Carlton CG, Clarkson CW (2001) J Pharmacol Exp Ther 299:220-226
59. Guo L, Guthrie H (2005) Pharmacol J Toxicol Methods 52:123-135
60. Tie H, Walker BD, Valenzuela SM, Breit SN, Campbell TJ (2000) Lancet 355:1825
61. Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA (2004) Naunyn Schmiedebergs Arch Pharmacol 369:462-472
62. Katchman AN, McGroary KA, Kilborn MJ, Kornick CA, Manfredi PL, Woosley RL, Ebert SN (2002) J Pharmacol Exp Ther 303:688-694
63. Rajamani S, Eckhardt LL, Valdivia CR, Klemens CA, Gillman BM, Anderson CL, Holzem KM, Delisle BP, Anson BD, Makielski JC, January CT (2006) Br J Pharmacol 149:481-489
64. Lee SY, Kim YJ, Kim KT, Choe H, Jo SH (2006) Br J Pharmacol 148:499-509
65. Zitron E, Kiesecker C, Scholz E, Luck S, Bloehs R, Kathofer S, Thomas D, Kiehn J, Kreye VA, Katus HA, Schoels W, Karle CA (2004) Naunyn Schmiedebergs Arch Pharmacol 370:146-156
66. Rodriguez-Menchaca A, Ferrer-Villada T, Lara J, Fernandez D, Navarro-Polanco RA, Sanchez-Chapula JA (2006) J Cardiovasc Pharmacol 47:21-29
67. Hiramatsu M, Wu LM, Hirano Y, Kawano S, Furukawa T, Hiraoka M (2004) Hear Vessel 19:137-143
68. Kuryshev YA, Brown AM, Wang L, Benedict CR, Rampe D (2000) J Pharmacol Exp Ther 295:614-620
69. Paul AA, Witchel HJ, Hancox JC (2002) Br J Pharmacol 136:717-729
70. Kawakami K, Nagatomo T, Abe H, Kikuchi K, Takemasa H, Anson BD, Delisle BP, January CT, Nakashima Y (2006) Br J Pharmacol 147:642-652
71. Witchel HJ, Pabbathi VK, Hofmann G, Paul AA, Hancox JC (2002) FEBS Lett 512:59-66
72. Kuryshev YA, Ficker E, Wang L, Hawryluk P, Dennis AT, Wible BA, Brown AM, Kang J, Chen XL, Sawamura K, Reynolds W, Rampe D (2005) Pharmacol Exp Ther 312:316-323
73. Ferrer-Villada T, Navarro-Polanco RA, Rodriguez-Menchaca AA, Benavides-Haro DE, Sanchez-Chapula JA (2006) Eur J Pharmacol 531:1-8
74. Claassen S, Zunkler BJ (2005) Pharmacology 74:31-36
75. Duncan RS, McPate MJ, Ridley JM, Gao Z, James AF, Leishman DJ, Leaney JL, Witchel HJ, Hancox JC (2007) Biochem Pharmacol 74:425-437
76. Paul AA, Witchel HJ, Hancox JC (2001) Biochem Biophys Res Commun 280:1243-1250
77. Walker BD, Valenzuela SM, Singleton CB, Tie H, Bursill JA, Wyse KR, Qiu MR, Breit SN, Campbell TJ (1999) Br J Pharmacol 127:243-251
78. Gonzalez T, Arias C, Caballero R, Moreno I, Delpon E, Tamargo J, Valenzuela C (2002) Br J Pharmacol 137:1269-1279
79. Wang L, Wible BA, Wan X, Ficker E (2007) J Pharmacol Exp Ther 320:525-534
80. Tie H (2002) Cellular mechanisms of QT prolongation and proarrhythmia induced by non-antiarrhythmic drugs. University of New South Wales
81. Kang J, Wang L, Chen XL, Triggle DJ, Rampe D (2001) Mol Pharmacol 59:122-126
82. Wu LM, Orikabe M, Hirano Y, Kawano S, Hiraoka M (2003) J Cardiovasc Pharmacol 42:410-418
83. Caballero R, Moreno I, Gonzalez T, Arias C, Valenzuela C, Delpon E, Tamargo J (2003) Circulation 107:889-895
84. Bischoff U, Schmidt C, Netzer R, Pongs O (2000) Eur J Pharmacol 406:341-343
85. Dustan Sarazan R, Crumb WJ Jr, Beasley CM Jr, Emmick JT, Ferguson KM, Strnat CA, Sausen PJ (2004) Eur J Pharmacol 502:163-167
86. Volberg WA, Koci BJ, Su W, Lin J, Zhou J (2002) J Pharmacol Exp Ther 302:320-327
87. Lacroix P, Crumb WJ, Durando L, Ciottoli GB (2003) Eur J Pharmacol 477:69-72
88. Lu HR, Vlaminckx E, van de Water A, Rohrbacher J, Hermans A, Gallacher DJ (2007) Eur J Pharmacol 577:222-232
89. Ridley JM, Milnes JT, Benest AV, Masters JD, Witchel HJ, Hancox JC (2003) Biochem Biophys Res Commun 306:388-393
90. Saenen JB, Paulussen AD, Jongbloed RJ, Marcelis CL, Gilissen RA, Aerssens J, Snyders DJ, Raes AL (2007) J Mol Cell Cardiol 43:63-72
91. Siebrands CC, Friederich P (2007) Eur J Anaesthesiol 24:148-153
92. Danielsson BR, Lansdell K, Patmore L, Tomson T (2005) Epilepsy Res 63:17-25
93. Danielsson BR, Lansdell K, Patmore L, Tomson T (2003) Epilepsy Res 55:147-157
94. Ridley JM, Milnes JT, Zhang YH, Witchel HJ, Hancox JC (2003) J Physiol 549:667-672
95. Tripos (2010) SYBYL-X 1.1. Tripos, St. Louis
96. Topliss JG, Edwards RP (1979) J Med Chem 22:1238-1244
97. Hancox JC, James AF (2008) Mol Pharmacol 73:1592-1595
98. Aronov AM (2006) J Med Chem 49:6917-6921
99. Garg D, Gandhi T, Gopi Mohan C (2008) J Mol Graph Model 26:966-976
100. Durdagi S, Duff HJ, Noskov SY (2011) J Chem Inf Model 51:463-474