Discovery of spiro-piperidine inhibitors and their modulation of the dynamics of the M2 proton channel from influenza A virus

Journal of the American Chemical Society

Volumn 131, Issue 23, 2009, Pages 8066-8076

  Wang, Jun ^a   Cady, Sarah D ^b   Balannik, Victoria ^c   Pinto, Lawrence H ^c   DeGrado, William F ^a   Hong, Mei ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b IOWA STATE UNIVERSITY   (United States)

^c NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE COMPOUNDS; AMANTADINE; CENTRAL NERVOUS SYSTEMS; CLINICAL USE; DRUG-RESISTANT STRAINS; DYNAMIC DISORDER; ELECTRODE VOLTAGE; HELICAL BUNDLE; INFLUENZA A; INFLUENZA A VIRUS; MAGNETIC ENVIRONMENTS; NEW CLASS; ORDER OF MAGNITUDE; PHOSPHOLIPID BILAYER; PROTON CHANNELS; SIDE EFFECT; SOLID STATE NMR; STRUCTURE AND DYNAMICS; STRUCTURE-ACTIVITY RELATION; TRANS-MEMBRANE DOMAINS; TRANSMEMBRANE HELICES;

ACTIVATION ANALYSIS; CELL MEMBRANES; DYNAMICS; ELECTRIC POTENTIAL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHOLIPIDS;

AMINES;

1,5 DIOXA 9 AZASPIRO(5,5)UNDECANE; 1,5 DITHIA 9 AZASPIRO(5,5)UNDECANE; 2 [3 AZASPIRO(5,5)UNDECANOL] 2 IMIDAZOLINE; 2 AZONIASPIRO(4,5)DECANE CHLRORIDE; 3 (CYCLOPENTYLMETHYL) 3 AZASPIRO(5,5)UNDECANE; 3 (CYCLOPROPYLMETHYL) 3 AZASPIRO(5,5)UNDECANE; 3 (PYRIDIN 2 YLMETHYL) 3 AZASPIRO(5,5)UNDECANE; 3 (THIOPHEN 3 YLMETHYL) 3 AZASPIRO(5,5)UNDECANE; 3 [(1 METHYL 1H PYRAZOL 4 YL)METHYL] 3 AZASPIRO(5,5)UNDECANE; 3 [(1H IMIDAZOL 2 YL)METHYL] 3 AZASPIRO(5,5)UNDECANE; 3 [(1H IMIDAZOL 4 YL)METHYL] 3 AZASPIRO(5,5)UNDECANE; 3 [3 AZASPIRO(5,5)UNDECAN 3 YLMETHYL] 5 METHYLISOXAZOLE; 3 AZASPIRO(5,5)UNDECANE 3 CARBOTHIOAMIDE; 3 AZASPIRO(5,5)UNDECANE 3 CARBOXAMIDE; 3 AZASPIRO(5,5)UNDECANE 3 CARBOXIMIDAMIDE; 3 AZASPIRO(5,5)UNDECANE 3 SULFONAMIDE; 3 AZASPIRO(5,5)UNDECANE HYDROCHLORIDE; 3 METHYL 3 AZONIASPIRO(5,5)UNDECANE CHLORIDE; 4 ETHYL 4 METHYLPIPERIDINIUM CHLORIDE; 4,4 DIMETHYLPIPERIDINIUM CHLROIDE; 8 AZONIASPIRO(4,5)DECANE CHLORIDE; AMANTADINE; ANTIVIRUS AGENT; BL 1743; PROTEIN M2; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SYNTHESIS; IC 50; INFLUENZA VIRUS A; MAGNETIC FIELD; PROTEIN CONFORMATION; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION; VIRUS ENVELOPE; VIRUS INHIBITION; VOLTAGE CLAMP;

AMANTADINE; ANIMALS; ANTIVIRAL AGENTS; HUMANS; IMIDAZOLES; INFLUENZA A VIRUS; OOCYTES; PIPERIDINES; PROTEIN CONFORMATION; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL MATRIX PROTEINS; XENOPUS;

EID: 67650540781     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900063s     Document Type: Article

References (55)

1. De Clercq, E. Nat. Rev. Drug Discovery 2006, 5, 1015-1025.
2. Lagoja, I. M.; De Clercq, E. Med. Res. Rev. 2008, 28, 1-38.
3. Zhirnov, O. P. Virology 1990, 176, 274-279.
4. Martin, K.; Helenius, A. Cell 1991, 67, 117-130.
5. Ciampor, F.; Bayley, P. M.; Nermut, M. V.; Hirst, E. M. A.; Sugrue, R. J.; Hay, A. J. Virology. 1992, 188, 14-24.
6. Grambas, S.; Hay, A. J. Virology 1992, 190, 11-18.
7. Lamb, R. A.; Zebedee, S. L.; Richardson, C. D. Cell 1985, 40, 627-633.
8. Stouffer, A. L.; Acharya, R.; Salom, D.; Levine, A. S.; Di Costanzo, L.; Soto, C. S.; Tereshko, V.; Nanda, V.; Stayrook, S.; DeGrado, W. F. Nature 2008, 451, 596-599.
9. Czabotar, P. E.; Martin, S. R.; Hay, A. J. Virus Res. 2004, 99, 57-61.
10. Wang, C.; Takeuchi, K.; Pinto, L. H.; Lamb, R. A. J. Virol 1993, 67, 5585-5594.
11. Schnell, J. R.; Chou, J. J. Nature 2008, 451, 591-595.
12. Jing, X. H.; Ma, C. L.; Ohigashi, Y.; Oliveira, F. A.; Jardetzky, T. S.; Pinto, L. H.; Lamb, R. A. Proc. Natl. Acad. Sci. U.S.A 2008, 105, 10967-10972.
13. Hay, A. J.; Wolstenholme, A. J.; Skehel, J. J.; Smith, M. H. EMBO J. 1985, 4, 3021-3024.
14. Bright, R. A.; Medina, M. J.; Xu, X. Y.; Perez-Oronoz, G.; Wallis, T. R.; Davis, X. H. M.; Povinelli, L.; Cox, N. J.; Klimov, A. I. Lancet 2005, 366, 1175-1181.
15. Bright, R. A.; Shay, D. K.; Shu, B.; Cox, N. J.; Klimov, A. I. JAMA J. Am. Med. Assoc. 2006, 295, 891-894.
16. Deyde, V. M.; Xu, X. Y.; Bright, R. A.; Shaw, M.; Smith, C. B.; Zhang, Y.; Shu, Y. L.; Gubareva, L. V.; Cox, N. J.; Klimov, A. I. J. Infect. Dis. 2007, 196, 249-257.
17. Stamatiou, G.; Foscolos, G. B.; Fytas, G.; Kolocouris, A.; Kolocouris, N.; Pannecouque, C.; Witvrouw, M.; Padalko, E.; Neyts, J.; De Clercq, E. Bioorg. Med. Chem. 2003, 11, 5485-5492.
18. Zoidis, G.; Fytas, C.; Papanastasiou, L.; Foscolos, G. B.; Fytas, G.; Padalko, E.; de Clercq, E.; Naesens, L.; Neyts, J.; Kolocouris, N. Bioorg. Med. Chem. 2006, 14, 3341-3348.
19. Kolocouris, A.; Tataridis, D.; Fytas, G.; Mavromoustakos, T.; Foscolos, G. B.; Kolocouris, N.; De Clercq, E. Bioorg. Med. Chem. Lett. 1999, 9, 3465-3470.
20. Kolocouris, N.; Zoidis, G.; Foscolos, G. B.; Fytas, G.; Prathalingham, S. R.; Kelly, J. M.; Naesens, L.; De Clercq, E. Bioorg. Med. Chem. Lett. 2007, 17, 4358-4362.
21. Stamatiou, G.; Kolocouris, A.; Kolocouris, N.; Fytas, G.; Foscolos, G. B.; Neyts, J.; De Clercq, E. Bioorg. Med. Chem. Lett. 2001, 11, 2137-2142.
22. Tataridis, D.; Fytas, G.; Kolocouris, A.; Fytas, C.; Kolocouris, N.; Foscolos, G. B.; Padalko, E.; Neyts, J.; De Clercq, E. Bioorg. Med. Chem. Lett. 2007, 17, 692-696.
23. Kolocouris, N.; Foscolos, G. B.; Kolocouris, A.; Marakos, P.; Pouli, N.; Fytas, G.; Ikeda, S.; Declercq, E. J. Med. Chem. 1994, 37, 2896-2902.
24. Kolocouris, N.; Kolocouris, A.; Foscolos, G. B.; Fytas, G.; Neyts, J.; Padalko, E.; Balzarini, J.; Snoeck, R.; Andrei, G.; DeClercq, E. J. Med. Chem. 1996, 39, 3307-3318.
25. Zoidis, G.; Tsotinis, A.; Kolocouris, N.; Kelly, J. M.; Prathalingam, S. R.; Naesens, L.; De Clercq, E. Org. Biomol. Chem. 2008, 6, 3177-3185.
26. Kurtz, S.; Luo, G. X.; Hahnenberger, K. M.; Brooks, C.; Gecha, O.; Ingalls, K.; Numata, K. I.; Krystal, M. Antimicrob. Agents Chemother. 1995, 39, 2204-2209.
27. Ochiai, H.; Sakai, S.; Hirabayashi, T.; Shimizu, Y.; Terasawa, K. Antiviral Res. 1995, 27, 425-430.
28. Alnakib, W.; Higgins, P. G.; Willman, J.; Tyrrell, D. A. J.; Swallow, D. L.; Hurst, B. C.; Rushton, A. J. Antimicrob. Chemother. 1986, 18, 119-129.
29. Garcia Martinez, A.; Teso Vilar, E.; Garcia Fraile, A.; de la Cerero, S.; Rodriguez Herrero, M. E.; Martinez Ruiz, P.; Subramanian, L. R.; Garcia Gancedo, A. J. Med. Chem. 1995, 38, 4474-4477.
30. Tu, Q.; Pinto, L. H.; Luo, G. X.; Shaughnessy, M. A.; Mullaney, D.; Kurtz, S.; Krystal, M.; Lamb, R. A. J. Virol. 1996, 70, 4246-4252.
31. Gandhi, C. S.; Shuck, K.; Lear, J. D.; Dieckmann, G. R.; DeGrado, W. F.; Lamb, R. A.; Pinto, L. H. J. Biol. Chem. 1999, 274, 5474-5482.
32. Cady, S. D.; Goodman, C.; Tatko, C. D.; DeGrado, W. F.; Hong, M. J. Am. Chem. Soc. 2007, 129, 5719-5729.
33. Wang, J.; Kim, S.; Kovacs, F.; Cross, T. A. Protein Sci. 2001, 10, 2241-2250.
34. Hu, J.; Fu, R.; Nishimura, K.; Zhang, L.; Zhou, H. X.; Busath, D. D.; Vijayvergiya, V.; Cross, T. A. Proc. Natl. Acad. Sci. U.S.A 2006, 103, 6865-6870.
35. Nishimura, K.; Kim, S.; Zhang, L.; Cross, T. A. Biochemistry 2002, 41, 13170-13177.
36. Cady, S. D.; Hong, M. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 1483-1488.
37. Hu, J.; Asbury, T.; Achuthan, S.; Li, C.; Bertram, R.; Quine, J. R.; Fu, R.; Cross, T. A. Biophys. J. 2007, 92, 4335-4343.
38. Giffin, K.; Rader, R. K.; Marino, M. H.; Forgey, R. W. FEBS J. 1995, 357, 269-274.
39. Aspinall, S. R.; Bianco, E. J. J. Am. Chem. Soc. 1951, 73, 602-603.
40. AbdelMagid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849-3862.
41. Winum, J. Y.; Toupet, L.; Barragan, V.; Dewynter, G.; Montero, J. L. Org. Lett. 2001, 3, 2241-2243.
42. Weerawarna, S. A.; Jewell, R. A. Preparation of piperidone ketal used as primary oxidant of cellulose fiber, involves condensing alcohol with piperidone in presence of polyphosphoric acid. EP1457491-A1; US2004192920-A1; CA2458736-A1; JP2004307478-A; US6852860-B2.
43. Luo, W.; Hong, M. J. Am. Chem. Soc. 2006, 128, 7242-7251.
44. London, R. E.; Wingad, B. D.; Mueller, G. A. J. Am. Chem. Soc. 2008, 130, 11097-11105.
45. Li, C.; Qin, H.; Gao, F. P.; Cross, T. A. Biochim. Biophys. Acta 2007, 1768, 3162-3170.
46. Shimbo, K.; Brassard, D. L.; Lamb, R. A.; Pinto, L. H. Biophys. J. 1996, 70, 1335-1346.
47. Ito, T.; Gorman, O. T.; Kawaoka, Y.; Bean, W. J.; Webster, R. G. J. Virol. 1991, 65, 5491-5498.
48. Cady, S. D.; Mishanina, T. V.; Hong, M. J. Mol. Biol. 2009, 385, 1127-1141.
49. Bennett, A. E.; Rienstra, C. M.; Auger, M.; Lakshmi, K. V.; Griffin, R. G. J. Chem. Phys. 1995, 103, 6951-6958.
50. Fung, B. M.; Khitrin, A. K.; Ermolaev, K. J. Magn. Reson. 2000, 142, 97-101.
51. Bax, A.; Freeman, R.; Kempsell, S. P. J. Am. Chem. Soc. 1980, 102, 4849-4851.
52. Hong, M. J. Magn. Reson. 1999, 136, 86-91.
53. Hong, M.; Griffin, R. G. J. Am. Chem. Soc. 1998, 120, 7113-7114.
54. Gullion, T.; Schaefer, J. J. Magn. Reson. 1989, 81, 196-200.
55. Hong, M.; Mishanina, T. V.; Cady, S. D. J. Am. Chem. Soc. 2009, in press.