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Volumn 56, Issue 7, 2013, Pages 2804-2812

Discovery of novel dual inhibitors of the wild-type and the most prevalent drug-resistant mutant, S31N, of the M2 proton channel from influenza A virus

Author keywords

[No Author keywords available]

Indexed keywords

4 (ADAMANTAN 1 YLAMINOMETHYL)BENZENE 1,3 DIOL; AMANTADINE DERIVATIVE; ANTIVIRUS AGENT; BENZYL DERIVATIVE; PROTEIN M2; UNCLASSIFIED DRUG;

EID: 84876266002     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301538e     Document Type: Article
Times cited : (92)

References (58)
  • 1
    • 25844438380 scopus 로고    scopus 로고
    • Incidence of adamantane resistance among influenza A (H3N2) viruses isolated worldwide from 1994 to 2005: A cause for concern
    • 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. Incidence of adamantane resistance among influenza A (H3N2) viruses isolated worldwide from 1994 to 2005: a cause for concern Lancet 2005, 366, 1175-1181
    • (2005) Lancet , vol.366 , pp. 1175-1181
    • Bright, R.A.1    Medina, M.J.2    Xu, X.Y.3    Perez-Oronoz, G.4    Wallis, T.R.5    Davis, X.H.M.6    Povinelli, L.7    Cox, N.J.8    Klimov, A.I.9
  • 2
    • 33644536465 scopus 로고    scopus 로고
    • Adamantane resistance among influenza A viruses isolated early during the 2005-2006 influenza season in the United States
    • Bright, R. A.; Shay, D. K.; Shu, B.; Cox, N. J.; Klimov, A. I. Adamantane resistance among influenza A viruses isolated early during the 2005-2006 influenza season in the United States JAMA 2006, 295, 891-894
    • (2006) JAMA , vol.295 , pp. 891-894
    • Bright, R.A.1    Shay, D.K.2    Shu, B.3    Cox, N.J.4    Klimov, A.I.5
  • 4
    • 50949106863 scopus 로고    scopus 로고
    • Surveillance for neuraminidase inhibitor resistance among human influenza A and B viruses circulating worldwide from 2004 to 2008
    • Sheu, T. G.; Deyde, V. M.; Okomo-Adhiambo, M., e. a. Surveillance for neuraminidase inhibitor resistance among human influenza A and B viruses circulating worldwide from 2004 to 2008 Antimicrob. Agents Chemother. 2008, 52, 3284-3292
    • (2008) Antimicrob. Agents Chemother. , vol.52 , pp. 3284-3292
    • Sheu, T.G.1    Deyde, V.M.2    Okomo-Adhiambo, M.3
  • 5
    • 61849118968 scopus 로고    scopus 로고
    • Global transmission of oseltamivir-resistant influenza
    • Moscona, A. Global transmission of oseltamivir-resistant influenza N. Engl. J. Med. 2009, 360, 953-956
    • (2009) N. Engl. J. Med. , vol.360 , pp. 953-956
    • Moscona, A.1
  • 7
    • 79851496686 scopus 로고    scopus 로고
    • Emerging influenza antiviral resistance threats
    • Hayden, F. G.; deJong, M. D. Emerging influenza antiviral resistance threats J. Infect. Dis. 2011, 203, 6-10
    • (2011) J. Infect. Dis. , vol.203 , pp. 6-10
    • Hayden, F.G.1    Dejong, M.D.2
  • 8
    • 73349123478 scopus 로고    scopus 로고
    • Emergence of oseltamivir-resistant pandemic H1N1 virus during prophylaxis
    • Baz, M. Emergence of oseltamivir-resistant pandemic H1N1 virus during prophylaxis N. Engl. J. Med. 2009, 361, 2296-2297
    • (2009) N. Engl. J. Med. , vol.361 , pp. 2296-2297
    • Baz, M.1
  • 11
    • 0022157043 scopus 로고
    • The molecular-basis of the specific anti-influenza action of amantadine
    • Hay, A. J.; Wolstenholme, A. J.; Skehel, J. J.; Smith, M. H. The molecular-basis of the specific anti-influenza action of amantadine EMBO J. 1985, 4, 3021-3024
    • (1985) EMBO J. , vol.4 , pp. 3021-3024
    • Hay, A.J.1    Wolstenholme, A.J.2    Skehel, J.J.3    Smith, M.H.4
  • 12
    • 0026787707 scopus 로고
    • Maturation of influenza A virus hemagglutinin-Estimates of the pH encountered during transport and its regulation by the M2 protein
    • Grambas, S.; Hay, A. J. Maturation of influenza A virus hemagglutinin-Estimates of the pH encountered during transport and its regulation by the M2 protein Virology 1992, 190, 11-18
    • (1992) Virology , vol.190 , pp. 11-18
    • Grambas, S.1    Hay, A.J.2
  • 13
    • 77952089169 scopus 로고    scopus 로고
    • Identification of hits as matrix-2 protein inhibitors through the focused screening of a small primary amine library
    • Hu, W.; Zeng, S.; Li, C.; Jie, Y.; Li, Z.; Chen, L. Identification of hits as matrix-2 protein inhibitors through the focused screening of a small primary amine library J. Med. Chem. 2010, 53, 3831-3834
    • (2010) J. Med. Chem. , vol.53 , pp. 3831-3834
    • Hu, W.1    Zeng, S.2    Li, C.3    Jie, Y.4    Li, Z.5    Chen, L.6
  • 14
    • 79954623305 scopus 로고    scopus 로고
    • Exploring the requirements for the hydrophobic scaffold and polar amine in inhibitors of M2 from Influenza A virus
    • Wang, J.; Ma, C.; Balannik, V.; Pinto, L. H.; Lamb, R. A.; Degrado, W. F. Exploring the requirements for the hydrophobic scaffold and polar amine in inhibitors of M2 from Influenza A virus ACS Med. Chem. Lett. 2011, 2, 307-312
    • (2011) ACS Med. Chem. Lett. , vol.2 , pp. 307-312
    • Wang, J.1    Ma, C.2    Balannik, V.3    Pinto, L.H.4    Lamb, R.A.5    Degrado, W.F.6
  • 16
    • 0029117350 scopus 로고
    • Growth impairment resulting from expression of influenza virus M2 protein in Saccharomyces cerevisiae: Identification of a novel inhibitor of influenza virus
    • Kurtz, S.; Luo, G.; Hahnenberger, K. M.; Brooks, C.; Gecha, O.; Ingalls, K.; Numata, K.; Krystal, M. Growth impairment resulting from expression of influenza virus M2 protein in Saccharomyces cerevisiae: identification of a novel inhibitor of influenza virus Antimicrob. Agents Chemother. 1995, 39, 2204-2209
    • (1995) Antimicrob. Agents Chemother. , vol.39 , pp. 2204-2209
    • Kurtz, S.1    Luo, G.2    Hahnenberger, K.M.3    Brooks, C.4    Gecha, O.5    Ingalls, K.6    Numata, K.7    Krystal, M.8
  • 17
    • 33751517736 scopus 로고    scopus 로고
    • Antiviral agents active against influenza A viruses
    • De Clercq, E. Antiviral agents active against influenza A viruses Nat. Rev. Drug Discovery 2006, 5, 1015-1025
    • (2006) Nat. Rev. Drug Discovery , vol.5 , pp. 1015-1025
    • De Clercq, E.1
  • 19
    • 37249016414 scopus 로고    scopus 로고
    • Anti-influenza virus agents: Synthesis and mode of action
    • Lagoja, I. M.; De Clercq, E. Anti-influenza virus agents: Synthesis and mode of action Med. Res. Rev. 2008, 28, 1-38
    • (2008) Med. Res. Rev. , vol.28 , pp. 1-38
    • Lagoja, I.M.1    De Clercq, E.2
  • 20
    • 84864228530 scopus 로고    scopus 로고
    • Antivirals targeting influenza A virus
    • Das, K. Antivirals targeting influenza A virus J. Med. Chem. 2012, 55, 6263-6277
    • (2012) J. Med. Chem. , vol.55 , pp. 6263-6277
    • Das, K.1
  • 21
    • 49449093199 scopus 로고    scopus 로고
    • Functional studies indicate amantadine binds to the pore of the influenza A virus M2 proton-selective ion channel
    • Jing, X.; Ma, C.; Ohigashi, Y.; Oliveira, F. A.; Jardetzky, T. S.; Pinto, L. H.; Lamb, R. A. Functional studies indicate amantadine binds to the pore of the influenza A virus M2 proton-selective ion channel Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 10967-10972
    • (2008) Proc. Natl. Acad. Sci. U.S.A. , vol.105 , pp. 10967-10972
    • Jing, X.1    Ma, C.2    Ohigashi, Y.3    Oliveira, F.A.4    Jardetzky, T.S.5    Pinto, L.H.6    Lamb, R.A.7
  • 23
    • 84876244443 scopus 로고    scopus 로고
    • Unpublished results
    • Ma, C. Unpublished results.
    • Ma, C.1
  • 25
    • 38749106195 scopus 로고    scopus 로고
    • Structure and mechanism of the M2 proton channel of influenza A virus
    • Schnell, J. R.; Chou, J. J. Structure and mechanism of the M2 proton channel of influenza A virus Nature 2008, 451, 591-593
    • (2008) Nature , vol.451 , pp. 591-593
    • Schnell, J.R.1    Chou, J.J.2
  • 26
    • 68249121326 scopus 로고    scopus 로고
    • Structure and function of the influenza A M2 proton channel
    • Cady, S. D.; Luo, W.; Hu, F.; Hong, M. Structure and function of the influenza A M2 proton channel Biochemistry 2009, 48, 7356-7364
    • (2009) Biochemistry , vol.48 , pp. 7356-7364
    • Cady, S.D.1    Luo, W.2    Hu, F.3    Hong, M.4
  • 27
    • 58149345493 scopus 로고    scopus 로고
    • Structure of amantadine-bound M2 transmembrane peptide of influenza A in lipid bilayers from magic-angle-spinning solid-state NMR: The role of Ser31 in amantadine binding
    • Cady, S. D.; Mishanina, T. V.; Hong, M. Structure of amantadine-bound M2 transmembrane peptide of influenza A in lipid bilayers from magic-angle-spinning solid-state NMR: the role of Ser31 in amantadine binding J. Mol. Biol. 2009, 385, 1127-1141
    • (2009) J. Mol. Biol. , vol.385 , pp. 1127-1141
    • Cady, S.D.1    Mishanina, T.V.2    Hong, M.3
  • 28
    • 76249125649 scopus 로고    scopus 로고
    • Structure of the amantadine binding site of influenza M2 proton channels in lipid bilayers
    • Cady, S. D.; Schmidt-Rohr, K.; Wang, J.; Soto, C. S.; DeGrado, W. F.; Hong, M. Structure of the amantadine binding site of influenza M2 proton channels in lipid bilayers Nature 2010, 463, 689-692
    • (2010) Nature , vol.463 , pp. 689-692
    • Cady, S.D.1    Schmidt-Rohr, K.2    Wang, J.3    Soto, C.S.4    Degrado, W.F.5    Hong, M.6
  • 29
    • 77958156306 scopus 로고    scopus 로고
    • Insight into the mechanism of the influenza a proton channel from a structure in a lipid bilayer
    • Sharma, M.; Yi, M.; Dong, H.; Qin, H.; Peterson, E.; Busath, D. D.; Zhou, H. X.; Cross, T. A. Insight into the mechanism of the influenza a proton channel from a structure in a lipid bilayer Science 2010, 330, 509-512
    • (2010) Science , vol.330 , pp. 509-512
    • Sharma, M.1    Yi, M.2    Dong, H.3    Qin, H.4    Peterson, E.5    Busath, D.D.6    Zhou, H.X.7    Cross, T.A.8
  • 31
    • 80855128789 scopus 로고    scopus 로고
    • Structural investigation of rimantadine inhibition of the AM2-BM2 chimera channel of influenza viruses
    • Pielak, R. M.; Oxenoid, K.; Chou, J. J. Structural investigation of rimantadine inhibition of the AM2-BM2 chimera channel of influenza viruses Structure 2011, 19, 1655-1663
    • (2011) Structure , vol.19 , pp. 1655-1663
    • Pielak, R.M.1    Oxenoid, K.2    Chou, J.J.3
  • 32
    • 79953041331 scopus 로고    scopus 로고
    • Specific binding of adamantane drugs and direction of their polar amines in the pore of the influenza M2 transmembrane domain in lipid bilayers and dodecylphosphocholine micelles determined by NMR spectroscopy
    • Cady, S. D.; Wang, J.; Wu, Y.; DeGrado, W. F.; Hong, M. Specific binding of adamantane drugs and direction of their polar amines in the pore of the influenza M2 transmembrane domain in lipid bilayers and dodecylphosphocholine micelles determined by NMR spectroscopy J. Am. Chem. Soc. 2011, 133, 4274-4284
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 4274-4284
    • Cady, S.D.1    Wang, J.2    Wu, Y.3    Degrado, W.F.4    Hong, M.5
  • 33
    • 84860797609 scopus 로고    scopus 로고
    • Magic-angle-spinning NMR of the Drug Resistant S31N M2 Proton Transporter from Influenza A
    • Andreas, L. B.; Eddy, M. T.; Chou, J. J.; Griffin, R. G. Magic-angle-spinning NMR of the Drug Resistant S31N M2 Proton Transporter from Influenza A J. Am. Chem. Soc. 2012, 134, 7215-7218
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 7215-7218
    • Andreas, L.B.1    Eddy, M.T.2    Chou, J.J.3    Griffin, R.G.4
  • 34
    • 66149112971 scopus 로고    scopus 로고
    • Mechanism of drug inhibition and drug resistance of influenza A M2 channel
    • Pielak, R. M.; Schnell, J. R.; Chou, J. J. Mechanism of drug inhibition and drug resistance of influenza A M2 channel Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 7379-7384
    • (2009) Proc. Natl. Acad. Sci. U.S.A. , vol.106 , pp. 7379-7384
    • Pielak, R.M.1    Schnell, J.R.2    Chou, J.J.3
  • 35
    • 72449187005 scopus 로고    scopus 로고
    • Design and pharmacological characterization of inhibitors of amantadine-resistant mutants of the M2 ion channel of influenza A virus
    • Balannik, V.; Wang, J.; Ohigashi, Y.; Jing, X.; Magavern, E.; Lamb, R. A.; DeGrado, W. F.; Pinto, L. H. Design and pharmacological characterization of inhibitors of amantadine-resistant mutants of the M2 ion channel of influenza A virus Biochemistry 2009, 48, 11872-11882
    • (2009) Biochemistry , vol.48 , pp. 11872-11882
    • Balannik, V.1    Wang, J.2    Ohigashi, Y.3    Jing, X.4    Magavern, E.5    Lamb, R.A.6    Degrado, W.F.7    Pinto, L.H.8
  • 38
    • 80052318334 scopus 로고    scopus 로고
    • Exploring organosilane amines as potent inhibitors and structural probes of influenza a virus M2 proton channel
    • Wang, J.; Ma, C.; Wu, Y.; Lamb, R. A.; Pinto, L. H.; DeGrado, W. F. Exploring organosilane amines as potent inhibitors and structural probes of influenza a virus M2 proton channel J. Am. Chem. Soc. 2011, 133, 13844-13847
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 13844-13847
    • Wang, J.1    Ma, C.2    Wu, Y.3    Lamb, R.A.4    Pinto, L.H.5    Degrado, W.F.6
  • 39
    • 77956574180 scopus 로고    scopus 로고
    • Heterodimers of histidine and amantadine as inhibitors for wild type and mutant M2 channels of influenza A
    • Zhang, W.; Xu, J.; Liu, F.; Li, C.; Jie, Y.; Chen, S.; Li, Z.; Liu, J.; Chen, Ling; Zhou, G. Heterodimers of histidine and amantadine as inhibitors for wild type and mutant M2 channels of influenza A Chin. J. Chem. 2010, 28, 1417-1423
    • (2010) Chin. J. Chem. , vol.28 , pp. 1417-1423
    • Zhang, W.1    Xu, J.2    Liu, F.3    Li, C.4    Jie, Y.5    Chen, S.6    Li, Z.7    Liu, J.8    Chen, L.9    Zhou, G.10
  • 40
    • 78650515603 scopus 로고    scopus 로고
    • Discovery of highly potent agents against influenza A virus
    • Zhao, X.; Li, C.; Zeng, S.; Hu, W. Discovery of highly potent agents against influenza A virus Eur. J. Med. Chem. 2011, 46, 52-57
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 52-57
    • Zhao, X.1    Li, C.2    Zeng, S.3    Hu, W.4
  • 43
    • 33745328312 scopus 로고    scopus 로고
    • In vitro inhibition of human influenza A virus replication by chloroquine
    • Ooi, E. E.; Chew, J. S.; Loh, J. P.; Chua, R. C. In vitro inhibition of human influenza A virus replication by chloroquine Virol. J. 2006, 3, 39
    • (2006) Virol. J. , vol.3 , pp. 39
    • Ooi, E.E.1    Chew, J.S.2    Loh, J.P.3    Chua, R.C.4
  • 45
    • 0000844109 scopus 로고    scopus 로고
    • Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures (1)
    • Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures (1) J. Org. Chem. 1996, 61, 3849-3862
    • (1996) J. Org. Chem. , vol.61 , pp. 3849-3862
    • Abdel-Magid, A.F.1    Carson, K.G.2    Harris, B.D.3    Maryanoff, C.A.4    Shah, R.D.5
  • 47
    • 41549144697 scopus 로고    scopus 로고
    • Efficient preparation of secondary aminoalcohols through a Ti(IV) reductive amination procedure. Application to the synthesis and antibacterial evaluation of new 3 beta-N-[hydroxyalkyl]aminosteroid derivatives
    • Salmi, C.; Loncle, C.; Letourneux, Y.; Brunel, J. M. Efficient preparation of secondary aminoalcohols through a Ti(IV) reductive amination procedure. Application to the synthesis and antibacterial evaluation of new 3 beta-N-[hydroxyalkyl]aminosteroid derivatives Tetrahedron 2008, 64, 4453-4459
    • (2008) Tetrahedron , vol.64 , pp. 4453-4459
    • Salmi, C.1    Loncle, C.2    Letourneux, Y.3    Brunel, J.M.4
  • 48
    • 0025831274 scopus 로고
    • Conformationally restricted arginine analogues
    • Webb, T. R.; Eigenbrot, C. Conformationally restricted arginine analogues J. Org. Chem. 1991, 56, 3009-3016
    • (1991) J. Org. Chem. , vol.56 , pp. 3009-3016
    • Webb, T.R.1    Eigenbrot, C.2
  • 49
    • 0000087953 scopus 로고
    • Improved synthesis of symmetrical and unsymmetrical 5,11 methanodibenzo[b,f][1,5]diazocines. Readily available nanoscale structural units
    • Webb, T. H.; Wilcox, C. S. Improved synthesis of symmetrical and unsymmetrical 5,11 methanodibenzo[b,f][1,5]diazocines. Readily available nanoscale structural units J. Org. Chem. 1990, 363-365
    • (1990) J. Org. Chem. , pp. 363-365
    • Webb, T.H.1    Wilcox, C.S.2
  • 50
    • 2942532178 scopus 로고    scopus 로고
    • Redox behavior of ferrocene-containing rotaxane: Transposition of the rotaxane wheel by redox reaction of a ferrocene moiety tethered at the end of the axle
    • Kihara, N.; Hashimoto, M.; Takata, T. Redox behavior of ferrocene-containing rotaxane: Transposition of the rotaxane wheel by redox reaction of a ferrocene moiety tethered at the end of the axle Org. Lett. 2004, 6, 1693-1696
    • (2004) Org. Lett. , vol.6 , pp. 1693-1696
    • Kihara, N.1    Hashimoto, M.2    Takata, T.3
  • 51
    • 84862777605 scopus 로고    scopus 로고
    • Palladium-catalyzed regioselective arylation of arene C-H bond assisted by the removable 2-pyridylsulfinyl group
    • Zhang, X.; Yu, M.; Yao, J.; Zhang, Y. Palladium-catalyzed regioselective arylation of arene C-H bond assisted by the removable 2-pyridylsulfinyl group Synlett 2012, 23, 463-467
    • (2012) Synlett , vol.23 , pp. 463-467
    • Zhang, X.1    Yu, M.2    Yao, J.3    Zhang, Y.4
  • 52
    • 0010114968 scopus 로고
    • An improved synthesis of 5-substituted tetrazoles
    • Finnegan, W. G.; Hennry, R. A.; Lofquist, R. An improved synthesis of 5-substituted tetrazoles J. Am. Chem. Soc. 1958, 80, 3908-3911
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 3908-3911
    • Finnegan, W.G.1    Hennry, R.A.2    Lofquist, R.3
  • 53
    • 84862018685 scopus 로고    scopus 로고
    • Synthesis of substituted asymmetrical biphenyl amino esters as alpha helix mimetics
    • Williams, A. B.; Hanson, R. N. Synthesis of substituted asymmetrical biphenyl amino esters as alpha helix mimetics Tetrahedron 2012, 68, 5406-5414
    • (2012) Tetrahedron , vol.68 , pp. 5406-5414
    • Williams, A.B.1    Hanson, R.N.2
  • 54
    • 41949105441 scopus 로고    scopus 로고
    • The oligomeric state of the active BM2 ion channel protein of influenza B virus
    • Balannik, V.; Lamb, R. A.; Pinto, L. H. The oligomeric state of the active BM2 ion channel protein of influenza B virus J. Bio.l Chem. 2008, 283, 4895-4904
    • (2008) J. Bio.l Chem. , vol.283 , pp. 4895-4904
    • Balannik, V.1    Lamb, R.A.2    Pinto, L.H.3
  • 55
    • 0027185716 scopus 로고
    • Ion channel activity of influenza A virus M2 protein: Characterization of the amantadine block
    • Wang, C.; Takeuchi, K.; Pinto, L. H.; Lamb, R. A. Ion channel activity of influenza A virus M2 protein: characterization of the amantadine block J. Virol. 1993, 67, 5585-5594
    • (1993) J. Virol. , vol.67 , pp. 5585-5594
    • Wang, C.1    Takeuchi, K.2    Pinto, L.H.3    Lamb, R.A.4
  • 56
    • 0026612385 scopus 로고
    • Influenza virus M2 protein has ion channel activity
    • Pinto, L. H.; Holsinger, L. J.; Lamb, R. A. Influenza virus M2 protein has ion channel activity Cell 1992, 69, 517-528
    • (1992) Cell , vol.69 , pp. 517-528
    • Pinto, L.H.1    Holsinger, L.J.2    Lamb, R.A.3


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