Inhibition of enterovirus 71 replication by 7-hydroxyflavone and diisopropyl-flavon7-yl phosphate

PLoS ONE

Volumn 9, Issue 3, 2014, Pages

  Wang, Jianmin ^a   Su, Haoxiang ^a   Zhang, Ting ^a   Du, Jiang ^a   Cui, Sheng ^a   Yang, Fan ^a   Jin, Qi ^a  

^a INSTITUTE OF PATHOGEN BIOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

7 HYDROXYFLAVONE; DIISOPROPYL ETHER; DIISOPROPYL FLAVON7 YL PHOSPHATE; ORGANOPHOSPHATE; PROTEINASE; RNA; UNCLASSIFIED DRUG; 3C PROTEASES; 7-HYDROXYFLAVONE; ANTIVIRUS AGENT; CYSTEINE PROTEINASE; DIISOPROPYL-FLAVON-7-YL PHOSPHATE; FLAVONE DERIVATIVE; FLAVONOID; VIRUS PROTEIN;

ARTICLE; CONTROLLED STUDY; CYTOPATHOGENIC EFFECT; DRUG EFFECT; ENTEROVIRUS 71; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INHIBITION; ENZYME INHIBITION ASSAY; IN VITRO STUDY; MOLECULAR DOCKING; NONHUMAN; NUCLEOTIDE SEQUENCE; PROTEIN CONFORMATION; RNA REPLICATION; VIRUS INHIBITION; VIRUS REPLICATION; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; ENTEROVIRUS; ENZYMOLOGY; HUMAN; METABOLISM; PHYSIOLOGY; TUMOR CELL LINE;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; CYSTEINE ENDOPEPTIDASES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENTEROVIRUS A, HUMAN; ENTEROVIRUS B, HUMAN; FLAVONES; FLAVONOIDS; HUMANS; MOLECULAR DOCKING SIMULATION; ORGANOPHOSPHATES; PROTEIN CONFORMATION; VIRAL PROTEINS; VIRUS REPLICATION;

EID: 84899708443     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0092565     Document Type: Article

References (46)

1. Schmidt NJ, Lennette EH, Ho HH (1974) An apparently new enterovirus isolated from patients with disease of the central nervous system. J Infect Dis 129: 304-309.
2. Solomon T, Lewthwaite P, Perera D, Cardosa MJ, McMinn P, et al. (2010) Virology, epidemiology, pathogenesis, and control of enterovirus 71. Lancet Infect Dis 10: 778-790.
3. Huang SW, Hsu YW, Smith DJ, Kiang D, Tsai HP, et al. (2009) Reemergence of enterovirus 71 in 2008 in taiwan: dynamics of genetic and antigenic evolution from 1998 to 2008. J Clin Microbiol 47: 3653-3662.
4. Tyler KL (2009) Emerging viral infections of the central nervous system: part 1. Arch Neurol 66: 939-948.
5. Yang F, Ren L, Xiong Z, Li J, Xiao Y, et al. (2009) Enterovirus 71 outbreak in the People's Republic of China in 2008. J Clin Microbiol 47: 2351.
6. Plevka P, Perera R, Cardosa J, Kuhn RJ, Rossmann MG (2012) Crystal structure of human enterovirus 71. Science 336: 1274.
7. Wang X, Peng W, Ren J, Hu Z, Xu J, et al. (2012) A sensor-adaptor mechanism for enterovirus uncoating from structures of EV71. Nat Struct Mol Biol 19: 424-429.
8. Hwang YC, Chen W, Yates MV (2006) Use of fluorescence resonance energy transfer for rapid detection of enteroviral infection in vivo. Appl Environ Microbiol 72: 3710-3715. (Pubitemid 43728029)
9. Hu YC, Hsu JT, Huang JH, Ho MS, Ho YC (2003) Formation of enterovirus-like particle aggregates by recombinant baculoviruses co-expressing P1 and 3CD in insect cells. Biotechnol Lett 25: 919-925. (Pubitemid 36796909)
10. Cui S, Wang J, Fan T, Qin B, Guo L, et al. (2011) Crystal structure of human enterovirus 71 3C protease. J Mol Biol 408: 449-461.
11. Parsley TB, Towner JS, Blyn LB, Ehrenfeld E, Semler BL (1997) Poly (rC) binding protein 2 forms a ternary complex with the 59-terminal sequences of poliovirus RNA and the viral 3CD proteinase. RNA 3: 1124-1134.
12. Harris KS, Reddigari SR, Nicklin MJ, Hammerle T, Wimmer E (1992) Purification and characterization of poliovirus polypeptide 3CD, a proteinase and a precursor for RNA polymerase. J Virol 66: 7481-7489.
13. Li ML, Hsu TA, Chen TC, Chang SC, Lee JC, et al. (2002) The 3C protease activity of enterovirus 71 induces human neural cell apoptosis. Virology 293: 386-395.
14. Weng KF, Li ML, Hung CT, Shih SR (2009) Enterovirus 71 3C protease cleaves a novel target CstF-64 and inhibits cellular polyadenylation. PLoS Pathog 5: e1000593.
15. Lei X, Sun Z, Liu X, Jin Q, He B, et al. (2011) Cleavage of the adaptor protein TRIF by enterovirus 71 3C inhibits antiviral responses mediated by Toll-like receptor 3. J Virol 85: 8811-8818.
16. Lei X, Liu X, Ma Y, Sun Z, Yang Y, et al. (2010) The 3C protein of enterovirus 71 inhibits retinoid acid-inducible gene I-mediated interferon regulatory factor 3 activation and type I interferon responses. J Virol 84: 8051-8061.
17. Lei X, Xiao X, Xue Q, Jin Q, He B, et al. (2013) Cleavage of interferon regulatory factor 7 by enterovirus 71 3C suppresses cellular responses. J Virol 87: 1690-1698.
18. Allaire M, Chernaia MM, Malcolm BA, James MN (1994) Picornaviral 3C cysteine proteinases have a fold similar to chymotrypsin-like serine proteinases. Nature 369: 72-76. (Pubitemid 24144357)
19. Malcolm BA (1995) The picornaviral 3C proteinases: cysteine nucleophiles in serine proteinase folds. Protein Sci 4: 1439-1445.
20. Birtley JR, Knox SR, Jaulent AM, Brick P, Leatherbarrow RJ, et al. (2005) Crystal structure of foot-and-mouth disease virus 3C protease. New insights into catalytic mechanism and cleavage specificity. J Biol Chem 280: 11520-11527. (Pubitemid 40418463)
21. Lee CC, Kuo CJ, Ko TP, Hsu MF, Tsui YC, et al. (2009) Structural basis of inhibition specificities of 3C and 3C-like proteases by zinc-coordinating and peptidomimetic compounds. J Biol Chem 284: 7646-7655.
22. Mosimann SC, Cherney MM, Sia S, Plotch S, James MN (1997) Refined X-ray crystallographic structure of the poliovirus 3C gene product. J Mol Biol 273: 1032-1047. (Pubitemid 27501158)
23. Wang J, Fan T, Yao X, Wu Z, Guo L, et al. (2011) Crystal structures of enterovirus 71 3C protease complexed with rupintrivir reveal the roles of catalytically important residues. J Virol 85: 10021-10030.
24. Matthews DA, Dragovich PS, Webber SE, Fuhrman SA, Patick AK, et al. (1999) Structure-assisted design of mechanism-based irreversible inhibitors of human rhinovirus 3C protease with potent antiviral activity against multiple rhinovirus serotypes. Proc Natl Acad Sci U S A 96: 11000-11007. (Pubitemid 29487318)
25. Chen X, Yu Z, Qu L, Yuan J, Lu J, et al. (2007) Phosphorylated modification of genistein and their interaction with lysozyme]. Yao xue xue bao = Acta pharmaceutica Sinica 42: 396.
26. Chen X-L, Qu L-B, Zhang T, Liu H-X, Yu F, et al. (2004) The nature of phosphorylated chrysin-protein interactions involved in noncovalent complex formation by electrospray ionization mass spectroscopy. Anal Chem 76: 211-217. (Pubitemid 38040652)
27. Zhang T, Chen X, Qu L, Wu J, Cui R, et al. (2004) Chrysin and its phosphate ester inhibit cell proliferation and induce apoptosis in Hela cells. Bioorg Med Chem 12: 6097-6105. (Pubitemid 39440450)
28. McMinn P, Stratov I, Nagarajan L, Davis S (2001) Neurological manifestations of enterovirus 71 infection in children during an outbreak of hand, foot, and mouth disease in Western Australia. Clin Infect Dis 32: 236-242. (Pubitemid 32524793)
29. Ho M, Chen ER, Hsu KH, Twu SJ, Chen KT, et al. (1999) An epidemic of enterovirus 71 infection in Taiwan. Taiwan Enterovirus Epidemic Working Group. N Engl J Med 341: 929-935. (Pubitemid 29441546)
30. Zhang SB, Liao H, Huang CH, Tan QY, Zhang WL, et al. (2008) [Serum types of enterovirus and clinical characteristics of 237 children with hand, foot and mouth disease in Shenzhen]. Zhongguo Dang Dai Er Ke Za Zhi 10: 38-41.
31. Kehle J, Roth B, Metzger C, Pfitzner A, Enders G (2003) Molecular characterization of an Enterovirus 71 causing neurological disease in Germany. J Neurovirol 9: 126-128. (Pubitemid 36372552)
32. Alexander JP Jr, Baden L, Pallansch MA, Anderson LJ (1994) Enterovirus 71 infections and neurologic disease - United States, 1977-1991. J Infect Dis 169: 905-908.
33. Nolan MA, Craig ME, Lahra MM, Rawlinson WD, Prager PC, et al. (2003) Survival after pulmonary edema due to enterovirus 71 encephalitis. Neurology 60: 1651-1656. (Pubitemid 36618093)
34. Harborne JB, Williams CA (2000) Advances in flavonoid research since 1992. Phytochemistry 55: 481-504.
35. Lyu SY, Rhim JY, Park WB (2005) Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro. Arch Pharm Res 28: 1293-1301.
36. Johari J, Kianmehr A, Mustafa MR, Abubakar S, Zandi K (2012) Antiviral Activity of Baicalein and Quercetin against the Japanese Encephalitis Virus. Int J Mol Sci 13: 16785-16795.
37. Liu AL, Wang HD, Lee SM, Wang YT, Du GH (2008) Structure-activity relationship of flavonoids as influenza virus neuraminidase inhibitors and their in vitro anti-viral activities. Bioorg Med Chem 16: 7141-7147.
38. Zandi K, Teoh BT, Sam SS, Wong PF, Mustafa MR, et al. (2011) Antiviral activity of four types of bioflavonoid against dengue virus type-2. Virol J 8: 560.
39. Zhang T, Wu Z, Du J, Hu Y, Liu L, et al. (2012) Anti-Japanese- encephalitis-viral effects of kaempferol and daidzin and their RNA-binding characteristics. PLoS One 7: e30259.
40. Lu G, Qi J, Chen Z, Xu X, Gao F, et al. (2011) Enterovirus 71 and coxsackievirus A16 3C proteases: binding to rupintrivir and their substrates and anti-hand, foot, and mouth disease virus drug design. J Virol 85: 10319-10331.
41. Kuo CJ, Shie JJ, Fang JM, Yen GR, Hsu JT, et al. (2008) Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents. Bioorg Med Chem 16: 7388-7398.
42. Jung HA, Moon HE, Oh SH, Kim BW, Sohn HS, et al. (2012) Kinetics and molecular docking studies of kaempferol and its prenylated derivatives as aldose reductase inhibitors. Chem Biol Interact 197: 110-118.
43. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, et al. (2009) AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 30: 2785-2791.
44. Reed LJ, Muench H (1938) A simple method of estimating fifty per cent endpoints. American Journal of Epidemiology 27: 493.
45. Malich G, Markovic B, Winder C (1997) The sensitivity and specificity of the MTS tetrazolium assay for detecting the in vitro cytotoxicity of 20 chemicals using human cell lines. Toxicology 124: 179-192. (Pubitemid 28055528)
46. Wang J, Wu Z, Jin Q (2012) COPI is required for enterovirus 71 replication. PLoS One 7: e38035.