Discovery of gramine derivatives that inhibit the early stage of EV71 replication in vitro

Molecules

Volumn 19, Issue 7, 2014, Pages 8949-8964

  Wei, Yanhong ^a   Shi, Liqiao ^b   Wang, Kaimei ^b   Liu, Manli ^b   Yang, Qingyu ^a   Yang, Ziwen ^a,b   Ke, Shaoyong ^b  

^a WUHAN UNIVERSITY   (China)

^b INSTITUTE OF PLANT PROTECTION   (China)

Author keywords

Antiviral activity; Enterovirus 71; Gramine derivatives

Indexed keywords

ANTIVIRUS AGENT; FURAN DERIVATIVE;

ANIMAL; APOPTOSIS; CHEMISTRY; CHLOROCEBUS AETHIOPS; DRUG EFFECTS; ENTEROVIRUS A; IC50; PHYSIOLOGY; VERO CELL LINE; VIRUS REPLICATION;

ANIMALS; ANTIVIRAL AGENTS; APOPTOSIS; CERCOPITHECUS AETHIOPS; ENTEROVIRUS A, HUMAN; FURANS; INHIBITORY CONCENTRATION 50; VERO CELLS; VIRUS REPLICATION;

EID: 84904790488     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19078949     Document Type: Article

References (30)

1. Schmidt, N.J.; Lennette, E.H.; Ho, H.H. An apparently new enterovirus isolated from patients with disease of the central nervous system. J. Infect. Dis. 1974, 129, 304-309.
2. AbuBakar, S.; Chee, H.Y.; Al-Kobaisi, M.F.; Jiang, X.S.; Chua, K.B.; Lam, S.K. Identification of enterovirus 71 isolates from an outbreak of hand, foot and mouth disease (HFMD) with fatal cases of encephalomyelitis in Malaysia. Virus Res. 1999, 61, 1-9.
3. McMinn, P.; Stratov, I.; Nagarajan, L.; Davis, S. Neurological manifestations of enterovirus 71 infection in children during an outbreak of hand, foot, and mouth disease in Western Australia. Clin. Infect. Dis. 2001, 32, 236-242.
4. Kehle, J.; Roth, B.; Metzger, C.; Pfitzner, A.; Enders, G. Molecular characterization of an Enterovirus 71 causing neurological disease in Germany. J. Neurovirol. 2003, 9, 126-128.
5. Hosoya, M.; Kawasaki, Y.; Sato, M.; Honzumi, K.; Kato, A.; Hiroshima, T.; Ishiko, H.; Suzuki, H. Genetic diversity of enterovirus 71 associated with hand, foot and mouth disease epidemics in Japan from 1983 to 2003. Pediatr. Infect. Dis. J. 2006, 25, 691-694.
6. Bible, J.M.; Iturriza-Gomara, M.; Megson, B.; Brown, D.; Pantelidis, P.; Earl, P.; Ishiko, H.; Suzuki, H. Molecular epidemiology of human enterovirus 71 in the United Kingdom from 1998 to 2006. J. Clin. Microbiol. 2008, 46, 3192-3200.
7. Ho, M.; Chen, E.R.; Hsu, K.H.; Twu, S.J.; Chen, K.T.; Tsai, S.F.; Wang, J.R.; Shih, S.R. An epidemic of enterovirus 71 infection in Taiwan. N. Engl. J. Med. 1999, 341, 929-935.
8. Ding, N.Z.; Wang, X.M.; Sun, S.W.; Song, Q.; Li, S.N.; He, C.Q. Appearance of mosaic enterovirus 71 in the 2008 outbreak of China. Virus Res. 2009, 145, 157-161.
9. Li, J.; Huo, X.X.; Dai, Y.; Yang, Z.H.; Lei, Y.K.; Jiang, Y.Z.; Li, G.; Zhan, J.; Zhan, F. Evidences for intertypic and intratypic recombinant events in EV71 of hand, foot and mouth disease during an epidemic in Hubei Province, China, 2011. Virus Res. 2012, 16, 195-202.
10. Chang, L.Y.; Huang, L.M.; Gau, S.S.; Wu, Y.Y.; Hsia, S.H.; Fan, T.Y.; Lin, K.L.; Huang, Y.C.; Lu, C.Y.; Lin, T.Y. Neurodevelopment and cognition in children after enterovirus 71 infection. N. Engl. J. Med. 2007, 356, 1226-1234.
11. Xu, J.; Qian, Y.; Wang, S.X.; Serrano, J.M.; Li, W.; Huang, Z.H.; Lu, S. EV71: An emerging infectious disease vaccine target in the Far East? Vaccine 2010, 28, 3516-3521.
12. Shang, L.Q.; Xu, M.Y.; Yin, Z. Antiviral drug discovery for the treatment of entero-virus 71 infections. Antivir. Res. 2013, 97, 183-194.
13. Li, Z.H.; Li, C.M.; Ling, P.; Shen, F.H.; Chen, S.H.; Liu, C.C.; Yu, C.K.; Chen, S.H. Ribavirin reduces mortality in enterovirus 71-infected mice by decreasing viral replication. J. Infect. Dis. 2008, 197, 854-857.
14. Liu, M.L.; Lee, Y.P.; Wang, Y.F.; Lei, H.Y.; Liu, C.C.; Wang, S.M.; Su, I.J.; Wang, J.R.; Yeh, T.M.; Chen, S.H.; et al. Type I interferons protect mice against enterovirus 71 infection. J. Gen. Virol. 2005, 86, 3263-3269.
15. Pevear, D.C.; Tull, T.M.; Seipel, M.E.; Groarke, J.M. Activity of pleconaril against enteroviruses. Antimicrob. Agents Chemother. 1999, 43, 2109-2115.
16. Iwata, S.; Saito, S.; Kon-ya, K.; Shizuri, Y.; Ohizumi, Y. Novel marine-derived halogen-containing gramine analogues induce vasorelaxation in isolated rat aorta. Eur. J. Pharmacol. 2001, 432, 63-70.
17. Nakahata, N.; Harada, Y.; Tsuji, M.; Kon-ya, K.; Shizuri, Y.; Ohizumi, Y. Structure- Activity relationship of gramine derivatives in Ca2q release from sarcoplasmic reticulum. Eur. J. Pharmacol. 1999, 382, 129-132.
18. Grün, S.; Frey, M.; Gierl, A. Evolution of the indole alkaloid biosynthesis in the genus Hordeum: Distribution of gramine and DIBOA and isolation of the benzoxazinoid biosynthesis genes from Hordeum lechleri. Phytochemistry 2005, 66, 1264-1272.
19. Katritzky, A.R.; Khelashvili, L.; Munawar, M.A. Syntheses of IAA- And IPA-Amino Acid Conjugates. J. Org. Chem. 2008, 73, 9171-9173.
20. Zheng, M.F.; Zheng, M.Y.; Ye, D.J.; Deng, Y.M.; Qiu, S.F.; Luo, X.M.; Chen, K.; Liu, H.; Jiang, H. Indole derivatives as potent inhibitors of 5-lipoxygenase: Design, synthesis, biological evaluation, and molecular modeling. Bioorg. Med. Chem. Lett. 2007, 17, 2414-2420.
21. Giampieri, M.; Balbi, A.; Mazzei, M.; Colla, P.L.; Ibba, C.; Loddo, R. Antiviral activity of indole derivatives. Antiviral Res. 2009, 83, 179-185.
22. Wang, R.; Shi, H.F.; Zhao, J.F.; He, Y.P.; Zhang, H.B.; Liu, J.P. Design, synthesis and aromatase inhibitory activities of novel indole-imidazole derivatives. Bioorg. Med. Chem. Lett. 2013, 23, 1760-1762.
23. Ke, S.Y.; Shi, L.Q.; Cao, X.F.; Yang, Q.Y.; Liang, Y.; Yang, Z.W. Heterocycle- functional gramine analogues: Solvent- And catalyst-free synthesis and their inhibition activities against cell proliferation. Eur. J. Med. Chem. 2012, 54, 248-254.
24. Reed, L.J.; Muench, H. A simple method of estimating fifty percent endpoints. Am. J. Epidemiol. 1938, 27, 493-497.
25. Weng, K.F.; Chen, L.L.; Huang, P.N.; Shih, S.R. Neural pathogenesis of enterovirus71 infection. Microbes Infect. 2010, 12, 505-510.
26. Shih, S.R.; Weng, K.F.; Stollar, V.; Li, M.L. Viral protein synthesis is required for Enterovirus71 to induce apoptosis in human glioblastoma cells. J. Neurovirol. 2008, 14, 53-61.
27. Shih, S.R.; Stollar, V.; Li, M.L. Host Factors in Enterovirus 71 Replication. J. Virol. 2011, 85, 9658-9666.
28. Chen, T.C.; Weng, K.F.; Chang, S.C.; Lin, J.Y.; Huang, P.N.; Shih, S.R. Development of antiviral agents for enteroviruses. J. Antimicrob. Chemother. 2008, 62, 1169-1173.
29. Microbiology Bytes. Available online: http://www.microbiologybytes.com/ virology/Picornaviruses.html (accessed on 17 August 2013).
30. Shih, S.R.; Tsai, K.N.; Li, Y.S.; Chueh, C.C.; Chan, E.C. Inhibition of Enterovirus 71-Induced Apoptosis by Allophycocyanin Isolated From a Blue-Green Alga Spirulina platensis. J. Med. Virol. 2003, 70, 119-125.