Benzimidazole derivative, BM601, a novel inhibitor of hepatitis B virus and HBsAg secretion

Antiviral Research

Volumn 107, Issue 1, 2014, Pages 6-15

  Xu, Yi Bin ^a   Yang, Li ^a   Wang, Gui Feng ^a   Tong, Xian Kun ^a   Wang, Ya Juan ^a   Yu, Ye ^a   Jing, Jing Feng ^a   Feng, Chun Lan ^a   He, Pei Lan ^a   Lu, Wei ^b   Tang, Wei ^a   Zuo, Jian Ping ^a,c  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

^c SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

Anti hepatitis B virus compound; Benzimidazole derivative; Secretion inhibitor

Indexed keywords

ANTIVIRUS AGENT; BENZIMIDAZOLE DERIVATIVE; BM 601; HEPATITIS B SURFACE ANTIGEN; LAMIVUDINE; MEMBRANE PROTEIN; UNCLASSIFIED DRUG; VIRUS DNA; VIRUS RNA;

ANTIVIRAL ACTIVITY; ARTICLE; CELL COUNTING; CELLULAR STRESS RESPONSE; CONTROLLED STUDY; DNA REPLICATION; DNA SYNTHESIS; DOWN REGULATION; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG STRUCTURE; ENDOPLASMIC RETICULUM; ENZYME LINKED IMMUNOSORBENT ASSAY; GOLGI COMPLEX; HEPATITIS B; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; IMMUNOFLUORESCENCE; IMMUNOPRECIPITATION; MOLECULAR WEIGHT; NONHUMAN; NUCLEOTIDE SEQUENCE; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYADENYLATION; PRIORITY JOURNAL; PROTEIN AGGREGATION; PROTEIN SECRETION; RNA TRANSCRIPTION; SECRETORY PATHWAY; VIRION; VIRUS NUCLEOCAPSID; VIRUS PARTICLE; VIRUS RELEASE; CELL SURVIVAL; DRUG EFFECTS; ISOLATION AND PURIFICATION; METABOLISM; PHYSIOLOGY; PROTEIN TRANSPORT; TOXICITY; VIRUS ASSEMBLY;

ANTIVIRAL AGENTS; BENZIMIDAZOLES; CELL SURVIVAL; HEPATITIS B SURFACE ANTIGENS; HEPATITIS B VIRUS; HUMANS; PROTEIN TRANSPORT; VIRUS ASSEMBLY;

EID: 84899625639     PISSN: 01663542     EISSN: 18729096     Source Type: Journal    
DOI: 10.1016/j.antiviral.2014.04.002     Document Type: Article

References (59)

1. I. Antonini, and F. Claudi et al. Heterocyclic quinones with potential antitumor activity. 2. Synthesis and antitumor activity of some benzimidazole-4,7-dione derivatives J. Med. Chem. 31 1 1988 260 264
2. M. Asif-Ullah, and K.J. Choi et al. Identification of compounds that inhibit the interaction between core and surface protein of hepatitis B virus Antiviral Res. 70 2 2006 85 90
3. N. Awata, and H. Takahashi et al. Identification of the metabolites of an antiallergic agent, 1-(2-ethoxyethyl)-2-(hexahydro-4-methyl-1H-1,4-diazepine-1- yl)-1H-benzimidazole difumarate (KG-2413), in rats Yakugaku Zasshi 109 5 1989 318 328
4. J. Berger, and J. Hauber et al. Secreted placental alkaline phosphatase: a powerful new quantitative indicator of gene expression in eukaryotic cells Gene 66 1 1988 1 10
5. T.M. Block, and R. Jordan Iminosugars as possible broad spectrum anti hepatitis virus agents: the glucovirs and alkovirs Antivir. Chem. Chemother. 12 6 2001 317 325
6. T.M. Block, and X. Lu et al. Secretion of human hepatitis B virus is inhibited by the imino sugar N-butyldeoxynojirimycin Proc. Natl. Acad. Sci. U.S.A. 91 6 1994 2235 2239
7. T.M. Block, and X. Lu et al. Treatment of chronic hepadnavirus infection in a woodchuck animal model with an inhibitor of protein folding and trafficking Nat. Med. 4 5 1998 610 614
8. M. Bruns, and S. Miska et al. Enhancement of hepatitis B virus infection by noninfectious subviral particles J. Virol. 72 2 1998 1462 1468
9. V. Bruss A short linear sequence in the pre-S domain of the large hepatitis B virus envelope protein required for virion formation J. Virol. 71 12 1997 9350 9357
10. V. Bruss Envelopment of the hepatitis B virus nucleocapsid Virus Res. 106 2 2004 199 209
11. F.V. Chisari, and P. Filippi et al. Expression of hepatitis B virus large envelope polypeptide inhibits hepatitis B surface antigen secretion in transgenic mice J. Virol. 60 3 1986 880 887
12. F.V. Chisari, and K. Klopchin et al. Molecular pathogenesis of hepatocellular carcinoma in hepatitis B virus transgenic mice Cell 59 6 1989 1145 1156
13. P.K. Chua, and M.H. Lin et al. Potent inhibition of human Hepatitis B virus replication by a host factor Vps4 Virology 354 1 2006 1 6
14. A.M. Dougherty, and H. Guo et al. A substituted tetrahydro-tetrazolo- pyrimidine is a specific and novel inhibitor of hepatitis B virus surface antigen secretion Antimicrob. Agents Chemother. 51 12 2007 4427 4437
15. B.E. Eble, and D.R. MacRae et al. Multiple topogenic sequences determine the transmembrane orientation of the hepatitis B surface antigen Mol. Cell. Biol. 7 10 1987 3591 3601
16. B.E. Eble, and V.R. Lingappa et al. The N-terminal (pre-S2) domain of a hepatitis B virus surface glycoprotein is translocated across membranes by downstream signal sequences J. Virol. 64 3 1990 1414 1419
17. H.B. El-Nassan Synthesis, antitumor activity and SAR study of novel [1,2,4]triazino[4,5-a]benzimidazole derivatives Eur. J. Med. Chem. 53 2012 22 27
18. D. Ganem, and A.M. Prince Hepatitis B virus infection - natural history and clinical consequences N. Engl. J. Med. 350 11 2004 1118 1129
19. T. Garcia, and J. Li et al. Drastic reduction in the production of subviral particles does not impair hepatitis B virus virion secretion J. Virol. 83 21 2009 11152 11165
20. G. Griffiths, and P. Quinn et al. Dissection of the Golgi complex. I. Monensin inhibits the transport of viral membrane proteins from medial to trans Golgi cisternae in baby hamster kidney cells infected with Semliki Forest virus J. Cell Biol. 96 3 1983 835 850
21. H.S. Gunes, and G. Cosar Synthesis of some hydroxamic acid derivatives of benzimidazole and their antibacterial and antifungal activities Arzneimittelforschung 42 8 1992 1045 1048
22. N. Hiramatsu, and A. Kasai et al. Real-time detection and continuous monitoring of ER stress in vitro and in vivo by ES-TRAP: evidence for systemic, transient ER stress during endotoxemia Nucleic Acids Res. 34 13 2006 e93
23. M. Hranjec, and G. Pavlovic et al. Benzimidazole derivatives related to 2,3-acrylonitriles, benzimidazo[1,2-a]quinolines and fluorenes: synthesis, antitumor evaluation in vitro and crystal structure determination Eur. J. Med. Chem. 45 6 2010 2405 2417
24. K.L. Huang, and Y.K. Lai et al. Involvement of GRP78 in inhibition of HBV secretion by Boehmeria nivea extract in human HepG2 2.2.15 cells J. Viral Hepat. 16 5 2009 367 375
25. A.P. Huovila, and A.M. Eder et al. Hepatitis B surface antigen assembles in a post-ER, pre-Golgi compartment J. Cell Biol. 118 6 1992 1305 1320
26. K. Ito, and Y. Qin et al. Impairment of hepatitis B virus virion secretion by single-amino-acid substitutions in the small envelope protein and rescue by a novel glycosylation site J. Virol. 84 24 2010 12850 12861
27. H. Kucukbay, and R. Durmaz et al. Synthesis of some benzimidazole derivatives and their antibacterial and antifungal activities Arzneimittelforschung 51 5 2001 420 424
28. C. Lambert, and T. Doring et al. Hepatitis B virus maturation is sensitive to functional inhibition of ESCRT-III, vps4, and gamma 2-adaptin J. Virol. 81 17 2007 9050 9060
29. D. Lavanchy Worldwide epidemiology of HBV infection, disease burden, and vaccine prevention J. Clin. Virol. 34 Suppl. 1 2005 S1 S3
30. A.S. Lee The ER chaperone and signaling regulator GRP78/BiP as a monitor of endoplasmic reticulum stress Methods 35 4 2005 373 381
31. Y.F. Li, G.F. Wang, P.L. He, W.G. Huang, F.H. Zhu, H.Y. Gao, W. Tang, Y. Luo, C.L. Feng, L.P. Shi, Y.D. Ren, W. Lu, and J.P. Zuo Synthesis and anti-hepatitis B virus activity of novel benzimidazole derivatives J. Med. Chem. 49 2006 4790 4794
32. J. Li, and Y. Liu et al. Subversion of cellular autophagy machinery by hepatitis B virus for viral envelopment J. Virol. 85 13 2011 6319 6333
33. W. Lim, and S.H. Kwon et al. HBx targeting to mitochondria and ROS generation are necessary but insufficient for HBV-induced cyclooxygenase-2 expression J. Mol. Med. (Berl.) 88 4 2010 359 369
34. H. Lunsdorf, C. Gurramkonda, A. Adnan, N. Khanna, and U. Rinas Virus-like particle production with yeast: ultrastructural and immunocytochemical insights into Pichia pastoris producing high levels of the hepatitis B surface antigen Microb. Cell Fact. 10 2011 48
35. T. Miyata, and K. Kokame et al. Analysis of gene expression in homocysteine-injured vascular endothelial cells: demonstration of GRP78/BiP expression, cloning and characterization of a novel reducing agent-tunicamycin regulated gene Semin. Thromb. Hemost. 24 3 1998 285 291
36. A. Naitoh, Y. Aoyagi, and H. Asakura Highly enhanced fucosylation of serum glycoproteins in patients with hepatocellular carcinoma J. Gastroenterol. Hepatol. 14 1999 436 445
37. H. Nakano, and T. Inoue et al. Synthesis of benzimidazole derivatives as antiallergic agents with 5-lipoxygenase inhibiting action Chem. Pharm. Bull. (Tokyo) 47 11 1999 1573 1578
38. M. Nassal Hepatitis B virus replication: novel roles for virus-host interactions Intervirology 42 2-3 1999 100 116
39. M.L. Op den Brouw, and R.S. Binda et al. Hepatitis B virus surface antigen impairs myeloid dendritic cell function: a possible immune escape mechanism of hepatitis B virus Immunology 126 2 2009 280 289
40. D.G. O'Sullivan, and C.M. Ludlow Antiviral properties of 1-allyl and 1-crotyl derivatives of 2-(-hydroxybenzyl) benzimidazole Experientia 28 8 1972 889 890
41. R. Patient, and C. Hourioux et al. Hepatitis B virus subviral envelope particle morphogenesis and intracellular trafficking J. Virol. 81 8 2007 3842 3851
42. R. Prange Host factors involved in hepatitis B virus maturation, assembly, and egress Med. Microbiol. Immunol. 201 4 2012 449 461
43. J. Qiu, and B. Qin et al. Novel evidence suggests Hepatitis B virus surface proteins participate in regulation of HBV genome replication Virol. Sin. 26 2 2011 131 138
44. M. Rost, and S. Mann et al. Gamma 2-adaptin, a novel ubiquitin- interacting adaptor, and Nedd4 ubiquitin ligase control hepatitis B virus maturation J. Biol. Chem. 281 39 2006 29297 29308
45. S. Schmitt, and D. Glebe et al. Structure of pre-S2 N- and O-linked glycans in surface proteins from different genotypes of hepatitis B virus J. Gen. Virol. 85 Pt. 7 2004 2045 2053
46. M.A. Sells, and M.L. Chen et al. Production of hepatitis B virus particles in Hep G2 cells transfected with cloned hepatitis B virus DNA Proc. Natl. Acad. Sci. U.S.A. 84 4 1987 1005 1009
47. B. Serruys, and F. Van Houtte et al. Llama-derived single-domain intrabodies inhibit secretion of hepatitis B virions in mice Hepatology 49 1 2009 39 49
48. A.A. Spasov, and I.N. Yozhitsa et al. Benzimidazole derivatives: spectrum of pharmacological activity and toxicological properties Pharm. Chem. J. 33 5 1999 232 243
49. M. Tonelli, and G. Paglietti et al. Antiviral activity of benzimidazole derivatives. I. Antiviral activity of 1-substituted-2-[(benzotriazol-1/2-yl) methyl]benzimidazoles Chem. Biodivers. 5 11 2008 2386 2401
50. X.K. Tong, and H. Qiu et al. WSS45, a sulfated alpha-d-glucan, strongly interferes with Dengue 2 virus infection in vitro Acta Pharmacol. Sin. 31 5 2010 585 592
51. P. Vanlandschoot, and F. Van Houtte et al. Hepatitis B virus surface antigen suppresses the activation of monocytes through interaction with a serum protein and a monocyte-specific receptor J. Gen. Virol. 83 Pt. 6 2002 1281 1289
52. Y. Wang, and F. Cui et al. HBsAg and HBx knocked into the p21 locus causes hepatocellular carcinoma in mice Hepatology 39 2 2004 318 324
53. G.F. Wang, and L.P. Shi et al. Anti-hepatitis B virus activity of chlorogenic acid, quinic acid and caffeic acid in vivo and in vitro Antiviral Res. 83 2 2009 186 190
54. T. Watanabe, and E.M. Sorensen et al. Involvement of host cellular multivesicular body functions in hepatitis B virus budding Proc. Natl. Acad. Sci. U.S.A. 104 24 2007 10205 10210
55. C. Wu, and W. Deng et al. Amino acid substitutions at positions 122 and 145 of hepatitis B virus surface antigen (HBsAg) determine the antigenicity and immunogenicity of HBsAg and influence in vivo HBsAg clearance J. Virol. 86 8 2012 4658 4669
56. J. Wu, X.J. Zhang, K.Q. Shi, Y.P. Chen, Y.F. Ren, Y.J. Song, G. Li, Y.F. Xue, Y.X. Fang, Z.J. Deng, X. Xu, J. Gao, and K.F. Tang Hepatitis B surface antigen inhibits MICA and MICB expression via induction of cellular miRNAs in hepatocellular carcinoma cells Carcinogenesis 35 2014 155 163
57. J.C. Yang, and C.F. Teng et al. Enhanced expression of vascular endothelial growth factor-A in ground glass hepatocytes and its implication in hepatitis B virus hepatocarcinogenesis Hepatology 49 6 2009 1962 1971
58. L. Yang, L. Shi, H.J. Chen, X.K. Tong, G.F. Wang, Y.M. Zhang, W.L. Wang, C.L. Feng, P.L. He, F.H. Zhu, Y.H. Hao, B.J. Wang, D.L. Yang, W. Tang, F.J. Nan, and J.P. Zuo Isothiafludine, a novel non-nucleoside compound, inhibits hepatitis B virus replication through blocking pregenomic RNA encapsidation. Acta Pharmacol. Sin. 35 2014 410 418
59. W. Yu, and C. Goddard et al. Design, synthesis, and biological evaluation of triazolo-pyrimidine derivatives as novel inhibitors of hepatitis B virus surface antigen (HBsAg) secretion J. Med. Chem. 54 16 2011 5660 5670