Hepatitis B virus replication is blocked by a 2-hydroxyisoquinoline-1,3(2H, 4H)-dione (HID) inhibitor of the viral ribonuclease H activity

Antiviral Research

Volumn 108, Issue 1, 2014, Pages 48-55

  Cai, Catherine W ^a   Lomonosova, Elena ^a,b   Moran, Eileen A ^a   Cheng, Xiaohong ^a   Patel, Kunjan B ^a   Bailly, Fabrice ^c   Cotelle, Philippe ^c   Meyers, Marvin J ^d   Tavis, John E ^a,b  

^a SAINT LOUIS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Saint Louis University   (United States)

^c UNIV LILLE   (France)

^d SAINT LOUIS UNIVERSITY   (United States)

Author keywords

2 Hydroxyisoquinoline 13(2H,4H) diones; Hepatitis B virus; Ribonuclease H; Viral replication

Indexed keywords

6325462; ANTIVIRUS AGENT; CHEMBRIDGE 6325462; CICLOPIROX; COMPLEMENTARY DNA; ESTERASE INHIBITOR; LABOTEST 12243782; LABOTEST 72543251; MB 1; MB 103; MB 104; MB 105; MB 106; MB 2; MB 3; MB 4; MB 71; MB 88; RIBONUCLEASE H; SIGMA 130672; SIGMA H 53704; SIGMA PH 008969; TCI AMERICA H 1040; TRC 939800; UNCLASSIFIED DRUG; VIRUS DNA; VIRUS ENZYME; VIRUS RNA; VS 42; VS 45; VS 51; VS 55; 2-HYDROXYISOQUINOLINE-1,3(2H,4H)-DIONE; ISOQUINOLINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DNA STRAND; DNA SYNTHESIS INHIBITION; DRUG CYTOTOXICITY; DRUG SCREENING; ENZYME ACTIVITY; HEPATITIS B VIRUS; HUMAN; IC 50; NONHUMAN; PRIORITY JOURNAL; RNA CLEAVAGE; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION; ANTAGONISTS AND INHIBITORS; CELL LINE; CHEMICAL STRUCTURE; DRUG EFFECTS; ENZYMOLOGY; IC50; MICROBIAL SENSITIVITY TEST; PHYSIOLOGY;

ANTIVIRAL AGENTS; CELL LINE; HEPATITIS B VIRUS; HUMANS; INHIBITORY CONCENTRATION 50; ISOQUINOLINES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; RIBONUCLEASE H; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 84902117159     PISSN: 01663542     EISSN: 18729096     Source Type: Journal    
DOI: 10.1016/j.antiviral.2014.05.007     Document Type: Article

References (34)

1. M. Billamboz, F. Bailly, M.L. Barreca, L.L. De, J.F. Mouscadet, C. Calmels, M.L. Andreola, M. Witvrouw, F. Christ, Z. Debyser, and P. Cotelle Design, synthesis, and biological evaluation of a series of 2- hydroxyisoquinoline-1,3(2H,4H)-diones as dual inhibitors of human immunodeficiency virus type 1 integrase and the reverse transcriptase RNase H domain J. Med. Chem. 51 2008 7717 7730
2. M. Billamboz, F. Bailly, C. Lion, C. Calmels, M.L. Andreola, M. Witvrouw, F. Christ, Z. Debyser, L. De Luca, A. Chimirri, and P. Cotelle 2-hydroxyisoquinoline-1,3(2H,4H)-diones as inhibitors of HIV-1 integrase and reverse transcriptase RNase H domain: influence of the alkylation of position 4 Eur. J. Med. Chem. 46 2011 535 546
3. M. Billamboz, F. Bailly, C. Lion, N. Touati, H. Vezin, C. Calmels, M.L. Andreola, F. Christ, Z. Debyser, and P. Cotelle Magnesium chelating 2-hydroxyisoquinoline-1,3(2H,4H)-diones, as inhibitors of HIV-1 integrase and/or the HIV-1 reverse transcriptase ribonuclease H domain: discovery of a novel selective inhibitor of the ribonuclease H function J. Med. Chem. 54 2011 1812 1824
4. M. Billamboz, V. Suchaud, F. Bailly, C. Lion, J. Demeulemeester, C. Calmels, M.L. Andreola, F. Christ, Z. Debyser, and P. Cotelle 4-Substituted 2-hydroxyisoquinoline-1,3(2H,4H)-diones, as a novel class of HIV-1 integrase inhibitors ACS. Med. Chem. Lett. 4 2013 606 611
5. T.M. Block, R. Gish, H. Guo, A. Mehta, A. Cuconati, W. Thomas London, and J.T. Guo Chronic hepatitis B: what should be the goal for new therapies? Antiviral Res. 98 2013 27 34
6. M. Buti, M. Brosa, M.A. Casado, M. Rueda, and R. Esteban Modeling the cost-effectiveness of different oral antiviral therapies in patients with chronic hepatitis B J. Hepatol. 51 2009 640 646
7. Y. Chen, W.S. Robinson, and P.L. Marion Selected mutations of the duck hepatitis B virus P gene RNase H domain affect both RNA packaging and priming of minus-strand DNA synthesis J. Virol. 68 1994 5232 5238
8. B.A. Desimmie, J. Demeulemeester, V. Suchaud, O. Taltynov, M. Billamboz, C. Lion, F. Bailly, S.V. Strelkov, Z. Debyser, P. Cotelle, and F. Christ 2-Hydroxyisoquinoline-1,3(2H,4H)-diones (HIDs), novel inhibitors of HIV integrase with a high barrier to resistance ACS Chem. Biol. 8 2013 1187 1194
9. D. Ganem, and A.M. Prince Hepatitis B virus infection-natural history and clinical consequences N. Engl. J. Med. 350 2004 1118 1129
10. W.H. Gerlich Medical virology of hepatitis B: how it began and where we are now Virol. J. 10 2013 239
11. M. Ghany, and T.J. Liang Drug targets and molecular mechanisms of drug resistance in chronic hepatitis B Gastroenterology 132 2007 1574 1585
12. R.G. Gish, T.T. Chang, C.L. Lai, R. de Man, A. Gadano, F. Poordad, J. Yang, H. Brett-Smith, and R. Tamez Loss of HBsAg antigen during treatment with entecavir or lamivudine in nucleoside-naive HBeAg-positive patients with chronic hepatitis B J. Viral Hepat. 17 2010 16 22
13. H. Guo, D. Jiang, T. Zhou, A. Cuconati, T.M. Block, and J.T. Guo Characterization of the intracellular deproteinized relaxed circular DNA of hepatitis B virus: an intermediate of covalently closed circular DNA formation J. Virol. 81 2007 12472 12484
14. J.Q. Hang, S. Rajendran, Y. Yang, Y. Li, P.W. In, H. Overton, K.E. Parkes, N. Cammack, J.A. Martin, and K. Klumpp Activity of the isolated HIV RNase H domain and specific inhibition by N-hydroxyimides Biochem. Biophys. Res. Commun. 317 2004 321 329
15. Y. Hu, X. Cheng, F. Cao, A. Huang, and J.E. Tavis Beta-thujaplicinol inhibits hepatitis B virus replication by blocking the viral ribonuclease H activity Antiviral Res. 99 2013 221 229
16. T. Ilina, K. Labarge, S.G. Sarafianos, R. Ishima, and M.A. Parniak Inhibitors of HIV-1 reverse transcriptase-associated ribonuclease H activity Biology 1 2012 521 541
17. K. Klumpp, J.Q. Hang, S. Rajendran, Y. Yang, A. Derosier, K.I. Wong, H. Overton, K.E. Parkes, N. Cammack, and J.A. Martin Two-metal ion mechanism of RNA cleavage by HIV RNase H and mechanism-based design of selective HIV RNase H inhibitors Nucleic Acids Res. 31 2003 6852 6859
18. K. Klumpp, and T. Mirzadegan Recent progress in the design of small molecule inhibitors of HIV RNase H Curr. Pharm. Des. 12 2006 1909 1922
19. H. Kwon, and A.S. Lok Hepatitis B therapy Nat. Rev. Gastroenterol. Hepatol. 8 2011 275 284
20. P. Marcellin, E.J. Heathcote, M. Buti, E. Gane, R.A. De Man, Z. Krastev, G. Germanidis, S.S. Lee, R. Flisiak, K. Kaita, M. Manns, I. Kotzev, K. Tchernev, P. Buggisch, F. Weilert, O.O. Kurdas, M.L. Shiffman, H. Trinh, M.K. Washington, J. Sorbel, J. Anderson, A. Snow-Lampart, E. Mondou, J. Quinn, and F. Rousseau Tenofovir disoproxil fumarate versus adefovir dipivoxil for chronic hepatitis B N. Engl. J. Med. 359 2008 2442 2455
21. K.E. Parkes, P. Ermert, J. Fassler, J. Ives, J.A. Martin, J.H. Merrett, D. Obrecht, G. Williams, and K. Klumpp Use of a pharmacophore model to discover a new class of influenza endonuclease inhibitors J. Med. Chem. 46 2003 1153 1164
22. T. Shaw, A. Bartholomeusz, and S. Locarnini HBV drug resistance. mechanisms, detection and interpretation J. Hepatol. 44 2006 593 606
23. M.F. Sorrell, E.A. Belongia, J. Costa, I.F. Gareen, J.L. Grem, J.M. Inadomi, E.R. Kern, J.A. McHugh, G.M. Petersen, M.F. Rein, D.B. Strader, and H.T. Trotter National Institutes Of Health Consensus Development Conference Statement: management of hepatitis B Ann. Intern. Med. 150 2009 104 110
24. V. Suchaud, F. Bailly, C. Lion, C. Calmels, M.L. Andreola, F. Christ, Z. Debyser, and P. Cotelle Investigation of a novel series of 2- hydroxyisoquinoline-1,3-(2H,4H)-diones as human immunodeficiency virus type 1 integrase inhibitors J. Med. Chem. 2014 http://dx.doi.org/10.1021/jm500109z
25. J.E. Tavis, and M.P. Badtke Hepadnaviral genomic replication C.E. Cameron, M. Götte, K.D. Raney, Viral Genome Replication 2009 Springer Science+Business Media LLC, New York 129 143
26. J.E. Tavis, X. Cheng, Y. Hu, M. Totten, F. Cao, E. Michailidis, R. Aurora, M.J. Meyers, E.J. Jacobsen, M.A. Parniak, and S.G. Sarafianos The hepatitis B virus ribonuclease H is sensitive to inhibitors of the human immunodeficiency virus ribonuclease H and integrase enzymes PLoS Pathog. 9 2013 e1003125
27. J.E. Tavis, A.J. Gehring, and Y. Hu How further suppression of virus replication could improve current HBV treatment Expert Rev. Anti Infect. Ther. 11 2013 755 757
28. M. Toy Cost-effectiveness of viral hepatitis B & C treatment Best Pract. Res. Clin. Gastroenterol. 27 2013 973 985
29. E. Tramontano, and R. Di Santo HIV-1 RT-associated RNase H function inhibitors: recent advances in drug development Curr. Med. Chem. 17 2010 2837 2853
30. F. van Bommel, R.A. De Man, H. Wedemeyer, K. Deterding, J. Petersen, P. Buggisch, A. Erhardt, D. Huppe, K. Stein, J. Trojan, C. Sarrazin, W.O. Bocher, U. Spengler, H.E. Wasmuth, J.G. Reinders, B. Moller, P. Rhode, H.H. Feucht, B. Wiedenmann, and T. Berg Long-term efficacy of tenofovir monotherapy for hepatitis B virus-monoinfected patients after failure of nucleoside/nucleotide analogues Hepatology 51 2010 73 80
31. G. Woo, G. Tomlinson, Y. Nishikawa, M. Kowgier, M. Sherman, D.K. Wong, B. Pham, W.J. Ungar, T.R. Einarson, E.J. Heathcote, and M. Krahn Tenofovir and entecavir are the most effective antiviral agents for chronic hepatitis B: a systematic review and Bayesian meta-analyses Gastroenterology 139 2010 1218 1229
32. K. Wursthorn, M. Jung, A. Riva, Z.D. Goodman, P. Lopez, W. Bao, M.P. Manns, H. Wedemeyer, and N.V. Naoumov Kinetics of hepatitis B surface antigen decline during 3 years of telbivudine treatment in hepatitis B e antigen-positive patients Hepatology 52 2010 1611 1620
33. F. Yu, X. Liu, P. Zhan, and E. De Clercq Recent advances in the research of HIV-1 RNase H inhibitors Mini Rev. Med. Chem. 8 2008 1243 1251
34. F. Zoulim, and S. Locarnini Hepatitis B virus resistance to nucleos(t)ide analogues Gastroenterology 137 2009 1593 1608