Perspectives for the treatment of hepatitis B virus infections

International Journal of Antimicrobial Agents

Volumn 12, Issue 2, 1999, Pages 81-95

  De Clercq, Erik ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; ACICLOVIR DERIVATIVE; ADEFOVIR; ADEFOVIR DIPIVOXIL; ALPHA INTERFERON; ANTIVIRUS AGENT; ARISTEROMYCIN; CIRCULAR DNA; CYTIDINE DERIVATIVE; DNA POLYMERASE; ELVUCITABINE; ENTECAVIR; ENZYME INHIBITOR; FAMCICLOVIR; GANCICLOVIR; HEPATITIS B CORE ANTIGEN; HEPATITIS B SURFACE ANTIGEN; HEPATITIS B VACCINE; LAMIVUDINE; LOBUCAVIR; PENCICLOVIR; STAVUDINE; TRANSACTIVATOR PROTEIN; VIRUS DNA; ZALCITABINE; ZIDOVUDINE DERIVATIVE;

ANIMAL CELL; ANIMAL MODEL; CONTROLLED STUDY; DRUG DEVELOPMENT; DRUG TARGETING; DUCK; GENETIC ANALYSIS; HEPATITIS B; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; IN VITRO STUDY; LIVER CELL CARCINOMA; LIVER CELL CULTURE; LIVER CIRRHOSIS; NONHUMAN; OPEN READING FRAME; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; REVIEW; SERODIAGNOSIS; VIRUS REPLICATION; WOODCHUCK;

ACUTE DISEASE; ANIMALS; ANTI-HIV AGENTS; ANTIVIRAL AGENTS; CELL LINE; CLINICAL TRIALS; DISEASE MODELS, ANIMAL; DNA, VIRAL; DRUG RESISTANCE, MICROBIAL; DUCKS; HEPADNAVIRIDAE INFECTIONS; HEPATITIS B VIRUS; HEPATITIS B VIRUS, DUCK; HEPATITIS B VIRUS, WOODCHUCK; HEPATITIS B, CHRONIC; HEPATITIS, VIRAL, ANIMAL; HUMANS; MARMOTA; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 0033027137     PISSN: 09248579     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0924-8579(99)00060-6     Document Type: Review

References (72)

1. Dusheiko G.M. Treatment and prevention of chronic viral hepatitis. Pharmacol. Ther. 65:1995;47-73.
2. Lai C.L., Chien R.N., Leung N.W.Y. et al. A 1-year trial of lamivudine for chronic hepatitis B. N. Engl. J. Med. 339:1998;61-68.
3. Lin E., Luscombe C., Colledge D., Wang Y.Y., Locarnini S. Long-term therapy with the guanine nucleoside analog penciclovir controls chronic duck hepatitis B virus infection in vivo. Antimicrob. Agents Chemother. 42:1998;2132-2137.
4. Ganem D., Varmus H.E. The molecular biology of the hepatitis B viruses. Ann. Rev. Biochem. 56:1987;651-693.
5. Yokota T., Mochizuki S., Konno K., Mori S., Shigeta S., DeClercq E. Inhibitory effects of selected antiviral compounds on human hepatitis B virus DNA synthesis. Antimicrob. Agents Chemother. 35:1991;394-397.
6. Korba B.E., Boyd M.R. Penciclovir is a selective inhibitor of hepatitis B virus replication in cultured human hepatoblastoma cells. Antimicrob. Agents Chemother. 40:1996;1282-1284.
7. Innaimo S.F., Seifer M., Bisacchi G.S., Standring D.N., Zahler R., Colonno R.J. Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus. Antimicrob. Agents Chemother. 41:1997;1444-1448.
8. Ying C, Van Pelt J, Yap P, DeClercq E, Neyts J. Digoxigenin labelled probes for the detection of HBV-DNA in antiviral evaluation. Symposium on Emerging Therapies for Chronic Viral Hepatitis (Abstracts) Marriott Chateau Champlain Hotel, Montreal, Quebec, Canada, October 2-4, 1998.
9. Lin T.S., Luo M.Z., Liu M.C. et al. Design and synthesis of 2′,3′-dideoxy-2′,3′-dehydro-β-L-cytidine (β-L-d4C) and 2′,3′-dideoxy-2′,3′-didehydro-β-L-5-fluorocytidine (β-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human immunodeficiency virus (HIV) in vitro. J. Med. Chem. 39:1996;1757-1759.
10. Furman P.A., Davis M., Liotta D.C. et al. The anti-hepatitis B virus activities, cytotoxicities, and anabolic profiles of the (-) and (+) enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine. Antimicrob. Agents Chemother. 36:1992;2682-2692.
11. Balzarini J., Wedgwood O., Kruining J., Pelemans H., Heijtink R., De Clercq E., McGuigan C. Anti-HIV and anti-HBV activity and resistance profile of 2′,3′-dideoxy-3′-thiacytidine (3TC) and its arylphosphoramidate derivative CF 1109. Biochem. Biophys. Res. Commun. 225:1996;363-369.
12. Staschke K.A., Colacino J.M., Mabry T.E., Jones C.D. The in vitro anti-hepatitis B virus activity of FIAU [1-(2′-deoxy-2′-fluoro-1-β-D-arabinofuranosyl-5-iodo)uracil] is selective, reversible, and determined, at least in part, by the host cell. Antiviral. Res. 23:1994;45-61.
13. Pai S.B., Liu S.H., Zhu Y.L., Chu C.K., Cheng Y.C. Inhibition of hepatitis B virus by a novel L-nucleoside, 2′-fluoro-5-methyl-β-L-arabinofuranosyl uracil. Antimicrob. Agents Chemother. 40:1996;380-386.
14. Balzarini J., Kruining J., Wedgwood O. et al. Conversion of 2′,3′-dideoxyadenosine (ddA) and 2′,3′-didehydro-2′,3′-dideoxyadenosine (d4A) to their corresponding aryloxyphosphoramidate derivatives markedly potentiates their activity against human immunodeficiency virus and hepatitis B virus. FEBS. Lett. 410:1997;324-328.
15. Ma T., Lin J.S., Newton M.G., Cheng Y.C., Chu C.K. Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoro-β-L-arabinofuranosyl)purine nucleosides. J. Med. Chem. 40:1997;2750-2754.
16. Chen H., Boudinot F.D., Chu C.K., McClure H.M., Schinazi R.F. Pharmacokinetics of (-)-β-D-2-aminopurine dioxolane and (-)-β-D-2-amino-6-chloropurine dioxolane and their antiviral metabolite (-)-β-D-dioxolane guanine in rhesus monkeys. Antimicrob. Agents Chemother. 40:1996;2332-2336.
17. Yokota T., Konno K., Shigeta S., Holý A., Balzarini J., DeClercq E. Inhibitory effects of acyclic nucleoside phosphonate analogues on hepatitis B virus DNA synthesis in HB611 cells. Antiviral. Chem. Chemother. 5:1994;57-63.
18. Heijtink R.A., Kruining J., de Wilde G.A., Balzarini J., DeClercq E., Schalm S.W. Inhibitory effects of acyclic nucleoside phosphonates on human hepatitis B virus and duck hepatitis B virus infections in tissue culture. Antimicrob. Agents Chemother. 38:1994;2180-2182.
19. Heijtink R.A., deWilde G.A., Kruining J. et al. Inhibitory effect of 9-(2-phosphonylmethoxyethyl)adenine (PMEA) on human and duck hepatitis B virus infection. Antiviral. Res. 21:1993;141-153.
20. Yokota T., Konno K., Chonan E. et al. Comparative activities of several nucleoside analogs against duck hepatitis B virus in vitro. Antimicrob. Agents Chemother. 34:1990;1326-1330.
21. Wang G.H., Seeger C. The reverse transcriptase of hepatitis B virus acts as a protein primer for viral DNA synthesis. Cell. 71:1992;663-670.
22. Shaw T., Mok S.S., Locarnini S.A. Inhibition of hepatitis B virus DNA polymerase by enantiomers of penciclovir triphosphate and metabolic basis for selective inhibition of HBV replication by penciclovir. Hepatology. 24:1996;996-1002.
23. Liu S.H., Grove K.L., Cheng Y.C. Unique metabolism of a novel antiviral L-nucleoside analog, 2′-fluoro-5-methyl-β-L-arabinofuranosyluracil: a substrate for both thymidine kinase and deoxycytidine kinase. Antimicrob. Agents Chemother. 42:1998;833-839.
24. Severini A., Liu X.Y., Wilson J.S., Tyrrell D.L.J. Mechanism of inhibition of duck hepatitis B virus polymerase by (-)-β-L-2′,3′-dideoxy-3′-thiacytidine. Antimicrob. Agents Chemother. 39:1995;1430-1435.
25. Kukhanova M., Li X., Chen S.H. et al. Interaction of β-L-2′,3′-dideoxy-2′,3′-didehydro-5-fluoro-CTP with human immunodeficiency virus-1 reverse transcriptase and human DNA polymerases: implications for human immunodeficiency virus drug design. Mol. Pharmacol. 53:1998;801-807.
26. Kukhanova M., Lin Z.Y., Yas'co M., Cheng Y.C. Unique inhibitory effect of 1-(2′-deoxy-2′-fluoro-β-L-arabinofuranosyl)-5-methyluracil 5′-triphosphate on Epstein-Barr virus and human DNA polymerases. Biochem. Pharmacol. 55:1998;1181-1187.
27. Zhu Y.L., Dutschman G.E., Liu S.H., Bridges E.G., Cheng Y.C. Anti-hepatitis B virus activity and metabolism of 2′,3′-dideoxy-2′,3′-didehydro-β-L(-)-5- fluorocytidine. Antimicrob. Agents Chemother. 42:1998;1805-1810.
28. Balzarini J., Navé J.F., Becker M.A., Tatibana M., DeClercq E. Kinetic properties of adenine nucleotide analogues against purified 5-phosphoribosyl-1-pyrophosphate synthetases from E. coli, rat liver and human erythrocytes. Nucleosides Nucleotides. 14:1995;1861-1871.
29. Merta A., Votruba I., Jindrich J. et al. Phosphorylation of 9-(2-phosphonomethoxyethyl)adenine and 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)-adenine by AMP(dAMP) kinase from L1210 cells. Biochem. Pharmacol. 44:1992;2067-2077.
30. Naesens L., Snoeck R., Andrei G., Balzarini J., Neyts J., DeClercq E. HPMPC (cidofovir), PMEA (adefovir) and related acyclic nucleoside phosphonate analogues: a review of their pharmacology and clinical potential in the treatment of viral infections. Antiviral. Chem. Chemother. 8:1997;1-23.
31. Kramata P., Votruba I., Otova B., Holý A. Different inhibitory potencies of acyclic phosphonomethoxyalkyl nucleotide analogs towards DNA polymerases alpha, delta and epsilon. Mol. Pharmacol. 49:1996;1005-1011.
32. Cihlar T., Chen M.S. Incorporation of selected nucleoside phosphonates and anti-human immunodeficiency virus nucleotide analogues into DNA by human DNA polymerases α, β and γ Antiviral. Chem. Chemother. 8:1997;187-195.
33. Tsiquaye K.N., Sutton D., Maung M., Boyd M.R. Antiviral activities and pharmacokinetics of penciclovir and famciclovir in Pekin ducks chronically infected with duck hepatitis B virus. Antiviral. Chem. Chemother. 7:1996;153-159.
34. Lin E., Luscombe C., Wang Y.Y., Shaw T., Locarnini S. The guanine nucleoside analog penciclovir is active against chronic duck hepatitis B virus infection in vivo. Antimicrob. Agents Chemother. 40:1996;413-418.
35. Zoulim F., Dannaoui E., Borel C. et al. 2′,3′-Dideoxy-β-L-5-fluorocytidine inhibits duck hepatitis B virus reverse transcription and suppresses viral DNA synthesis in hepatocytes, both in vitro and in vivo. Antimicrob. Agents Chemother. 40:1996;448-453.
36. Aguesse-Germon S., Liu S.H., Chevallier M. et al. Inhibitory effect of 2′-fluoro-5-methyl-β-L-arabinofuranosyluracil on duck hepatitis B virus replication. Antimicrob. Agents Chemother. 42:1998;369-376.
37. Cullen J.M., Smith S.L., Davis M.G. et al. In vivo antiviral activity and pharmacokinetics of (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine in woodchuck hepatitis virus-infected woodchucks. Antimicrob. Agents Chemother. 41:1997;2076-2082.
38. Mason W.S., Cullen J., Moraleda G. et al. Lamivudine therapy of WHV-infected woodchucks. Virology. 245:1998;18-32.
39. Korba BE, Peek SF, Toshkov IA et al. Treatment with lamivudine (3TC, 3′-thiacytidine) delays development of hepatocellular carcinoma (HCC) in woodchucks chronically infected with woodchuck hepatitis B virus (WHV). Abstracts of the 38th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego, CA, September 24-27, 1998, Abstract no. H-54.
40. Boker K.H., Ringe K., Kruger M., Pichlmayr R., Manns M.P. Prostaglancin E plus famciclovir - a new concept for the treatment of severe hepatitis B after liver transplantation. Transplantation. 57:1994;1706-1708.
41. Kruger M., Tillmann H.L., Trautwein C. et al. Famciclovir treatment of hepatitis B virus recurrence after liver transplantation: a pilot study. Liver. Transpl. Surg. 2:1996;253-262.
42. Main J., Brown J.L., Howells C. et al. A double blind, placebo-controlled study to assess the effect of famciclovir on virus replication in patients with chronic hepatitis B virus infection. J. Viral. Hepatitis. 3:1996;211-215.
43. Singh N., Gayowski T., Wannstedt C.F., Wagener M.M., Marino I.R. Pretransplant famciclovir as prophylaxis for hepatitis B virus recurrence after liver transplantation. Transplantation. 63:1997;1415-1419.
44. Krüger M., Böker K.H.W., Zeidler H., Manns M.P. Treatment of hepatitis B-related polyarteritis nodosa with famciclovir and interferon α-2b. J. Hepatol. 26:1997;935-939.
45. Milich D.R., Jones J.E., Hughes J.L., Price J., Raney A.K., McLachlan A. Is a function of the secreted hepatitis B e antigen to induce immunologic tolerance in utero? Proc. Natl. Acad. Sci. USA. 87:1990;6599-6603.
46. Deeks S.G., Collier A., Lalezari J. et al. The safety and efficacy of adefovir dipivoxil, a novel anti-human immunodeficiency virus (HIV) therapy, in HIV-infected adults: a randomized, double-blind, placebo-controlled trial. J. Infect. Dis. 176:1997;1517-1523.
47. Barditch-Crovo P., Toole J., Hendrix C.W. et al. Anti-human immunodeficiency virus (HIV) activity, safety, and pharmacokinetics of adefovir dipivoxyl (9-[2-bis-pivaloyloxymethyl)phosphonylmethoxyethyl]adenine) in HIV-infected patients. J. Infect. Dis. 176:1997;406-413.
48. Gilson RJ, Chopra K, Murray-Lyon I, et al. Adefovir dipivoxil (Bis-POM PMEA) treatment for chronic hepatitis B infection: a placebo-controlled phase I/II study. 36th Annual Meeting of the American Society for Microbiology, New Orleans, LO, September 15-18, 1996, Late Breakers, p. 7, no. LB1.
49. Jeffers L, Heathcote E, Wright T et al. A phase II dose-ranging, placebo-controlled trial of adefovir dipivoxil for the treatment of chronic hepatitis B virus infection. Abstracts of the Eleventh International Conference on Antiviral Research, San Diego, California, April 5-10, 1998, Late Breakers, p. 9, no. 197.
50. Ling R., Mutimer D., Ahmed M. et al. Selection of mutations in the hepatitis B virus polymerase during therapy of transplant recipients with lamivudine. Hepatology. 24:1996;711-713.
51. Tipples G.A., Ma M.M., Fischer K.P., Bain V.G., Kneteman N.M., Tyrrell D.L. Mutation in HBV RNA-dependent DNA polymerase confers resistance to lamivudine in vivo. Hepatology. 24:1996;714-717.
52. Bartholomew M.M., Jansen R.W., Jeffers L.J. et al. Hepatitis-B-virus resistance to lamivudine given for recurrent infection after orthotopic liver transplantation. Lancet. 349:1997;20-22.
53. Honkoop P., Niesters H.G., deMan R.A., Osterhaus A.D., Schalm S.W. Lamivudine resistance in immunocompetent chronic hepatitis B. Incidence and patterns. J. Hepatol. 26:1997;1393-1395.
54. Fischer K.P., Tyrrell D.L.J. Generation of duck hepatitis B virus polymerase mutants through site-directed mutagenesis which demonstrate resistance to lamivudine [(-)-β-L-2′,3′-dideoxy-3′-thiacytidine] in vitro. Antimicrob. Agents Chemother. 40:1996;1957-1960.
55. Fu L., Cheng Y.C. Role of additional mutations outside the YMDD motif of hepatitis B virus polymerase in L(-)SddC (3TC) resistance. Biochem. Pharmacol. 55:1998;1567-1572.
56. Niesters H.G.M., Honkoop P., Haagsma E.B. et al. Identification of more than one mutation in the hepatitis B virus polymerase gene arising during prolonged lamivudine treatment. J. Infect. Dis. 177:1998;1382-1385.
57. Ladner S.K., Miller T.J., King R.W. The M539V polymerase variant of human hepatitis B virus demonstrates resistance to 2′-deoxy-3′-thiacytidine and a reduced ability to synthesize viral DNA. Antimicrob. Agents Chemother. 42:1998;2128-2131.
58. Ladner S.K., Miller T.J., Otto M.J., King R.W. The hepatitis B virus M539V polymerase variation responsible for 3TC resistance also confers cross-resistance to other nucleoside analogues. Antiviral. Chem. Chemother. 9:1998;65-72.
59. Aye T.T., Bartholomeusz A., Shaw T. et al. Hepatitis B virus polymerase mutations during antiviral therapy in a patient following liver transplantation. J. Hepatol. 26:1997;1148-1153.
60. Mulato A.S., Lamy P.D., Miller M.D. et al. Genotypic and phenotypic characterization of human immunodeficiency virus type 1 variants isolated from AIDS patients after prolonged adefovir dipivoxil therapy. Antimicrob. Agents Chemother. 42:1998;1620-1628.
61. Naesens L., Bischofberger N., Augustijns P. et al. Antiretroviral efficacy and pharmacokinetics of oral bis(isopropyloxycarbonyloxymethyl)-9-(2-phosphonylmethoxy-propyl)adenine in mice. Antimicrob. Agents Chemother. 42:1998;1568-1573.
62. Robbins B.L., Srinivas R.V., Kim C., Bischofberger N., Fridland A. Anti-human immunodeficiency virus activity and cellular metabolism of a potential prodrug of the acyclic nucleoside phosphonate 9-R-(2-phosphonomethoxypropyl)adenine (PMPA), bis(isopropyloxymethylcarbonyl)PMPA. Antimicrob. Agents Chemother. 42:1998;612-617.
63. Tsai C.C., Follis K.E., Sabo A. et al. Prevention of SIV infection in macaques by (R)-9-(2-phosphonylmethoxypropyl)adenine. Science. 270:1995;1197-1199.
64. Van Rompay K.K.A., Marthas M.L., Lifson J.D. et al. Administration of 9-[2-(phosphonomethoxy)propyl]adenine (PMPA) for prevention of perinatal simian immunodeficiency virus infection in rhesus macaques. AIDS. Res. Hum. Retrovir. 14:1998;761-772.
65. Van Rompay KKA, Berardi CJ, Aguirre NL, et al. Two doses of PMPA protect newborn macaques against oral simian immunodeficiency virus infection. AIDS 1998;12: F79-F83.
66. Havlir D.V., Richman D.D. Viral dynamics of HIV: implications for drug development and therapeutic strategies. Ann. Intern. Med. 124:1996;984-994.
67. Shaw T, Colledge D, Locarnini SA. Synergistic inhibition of in vitro hepadnaviral replication by PMEA and penciclovir or lamivudine. Abstracts of the Tenth International Conference on Antiviral Research, Atlanta, Georgia, April 6-11, 1997, Abstract no. 33, p. A51.
68. Zembower D.E., Lin Y.M., Flavin M.T., Chen F.C., Korba B.E. Robustaflavone, a potential non-nucleoside anti-hepatitis B agent. Antiviral. Res. 39:1998;81-88.
69. Dutschman G.E., Bridges E.G., Liu S.H. et al. Metabolism of 2′,3′-dideoxy-2′,3′-didehydro-β-L-(-)-5- fluorocytidine and its activity in combination with clinically approved anti-human immunodeficiency virus β-D(+) nucleoside analogs in vitro. Antimicrob. Agents Chemother. 42:1998;1799-1804.
70. Colledge D., Locarnini S., Shaw T. Synergistic inhibition of hepadnaviral replication by lamivudine in combination with penciclovir in vitro. Hepatology. 26:1997;216-225.
71. Xiong X, Flores C, Yang H, Toole JJ, Gibbs CS. Mutations in hepatitis B DNA polymerase associated with resistance to lamivudine do not confer resistance to adefovir in vitro. Hepatology 1998;27 (in press).
72. Block T.M., Lu X., Mehta A.S. et al. Treatment of chronic hepadnavirus infection in a woodchuck animal model with an inhibitor of protein folding and trafficking. Nat. Med. 4:1998;610-614.