Inhibition of hepatitis B virus DNA polymerase by enantiomers of penciclovir triphosphate and metabolic basis for selective inhibition of HBV replication by penciclovir

Hepatology

Volumn 24, Issue 5, 1996, Pages 996-1002

  Shaw, Tim ^a   Mok, Su San ^a,b   Locarnini, Stephen A ^a  

^a FAIRFIELD HOSPITAL   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; DEOXYGUANOSINE TRIPHOSPHATE; DNA POLYMERASE; FAMCICLOVIR; GANCICLOVIR; PENCICLOVIR; RNA DIRECTED DNA POLYMERASE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; DRUG METABOLISM; ENANTIOMER; ENZYME INHIBITION; HEPATITIS B VIRUS; HERPES SIMPLEX VIRUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; PHOSPHORYLATION; PRIORITY JOURNAL; VIRUS CORE; VIRUS REPLICATION;

EID: 16044369181     PISSN: 02709139     EISSN: None     Source Type: Journal    
DOI: 10.1053/jhep.1996.v24.pm0008903366     Document Type: Article

References (47)

1. Ayoola EA, Balayan MS, Deinhardt F, Gust I, Kureshi AW, Maynard JE, Nayak NC, et al. Progress in the control of viral hepatitis: memorandum from a WHO meeting. Bull World Health Organ 1988;66:443-455.
2. Shaw T, Locarnini S. Hepatic purine and pyrimidine metabolism: implications for antiviral chemotherapy in viral hepatitis. Liver 1995;15:169-184.
3. Sommadossi J-P. Treatment of hepatitis B by nucleoside analogs: still a reality. Curr Opin Infect Dis 1994;7:678-682.
4. Summers J, Mason WS. Replication of the genome of a hepatitis B-like virus by reverse transcription of an RNA intermediate. Cell 1982;29:403-415.
5. Ganem D, Pollack JR, Tavis J. Hepatitis B virus reverse transcriptase and its many roles in hepadnaviral genome replication. Infect Agents Dis 1994;3:85-93.
6. Zoulim F, Dannaoui E, Trepo C. Inhibitory effect of penciclovir on the priming of hepadnavirus reverse transcription. Abstracts of the 35th Interscience conference on antimicrobial agents and chemotherapy [Abstract]. 1995:182A.
7. Wang G-H, Seeger C. The reverse transcriptase of hepatitis B virus acts as a protein primer for viral DNA synthesis. Cell 1992;71:663-670.
8. Doong S-L, Tsai C-H, Schinazi RF, Liotta DC, Cheng Y-C. Inhibition of the replication of hepatitis B virus in vitro by 2′,3′-dideoxy-3′-thiacytidine and related analogues. Proc Natl Acad Sci U S A 1991;88:8495-8499.
9. Dienstag JL, Perrillo RP, Schiff ER, Bartholomew M, Vicary C, Rubin M. A preliminary trial of lamivudine for chronic hepatitis B infection. New Engl J Med 1995;333:1657-1661.
10. Fourel I, Hantz O, Cova L, Allaudeen HS, Trepo C. Main properties of duck hepatitis B virus DNA polymerase: comparison with the human and woodchuck hepatitis B virus DNA polymerases. Antiviral Res 1987;8:189-199.
11. Aoki-Sei S, O'Brien MC, Ford H, Fujii H, Gilbert DA, Cooney DA, Johns DG, et al. In vitro inhibition of hepatitis B virus replication by 2′,3′-dideoxyguanosine, 2′,3′-dideoxyinosine, and 3′-azido-2′,3′-dideoxythymidine in 2.2.15 (PR) cells. J Infect Dis 1991;164:843-851.
12. Howe AY, Robins MJ, Wilson JS, Tyrrell DLJ. Selective inhibition of the reverse transcriptase of duck hepatitis B virus by binding of 2′,3′-dideoxyguanosine-5′-triphosphate to the viral polymerase. HEPATOLOGY 1996;23: 87-96.
13. Locarnini SA, Guo K, Lucas CR, Gust ID. Inhibition of HBV DNA replication by ganciclovir in patients with AIDS. Lancet 1989;2:1225-1226.
14. Wang Y, Bowden S, Shaw T, Civitico G, Chan Y, Qiao M, Locarnini S. Inhibition of duck hepatitis B virus replication in vivo by the nucleoside analogue ganciclovir (9-[2-hydroxy-1-(hydroxymethyl) ethoxymethyl] guanine. Antiviral Chem Chemotherapy 1991;2:107-114.
15. Luscombe C, Pedersen J, Bowden S, Locarnini S. Alterations in intrahepatic expression of duck hepatitis B viral markers with ganciclovir therapy. Liver 1994;14:182-192.
16. MacMillan JS, Shaw T, Angus PW, Locarnini S. Effect of immunosuppressive and antiviral agents on hepatitis B virus replication in vitro. HEPATOLOGY 1995;22:36-43.
17. Gish RG, Lau JYN, Brooks L, Fang JWS, Steady SL, Imperial JC, Garcia-Kennedy R, et al. Ganciclovir treatment of hepatitis B virus infection in liver transplant recipients. HEPATOLOGY 1996;23:1-7.
18. Shaw T, Amor P, Civitico G, Boyd M, Locarnini S. In vitro antiviral activity of penciclovir, a novel purine nucleoside, against duck hepatitis B virus. Antimicrob Agents Chemotherapy 1994;38:719-723.
19. Tsiquaye KN, Slomka MJ, Muang M. Oral famciclovir against hepatitis B virus replication in hepatic and nonhepatic tissues of ducklings infected in ovo. J Med Virol 1994;42:306-310.
20. Lin E, Luscombe C, Wang YY, Shaw T, Locarnini S. The guanine nucleoside analogue penciclovir is active against chronic duck hepatitis B virus infection in vivo. Antimicrob Agents Chemotherapy 1995;40:413-418.
21. Korba BE, Boyd MR. Penciclovir is a selective inhibitor of hepatitis B virus replication in cultured human hepatoblastoma cells. Antimicrobial Agents Chemotherapy 1996;40:1282-1284.
22. Tsiquaye K, Sutton D, Maung M, Boyd M. Antiviral activities and pharmacokinetics of penciclovir and famciclovir in Pekin ducks chronically infected with duck hepatitis B virus. Antiviral Chem Chemotherapy 1996; 7:153-159.
23. Mason WS, Cullen J, Saputelli J, Wu TT, Liu C, London WT, Lustbader E, et al. Characterization of the antiviral effects of 2′-carbodeoxyguanosine in ducks chronically infected with duck hepatitis B virus. HEPATOLOGY 1995;22:36-43.
24. Price PM, Banerjee R, Jeffrey AM, Acs G. The mechanism of inhibition of hepatitis B virus replication by the carbocyclic analog of 2′-deoxyguanosine. HEPATOLOGY 1992;16:8-12.
25. Hannah J, Tolman RL, Karkas JD, Liou R, Perry HC, Field AK. Carbaacyclonucleoside antiherpetic agents. Journal of Heterocyclic Chemistry 1989;2:1261-1271.
26. Ilsley DD, Lee S-H, Miller WH, Kuchta RD. Acyclic guanosine analogs inhibit DNA polymerases α, δ and ∈ with very different potencies and have unique mechanisms of action. Biochemistry 1995;34:2504-2510.
27. Lowe DM, Alderton WK, Ellis MR, Palmer V, Miller WH, Roberts GB, Fyfe JA, et al. Mode of action of (R)-9-[4-hydroxy-2-(hydroxymethyl)butyl]-guanine against herpesviruses. Antimicrob Agents Chemotherapy 1995; 39:1802-1808.
28. Earnshaw DL, Bacon TH, Darlison SJ, Edmonds K, Perkins RM, Vere Hodge A. Mode of action of penciclovir in MRC-5 cells infected with herpes simplex virus type 1 (HSV-1), HSV-2 and varicella-zoster virus. Antimicrob Agents Chemotherapy 1992;26:2747-2757.
29. 13C NMR to determine the specificity and absolute configuration of penciclovir phosphate esters formed in HSV-1 and HSV-2 infected cells and by HSV-1 encoded thymidine kinase. Chirality 1993;5:583-588.
30. Vere Hodge RA. Famciclovir and penciclovir. The mode of action of famciclovir including its conversion to penciclovir. Antiviral Chem Chemotherapy 1993;4:67-84.
31. Schinazi RF, Juodawlkis AS, Lloyd RM Jr, Lesnikowski J. Differential inhibition of viral polymerases by enantiomers of penciclovir triphosphate. Abstracts of the 35th Interscience conference on antimicrobial agents and chemotherapy [Abstract 104]. Amer Soc Microbiol 1995:123A.
32. Delarue M, Poch O, Tordo N, Moras D, Argos P. An attempt to unify the structure of polymerases. Protein Eng 1990;3:461-467.
33. Heringa J, Argos P. Evolution of viruses as recorded by the polymerase sequences. In: Morse SS, ed. The evolutionary biology of viruses. New York, 1994:87-103.
34. Mok SS, Shaw T, Locarnini S. Preferential inhibition of human hepatitis B virus (HBV) DNA polymerase by the (R)-enantiomer of penciclovir triphosphate. Abstracts of the 35th Interscience conference on antimicrobial agents and chemotherapy [Abstract 66]. Amer Soc Microbiol 1995:191A.
35. Shaw T, Mok SS, Locarnini S. Penciclovir metabolism in human hepatoblastoma cells and preferential inhibition of human hepatitis B virus (HBV) DNA polymerase by the (R)-enantiomer of penciclovir triphosphate [Abstract 50]. Hawaii, 1995.
36. Sells MA, Chen M, Acs G. Production of hepatitis B virus particles in HepG2 cells transfected with cloned hepatitis B virus DNA. Proc Natl Acad Sci U S A 1987;84:1005-1009.
37. Vere Hodge R, Perkins RM. Mode of action of 9-(4-hydroxy-3-hydroxymethyl-but-1-yl)guanine (BRL 39123) against herpes simplex virus in MRC-5 cells. Antimicrob Agents Chemother 1989;33:223-229.
38. Fautz R, Husein B, Hechenberger C. Application of the neutral red assay (NR assay) to monolayer cultures of primary hepatocytes: rapid colorimetric viability determination for the unscheduled DNA synthesis test (UDS). Mutat Res 1991:173-179.
39. Eriksson S, Arner E, Spasokoukotskaja T, Wang L, Karlsson A, Brosjo O, Gunven P, et al. Properties and levels of deoxynucleoside kinases in normal and tumor cells; implications for chemotherapy. Adv Enzyme Regul 1994; 34:13-25.
40. Smee DF. Interaction of 9-(1,3-dihydroxy-2-propoxymethyl)guanine with cytosol and mitochondrial deoxyguanosine kinases:possible role in anticytomegalovirus activity. Mol Cell Biochem 1985;69:75-81.
41. Wang L, Karlsson A, Arner ESJ, Eriksson S. Substrate specificity of mitochondrial 2′-deoxyguanosine kinase. Efficient phosphorylation of 2-chloroadenosine. J Biol Chem 1993;268:22847-22852.
42. Brass CA, Mody MG. Evaluation of purine nucleoside phosphorylase release as a measure of hepatic endothelial cell injury. HEPATOLOGY 1995; 21:174-179.
43. Tuttle J, Krenitsky TA. Effects of acyclovir and its metabolites on purine nucleoside phosphorylase. J Biol Chem 1984;259:4065-4069.
44. Marr CLP, Penn CR. Stability of carbovir, a potent inhibitor of HIV, to phosphorolysis by human purine nucleoside phosphorylase. Antiviral Chem Chemother 1992;3:121-124.
45. Reichard P. Interactions between deoxyribonucleotide and DNA synthesis. Annu Rev Biochem 1988;57:349-374.
46. Cirelli R, Herne H, McCrary M, Lee P, Tyring SK. Famciclovir: review of clinical efficacy and safety. Antiviral Res 1996;29:141-151.
47. Martin JL, Brown CE, Matthews-Davis N, Reardon JE. Effects of antiviral nucleoside analogs on human DNA polymerases and mitochondrial DNA synthesis. Antimicrob Agents Chemother 1994;38:2743-2749.