DNA polymerase activity of hepatitis B virus particles: Differential inhibition by L-enantiomers of nucleotide analogs

Antiviral Research

Volumn 30, Issue 2-3, 1996, Pages 133-145

  Davis, Michelle G ^a   Wilson, Jeanne E ^a   VanDraanen, Nanine A ^a   Miller, Wayne H ^a   Freeman, George A ^a   Daluge, Susan M ^a   Boyd, Frank L ^a   Aulabaugh, Ann E ^a   Painter, George R ^a   Boone, Lawrence R ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Hepatitis B virus; L Nucleotide; Polymerase

Indexed keywords

1,3 DIMETHYL 3,4,5,6 TETRAHYDRO 2(1H) PYRIMIDONE; 2',3' DIDEOXYNUCLEOTIDE; 5 FLUORO 1 [2 (HYDROXYMETHYL) 1,3 OXATHIOLAN 5 YL]CYTOSINE TRIPHOSPHATE; 5 FLUORO 1 [2 (HYDROXYMETHYL) 1,3 OXATHYIOLAN 5 YL]CYTOSINE; ACICLOVIR; ACICLOVIR TRIPHOSPHATE; ANTIVIRUS AGENT; CARBOVIR TRIPHOSPHATE; DEOXYADENOSINE TRIPHOSPHATE; DEOXYCYTIDINE TRIPHOSPHATE; DEOXYGUANOSINE TRIPHOSPHATE; DNA POLYMERASE; GANCICLOVIR; GANCICLOVIR TRIPHOSPHATE; LAMIVUDINE; LAMIVUDINE TRIPHOSPHATE; NUCLEOTIDE DERIVATIVE; PENCICLOVIR; PENCICLOVIR TRIPHOSPHATE; RNA DIRECTED DNA POLYMERASE; STAVUDINE TRIPHOSPHATE; THYMIDINE TRIPHOSPHATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIRUS ENZYME; ZALCITABINE;

ARTICLE; CELL CULTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME SUBSTRATE; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; PHOSPHORYLATION; PRIORITY JOURNAL;

HEPATITIS B VIRUS; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0029938508     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/0166-3542(96)00938-2     Document Type: Article

References (34)

1. Choi, W.B., Wilson, L.J., Yeola, S., Liotta D.C. and Schinazi, R.F. (1991) In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of thialanyl and dioxolanyl nucleoside analogs. J. Am. Chem. Soc. 113, 9377-9379.
2. Davis, M.G. and Jansen, R.W. (1994) Inhibition of hepatitis B virus in tissue culture by alpha interferon. Antiviral Agents Chemother. 38, 2921-2924.
3. Davis, M.G., Smith, S.L., Wilson, J.E., Aulabaugh, A., Daluge, S.M., VanDraanen, N.A., Boyd, F.L., Miller, W.H. and Cullen, J.M. (1994) Inhibition of HBV polymerase by nucleotide analogs: differential activity of enantiomers. Antiviral Res. 23 (Suppl.), 125.
4. Furman, P.A., Davis, M., Liotta, D.C., Paff, M., Frick, L.W., Nelson, D.J., Dornsife, R.E., Wurster, J.A., Wilson, L.J., Fyfe, J.A., Tuttle, J.V., Miller, W.H., Condreay, L., Averett, D.R., Schinazi, R.F. and Painter, G.R. (1992) 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, 2686-2692.
5. Hager, M.W. and Liotta, D.C. (1991) Cyclization protocols for controlling the glycosidic stereochemistry of nucleosides. Application to the synthesis of the antiviral agent 3′-azido-3′-deoxythymidine (AZT). J. Am. Chem. Soc. 113, 5117-5119.
6. Hantz, O., Cova, L., Allaudeen, H.S. and Trepo, C. (1987) Main properties of duck hepatitis B virus DNA polymerase: comparison with the human and woodchuck hepatitis B virus DNA polymerases. Antiviral Res. 8, 189-199.
7. Hoong, L.K., Strange, L.E., Liotta, D.C., Kozalka, G.W., Burns, C.L. and Schinazi, R.F. (1992) Enzyme-mediated enantioselective preparation of pure enantiomers of the antiviral agent 2′,3′-dideoxy-5-fluoro-3′-thiacytidine (FTC) and related compounds. J. Org. Chem. 57, 5563-5565.
8. Hruska, J.F., Clayton, D.A., Rubenstein, J.L.R. and Robinson, W.S. (1977) Structure of hepatitis B Dane particle DNA before and after the Dane particle DNA polymerase reaction. J. Virol. 21, 666-672.
9. Kaplan, P.M., Greenman, R.L., Gerin, J.L., Purcell, R.H. and Robinson, W.S. (1973) DNA polymerase associated with human hepatitis B antigen. J. Virol. 12, 995-1005.
10. Larder, B., Purifoy, D., Powell, K. and Darby, G. (1987) Site-specific mutagenesis of AIDS virus reverse transcriptase. Nature 327, 716.
11. Littler, E., Sangar, D., Miller, W., Ellis, M., Parmer, V., Aldenton, W. and Lowe, D. (1994) Studies on the in vivo synthesis and in vitro biochemical properties of penciclovir triphosphate. Antiviral Res. 23 (Suppl.), 126.
12. Lofgren, B., Nordenfelt, E. and Oberg, B. (1989) Inhibition of RNA-and DNA-dependent duck hepatitis B virus DNA polymerase activity by nucleotiside and pyrophosphate analogs. Antiviral Res. 12, 301-310.
13. Matthes, E., Reimer, K., von Janta-Lipinski, M., Meisel, H. and Lehmann, C. (1991) Comparative inhibition of hepatitis B virus DNA polymerase and cellular DNA polymerases by triphosphates of sugar-modified 5-methyldeoxycytidines and of other nucleoside analogs. Antimicrob. Agents Chemother. 35, 1254-1257.
14. Matthes, E., von Janta-Lipinski, M., Will, H., Schroder, H.C., Merz, H., Steffen, R. and Muller, W.E.G. (1992) Inhibition of hepatitis B virus production by modified 2′-3′-dideoxythymidine and 2′-3′-dideoxy-5-methylcytidine derivatives. Biochem. Pharmacol. 43, 1571-1577.
15. McLachlan, A. (Ed.) (1991) Molecular Biology of the Hepatitis B Virus. CRC Press, Boca Raton, FL.
16. Miller, R.H., Marion, P.L. and Robinson, W.S. (1984a) Hepatitis B viral DNA-RNA hybrid molecules in particles from infected liver are converted to viral DNA molecules during an endogeneous DNA polymerase reaction. Virology 139, 64-72.
17. Miller, R.H., Tran, C.-T. and Robinson, W.S. (1984b) Hepatitis B virus particles of plasma and liver contain DNA-RNA hybrid molecules. Virology 139, 53-63.
18. Miller, W.H., Daluge, S.M., Garvey, E.P., Hopkins, S., Reardon, J.E., Boyd, F.L. and Miller, R.L. (1993) Phosphorylation of carbovir enantiomers by cellular enzymes determines the stereoselectivity of antiviral activity. J. Biol. Chem. 267, 21 220-21 224.
19. Radziwill, G., Tucker, W. and Schaller, H. (1990) Mutational analysis of the hepatitis B virus P gene product: domain structure and RNase H activity. J. Virol. 64, 613-620.
20. Reimer, K., Matthes, E., von Janta-Lipinski, M. and Meisel, H. (1991) Inhibition of hepatitis B virus DNA polymerase by thymidine triphosphate analogues in vitro. Antiviral Chem. Chemother. 2, 249-253.
21. Schinazi, R.F., Lloyd, R.M., Nguyen, M.-H., Cannon, D.L., McMillan, A., Ilksoy, N., Chu, C.K., Liotta, D.C., Bazmi, H.Z. and Mellors, J.W. (1993) Characterization of human immunodeficiency viruses resistant to oxathiolane-cytosine nucleosides. Antimicrob. Agents Chemother. 37, 875-881.
22. Schinazi, R.F., Gosselin, G., Faraj, A., Korba, B.E., Liotta, D.C., Chu, C.K., Mathe, C., Imbach, J.-L. and Sommadossi, J.-P. (1994) Pure nucleoside enantiomers of b-2′,3′-dideoxycytidine analogs are selective inhibitors of hepatitis B virus in vitro. Antimicrob. Agents Chemother. 38, 2172-2174.
23. Seeger, C., Summers, J. and Mason, W.S. (1991) Viral DNA synthesis. Curr. Top. Microbiol. Immunol. 168, 41-60.
24. Sells, M.A., Chen, M.L. and Acs, G. (1987) Production of hepatitis B virus particles in HepG2 cells transfected with cloned hepatitis B virus DNA. Proc. Natl. Acad. Sci. U.S.A. 84, 1005-1009.
25. Summers, J. and Mason, W. (1982) Replication of the genome of a hepatitis B-like virus by reverse transcription of an RNA intermediate. Cell 29, 403-415.
26. Summers, J., Smolec, J.M. and Snyder, R. (1978) A virus similar to hepatitis B virus associated with hepatitis ansd hepatoma in woodchucks. Proc. Natl. Acad. Sci. U.S.A. 75, 4533-4537.
27. Tisdale, M., Kemp, S.D., Parry, N.R. and Larder, B.A. (1993) Rapid in vitro selection of human immunodeficiency virus type 1 resistant to 3′-thiacytidine inhibitors due to a mutation in the YMDD region of reverse transcriptase. Proc. Natl. Acad. Sci. U.S.A. 90, 5653-5656.
28. Tsurimoto, T., Fujiyama, A. and Matsubara, K. (1987) Stable expression and replication of hepatitis B virus genome in an integrated state in a human hepatoma cell line transfected with the cloned viral DNA. Proc. Natl. Acad. Sci. U.S.A. 84, 444-448.
29. VanDraanen, N.A., Tucker, S.C., Boyd, F.L., Trotter, B.W. and Reardon, J.E. (1992) β-L-thymidine 5′-triphosphate analogs as DNA polymerase substrates. J. Biol. Chem. 267, 25019-25024.
30. Wang, G.-H. and Seeger, C. (1992) The reverse transcriptase of hepatitis B virus acts as a protein primer for viral DNA synthesis. Cell 71, 633-670.
31. Wang, G.-H. and Seeger, C. (1993) Novel mechanism for reverse transcription in hepatitis B viruses. J. Virol. 67, 6507-6512.
32. White, E.L., Parker, W.B., Macy, L.J., Shaddix, S.C., McCaleb, G., Secrist, J.A., Vince, R. and Shannon, W.M. (1989) Comparison of the effect of carbovir, AZT and dideoxynucleoside triphosphates on the activity of human immunodeficiency virus reverse transcriptase and selected human polymerases. Biochem. Biophys. Res. Commun. 161, 393-398.
33. Wilson, J.E., Martin, J.L., Borroto-Esoda, K., Hopkins, S., Painter, G., Liotta, D.C. and Furman, P.A. (1993) The 5′ triphosphates of the (-) and (+) enantiomers of cis-5-fluoro-12-[2-(hydroxymethyl)]-1,3-oxathiolan-5-yl]cytosine equally inhibit human immunodeficiency virus type 1 reverse transcriptase. Antiviral Agents Chemother. 37, 1720-1722.
34. Zoulim, F and Seeger, C. (1994) Reverse transcription in hepatitis B viruses is primed by a tyrosine residue of the polymerase. J. Virol. 68, 6-13.