Inhibition of hepatitis B virus replication by nucleoside enantiomers of β-2',3'-dideoxypurine analogues

Antiviral Chemistry and Chemotherapy

Volumn 7, Issue 5, 1996, Pages 276-280

  El Alaoui, A M ^a   Faraj, A ^a   Pierra, C ^b   Boudou, V ^b   Johnson, R ^b   Mathe C ^b   Gosselin, G ^b   Korba, B E ^c   Imbach, J L ^b   Schinazi, R F ^d,e   Sommadossi, J P ^a  

^a University of Alabama at Birmingham   (United States)

^b CNRS   (France)

^c GEORGETOWN UNIVERSITY   (United States)

^d ATLANTA VA MEDICAL CENTER   (United States)

^e EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

L nucleosides; Hepatitis B virus; Purines

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; ANTIVIRUS AGENT; LAMIVUDINE; PURINE DERIVATIVE; VIRUS DNA;

ANTIVIRAL ACTIVITY; ARTICLE; CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENANTIOMER; GENETIC TRANSFECTION; HEPATITIS B VIRUS; HEPATOBLASTOMA; HUMAN; HUMAN CELL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION;

EID: 9544241432     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Ayoola, E.A., Balayan, M.S., Deinhardt, F., Gust, I., Kureshi, A.W., Maynard, J.E., Nayak, N.C., Brodley, D.W., Ferguson, M., Melnick, J., Purcell, R.H., and Zuckerman, A.J. (1988) Progress in the control of viral hepatitis: Memorandum from a WHO meeting. Bull World Health Org 66: 443-455.
2. Beasley, R.P., Hwang, L.-Y., Lin, C.-C., and Chien, C.-S. (1981) Hepatocellular carcinoma and hepatitis B virus. Lancet ii: 1129-1133.
3. Coates, J.A.V., Cammack, N., Jenkinson, H.J., Jowett, A.J., Jowett, M.I., Pearson, B.A., Penn, C.R., Rouse, P.L., Viner, K.C., and Cameron, J.M. (1992) (-)-2′-Deoxy-3′-thiacytidine is a potent, highly selective inhibitor of human immunodeficiency virus type 1 and type 2 replication in vitro. Antimicrob Agents Chemother 36: 733-739.
4. Davis, G.L., and Hoofnagle, J.H. (1986) Interferon in viral hepatitis: role in pathogenesis and treatment. Hepatol 6: 1038-1041.
5. van Draanen, N.A., Tisdale, M., Parry, N.R., Jansen, R., Dornsife, R.E., Tuttle, J.V., Averett, D.R., and Kozalka, G.W. (1994) Influence of stereochemistry on antiviral activities and resistance profiles of dideoxycytidine nucleosides. Antimicrob Agents Chemother 38: 868-871.
6. Faraj, A., Fowler, D.A., Brides, E.G., and Sommadossi, J.-P. (1994) Effects of 2′,3′-dideoxynucleosides on proliferation and differentiation of human pluripotent progenitors in liquid culture and their effects on mitochondrial DNA synthesis. Antimicrob Agents Chemother 38: 924-930.
7. Furman, P.A., Davis, M., Liotta, D.C., Paff, M., Frick, L.W., Nelson, D.J., Dornsif, 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-fiuoro-1-[2-(hydroxymethyl)-1,3-oxithiolan-5-yl]-cytosine (FTC). Antimicrob Agents Chemother 36: 2686-2692.
8. Furman, P.A., Wilson, J.E., Reardon, J.E., and Painter, G.R. (1995) The effect of absolute configuration on the anti-HIV and anti-HBV activity of nucleoside analogues. Antiviral Chem Chemother 6(6): 345-355.
9. Gosselin, G., Schinazi, R.F., Sommadossi, J.-P., Mathé, C., Bergogne, M.-C., Aubertin, A.M., Kim, A., and Imbach, J.-L. (1994a) Anti-human immunodeficiency virus activities of the J-L enantiomer of 2′,3′-dideoxycytidine and its 5-fluoro derivative in vitro. Antimicrob Agents Chemother 38: 1292-1297.
10. Gosselin, G., Mathe, C., Bergogne, M.-C., Aubertin, A.-M., Kirn, A., Schinazi, R.F., Sommadossi, J.-P., and Imbach, J.-L. (1994b) Enantiomeric 2′3′dideoxycytidine derivatives are potent human immunodeficiency virus inhibitors in cell cultures. C R Acad Sci Ser III 317: 85-89.
11. Hoofnagle, J.H., Hanson, R.G., Minuk, G.Y., Pappas, S.C., Schafer, D.F., Dusheiko, G.M., Staus, S.E., Popper, H., and Jones, E.A. (1984) Randomized controlled trial of adenine arabinoside monophosphate for chronic type B hepatitis. Gastroenterol 86: 150-157.
12. Johnson, M.A., Ahluwalia, G., Connelly, M.C., Cooney, D.A., Broder, S., Johns, D.G., and Fridland, A. (1988) Metabolic pathways for the activation of the antiretroviral agent 2′,3′-dideoxyadenosine in human lymphoid cells. J Biol Chem 263: 15354-15357.
13. Kassianides, C., Hoofnagle, J.H., Miller, R.H., Doo, E., Ford, H., Broder, S., and Mitsuya, H. (1989) Inhibition of duck hepatitis B virus replication by 2′,3′-dideoxycytidine. A potent inhibitor of reverse transcriptase. Gastroenterol 97: 1275-1280.
14. Korba, B.E., and Gerin, J.L. (1992) Use of standarized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication. Antiviral Res 19: 55-70.
15. Koszalka, G.W., Bums, C.L., St Clair, M., Frick, L.W., Lambe, C.U., Paff, M.T., Nelson, D.J., Korba, B., Ayers, K., and Krenitsky, T.A. (1995) Inhibition of HIV- and HBV-virus replication by 2,6-disubstituted purine 2′,3′-dideoxynucleosides. Antiviral Res 26(3): A228.
16. Lee, B., Luo, W., Suzuki, S., Robins, M.J., and Tyrrell, D.L.J. (1989) In vitro and in vivo comparison of the abilities of purine and pyrimidine 2′,3′-dideoxynucleosides to inhibit duck hepadnavirus. Antimicrob Agents and Chemother 33: 336-339.
17. Lin, T.-S., Luo, M.-Z., Liu, M.-C., Pai, S.B., Dutschman, G.E., and Cheng, Y.-C. (1994) Antiviral activity of 2′,3′-dideoxy-β-L-5-fluorocytidine (β-L-FddC) and 2′,3′-dideoxy-β-L-cytidine (β-L-ddC) against hepatitis B virus and human immunodeficiency virus type 1 in vitro. Biochem Pharmacol 47: 171-174.
18. Un, T.-S., Luo, M.-Z., Zhu, J.L., Liu, M.-C., Zhu, Y.-L., Dutschman, G.E., and Cheng, Y.-C. (1995) Synthesis of a series of purine 2′,3′-dideoxy-L-nucleoside analogues as potential antiviral agents. Nucleosides & Nucleotides 14: 1759-1783.
19. Mansour, T.S., Tse, A., and Charron, M. (1995) Anti-HIV and anti-HBV activities of L-2′,3′-dideoxynucleoside analogues: ddC, 5FddC, 5-azaddC and ddG. Med Chem Res 5: 417-425.
20. Parker, W.B., and Cheng, Y.-C. (1994) Mitochondrial toxicity of antiviral nucteoside analogues. The Journal of NIH Research 6: 57-61.
21. Perillo, R.P. (1989) Interferon therapy for chronic type B hepatitis: the promise comes of age. Gastroenterol 96: 532-536.
22. Schinazi, R.F., McMillan, A., Cannon, D., Mathis, R., Lioyd, R.M., Peck, A., Sommadossi, J.-P., St Clair, M., Wilson, J., Furman, P.A., Painter, G., Choi, W.-B., and Liotta, D.C. (1992) Selective inhibition of human immunodeficiency virus by racemates and enantiomer of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine. Antimicrob Agents Chemother 36: 2423-2431.
23. Schinazi, R.F., Gosselin, G., Faraj, A., Korba, B.E., Liotta, D.C., Chu, C.K., Mathé, C., Imbach, J.-L., and Sommadossi, J.-P. (1994) Pure nucleoside enantiomers of β-2′,3′-dideoxycytidine analogues are selective inhibitors of hepatitis B in vitro. Antimicrob Agents Chemother 38: 2172-2174.
24. Sommadossi, J.-P. (1994) Treatment of hepatitis B by nucleoside analogs: still a reality. Current Opinion in Infectious Diseases. 7: 678-682.
25. Staschke, K.A., Clacino, J.M., Mabry, T.E., and Jones, C.D. (1994) The in vitro anti-hepatitis B virus activity of FIAU [1-2′-deoxy-2′-fluoro-′-D-arabinofuranosyl)-5-iodouracil] is selective, reversible and determined, at least in part, by the host cell. Antiviral Res 23: 45-61.
26. Summers, J., and Mason, W.S. (1982) Replication of the genome of a hepatitis B-like virus by reverse transcription of an RNA intermediate. Cell 29: 403-415.
27. Suzuki, S., Lee, B., Luo, W., Tovell, D., Robins, M.J., and Tyrrell, D L.J. (1988) Inhibition of duck hepatitis B virus replication by purine 2′,3′-dideoxynucleosides. Biochem Biophys Res Comm 156: 1144-1151.
28. Yarchoan, R., Perno, C.F., Thomas, R.V., Klecker, R.W., Allain, J.-P., Wills, R.J., McAtee, N., Fischl, M.A., Dubinsky, R., McNealy, M.C., Mitsuya, H., Pluda, J.M., Lawley, T.J., Leuther, M., Safai, B., Collins, J.M., Myers, C.E., and Broder, S. (1988) Phase I studies of 2′,3′-dideoxycytidine in severe human immunodeficiency virus infection as a single agent and alternating with zidovudine (AZT). Lancet i, 76-81.