Inhibition of hepatitis B virus by a novel L-nucleoside, 2′-fluoro-5-methyl-β-L-arabinofuranosyl uracil

Antimicrobial Agents and Chemotherapy

Volumn 40, Issue 2, 1996, Pages 380-386

  Pai, S Balakrishna ^a   Liu, Shwu Huey ^a   Zhu, Yong Lian ^a   Chu, Chung K ^b   Cheng, Yung Chi ^a  

^a YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CLEVUDINE; DNA POLYMERASE; LACTIC ACID; MITOCHONDRIAL DNA; NUCLEOSIDE; VIRUS DNA;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DNA SYNTHESIS INHIBITION; DOSE RESPONSE; DRUG CYTOTOXICITY; DRUG METABOLISM; ENANTIOMER; HEPATITIS B VIRUS; HEPATOMA CELL; HUMAN; HUMAN CELL; PRIORITY JOURNAL; VIRUS INHIBITION;

ANTIVIRAL AGENTS; ARABINOFURANOSYLURACIL; CELL DIVISION; CELL LINE; DNA REPLICATION; DNA, VIRAL; DNA-DIRECTED DNA POLYMERASE; HEPATITIS B CORE ANTIGENS; HEPATITIS B SURFACE ANTIGENS; HEPATITIS B VIRUS; HUMANS; LACTIC ACID; STEREOISOMERISM; TRANSCRIPTION, GENETIC; VIRUS REPLICATION;

EID: 0030045732     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.40.2.380     Document Type: Article

References (33)

1. Ayoola, E. A., M. S. Balayan, F. Deinhart, I. Gust, A. W. Kureshi, J. E. Maynard, N. C. Nayak, D. W. Brodley, M. Ferguson, J. Melnick, R. H. Purcell, and A. J. Zuckerman. 1988. Progress in the control of viral hepatitis: memorandum from a WHO meeting. Bull. W H. O 66:443-455.
2. Beasley, R. P., L. Y. Hwang, C. C. Lin, and C. S. Chien. 1981. Hepatocellular carcinoma and hepatitis B virus. A retrospective study of 22,707 men in Taiwan. Lancet ii:1129-1133
3. Chang, C.-N., S.-L. Doong, J. H. Zhou, J. W. Beach, L. S. Jeong, C. K. Chu, C.-H. Tsai, and Y.-C. Cheng. 1992. Deoxycytidine deaminase-resistant stereoisomer is the active form of (±)-2′,3′-dideoxy-3′-thiacytidine in the inhibition of hepatitis B virus replication. J Biol. Chem 267:13938-13942.
4. Chang, C.-N., V. Skalaski, J. H. Zhou, and Y.-C. Cheng. 1992 Biochemical pharmacology of (+)- and (-)-2′-3′-dideoxy-3′-thiacytidine as anti-hepatitis B virus agents. J. Biol. Chem. 267:22414-22420.
5. Chen, C.-H., and Y.-C. Cheng. 1989. Delayed cytotoxicity and selective loss of mitochondrial DNA in cells treated with the anti-human immunodeficiency virus compound 2′-3′-dideoxycytidine J. Biol. Chem. 264:11934-11937.
6. Cheng, Y.-C., S. P. Grill, G. E. Dutschman, K. Nakayama, and K. F. Bastow. 1983. Metabolism of 9-(1,3-dihydroxy-2-propoxymethyl)guaninine, a new anti-herpes virus compound, in herpes simplex virus-infected cells. J. Biol. Chem. 258:12460-12464.
7. Chirgwin, J. M., A. K. Przybyla, R. J. MacDonald, and W. J. Rutter. 1979. Isolation of biologically active ribonucleic acid from sources enriched in ribonuclease. Biochemistry 18:5294.
8. Chu, C. K., T. Ma, K. Shanmuganathan, C. Wang, Y. Xiang, S. B. Pai, G.-Q. Yao, J.-P. Sommadossi, and Y.-C. Cheng. 1995. Use of 2′-fluoro-5-methyl-β-L-arabinofuranosyl uracil as a novel antiviral agent for hepatitis B virus and Epstein-Barr virus Antimicrob. Agents Chemother. 39:979-981.
9. Colcacino, J. M., S. K. Malcolm, and S. R. Jaskunas. 1994. Effect of fialuridine on replication of mitochondrial DNA in CEM cells and in human hepatoblastoma cells in culture. Antimicrob. Agents Chemother. 38:1997-2002
10. Cui, L., S. Yoon, R. F. Schinazi, and J.-P. Sommadossi. 1995. Cellular and molecular events leading to mitochondrial toxicity of 1-(2-deoxy-2-fluoro-1-beta-D-arabinofuranosyl)-5-iodouracil in human liver cells. J. Clin. Invest. 95:555-563.
11. Di Bisceglie, A. M., V. K. Rustgi, J. H. Hoofnagle, G. M. Dusheik, and M. T. Lotze. 1988. Hepatocellular carcinoma. Ann. Intern. Med. 108:390-401.
12. Doong, S.-L., C.-H. Tsai, R. F. Schinazi, D. C. Liotta, and Y.-C. Cheng. 1991. Inhibition of the replication of hepatitis B virus in vitro by 2′-3′-dideoxy-3′-thiacytidine and related analogs. Proc. Natl. Acad. Sci USA 88:8495-8499.
13. Fried, M. W., A. M. Di Bisceglie, S. E. Straus, B. Savarese, M. P. Bearnes, and J. H. Hoofnagle. 1992 FIAU, a new oral anti-viral agent, profoundly inhibits HBV DNA in patients with chronic hepatitis B. Hepatology 16:127A.
14. Gosselin, G., R. F. Schinazi, J.-P. Sommadossi, C. Mathe, M.-C. Bergogne, A. M. Auberlin, A. Kim, and J. L. Imbach. 1994. Anti-human immunodeficiency virus activities of the β-L-enantiomer of 2′,3′-dideoxycytidine and its 5-fluoro derivative in vitro. Antimicrob Agents Chemother. 28:1292-1297.
15. Kamali, F. 1993 Clinical pharmacology of zidovudine and other 2′,3′-dideoxynucleoside analogues. Clin Invest. 71:392-405.
16. Kim, H. O., K. Shanmuganathan, A. J. Alves, L. S. Jeong, J. W. Beach, R. F. Schinazi, C. N. Chang, Y.-C. Cheng, and C. K. Chu. 1992. Potent anti-HIV and anti-HBV activities of (-)-L-β-dioxolane-C and (+)-L-β-dioxolane-T and their asymmetric synthesis Tetrahedron Lett. 33:6899-6902.
17. Larder, B. A., B. Chesebro, and D. D. Richman. 1990. Susceptibilities of zidovudine-susceplible and -resistant human immunodeficiency virus isolates to antiviral agents determined by using a quantitative plaque reduction assay. Antimicrob. Agents Chemother. 34:436-441.
18. Lewis, W., R. R. Meyer, J. F. Simpson, J. M. Colcacino, and F. W. Perrino. 1994. Mammalian DNA polymerases α, β, γ, δ, and ε incorporate Fialuridine (FIAU) monophosphate into DNA and are inhibited competitively by FIAU triphosphate Biochemistry 33:14620-14624.
19. Lin, T.-S., X. Guo, M. Z. Luo, M.-C. Liu, Y.-L. Zhu, G. E. Dutschman, S. B. Pai, M. M. Li, and Y.-C. Cheng. 1995. Studies of the pharmacokinetics and toxicology of 2′,3′-dideoxy-β-L-5-fluorocytidine (β-L-FddC) and 2′,3′-dideoxy-β-L-5-azacytidine. Nucleosides Nucleotides 14:619-623
20. Lin, T. S., M. Z. Luo, M. C. Liu, S. B. Pai, G. E. Dutschman, and Y.-C. Cheng. 1994. Antiviral activity of 2′,3′-dideoxy-beta-L-5-fluorocytidine (beta-L-FddC) and 2′,3′-dideoxy-beta-L cytidine (beta-L-ddC) against hepatitis B virus and human immunodeficiency virus type 1 in vitro. Biochem. Pharmacol. 47:171-174.
21. Lin, T.-S., M. Z. Luo, M. C. Liu, S. B. Pai, G. E. Dutschman, and Y.-C. Cheng. 1994. Synthesis and biological evaluation of 2′,3′-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and human hepatitis B virus (HBV). J Med Chem. 37:798-803
22. Matthes, E., P. Langen, M. von Janata-Lipinski, H. Will, H. C. Schroder, H. Merz, B. E. Weiler, and W. E. G. Muller. 1990. Potent inhibition of hepatitis B virus production in vitro by modified pyrimidine nucleosides. Antimicrob. Agents Chemother 34:1986-1990
23. Matthes, E., K. Reimer, M. Von Janata-Lipinski, H. Meisel, and C. Lehmann. 1991. Comparative inhibition of hepatitis B virus DNA polymerase and cellular DNA polymerase by triphosphate of sugar-modified 5-methyl deoxycytidine and other modified nucleoside analogs. Antimicrob Agents Chemother. 35:1254-1257.
24. Meisel, H., K. Reimer, M. von Janata-Lipinski, D. Barwolf, and E. Matthes. 1990. Inhibition of hepatitis B virus DNA polymerase by 3′-fluorothymidine triphosphate and other modified nucleotide triphosphate analogs J Med. Virol. 30:137-141
25. Parker, W. B., and Y.-C. Cheng. 1994 Mitochondrial toxicity of antiviral nucleoside analogs J NIH Res. 6:57-61.
26. Price, P. M., R. Banerjee, and G. Acs. 1989. Inhibition of the replication of hepatitis B virus by the carboxylic analogue of 2′-deoxyguanosine. Proc Natl. Acad. Sci USA 86:8541-8544.
27. Ruth, J. L., and Y.-C. Cheng. 1981. Nucleoside analogues with clinical potential in antivirus chemotherapy. The effect of several thymidine and 2′-deoxcytidine analogue 5′-triphosphates on purified human (alpha, beta) and herpes simplex virus (types 1, 2) DNA polymerases Mol. Pharmacol. 20:415-422.
28. Sachs, M. K. 1992. Antiretroviral chemotherapy of human immunodeficiency virus infections other than with azidothymidine. Arch Intern. Med. 152:485-502
29. Sambrook, J., E. F. Fritsch, and T. Maniatis. 1989. Molecular cloning: a laboratory manual, 2nd ed. Cold Spring Harbor Laboratory, Cold Spring Harbor, N.Y.
30. Schinazi, R. F., G. Gosselin, A. Faraj, B. E. Korba, D. C. Liotta, C. K. Chu, C. Mathe, J. L. Imbach, and J. P. Sommadossi. 1994. Pure nucleoside enantiomers of beta-2′,3′-dideoxycytidine analogs are selective inhibitors of hepatitis B virus in vitro. Antimicrob. Agents Chemother. 38:2172-2174
31. Sells, M. A., M. L. Chen, and G. Acs. 1987. Production of hepatitis B virus particles in Hep G2 cells transformed with cloned hepatitis B virus DNA. Proc. Natl Acad. Sci. USA 84:1005-1009.
32. Yao, G.-Q., S.-H. Liu, E. Chou, M. Kukhanova, C. K. Chu, and Y.-C. Cheng. Inhibition of Epstein-Barr virus replication by a novel L-nucleoside, 2′-fluoro-5-methyl-β-L-arabinofuranosyl uracil Submitted for publication.
33. Yarchoan, R., J. M. Pluda, C. F. Perno, H. Mitsuya, R. V. Thomas, K. M. Wyvill, and S. Broder. 1990. Initial clinical experience with dideoxynucleotides as single agents and in combination therapy. Ann. N. Y. Acad. Sci. 616:328-343.