Antiviral activities of oral 1-O-hexadecylpropanediol-3-phosphoacyclovir and acyclovir in woodchucks with chronic woodchuck hepatitis virus infection

Antimicrobial Agents and Chemotherapy

Volumn 44, Issue 7, 2000, Pages 1964-1969

  Hostetler, Karl Y ^a,b   Beadle, James R ^a,b   Hornbuckle, William E ^c   Bellezza, Christine A ^c   Tochkov, Ilia A ^c   Cote, Paul J ^d   Gerin, John L ^d   Korba, Brent E ^d   Tennant, Bud C ^c  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b VA SAN DIEGO HEALTHCARE SYSTEM   (United States)

^c Department of Obstetrics Gynecology   (United States)

^d GEORGETOWN UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 O HEXADACYLPROPANEDIOL 3 PHOSPHOACYCLOVIR; ACICLOVIR; ACICLOVIR DERIVATIVE; UNCLASSIFIED DRUG; VIRUS DNA;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIBIOTIC THERAPY; ANTIVIRAL ACTIVITY; ARTICLE; CHRONIC HEPATITIS; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFICACY; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATITIS B VIRUS; HEPATITIS VIRUS; LIVER CELL; NONHUMAN; PRIORITY JOURNAL; TREATMENT OUTCOME; VIRUS HEPATITIS; VIRUS INHIBITION; VIRUS LOAD; VIRUS REPLICATION; WOODCHUCK;

ACYCLOVIR; ADMINISTRATION, ORAL; ANIMALS; ANTIVIRAL AGENTS; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; HEPATITIS B; HEPATITIS B VIRUS, WOODCHUCK; MALE; MARMOTA; TREATMENT OUTCOME;

EID: 0033917391     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.44.7.1964-1969.2000     Document Type: Article

References (31)

1. Alexander, G. J. M., E. A. Fagan, J. E. Hegarty, N. Rolando, P. Guarner, A. L. W. F. Eddleston, and R. Williams. 1986. A controlled trial of acyclovir in stable chronic HBsAg, HBeAg-positive carriers. J. Hepatol. 3(Suppl. 2): S123-S127.
2. Beadle, J. R., G. D. Kini, K. A. Aldern, M. F. Gardner, K. N. Wright, R. J. Ryback, and E. R. Kern. Synthesis and antiviral evaluation of 1-O-hexadecylpropanediol-3-P-acyclovir: efficacy against HSV-1 infection in mice. Nucleosides Nucleotides 19:471-479.
3. Berk, L., S. W. Schalm, R. A. de Man, R. A. Heytink, P. Berthelot, C. Brechot, B. Boboc, F. Degos, P. Marcellin, J. P. Benhamou, G. Hess, S. Rossol, K.-H. M. zum Büschenfelde, A. F. M. Chamuleau, P. L. M. Jansen, H. W. Reesink, B. Meyer, C. Beglinger, G. A. Stalder, J. W. den Ouden-Muller, and M. J. deJong. 1992. Failure of acyclovir to enhance the antiviral effect of α-lymphoblastoid interferon on HBe-seroconversion in chronic hepatitis B. A multi-centre randomized controlled trial. J. Hepatol. 14:305-309.
4. Berk, L., S. W. Schalm, and R. A. Heijtink. 1992. Zidovudine inhibits hepatitis B virus replication. Antivir. Res. 19:111-118.
5. Cullen, J. M., S. L. Smith, M. G. Davis, S. E. Dunn, C. Botteron, A. Cecchi, D. Linsey, D. Linzey, L. Frick, M. T. Paff, A. Goulding, and K. Biron. 1997. 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. 41:2076-2082.
6. Derse, D., Y.-C. Cheng, P. A. Furman, M. H. St. Clair, and G. B. Elion. 1981. Inhibition of purified human and herpes simplex virus-induced DNA polymerases by 9-(2-hydroxyethoxymethyl)guanine triphosphate. Effects on primer-template function. J. Biol. Chem. 256:11447-11451.
7. Elion, G. B., P. A. Furman, J. A. Fyfe, P. de Miranda, L. Beauchamp, and H. J. Schaeffer. 1977. Selectivity of action of an antiherpetic agent. 9-(2-hydroxyethoxymethyl)guanine. Proc. Natl. Acad. Sci. USA 74:5716-5720.
8. Fourel, I., O. Hantz, K. A. Watanabe, C. Jacquet, B. Chomel, J. J. Fox, and C. Trepo. 1990. Inhibitory effects of 2′-fluorinated arabinusyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks. Antimicrob. Agents Chemother. 34:473-475.
9. Fyfe, J. A., P. M. Keller, P. A. Furman, R. L. Miller, and G. B. Elion. 1978. Thymidine kinase from herpes simplex virus phosphorylates the new antiviral compound, 9-(2-hydroxyethoxymethyl)guanine. J. Biol. Chem. 253:8721-8727.
10. Genovesi, E. V., L. Lamb, I. Medina, D. Taylor, M. Seifer, S. Innalmo, R. J. Colonno, D. N. Standring, and J. M. Clark. 1998. Efficacy of the carbocyclic 2′-deoxyguanosine nucleoside BMS-200475 in the woodchuck model of hepatitis B virus infection. Antimicrob. Agents Chemother. 42:3209-3217.
11. Gerin, J. L. 1990. Experimental WHV infection of woodchucks: an animal model of hepadnavirus-induced liver cancer. Gastroenterol. Jpn. 25(Suppl.): 38-42.
12. Gilson, R. J., A. E. Hawkins, G. K. Kelly, S. K. Gill, and I. V. Weller. 1991. No effect of zidovudine on hepatitis B virus replication in homosexual men with symptomatic HIV-1 infection. AIDS 5:217-220.
13. Hantz, O., H. S. Allaudeen, T. Ooka, E. De Clercq, and C. Trepo. 1984. Inhibition of human and woodchuck hepatitis virus DNA polymerase by the triphosphates of acyclovir, 1-(2′-deoxy-2′-fluoro-β-D-arabinofuranosyl)-5-iodocytosine and E-5-(2-bromovinyl)-2′-deoxyuridine. Antivir. Res. 4:187-199.
14. Hantz, O., C. Perigaud, C. Borel, C. Jamard, F. Zoulim, C. Trepo, J.-L. Imbach, and G. Gosselin. 1999. The SATE pronucleotide approach applied to acyclovir. Part II. Effects of bis(SATE)phosphotriester derivatives of acyclovir on duck hepatitis B virus replication in vitro and in vivo. Antivir. Res. 40:179-187.
15. Hostetler, K. Y., J. R. Beadle, G. D. Kini, M. F. Gardner, K. N. Wright, T.-H. Wu, and B. A. Korba. 1997. Enhanced oral absorption and antiviral activity of 1-O-octadecyl-sn-glycero-3-phospho-acyclovir in hepatitis B virus infection, in vitro. Biochem. Pharmacol. 53:1815-1822.
16. Ilsley, D. D., S.-H. Lee, W. H. Miller, and R. D. Kuchta. 1995 Acyclic guanosine analogs inhibit DNA polymerases α, δ, ε with very different potencies and have unique mechanisms of action. Biochemistry 34:2504-2510.
17. Janssen, H. L., L. Berk, R. A. Heijtink, F. J. ten Kate, and S. W. Schalm. 1993. Interferon-α and zidovudine combination therapy for chronic hepatitis B: results of a randomized, placebo-controlled trial. Hepatology 17:383-388.
18. Kini, G. D., J. R. Beadle, K. A. Aldern, D. D. Richman, B. E. Korba, and K. Y. Hostetler. 1998. Anti-hepatilis B virus activity of 3-hexadecyloxypropane-1-phospho-penciclovir and 3-hexadecyloxypropane-1-phospho-dideoxyguanosine in 2.2.15 cells. Antivir. Res. 37:A65. (Abstract 92.)
19. Korba, B. A., H. Xie, K. N. Wright, W. E. Hombuckle, J. L. Gerin, B. C. Tennant, and K. Y. Hostetler. 1996. Liver-targeted antiviral nucleosides: enhanced antiviral activity of phosphatidyl-dideoxyguanosine versus dideoxyguanosine in woodchuck hepatitis virus infection in vivo. Hepatology 23: 958-963.
20. Korba, B. E., P. J. Cote, W. E. Hornbuckle, B. C. Tennant, and J. L. Gerin. 2000. Treatment of chronic WHV infection in the Eastern woodchuck (M. monax) with nucleoside analogs as a model for therapy of chronic hepatitis virus B infection in man. Hepatology 31:1165-1175.
21. Mason, W. S., J. Cullen, G. Moraleda, J. Saputelli, C. E. Aldrich, D. S. Miller, B. Tennant, L. Firck, D. Averett, L. D. Condreay, and A. R. Jilbert. 1998. Lamuvidine therapy of WHV-infected woodchucks. Virology 245:18-32.
22. Miller, W. H., and R. L. Miller. 1982. Phosphorylation of acyclovir diphosphate by cellular enzymes. Biochem. Pharmacol. 31:3879-3884.
23. Nilsson, A., and B. Borgstrom. 1967. Absorption and metabolism of lecithin and lysolecithin by intestinal slices. Biochim. Biophys. Acta 137:240-254.
24. Perigaud, C., G. Gosselin, J.-L. Girardet, B. E. Korba, and J.-L. Imbach. 1999. The S-acyl-2-thioethyl pronucleotide approach applied to acyclovir. Part I. Synthesis and in vitro anti-hepatitis B virus activity of bis(S-acyl-2-thioethyl)phosphotriester derivatives of acyclovir. Antivir. Res. 40:167-178.
25. Reardon, J. E. 1989. Herpes simplex virus type 1 and human DNA polymerase interactions with 2′-deoxyguanosine 5′-triphosphate analogues. Kinetics of incorporation into DNA and induction of inhibition. J. Biol. Chem. 264: 19039-19044.
26. Reardon, J. E., and T. Spector. 1989. Herpes simplex virus type 1 DNA polymerase. Mechanism of inhibition by acyclovir triphosphate. J. Biol. Chem. 264:7405-7411.
27. Schaeffer, H. J., L. Beauchamp, P. de Miranda, G. B. Elion, D. J. Bauer, and P. Collins. 1978. 9-(2-Hydroxyethoxymethyl)guanine activity against viruses of the herpes group. Nature 272:583-585.
28. Scow, R. O., Y. Stein, and O. Stein. 1967. Incorporation of dietary lecithin and lysolecithin into lymph chylomicrons in the rat. J. Biol. Chem. 242:4919-4924.
29. Shaw, T., S. S. Mok, and S. A. Locarnini. 1996. Inhibition of hepatitis B virus DNA polymerase by enantiomers of penciclovir triphosphate and metabolic basis selective inhibition of HBV replication by penciclovir. Hepatology 24:996-1002.
30. St. Clair, M. H., W. H. Miller, R. L. Miller, C. U. Lambe, and P. A. Furman. 1984. Inhibition of cellular α-DNA polymerase and herpes simplex virus-induced DNA polymerases by the triphosphate of BW759U. Antimicrob. Agents Chemother. 25:191-194.
31. Tennant, B. C., B. H. Baldwin, L. A. Graham, M. A. Ascenzi, W. E. Hornbuckle, P. H. Rowland, I. A. Tochkov, A. E. Yeager, H. N. Erb, J. M. Colacio, C. Lopez, J. A. Engelhardt, R. R. Bowsher, F. C. Richardson, W. Lewis, P. J. Cote, B. E. Korba, and J. L. Gerin. 1998. Antiviral activity and toxicity of fialuridine in the woodchuck model of hepatitis B virus infection. Hepatology 28:179-191.