Enhanced oral absorption and antiviral activity of 1-O-octadecyl-sn- glycero-3-phospho-acyclovir and related compounds in hepatitis B virus infection, in vitro

Biochemical Pharmacology

Volumn 53, Issue 12, 1997, Pages 1815-1822

  Hosteller, Karl Y ^a,b   Beadle, James R ^a   Kini, Ganesh D ^a   Gardner, Michael F ^a   Wright, Kristine N ^a   Wu, Tong Hau ^a   Korba, Brent A ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b VA SAN DIEGO HEALTHCARE SYSTEM   (United States)

^c GEORGETOWN UNIVERSITY   (United States)

Author keywords

Antiviral agents; Hepatitis B virus; Prodrugs

Indexed keywords

1 O HEXADECYLPROPANEDIOL 3 PHOSPHOACYCLOVIR; 1 O OCTADECYLGLYCERO 3 PHOSPHOACYCLOVIR; 1 O OCTADECYLGLYCERO 3 PHOSPHOAZIDOTHYMIDINE; ACICLOVIR TRIPHOSPHATE; DNA POLYMERASE; PRODRUG; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIVIRAL ACTIVITY; AREA UNDER THE CURVE; ARTICLE; DRUG METABOLISM; DRUG STRUCTURE; FEMALE; HEPATITIS B; HEPATITIS B VIRUS; HEPATOMA CELL; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; VIRUS INHIBITION; VIRUS REPLICATION;

EID: 0030786518     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)82446-X     Document Type: Article

References (34)

1. Popper H, Shafritz DA and Hoofnagle JH, Relation of the hepatitis B virus carrier state to hepatocellular carcinoma. Hepatology 7: 764-772, 1987.
2. Ayoola EA, Balayan MS, Deinhardt F, Gust I, Kureshi AW, Maynard JE, Nayak NC, Schatzmayr HG, Zhuang H, Beasley RP, Blueger AF, Bradley DW, Ferguson M, Melnick J, Purcell RH and Zuckerman AJ, Progress in the control of viral hepatitis: Memorandum from a WHO meeting. Bull World Health Organ 66: 443-445, 1988.
3. Ganem D, Pollack JR and Tavis J, Hepatitis B virus reverse transcriptase and its many roles in hepadnaviral genomic replication. Infect Agents Dis 3: 85-93, 1994.
4. Summers J and Orason WS, Replication of the genome of a hepatitis B-like virus by reverse transcription of an RNA intermediate. Cell 29: 403-415, 1982.
5. Aoki-Sel S, O'Brien MC, Ford H, Fujii H, Gilbert DA, Cooney DA, Johns DG, Broder S and Mitsuya H, In vitro inhibition of hepatitis B virus replication by 2′,3′-dide-oxyguanosine, 2′,3′-dideoxyinosine, and 3′-azido-2′,3′-dideoxythymidine in 2.2.15 (PR) cells. J Inject Dis 164: 843-851, 1991.
6. Berk L, Schalm SW and Heijtink RA, Zidovudine inhibits hepatitis B virus replication. Antiviral Res 19: 111-118, 1992.
7. Doong S-L, Tsai C-H, Schinazi RF, Liotta DC and Cheng Y-C, Inhibition of the replication of hepatitis B virus in vitro by 2′,3′-dideoxy-3′-thiacytidine and related analogues. Proc Nad Acad Sci USA 88: 8495-8499, 1991.
8. Heijtink RA, Kruining J, de Wilde GA, Balzarini J, de Clercq E and Schalm SW, Inhibitory effects of acyclic nucleoside phosphonates on human hepatitis B virus and duck hepatitis B virus infections in tissue culture. Antimicrob Agents Chemother 38: 2180-2182, 1994.
9. Korba BA and Gerin JL, Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication. Antiviral Res 19: 55-70, 1992.
10. Lee B, Luo W, Suzuki S, Robins MJ and Tyrrell DLJ, In vitro and in vivo comparison of the abilities of purine and pyrimidine 2′,3′-dideoxynucleosides to inhibit duck hepadnavirus. Antimicrob Agents Chemother 33: 336-339, 1989.
11. Matthes E, Langen P, von Janta-Lipinski M, Will H, Schroder HC, Merz H, Weiler BE and Müller WEG, Potent inhibition of hepatitis B virus production in vitro by modified pyrimidine nucleosides. Antimicrob Agents Chemother 34: 1986-1990, 1990.
12. Schinazi RF, Gosselin G, Faraj A, Korba BE, Liotta DC, Chu CK, Mathe C, Imbach J-L and Sommadossi J-P, Pure nucleoside enantiomers of β-2′,3′-dideoxycytidine analogs are selective inhibitors of hepatitis B virus in vitro. Antimicrob Agents Chemother 38: 2172-2174, 1994.
13. Hantz O, Allaudeen HS, Ooka T, De Clerco E and Trepo C, 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. Antiviral Res 4: 187-199, 1984.
14. Berk L, Schalm SW, de Man RA, Heytink RA, Berthelot P, Brechet C, Boboc B, Degos F, Marcellin P, Benhamou J-P, Hess G, Rossol S, zum Büschenfelde K-HM, Chamuleau RAFM, Jansen PLM, Reesink HW, Meyer B, Beglinger C, Stalder GA, den Ouden-Muller JW and de Jong M, Failure of acyclovir to enhance the antiviral effect of a-lymphoblastoid interferon on HBe-seroconversion in chronic hepatitis B. A multi-centre randomized controlled trial. J Hepatol 14: 305-309, 1992.
15. Gilson RJ, Hawkins AE, Kelly GK, Gill SK and Weller IV. No effect of zidovudine on hepatitis B virus replication in homosexual men with symptomatic HIV-1 infection. AIDS 5: 217-220, 1991.
16. Janssen HL, Berk L, Heijtink RA, ten Kate FJ and Schalm SW, Interferon-α and zidovudine combination therapy for chronic hepatitis B: Results of a randomized, placebo-controlled trial. Hepatology 17: 383-388, 1993.
17. 2-Acetylacyclovir and 6-deoxyacyclovir. Synthesis 6: 461-464, 1990.
18. Hostetler KY, Carson DA and Richman DD, Phosphatidyl-azidothymidine. Mechanism of antiretroviral action in CEM cells. J Biol Chem 266: 11714-11717, 1991.
19. Folch JM, Lees M and Sloane-Stanley GH, A single procedure for the isolation and purification of total lipids from animal tissues. J Biol Chem 226: 497-509, 1957.
20. Elion GB, Furman PA, Fyfe JA, de Miranda P, Beauchamp L and Schaeffer HJ, Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl) guanine. Proc Natl Acad Sci USA 74: 5716-5720, 1977.
21. Fyfe JA, Keller PM, Furman PA, Miller RL and Elion GB, Thymidine kinase from herpes simplex virus phosphorylates the new antiviral compound, 9-(2-hydroxyethoxymethyl)guanine. J Biol Chem 253: 8721-8727, 1978.
22. Field AK, Tuomari AV, McGeever-Rubin B, Terry BJ, Mazina KE, Haffey ML, Hagen ME, Clark JM, Braitman A, Slusarchyk WA, Young MG and Zahler R, (±)-(1α, 2β, 3α)-9-[2,3-bis(Hydroxymethyl)cyclobutyl]guanine [(±)-BHCG or SQ 33 054]: A potent and selective inhibitor of herpesviruses. Antiviral Res 13: 41-52, 1990.
23. Hostetler KY, Richman DD, Carson DA, Stuhmiller LM, van Wijk GMT and van den Bosch H, Greatly enhanced inhibition of human immunodeficiency virus type 1 replication in CEM and HT4-6C cells by 3′-deoxythymidine diphosphate dimyristoylglycerol, a lipid prodrug of 3′-deoxythymidine. Antimicrob Agents Chemother 36: 2025-2029, 1992.
24. Hostetler KY, Parker S, Sridhar CN, Martin MJ, Li J-L, Stuhmiller LM, van Wijk GMT, van den Bosch H, Gardner MF, Aldern KA and Richman DD, Acyclovir diphosphate dimyristoylglycerol: A phospholipid prodrug with activity against acyclovir-resistant herpes simplex virus. Proc Natl Acad Sci USA 90: 11835-11839, 1993.
25. van Wijk GMT, Hostetler KY and van den Bosch H, Lipid conjugates of antiretroviral agents: Release of antiretroviral nucleoside monophosphates by a nucleoside diphosphate diglyceride hydrolase activity from rat liver mitochondria. Biochim Biophys Acta 1084: 307-310, 1991.
26. Welch CJ, Larrson A, Ericson AC, Oberg B, Datema R and Chattopadhyaya J, The chemical synthesis and antiviral properties of an acyclovir-phospholipid conjugate. Acta Chem Scand B 39: 47-54, 1985.
27. Lefebvre I, Perigaud C, Pompon A, Aubertin A-M, Girardet J-L, Kirn A, Gosselin G and Imbach J-L, Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: Intracellular delivery of 3′-azido-2′,3′-dideoxythymidine 5′-monophosphate. J Med Chem 38: 3941-3950, 1995.
28. McGuigan C, Pathirana RN, Balzarini J and De Clercq E, Intracellular delivery of bioactive AZT nucleotides by aryl phosphate derivatives of AZT. J Med Chem 36: 1048-1052, 1993.
29. atsuzawa Y and Hostetler KY, Properties of phospholipase C isolated from rat liver lysosomes. J Biol Chem 255: 646-652, 1980.
30. Hostetler KY and Hall LB, Phospholipase C activity of rat tissues. Biochem Biophys Res Commun 96: 388-393, 1980.
31. Nishihira J and Ishibashi T, A phospholipase C with a high specificity for platelet-activating factor in rabbit liver light mitochondria. Lipids 21: 780-785, 1986.
32. Okayasu T, Hoshii K, Seyama K, Ishibashi T and Imai Y, Metabolism of platelet-activating factor in primary cultured adult rat hepatocytes by a new pathway involving phospholipase C and alkyl monooxygenase. Biochim Biophys Acta 876: 58-64, 1986.
33. Nilsson A and Borgstrom B, Absorption and metabolism of lecithin and lysolecithin by intestinal slices. Biochim Biophys Acta 137: 240-254, 1967.
34. Scow RO, Stein Y and Stein O, Incorporation of dietary lecithin and lysolecithin into lymph chylomicrons in the rat. J Biol Chem 242: 4919-4924, 1967.