In vitro antiviral activities of myristic acid analogs against human immunodeficiency and hepatitis B viruses

Antiviral Research

Volumn 34, Issue 3, 1997, Pages 75-90

  Parang, Keykavous ^a   Wiebe, Leonard I ^a   Knaus, Edward E ^a   Huang, Jyy Shiang ^a   Tyrrell, David L ^a   Csizmadia, Ferenc ^b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

DHBV; HBV; HIV; Myristic acid analogs

Indexed keywords

ANTIVIRUS AGENT; LAMIVUDINE; MYRISTIC ACID DERIVATIVE; ZIDOVUDINE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CELL CULTURE; CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HELPER CELL; HEPATITIS B VIRUS; HEPATOBLASTOMA; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; NONHUMAN; PARTITION COEFFICIENT; PHYSICS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; ANTI-HIV AGENTS; ANTIVIRAL AGENTS; CELL LINE; CHEMISTRY, PHYSICAL; DRUG EVALUATION, PRECLINICAL; FATTY ACIDS; HEPATITIS B VIRUS; HEPATITIS B VIRUS, DUCK; HIV-1; HUMANS; MYRISTIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFIDES; VIRAL PROTEINS; VIRUS REPLICATION;

EID: 0030961732     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-3542(96)01022-4     Document Type: Article

References (39)

1. Acs, G., Sells, M.A., Purcell, R.H., Price, P., Engle, R., Shapiro, M. and Popper, H. (1987) Hepatitis B virus produced by transfected Hep G2 cells causes hepatitis in chimpanzees. Proc. Natl. Acad. Sci. USA 84, 4641-4644.
2. Adams, S.P., Devadas, B. and Gordon, J.I. (April 15, 1992) Azido substituted fatty acid analog enzyme substrates. E.P. 0 480 901 A1.
3. Bryant, M.L., McWherter, C.A., Kishore, N.S., Gokel, G. W. and Gordon J.I. (1993) MyristoylCoA: protein N-myristoyltransferase as a therapeutic target for inhibiting replication of human immunodeficiency virus-1. Perspect. Drug Discovery Design 1, 193-209.
4. Bryant, M.L., Ratner, L., Duronio, R.J., Kishore, N.S., Devadas, B., Adams, S.P. and Gordon, J.I. (1991) Incorporation of 12-methoxydodecanoate into the human immunodeficiency virus 1 gag polyprotein precursor inhibits its proteolytic processing and virus production in a chronically infected human lymphoid cell line. Proc. Natl. Acad. Sci. USA 88, 2055-2059.
5. Bryant, M.L., Heuckeroth, R.O., Kimata, J.T., Ratner L. and Gordon, J.I. (1989) Replication of human immunodeficiency virus I and Moloney murine leukemia virus is inhibited by heteroatoms containing analogs of myristic acid. Proc. Natl. Acad. Sci. USA, 86, 8655-8659.
6. Devadas, B., Lu, T., Katoh, A., Kishore, N.S., Wade, A.C., Mehta, P. P., Rudnick, D.A., Bryant, M.L., Adams, S.P., Li, Q., Gokel, G.W. and Gordon, J.I. (1992) Substrate specificity of Saccharomyces cerevisiae myristoyl-CoA: protein N-myristoyltransferase: analysis of fatty acid analogs containing carbonyl groups, nitrogen heteroatoms, and nitrogen heterocycles in an in vitro enzyme assay and subsequent identification of inhibitors of human immunodeficiency virus-I replication. J. Biol. Chem. 267, 7224-7239.
7. Diekman, J., Thomson, J.B. and Djerassi, C. (1969) Trimethylsilyl esters of phenoxyalkanoic acids. J. Org. Chem. 34, 3147-3161.
8. Eisenhut, M. and Liefhold, J. (1988) p-Phenylene bridged fatty acids. Int. J. Radiat. Appl. Instrum. Part A. 39, 639-649.
9. Gordon, J.I., Adams, S.P. and Heuckeroth, R.O. (Washington University) (March 6, 1991) Oxy- or thio-substituted fatty acid analogs for use in the treatment of retroviral infections. E. P. 0 415 902 A1.
10. Goodman, M.M., Kirsch, G. and Knapp, F.F. (1984) Synthesis and evaluations of radioiodinated terminal p-iodophenyl-substituted and -methyl-branched fatty acids. J. Med. Chem. 27, 390-397.
11. Harper, D.R., Gilbert, R.L., O'Connor, T.J., Kinchington, D., Mahmood, N., McIlhinney, R.A.J. and Jeffries, D.J. (1996) Antiviral activity of 2-hydroxy fatty acids. Antiviral Chem. Chemother. 7, 138-141.
12. Heijtink, R.A., De Wilde, G.A., Kruining, J., Berk, L., Balzarini, J., De Clercq, E., Holy, A., Schalm, S.W. (1993) Inhibitory effect of 9-(2-phosphonylmethoxyethyl)adenine (PMEA) on human and duck hepatitis B virus infection. Antiviral Res. 21, 141-153.
13. Heuckeroth, R.O., Glaser, L. and Gordon, J.I. (1988) Heteroatom-substituted fatty acid analogs as substrates for N-myristoyltransferase: an approach for studying both the enzymology and function of protein acylation. Proc. Natl. Acad. Sci. USA 85, 8795-8799.
14. Johnson, D.R., Cox, A.D., Soski, P.A., Devadas, B., Adams, S.P., Leimgraber, R.M., Heuckeroth, R.O., Buss, J.E., Gordon and J.I. (1990) Functional analysis of protein N-myristoylation metabolic labeling studies using three oxygen-substituted analogs of myristic acid and cultured mammalian cells provide evidence for protein-sequence-specific incorporation and analog-specific redistribution. Proc. Natl. Acad. Sci. USA 87, 8511-8515.
15. Kishore, N.S., Lu, T., Knoll, L.J., Katoh, A., Rudnick, D.A., Mehta, P.P., Devadas, B., Huhn, M., Atwood, J.L., Adams, S.P., Gokel, G.W. and Gordon, J.I. (1991) The substrate specificity of S. cerevisiae myristoylCoA: protein N-myristoyltransferase: analysis of myristic acid analogs containing oxygen, sulfur, double bonds, triple bonds and/ or aromatic residue. J. Biol. Chem. 266, 8835-8855.
16. Kishore, N.S., Wood, D.C., Pramod, P.M., Arlene, C.W., Tianbao, L., GokeL, G.W. and Gordon, J.I. (1993) Comparison of the acyl chain specificities of human myristoyl-CoA synthetase and human myristoyl-CoA: protein N-myristoyltransferase. J. Biol. Chem. 268, 4889-4902.
17. Korba, B.E. and Gerin, J.L. (1992) Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication. Antiviral Res. 19, 55-70.
18. Korba, B.E. and Milman, G. (1991) A cell culture assay for compounds which inhibit hepatitis B virus replication. Antiviral Res. 15, 217-228.
19. Langner, C.A., Lodge, J.K., Travis, S.J., Caldwell, J.E., Tianbao, L., Li, Q., Bryant, M.L., Devadas, B., Gokel, G.W., Kobayashi, G.S. and Gordon, J.I. (1992) 4-Oxatetradecanoic acid is fungicidal for C. neoformans and inhibits replication of human immunodeficiency virus I. J. Biol. Chem. 267, 17159-17169.
20. Lee, B., Luo, W.X., Suzuki, S., Robins, M.J. and Tyrrell, D.L. (1989) In vitro and in vivo comparison of the abilities of purine and pyrimidine 2′-3′-dideoxynucleosides to inhibit duck hepadnavirus. Antimicrob. Chemother. 33, 336-339.
21. Lin, E., Luscombe, C., Wang, Y.Y., Shaw, T. and Locarnini, S. (1996) The guanine nucleoside analog penciclovir is active against chronic hepatitis B virus infection in vivo. J. Antimicrob. Chemother. 40, 413-418.
22. Mcllhinney, R.A. (1990) The fats of life: the importance and function of protein acylation. Trends Biochem. Sci. 15, 387-391.
23. Macrae, D.R., Bruss, V. and Ganem, D. (1991) Myristylation of a duck hepatitis B virus envelope is essential for infectivity but not for virus assembly. Virology 181, 359-63.
24. Marc, D., Masson, G., Girard, M. and Verf, S.V.D. (1990) Lack of myristylation of poliovirus capsid polypeptide VPO prevents the formation of virions or results in the assembly of noninfectious virus particles. J. Virol. 64, 4099-4107.
25. Nara, P.L., Hatch, W.C., Dunlop, N.M., Robey, W.G., Arthur, L. O., Gonda, M.A. and Fischinger, P.J. (1987) Simple, rapid, quantitative, syncytium-forming microassay for the detection of human immunodeficiency virus neutralizing antibody. AIDS Res. Hum. Retroviruses 3, 283-302.
26. Ozer, A., Knaoustov, V.I., Mearn, M., Lewis, D.E., Genta, R.M., Darlington, G.J. and Yoffe, B. (1996) Effect of hepatocyte proliferation and cellular DNA synthesis on hepatitis B virus replication. Gasteroenterology 110, 1519-1528.
27. Paige, L.A., Zheng, G., Shawn, A.D., Cassady, J.M. and Geahlen, R.L. (1990) Metabolic activation of 2-substituted derivatives of myristic acid to form potent inhibitors of myristoyl CoA:protein N-myristoyltransferase. Biochemistry 29, 10566-10573.
28. Parang, K., Knaus, E.E., Wiebe, L.I., Sardari, S., Daneshtalab, M. and Csizmadia, F. (1996) Synthesis and antifungal activities of myristic acid analogs. Arch. Pharm. Med. Chem. 329, 475-482.
29. Perrin, D.D., Dempsey, B. and Serjeant, E.P. (1981) pKa Prediction for Organic Acids and Bases, 27-52 pp. Chapman and Hall, London.
30. Persing, D.H., Varmus, H.E. and Ganem, D. (1987) The pre-S1 protein of hepatitis B virus is acylated at its amino terminus with myristic acid. J. Virol. 61, 1672-1677.
31. Rocque, W.J., McWherter, C.A., Wood, D.C. and Gordon, G.I. (1993) A comparative analysis of the kinetic mechanism and peptide substrate specificity of human and Sacchromyces cerevisiae acyl-CoA: protein N-myristoyltransferase. J. Biol. Chem. 268, 9964-9971.
32. Schinazi, R.F., Chu, K.C., Peck, A., McMillan, A., Mathis, R., Cannon, D., Jeong, L-S, Beach, J.W., Choi, W-B, Yeola, S. and Liotta, D.C. (1992) Activities of four optical isomers of 2′,3′-dideoxy-3′-thiacytidine (BCH-189) against human immunodeficiency virus type 1 in human lymphocytes. Antimicrob. Agents Chemother. 36, 672-676.
33. 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. USA 84, 1005-1009.
34. Sells, M.A., Zelent A.Z., Shvartsman, M. and Acs, G. (1988) Replicative intermediate of hepatitis B virus in HepG2 cells that produce infectious virions. J. Virol. 62, 2836-2844.
35. Staprans, A., Loeb, D.D. and Ganem, D. (1991) Mutations affecting hepadnavirus plus-strand DNA synthesis dissociate primer cleavage from translocation and reveal the origin of linear viral DNA. J. Virol. 65, 1255-1262.
36. Tuttleman, J.S., Pugh, J.C. and Summers, J.W. (1986) In vitro experimental infection of primary duck hepatocyte cultures with DHBV. J. Virol. 58, 17-25.
37. Valenzuela, P., Gray, P., Quiroga, M., Zaldivar, J., Goodman, H.M. and Rutter, W.J. (1979) Nucleotide sequence of the gene coding for the major protein of hepatitis B virus surface antigen. Nature 280, 815-819.
38. Weislow, O.W., Kiser, R., Fine, D., Bader, J., Shoemaker, R.H. and Boyd, M.R.. (1989) New soluble-formazan assay for HIV-1 cytopathic effects: Application to high-flux screening of synthetic and natural products for AIDS-antiviral activity. J. Natl. Cancer Instit. 81, 577-586.
39. Xie, H., Voronkov, M., Liotta, D.C., Korba, B.A., Schinazi, R.F., Richman, D. D. and Hostetler, K. Y. (1995) Phosphatidyl-2′,3′-dideoxy-3′-thiacytidine: synthesis and antiviral activity in hepatitis B- and HIV-1-infected cells. Antiviral Res. 28, 113-120.