Antiviral activities of nucleotide heterodimers against human immunodeficiency virus type 1 in vitro

Antiviral Research

Volumn 31, Issue 1-2, 1996, Pages 115-120

  Ijichi, Katsushi ^a   Fujiwara, Masatoshi ^a   Mori, Kenya ^b   Morozumi, Manami ^b   Machida, Haruhiko ^b   Shigeta, Shiro ^c   Konno, Kenji ^a   Yokota, Tomoyuki ^a   Baba, Masanori ^d  

^a Rational Drug Design Laboratories   (Japan)

^b YAMASA CORPORATION   (Japan)

^c FUKUSHIMA MEDICAL UNIVERSITY   (Japan)

^d KAGOSHIMA UNIVERSITY   (Japan)

Author keywords

Heterodimer; HIV 1; Reverse transcriptase inhibitor resistant mutants

Indexed keywords

DIDANOSINE; NUCLEOTIDE DERIVATIVE; RIBAVIRIN; RNA DIRECTED DNA POLYMERASE; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG RESISTANCE; DRUG STRUCTURE; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; PRIORITY JOURNAL; VIRUS INHIBITION;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0029944279     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/0166-3542(96)00945-X     Document Type: Article

References (20)

1. Baba, M., Pauwels, R., Balzarini, J., Herdewijn, P., De Clercq, E. and Desmyter, J. (1987) Ribavirin antagonizes inhibitory effects of pyrimidine 2′,3′-dideoxynucleosides but enhances inhibitory effects of purine 2′,3′-dideoxynucleosides on replication of human immunodeficiency virus in vitro. Antimicrob. Agents Chemother. 31, 1613-1617.
2. Baba, M., Shigeta, S., Yuasa, S., Takashima, H., Sekiya, K., Ubasawa, M., Tanaka, H., Miyasaka, T., Walker, R.T. and De Clercq, E. (1994) Preclinical evaluation of MKC-442, a highly potent and specific inhibitor of human immunodeficiency virus type 1 in vitro. Antimicrob. Agents Chemother. 38, 688-692.
3. Busso, M., Mian, A.M., Hahn, E.F. and Resnick, L. (1988) Nucleotide dimers suppress HIV expression in vitro. AIDS Res. Human Retroviruses 4, 449-455.
4. Gao, Q., Gu, Z., Hiscott, J., Dionne, G. and Wainberg, M.A. (1993a) Generation of drug-resistant variants of human immunodeficiency virus type 1 by in vitro passage in increasing concentrations of 2′,3′-dideoxycytidine and 2′,3′-dideoxy-3′-thiacytidine. Antimicrob. Agents Chemother. 37, 130-133.
5. Gao, W.-T., Shirasaka, T., Johns, D.G., Broder, S. and Mitsuya, H. (1993b) Differential phosphorylation of azidothymidine, dideoxycytidine, and dideoxyinosine in resting and activated peripheral blood mononuclear cells. J. Clin. Invest. 91, 2326-2333.
6. Hahn, E.F., Busso, M., Mian, A.M. and Resnick, L. (1989) Nucleotide dimers as anti-human immunodeficiency virus agents. In: J. Martin (Ed), Nucleotide Analogues as Antiviral Agents, pp. 156-169. American Chemical Society, Washington, D.C.
7. Hartman, N.R., Ahluwalia, G.S., Cooney, D.A., Mitsuya, H., Kageyama, S., Fridland, A., Broder, S. and Johns, D.G. (1991) Inhibition of IMP dehydrogenase stimulate the phosphorylation of the anti-human immunodeficiency virus nucleosides 2′,3′-dideoxyadenosine and 2′,3′-dideoxyinosine. Mol. Pharmacol. 40, 118-124.
8. Land, S., Treloar, G., McPhee, D., Birch, C., Doherty, R., Cooper, D. and Gust, I. (1990) Decreased in vitro susceptibility to zidovudine of HIV isolates obtained from patients with AIDS. J. Infect. Dis. 161, 326-329.
9. Larder, B.A., Darby, G. and Richman, D.D. (1989) HIV with reduced sensitivity to zidovudine (AZT) isolated during prolonged therapy. Science 243, 1731-1734.
10. Nanni, R.G., Ding, J., Jacobo-Molina, A., Hughes, S.H. and Arnold, E. (1993) Review of HIV-1 reverse transcriptase three-dimensional structure: implications for drug design. Perspect. Drug Dis. Des. 1, 129-150.
11. Pauwels, R., Balzarini, J., Baba, M., Snoeck, R., Schols, D., Herdewijn, P., Desmyter, J. and De Clercq, E. (1988) Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J. Virol. Methods 20, 309-321.
12. Puech, F., Pompon, A., Lefebvre, I., Gosselin, G. and Imbach, J. L. (1992) Nucleotidic prodrugs of anti-HIV dideoxynucleosides. Bioorg. Med. Chem. Lett. 2, 603-606.
13. Richman, D.D., Havlir, D., Corbeil, J., Looney, D., Ignacio, C., Spector, S.A., Sullivan, J., Cheeseman, S., Barringer, K., Pauletti, D., Shih, C.-K., Myers, M. and Griffin, J. (1994) Nevirapine resistance mutations of human immunodeficiency virus type 1 selected during therapy. J. Virol. 68, 1660-1666.
14. Schinazi, R.F., Sommadossi, J.-P., Saalmann, V., Cannon, D.L., Xie, M.-Y., Hart, G.C., Smith, G.A. and Hahn, E.F. (1990) Activities of 3′-azido-3′-deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 34, 1061-1067.
15. Shirasaka, T., Chokekijchai, S., Yamada, A., Gosselin, G., Imbach, J.-L. and Mitsuya, H. (1995) Comparative analysis of anti-human immunodeficiency virus type 1 activities of dideoxynucleoside analogs in resting and activated peripheral blood mononuclear cells. Antimicrob. Agents Chemother. 39, 2555-2559.
16. St. Clair, M.H., Martin, J.L., Tudor-Williams, G., Bach, M.C., Vavro, C.L., King, D.M., Kellam, P., Kemp, S.D. and Larder, B.A. (1991) Resistance to ddl and sensitivity to AZT induced by a mutation in HIV-1 reverse transcriptase. Science 253, 1557-1559.
17. Tanaka, H., Takashima, H., Ubasawa, M., Sekiya, K., Nitta, I., Baba, M., Shigeta, S., Walker, R.T., De Clercq, E. and Miyasaka, T. (1992) Structure-activity relationships of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine analogues: effect of substitutions at the C-6 phenyl ring and at the C-5 position on anti-HIV-1 activity. J. Med. Chem. 35, 337-345.
18. Tener, G.M. (1961) 2-Cyanoethyl phosphate and its use in the synthesis of phosphate esters. J. Am. Chem. Soc. 83, 159-163.
19. Velázquez, S., Alvarez, R., San-Félix, A., Jimeno, M.L., De Clercq, E., Balzarini, J. and Camarasa, M.J. (1995) Synthesis and anti-HIV activity of [AZT]-[TSAO-T] and [AZT]-[HEPT] dimers as potential multifunctional inhibitors of HIV-1 reverse transcriptase. J. Med. Chem. 38, 1641-1649.
20. Vogt, M.W., Hartshorn, K.L., Furman, P.A., Chou, T.-C., Fyfe, J.A., Coleman, L.A., Crumpacker, C., Schooley, P.T. and Hirsch, M.S. (1987) Ribavirin antagonizes the effect of azidothymidine on HIV replication. Science 235, 1376-1379.