Effects of nucleotide analogues on human immunodeficiency virus type 1 integrase

Molecular Pharmacology

Volumn 49, Issue 4, 1996, Pages 621-628

  Mazumder, Abhijit ^a   Neamati, Nouri ^a   Sommadossi, Jean Pierre ^b   Gosselin, Gilles ^c   Schinazi, Raymond F ^d,e   Imbach, Jean Louis ^c   Pommier, Yves ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b University of Alabama at Birmingham   (United States)

^c CNRS   (France)

^d ATLANTA VA MEDICAL CENTER   (United States)

^e EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXY 2' FLUOROADENOSINE; 2',3' DIDEOXY 2' FLUOROADENOSINE TRIPHOSPHATE; 2',3' DIDEOXYNUCLEOSIDE TRIPHOSPHATE; COUMAMYCIN; INTEGRASE; LAMIVUDINE; NICOTINAMIDE ADENINE DINUCLEOTIDE; STAVUDINE; UNCLASSIFIED DRUG; ZIDOVUDINE; ZIDOVUDINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG BINDING; DRUG DNA BINDING; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PRIORITY JOURNAL;

ANTIVIRAL AGENTS; BASE SEQUENCE; BINDING SITES; DNA; DNA NUCLEOTIDYLTRANSFERASES; ENZYME INHIBITORS; HIV-1; INTEGRASES; MOLECULAR SEQUENCE DATA; NUCLEOTIDES; VIRUS REPLICATION;

EID: 0029871472     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Katz, R. A., and A. M. Skalka The retroviral enzymes. Annu. Rev. Biochem. 63:133-173 (1994).
2. Engelman, A., G. Englund, J. M. Orenstein, M A. Martin, and R Craigie. Multiple effects of mutations in human immunodeficiency virus type 1 integrase on viral replication. J. Virol. 69:2729-2736 (1995).
3. Englund, G., T. S. Theodore, E. O. Freed, A. Engelman, and M. A. Martin. Integration is required for productive infection of monocyte-derived macrophages by human immunodeficiency virus type-1. J. Virol. 69:3216-3219 (1995).
4. Mazumder, A., M. Gupta, D. M. Perrin, D. S. Sigman, M. Rabinovitz, and Y. Pommier. Inhibition of human immunodeficiency virus type 1 integrase by a hydrophobic cation: the phenanthroline-cuprous complex. AIDS Res. Hum. Retroviruses 11:115-125 (1995).
5. Mazumder, A., K. Raghavan, J N. Weinstein, K. W. Kohn, and Y. Pommier. Inhibition of human immunodeficiency virus type 1 integrase by curcumin Biochem. Pharmacol. 49:1165-1170 (1995).
6. Mitsuya, H., and S. Broder. Inhibition of the in vitro infectivity and cytopathic effect of human T-lytnphotrophic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV) by 2′,3′-dideoxynucleosides. Proc. Natl Acad. Sci. USA 83:1911-1915 (1986).
7. Gosselin, G., C. Mathe, M.-C. Bergogne, A.-M. Aubertin, A. Kirn, R. F. Schinazi, J.-P. Sommadossi, and J.-L. Imbach. Enantiomeric 2′.3′-dideoxycytidine derivatives are potent human immunodeficiency virus inhibitors in cell culture. C. R. Acad. Sci. Ser. III Sci. Vie 317:85-89 (1994).
8. Faraj, A., L. A. Agrofoglio, J. K. Wakefield, S. McPherson, C. D. Morrow, G. Gosselin. C. Mathe, J.-L. Imbach, R. F. Schinazi, and J.-P. Sommadossi. Inhibition of human immunodeficiency virus type 1 reverse transcriptase by the 5′-triphosphate β enantiomers of cytidine analogs. Antimicrob. Agents Chemother. 38:2300-2305 (1994).
9. Schmazi, R. F., G. Gosselin, A. Faraj, B. E. Korba, D. C. Liotta, C. K. Chu, C. Mathe, J.-L. Imbach, and J.-P. Sommadossi. Pure nucleoside enantiomers of β-2′,3′-dideoxycytidine analogues are selective inhibitors of hepatitis B virus and human immunodeficiency virus in vitro. Antimicrob. Agents Chemother. 38:2172-2174 (1994).
10. Gao, W.-Y., R. Agbaria, J. S. Driscoll, and H. Mitsuya. Divergent antihuman immunodeficiency virus activity and anabolic phosphorylation of 2′:3′-dideoxynucleoside analogs in resting and activated human cells. J. Biol Chem. 269:12633-12638 (1994).
11. Matthes, E., C. Lehman, D. Scholz, H. A. Rosenthal, and P. Langen. Phosphorylation, anti-HIV activity and cytotoxicity of 3′-fluorothymidine. Biochem. Biophys Res. Commun. 153:825-831 (1988).
12. Sommadossi, J. P. Nucleoside analogs: similarities and differences. Clin. Infect. Dis. 16:S7-S15 (1993).
13. De Clercq, E. Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J. Med. Chem. 38:2491-2517 (1995).
14. Larder, B. A., S. D. Kemp, and P. R. Harrigan. Potential mechanism for sustained antiretroviral efficacy of AZT-3TC combination therapy. Science (Washington D. C.) 269:696-699 (1995).
15. Schinazi, R. F. Combined chemotherapeutic modalities for viral infections: rationale and clinical potential, in Synergism and Antagonism in Chemotherapy (T. C. Chou and D. C. Rideout, eds.). Academic Press, Orlando, FL, 109-181 (1991).
16. Johnson, V. A. Combination therapy: more effective control of HIV type 1? AIDS Res. Hum. Retrouiruses 10:907-912 (1994).
17. Mazumder, A., D. Cooney, R. Agbaria, M. Gupta, and Y. Pommier. Inhibition of human immunodeficiency virus type 1 integrase by 3′-azido-3′-deoxythymidylate. Proc. Natl Acad. Sci. USA 91:5771-5775 (1994).
18. Furman, P A., J. A. Fyfe, M. H. St. Clair, K. Weinhold, J. L. Rideout, G. A. Freeman, S. N. Lehrman, D P. Bolognesi, S. Broder, H. Mitsuya, and D. W. Barry. Phosphorylation of 3′-azido-3′-deoxythymidine and selective interaction of the 5′-triphosphate with human immunodeficiency virus reverse transcriptase. Proc. Nat. Acad. Sci. USA 83:8333-8337 (1986).
19. White, E. L., W. B. Parker, L. J. Macy, S. C. Shaddix, G. McCaleb, J. A. Secrist, R. Vince, and W. M. Shannon. Comparison of the effect of carbovir, AZT, and dideoxynucleoside triphosphates on the activity of HIV reverse transcriptase and selected human polymerases. Biochem. Biophys. Res. Commun. 161:393-398 (1989).
20. Meisel, H., K Reimer, M. von Janta-Lipinski, D. Barwolff, and E. Matthes. Inhibition of hepatitis B virus DNA polymerase by 3′-fluorothymidine triphosphate and other modified nucleoside triphosphate analogs. J. Med. Virol. 30:137-141 (1990).
21. Cretton, E. M., M. Y. Xie, R. J. Bevan, N. M. Goudgaon, R. F. Schinazi, and J. P. Sommadossi. Catabolism of 3′-azido-3′-deoxythymidine in hepatocytes and liver microsomes, with evidence of formation of 3′-amino-3′-deoxythymidine, a highly toxic catabolite for human bone marrow cells. Mol. Pharmacol. 39:258-266 (1991)
22. Schinazi, R. F , C. K. Chu, A. Peck, A. McMillan, R. Mathis, D. Cannon, L.-S. Jeong, J. W. Beach, W.-B Choi, S. Yeola, and D. C. Liotta. Activity of the 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 (1992)
23. Herdewijn, P. A. M. M. Novel nucleoside strategies for anti-HIV and anti-HSV therapy. Antiviral Res. 19:1-14 (1992)
24. Chang, C.-N., S.-L. Doong, J. H. Zhou, J. W. Beach, L. S. Jeong, C. K. Chu, C.-H. Tsai, R. F. Schinazi, D. C. Liotta, and Y.-C. Cheng. 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 (1992).
25. Schinazi, R. F., A. McMillan, D. Cannon, R. Mathis, R. M. Lloyd, A. Peck, J. P Sommadossi, M. St Clair, J. Wilson, P. A. Furman, G. Painter, W.-B. Choi, and D. C. Liotta. Selective inhibition of human immunodeficiency viruses by racemates and enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine. Antimicrob. Agents Chemother. 36:2423-2431 (1992)
26. Ahluwalia, G., D. A. Cooney, H. Mitsuya, A. Fridland, K. P. Flora, Z. Hao, M. Dalal, S. Broder, and D. G. Johns. Initial studies on the cellular pharmacology of 2′:3′-dideoxyinosine, an inhibitor of HIV infectivity. Biochem. Pharmacol. 36:3797-3800 (1987).
27. Meyerhans, A, J.-P. Vartanian, C. Hultgren, U. Plikat, A. Karlsson, L. Wang, S. Eriksson, and S. Wain-Hobson. Restriction and enhancement of human immunodeficiency virus type 1 replication by modulation of intracellular deoxynucleoside triphosphate pools. J. Virol. 68:535-540 (1994).
28. Brown, P. O., C. L. Peebles, and N R Cozzarelli. A topoisomerase from Escherichia coli related to DNA gyrase. Proc. Natl Acad. Sci. USA 76: 6110-6114 (1979).
29. Goto, T., P. Laipis, and J. C. Wang. The purification and characterization of DNA topoisomerases I and II of the yeast Saccharomyces cerevisiae. J. Biol. Chem. 259:10422-10429 (1984).
30. Lipford, J. R., S. T. Worland, and C. M. Farnet. Nucleotide binding by the HIV-1 integrase protein in vitro. J. Acquired Immune Defic. Syndr. 7:1215-1223 (1994).
31. Engelman, A., K. Mizuuchi, and R. Craigie. HIV-1 DNA integration: mechanism of viral DNA cleavage and DNA strand transfer. Cell 67:1211-1221 (1991).
32. Vink, C., E. Yeheskiely, G. A. van der Marel, J. H. van Boom, and R. H. Plasterk. Site-specific hydrolysis and alcoholysis of human immunodeficiency virus DNA termini mediated by the viral integrase protein. Nucleic Acids Res. 19:6691-6698 (1991).
33. Chow, S. A., K. A. Vincent, V. Ellison, and P. O. Brown. Reversal of integration and DNA splicing mediated by integrase of human immunodeficiency virus. Science (Washington D. C.) 255:723-726 (1992).
34. Bushman, F. D., A. Engelman, I. Palmer, P. Wingfield, and R. Craigie. Domains of the integrase protein of human immunodeficiency virus type 1 responsible for polynucleotidyl transfer and zinc binding. Proc. Natl. Acad. Sci. USA 90:3428-3432 (1993).
35. Chen, M. S., R. T. Suttman, E. Papp, P. D. Cannon, M. J. McRoberts, C. Bach, W. C. Copeland, and T. S.-F. Wang. Selective action of 4′-azidothymidine triphosphate on reverse transcriptase of human immunodeficiency virus type one and human DNA polymerases alpha and beta. Biochemistry 32:6002-6010 (1993).
36. Zhu, Z., H. T. Ho, M. J. Hitchcock, and J. P. Sommadossi. Cellular pharmacology of 2′:3′-didehydro-2′,3′-dideoxythymidine (D4T) in human peripheral blood mononuclear cells. Biochem. Pharmacol. 39:R15-R19 (1990).
37. Tornevik, Y., and S. Eriksson. 2′,3′-Dideoxycytidine toxicity in cultured human CEM T lymphoblasts: effects of combination with 3′-azido-3′-deoxythymidine and thymidine. Mol. Pharmacol. 38:237-243 (1990).
38. Tan, C.-K., R. Civil, A. M. Mian, A. G. So, and K. M. Downey. Inhibition of the RNase H activity of HIV reverse transcriptase by azidothymidylate. Biochemistry 30:4831-4835 (1991).
39. Bebenek, K., D. C. Thomas, J. D. Roberts, F. Eckstein, and T. A. Kunkel. Effects of 3′-azido-3′-deoxythymidine metabolites on simian virus 40 origin-dependent replication and heteroduplex repair in HeLa cell extracts. Mol. Pharmacol. 43:57-63 (1993).
40. Harrington, J. A., J. E. Reardon, and T. Spector. 3′-Azido-3′-deoxythymidine (AZT) monophosphate: an inhibitor of exonudeolytic repair of AZT-terminated DNA. Antimicrob. Agents Chemother. 37:918-920 (1993).
41. Bridges, E. G., A. Faraj, and J. P. Sommadossi. Inhibition of mammalian DNA polymerase-associated 3′ to 5′ exonuclease activity by 5′-monophosphates of 3′-azido-3′-deoxythymidine and 3′-amino-3′-deoxythymidine. Biochem. Pharmacol. 45:1571-1576 (1993).