Irreversible inhibition of human immunodeficiency virus type 1 integrase by dicaffeoylquinic acids

Journal of Virology

Volumn 73, Issue 4, 1999, Pages 3309-3316

  Zhu, Kai ^a   Cordeiro, Mara L ^a   Atienza, Jocelyn ^a   Edward Robinson Jr , W ^b   Chow, Samson A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAFFEIC ACID; CHLOROGENIC ACID; DICAFFEOYLQUINIC ACID; INTEGRASE INHIBITOR; QUINIC ACID; TRANSFERASE; UNCLASSIFIED DRUG; VIRUS DNA;

ARTICLE; DRUG ACTIVITY; DRUG EFFICACY; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; INHIBITION KINETICS; NONHUMAN; PRIORITY JOURNAL; VIRUS DNA CELL DNA INTERACTION; VIRUS GENOME; VIRUS INHIBITION; VIRUS REPLICATION;

EID: 0032976222     PISSN: 0022538X     EISSN: None     Source Type: Journal    
DOI: 10.1128/jvi.73.4.3309-3316.1999     Document Type: Article

References (65)

1. Adachi, A., H. E. Gendelman, S. Koenig, T. Folks, R. Willey, A. Rabson, and M. A. Martin. 1986. Production of acquired immunodeficiency syndrome-associated retrovirus in human and nonhuman cells transfected with an infectious molecular clone. J. Virol. 59:284-291.
2. Andrake, M. D., and A. M. Skalka. 1996. Retroviral integrase, putting the pieces together. J. Biol. Chem. 271:19633-19636.
3. Bartlett, J. G. 1996. Protease inhihitors for HIV infection. Ann. Intern. Med. 124:1086-1088.
4. Billich, A., M. Schauer, S. Frank, B. Rosenwirth, and S. Billich. 1992. HIV-1 integrase: high level production and screening assay for the endonucleolytic activity. Antivir. Chem. Chemother. 3:113-119.
5. Brown, P. O. 1997. Integration, p. 161-203. In J. M. Coffin, S. H. Hughes, and H. E. Varmus (ed.), Retroviruses. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
6. Burke, T. R., Jr., M. R. Fesen, A. Mazumder, J. Wang, A. M. Carothers, D. Grunberger, J. Driscoll, K. Kohn, and Y. Pommier. 1995. Hydroxylated aromatic inhibitors of HIV-1 integrase. J. Med. Chem. 38:4174-4178.
7. Bushman, F. D., A. Engelman, I. Palmer, P. Wingfield, and R. Craigie. 1993. 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.
8. Carteau, S., J. F. Mouscadet, H. Goulaouic, F. Subra, and C. Auclair. 1993. Effect of topoisomerase inhibitors on the in vitro HIV DNA integration reaction. Biochem. Biophys. Res. Commun. 192:1409-1414.
9. Carteau, S., J. F. Mouscadet, H. Goulaouic, F. Subra, and C. Auclair. 1994. Inhibition of the in vitro integration of Moloney murine leukemia virus DNA by the DNA minor groove binder netropsin. Biochem. Pharmacol. 47:1821-1826.
10. Chow, S. A., K. A. Vincent, V. Ellison, and P. O. Brown. 1992. Reversal of integration and DNA splicing mediated by integrase of human immunodeficiency virus. Science 255:723-726.
11. 10a. Chow, S. A. Unpublished data.
12. Coffin, J. M. 1995. HIV population dynamics in vivo: implications for genetic variation, pathogenesis, and therapy. Science 267:483-489.
13. Cohen, G. M., and M. d'Arcy Doherty. 1987. Free radical mediated cell toxicity by redox cycling chemicals. Br. J. Cancer 55:46-52.
14. 12a. Cordeiro, M. L., and S. A. Chow. Unpublished data.
15. Cushman, M., W. M. Golebiewski, Y. Pommier, A. Mazumder, D. Reymen, E. De Clercq, L. Graham, and W. G. Rice. 1995. Cosalane analogues with enhanced potencies as inhibitors of HIV-1 protease and integrase. J. Med. Chem. 38:443-452.
16. Cushman, M., and P. Sherman. 1992. Inhibition of HIV-1 integration protein by aurintricarboxylic acid monomers, monomer analogs, and polymer fractions. Biochem. Biophys. Res. Commun. 185:85-10.
17. Dotan, I., B. P. Scottoline, T. S. Heuer, and P. O. Brown. 1995. Characterization of recombinant murine leukemia virus integrase. J. Virol. 69:456-468.
18. Ellison, V., and P. O. Brown. 1994. A stable complex between integrase and viral DNA ends mediates HIV integration in vitro. Proc. Natl. Acad. Sci. USA 91:7316-7320.
19. Engelman, A., F. D. Bushman, and R. Craigie. 1993. Identification of discrete functional domains of HIV-1 integrase and their organization within an active multimeric complex. EMBO J. 12:3269-3275.
20. Engelman, A., K. Mizuuchi, and R. Craigie. 1991. HIV-1 DNA integration: mechanism of viral DNA cleavage and DNA strand transfer. Cell 67:1211-1221.
21. Englund, G., T. S. Theodore, E. O. Freed, A. Engelman, and M. A. Martin. 1995. Integration is required for productive infection of monocyte-derived macrophages by human immunodeficiency virus type 1. J. Virol. 69:3216-3219.
22. Farnet, C. M., and F. D. Bushman. 1996. HIV cDNA integration: molecular biology and inhibitor development. AIDS 10(Suppl. A):S3-S11.
23. Farnet, C. M., B. Wang, J. R. Lipford, and F. D. Bushman. 1996. Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules. Proc. Natl. Acad. Sci. USA 93:9742-9747.
24. Fesen, M. R., K. W. Kohn, F. Leteurtre, and Y. Pommier. 1993. Inhibitors of human immunodeficiency virus integrase. Proc. Natl. Acad. Sci. USA 90: 2399-2403.
25. Fesen, M. R., Y. Pommier, F. Leteurtre, S. Hiroguchi, J. Yung, and K. W. Kohn. 1994. Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. Biochem. Pharmacol. 48:595-608.
26. Finley, K. T. 1974. The addition and substitution chemistry of quinones, p. 878-1144. In S. Patai (ed.), The chemistry of the quinoid compounds. Wiley, London, England.
27. Goff, S. P. 1992. Genetics of retroviral integration. Annu. Rev. Genet. 26: 527-544.
28. Goulaouic, H., and S. A. Chow. 1996. Directed integration of viral DNA mediated by fusion proteins consisting of human immunodeficiency virus type 1 integrase and Escherichia coli LexA protein. J. Virol. 70:37-46.
29. Hazuda, D. J., P. J. Felock, J. C. Hastings, B. Pramanik, and A. L. Wolfe. 1997. Differential divalent cation requirements uncouple the assembly and catalytic reactions of human immunodeficiency virus type 1 integrase. J. Virol. 71:7005-7011.
30. Henderson, P. J. F. 1992. Statistical analysis of enzyme kinetic data. In D. Rickwood and B. Hames (ed.), Enzyme assays: a practical approach. IRL Press, Oxford, England.
31. Ho, D. D., A. U. Neumann, A. S. Perelson, W. Chen, J. M. Leonard, and M. Markowitz. 1995. Rapid turnover of plasma virions and CD4 lymphocytes in HIV-1 infection. Nature 373:123-126.
32. Johnson, M. S., M. A. McClure, D.-F. Feng, J. Gray, and R. F. Doolittle. 1986. Computer analysis of retroviral pol genes: assignment of enzymatic functions to specific sequences and homologies with nonviral enzymes. Proc. Natl. Acad. Sci. USA 83:7648-7652.
33. King, P. J., and W. E. Robinson, Jr. 1998. Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase. J. Virol. 72:8420-8424.
34. Kulkosky, J., K. S. Jones, R. A. Katz, J. P. G. Mack, and A. M. Skalka. 1992. Residues critical for retroviral integrative recombination in a region that is highly conserved among retroviral/retrotransposon integrases and bacterial insertion sequence transposases. Mol. Cell. Biol. 12:2331-2338.
35. LaFemina, R. L., P. L. Graham, K. LeGrow, J. C. Hastings, A. Wolfe, S. D. Young, E. A. Emini, and D. J. Hazuda. 1995. Inhibition of human immunodeficiency virus integrase by bis-catechols. Antimicrob. Agents Chemother. 39:320-324.
36. LaFemina, R. L., C. L. Schneider, H. L. Robbins, P. L. Callahan, K. LeGrow, E. Roth, W. A. Schleif, and E. A. Emini. 1992. Requirement of active human immunodeficiency virus type 1 integrase enzyme for productive infection of human T-lymphoid cells. J. Virol. 66:7414-7419.
37. Leavitt, A. D., L. Shiue, and H. E. Varmus. 1993. Site-directed mutagenesis of HIV-1 integrase demonstrates differential effects on integrase functions in vitro. J. Biol. Chem. 268:2113-2119.
38. Mazumder, A., N. Neamati, J. O. Ojwang, S. Sunder, R. F. Rando, and Y. Pommier. 1996. Inhibition of the human immunodeficiency virus type 1 integrase by guanosine quartet structures. Biochemistry 35:13762-13771.
39. Mazumder, A., N. Neamati, J. P. Sommadossi, G. Gosselin, R. F. Schinazi, J. L. Imbach, and Y. Pommier. 1996. Effects of nucleotide analogues on human immunodeficiency virus type 1 integrase. Mol. Pharmacol. 49:621-628.
40. Mazumder, A., N. Neamati, S. Sunder, J. Schulz, H. Pertz, E. Eich, and Y. Pommier. 1997. Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. J. Med. Chem. 40:3057-3063.
41. McDougall, B., P. J. King, B. W. Wu, Z. Hostomsky, M. G. Reinecke, and W. E. Robinson, Jr. 1998. Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. Antimicrob. Agents Chemother. 42:140-146.
42. Monks, T. J., R. P. Hanzlik, G. M. Cohen, D. Ross, and D. G. Graham. 1992. Quinone chemistry and toxicity. Toxicol. Appl. Pharmacol. 112:2-16.
43. Mouscadet, J.-F., S. Carteau, H. Goulaouic, F. Subra, and C. Auclair. 1994. Triplex-mediated inhibition of HIV DNA integration in vitro. J. Biol. Chem. 269:21635-21638.
44. Neamati, N., H. Hong, S. Sunder, G. W. A. Milne, and Y. Pommier. 1997. Potent inhibitors of human immunodeficiency virus type 1 integrase: identification of a novel four-point pharmacophore and tetracyclines as novel inhibitors. Mol. Pharmacol. 52:1041-1055.
45. Neamati, N., A. Mazumder, H. Zhao, S. Sunder, T. R. Burke, Jr., R. J. Schultz, and Y. Pommier. 1997. Diarylsulfones, a novel class of human immunodeficiency virus type 1 integrase inhibitors. Antimicrob. Agents Chemother. 41:385-393.
46. Paul, W. E. 1995. Reexamining AIDS research priorities. Science 267:633-636.
47. Perelson, A. S., A. U. Neumann, M. Markowitz, J. M. Leonard, and D. D. Ho. 1996. HIV-1 dynamics in vivo: virion clearance rate, infected cell life-span, and viral generation time. Science 271:1582-1586.
48. Polard, P., and M. Chandler. 1995. Bacterial transposases and retroviral integrases. Mol. Microbiol. 15:13-23.
49. Pommier, Y., A. A. Pilon, A. Mazumder, and N. Neamati. 1997. HIV-1 integrase as a target for antiviral drugs. Antivir. Chem. Chemother. 8:463-483.
50. Richman, D. D. 1996. HIV therapeutics. Science 272:1886-1888.
51. Robinson, W. E., Jr., M. Cordeiro, S. Abdel-Malek, Q. Jia, S. A. Chow, M. G. Reinecke, and W. M. Mitchell. 1996. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase. Mol. Pharmacol. 50: 846-855.
52. Robinson, W. E., Jr., M. G. Reinecke, S. Abdel-Malek, Q. Jia, and S. A. Chow. 1996. Inhibitors of HIV-1 replication that inhibits HIV integrase. Proc. Natl. Acad. Sci. USA 93:6326-6331.
53. Sakai, H., M. Kawamura, J.-I. Sakuragi, S. Sakuragi, R. Shibata, A. Ishimolo, N. Ono, S. Ueda, and A. Adachi. 1993. Integration is essential for efficient gene expression of human immunodeficiency virus type 1. J. Virol. 67:1169-1174.
54. Shibagaki, Y., M. L. Holmes, R. S. Appa, and S. A. Chow. 1997. Characterization of feline immunodeficiency virus integrase and analysis of functional domains. Virology 230:1-10.
55. Shin, C.-G., B. Taddeo, W. A. Haseltine, and C. M. Farnet. 1994. Genetic analysis of the human immunodeficiency virus type 1 integrase protein J. Virol. 68:1633-1642.
56. Shoemaker, C., J. Hoffman, S. P. Goff, and D. Baltimore. 1981. Intramolecular integration within Moloney murine leukemia virus. J. Virol. 40:164-172.
57. Talbott, R. L., E. E. Sparger, K. M. Lovelace, W. M. Fitch, N. C. Pedersen, P. A. Luciw, and J. H. Elder. 1989. Nucleotide sequence and genomic organization of feline immunodeficiency virus. Proc. Natl. Acad. Sci. USA 86:5743-5747.
58. Tse, D. C. S., R. L. McCreery, and R. N. Adams. 1976. Potential oxidative pathways of brain catecholamines. J. Med. Chem. 19:37-40.
59. van Gent, D., C. Vink, A. A. M. Oude Groeneger, and R. H. A. Plasterk. 1993. Complementation between HIV integrase proteins mutated in different domains. EMBO J. 12:3261-3267.
60. Vincent, K. A., V. Ellison, S. A. Chow, and P. O. Brown. 1993. Characterization of human immunodeficiency virus type 1 integrase expressed in Escherichia coli and analysis of variants with amino-terminal mutations. J. Virol. 67:425-437.
61. Vink, C., R. A. Puras Lutzke, and R. H. A. Plasterk. 1994. Formation of a stable complex between the human immunodeficiency virus integrase protein and viral DNA. Nucleic Acids Res. 22:4103-4110.
62. Wei, S.-Q., K. Mizuuchi, and R. Craigie. 1997. A large nucleoprotein assembly at the ends of the viral DNA mediates retroviral DNA integration. EMBO J. 16:7511-7520.
63. Wei, X., S. K. Ghosh, M. E. Taylor, V. A. Johnson, E. A. Emini, P. Deutsch, J. D. Lifson, S. Bonhoeffer, M. A. Nowak, B. H. Hahn, M. S. Saag, and G. M. Shaw. 1995. Viral dynamics in human immunodeficiency virus type 1 infection. Nature 373:117-122.
64. Zhao, H., N. Neamati, H. Hong, A. Mazumder, S. Wang, S. Sunder, G. W. A. Milne, Y. Pommier, and T. R. Burke, Jr. 1997. Coumarin-based inhibitors of HIV integrase. J. Med. Chem. 40:242-249.
65. Zhao, H., N. Neamati, A. Mazumder, S. Sunder, Y. Pommier, and T. R. Burke, Jr. 1997. Arylamide inhibitors of HIV-1 integrase. J. Med. Chem. 40:1186-1194.