Development of Resistance against Diketo Derivatives of Human Immunodeficiency Virus Type 1 by Progressive Accumulation of Integrase Mutations

Journal of Virology

Volumn 77, Issue 21, 2003, Pages 11459-11470

  Fikkert, Valery ^a   Van Maele, Bénédicte ^a   Vercammen, Jo ^b   Hantson, Anke ^a   Van Remoortel, Barbara ^a   Michiels, Martine ^a   Gurnari, Cristina ^a,c   Pannecouque, Christophe ^a   De Maeyer, Marc ^b   Engelborghs, Yves ^b   De Clercq, Erik ^a   Debyser, Zeger ^a   Witvrouw, Myriam ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 [5 (4 FLUOROBENZYL) 2 FURYL] 3 (1,2,4 TRIAZOL 3 YL) 1,3 PROPANEDIONE; 1,1' [1,4 PHENYLENEBIS(METHYLENE)]BIS(1,4,8,11 TETRAAZACYCLOTETRADECANE); DIKETONE; INTEGRASE; INTEGRASE INHIBITOR; L 708906; NEVIRAPINE; RITONAVIR; UNCLASSIFIED DRUG; V 165; ZIDOVUDINE;

ARTICLE; CONTROLLED STUDY; CROSS RESISTANCE; DRUG SENSITIVITY; ENZYME ACTIVITY; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; NUCLEOTIDE SEQUENCE; PHENOTYPE; PRIORITY JOURNAL; VIRUS DNA CELL DNA INTERACTION; VIRUS MUTATION; VIRUS REPLICATION; VIRUS STRAIN;

ACETOACETATES; ANTI-HIV AGENTS; CELL LINE; DRUG RESISTANCE, VIRAL; FURANS; HIV INTEGRASE; HIV INTEGRASE INHIBITORS; HIV-1; HUMANS; MODELS, MOLECULAR; MUTATION; RECOMBINATION, GENETIC; TRIAZOLES; VIRUS INTEGRATION; VIRUS REPLICATION;

EID: 10744226580     PISSN: 0022538X     EISSN: None     Source Type: Journal    
DOI: 10.1128/JVI.77.21.11459-11470.2003     Document Type: Article

References (37)

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. Billich, A. 2003. S-1360 Shionogi-GlaxoSmithKline. Curr. Opin. Investig. Drugs 4:206-209.
3. Bridger, G. J., R. T. Skerlj, S. Padmanabhan, S. A. Martellucci, G. W. Henson, S. Struyf, M. Witvrouw, D. Schols, and E. De Clercq. 1995. Synthesis and structure-activity relationship of phenylenebis(methylene)-linked bis-tetraazamacrocycles that inhibit HIV replication. Effect of heteroaromatic linkers on the activity of bicyclams. J. Med. Chem. 38:366-378.
4. Brown, P. O. 1997. Integration of retroviral DNA. Curr. Top. Microbiol. Immunol. 157:19-47.
5. Bushman, F. D., and R. Craigie. 1991. Activities of human immunodeficiency virus (HIV) integration protein in vitro: specific cleavage and integration of HIV DNA. Proc. Natl. Acad. Sci. USA 88:1339-1343.
6. Chen, J. C., J. Krucinski, L. J. Miercke, J. S. Finer-Moore, A. H. Tang, A. D. Leavitt, and R. M. Stroud. 2000. Crystal structure of the HIV-1 integrase catalytic core and C-terminal domains: a model for viral DNA binding. Proc. Natl. Acad. Sci. USA 97:8233-8238.
7. Cherepanov, P., J. A. Esté, R. F. Rando, J. O. Ojwang, G. Reekmans, R. Steinfeld, G. David, E. De Clercq, and Z. Debyser. 1997. Mode of interaction of G-quartets with the integrase of human immunodeficiency virus type 1 (HIV-1). Mol. Pharmacol. 52:771-780.
8. Chow, S. A., K. A. Vincent, V. Ellison, and P. O. Brown. 1992. Reversal of integration and DNA splicing mediated by integrase of HIV. Science 255:723-726.
9. Debyser, Z., P. Cherepanov, B. Van Maele, E. De Clercq, and M. Witvrouw. 2002. In search of authentic inhibitors of HIV-1 integration. Antivir. Chem. Chemother. 13:1-15.
10. Debyser, Z., P. Cherepanov, W. Pluymers, and E. De Clercq. 2001. Assays for the evaluation of HIV-1 integrase inhibitors. Methods Mol. Biol. 160:139-155.
11. De Clercq, E. 1995. Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J. Med. Chem. 38:2491-2517.
12. De Maeyer, M., J. Desmet, and I. Lasters. 2000. The dead-end elimination theorem: mathematical aspects, implementation, optimizations, evaluation, and performance. Methods Mol. Biol. 143:265-304.
13. Esté, J. A., D. Schols, K. De Vreese, P. Cherepanov, M. Witvrouw, C. Pannecouque, Z. Debyser, R. F. Rando, B. Clotet, J. Desmyter, and E. De Clercq. 1998. Human immunodeficiency virus glycoprotein gp120 as the primary target for the antiviral action of AR177 (zintevir). Mol. Pharmacol. 53:340-345.
14. Hazuda, D. J., P. Felock, M. Witmer, A. Wolfe, K. Stillmock, J. A. Grobler, A. Espeseth, L. Gabryelski, W. Schleif, C. Blau, and M. D. Miller. 2000. Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replication in cells. Science 287:646-650.
15. Horwitz, J. P., J. Chua, and M. Noel. 1964. Nucleosides. V. The monomesylates of 1-(2′-deoxy-β-D-lyxofuranosyl)thymidine. J. Org. Chem. 29:2076-2078.
16. Kikukawa, R., Y. Koyanagi, S. Harada, N. Kobayashi, M. Hatanaka, and N. Yamamoto. 1986. Differential susceptibility to the acquired immunodeficiency syndrome retrovirus in cloned cells of human leukemic T-cell line MOLT-4. J. Virol. 57:1159-1162.
17. 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.
18. King, P. J., D. J. Lee, R. A. Reinke, J. G. Victoria, K. Beale, and W. E. Robinson, Jr. 2003. Human immunodeficiency virus type 1 integrase containing a glycine to serine mutation at position 140 is attenuated for catalysis and resistant to integrase inhibitors. Virology 306:147-161.
19. Kuiken, C. L., B. Foley, B. Hahn, B. Korber, F. McCutchan, P. A. Marx, J. W. Mellors, J. I. Mullins, J. Sodroski, and S. Wolinsky. Human retroviruses and AIDS 2000: A compilation and analysis of nucleic acid and amino acid sequences. Theoretical Biology and Biophysics Group, Los Alamos National Laboratory, Los Alamos, N.Mex.
20. 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.
21. Miller, M. D., C. M. Farnet, and F. D. Bushman. 1997. Human immunodeficiency virus type 1 preintegration complexes: studies of organization and composition. J. Virol. 71:5382-5390.
22. Miyoshi, I., H. Taguchi, I. Kobonishi, S. Yoshimoto, Y. Ohtsuki, and Y. Shiraishi. 1982. Type C virus-producing cell lines derived from adult T cell leukemia. Gann. Monogr. 28:219-228.
23. Nakajima, N., R. Lu, and A. Engelman. 2001. Human immunodeficiency virus type 1 replication in the absence of integrase-mediated DNA recombination: definition of permissive and nonpermissive T-cell lines. J. Virol. 75:7944-7955.
24. Ojwang, J. O., R. W. Buckbeit, Y. Pommier, A. Mazumder, K. De Vreese, J. A. Esté, D. Reymen, L. A. Pallansch, C. Lackman-Smith, T. L. Wallace, E. De Clercq, M. S. McGrath, and R. F. Rando. 1995. T30177, an oligonucleotide stabilized by an intramolecular guanosine octet, is a potent inhibitor of laboratory strains and clinical isolates of human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 39:2426-2435.
25. Pannecouque, C., W. Pluymers, B. Van Maele, V. Tetz, P. Cherepanov, E. De Clercq, M. Witvrouw, and Z. Debyser. 2002. New class of HIV integrase inhibitors that block viral replication in cell culture. Curr. Biol. 12:1169-1177.
26. Pauwels, R., J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter, and E. De Clercq. 1988. Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J. Virol. Methods 20:309-321.
27. Pluymers, W., N. Neamati, C. Pannecouque, V. Fikkert, C. Marchand, T. R. Burke, Y. Pommier, D. Scols, E. De Clercq, Z. Debyser, and M. Witvrouw. 2000. Viral entry as the primary target for the anti-HIV activity of chicoric acid and its tetra-acetyl esters. Mol. Pharmacol. 58:641-648.
28. Pluymers, W., G. Pais, C. Pannecouque, V. Fikkert,Y. Pommier, T. R. Burke, Jr., E. De Clercq, M. Witvrouw, N. Neamati, and Z. Debyser. 2002. Inhibition of human immunodeficiency virus type 1 (HIV-1) integrase activity and HIV-1 replication by a series of diketo derivatives. Antimicrob. Agents Chemother. 46:3292-3297.
29. Pommier, Y., and N. Neamati. 1999. Inhibitors of human immunodeficiency virus integrase. Adv. Virus Res. 52:427-458.
30. Popovic, M., M. G. Sarngadharan, E. Read, and R. C. Gallo. 1984. Detection, isolation, and continuous production of cytopathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS. Science 224:497-500.
31. Richman, D. D. 2001. HIV chemotherapy. Nature 410:995-1001.
32. 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.
33. Sakai, H., M. Kawamura, J. Sakugari, S. Sakugari, R. Shibata, A. Ishimoto, 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.
34. Sherman, P. A., and J. A. Fyfe. 1990. Human immunodeficiency virus integration protein expressed in Escherichia coli possesses selective DNA cleaving activity. Proc. Natl. Acad. Sci. USA 87:5119-5123.
35. Wang, J. Y., H. Ling, W. Yang, and R. Craigie. 2001. Structure of a two-domain fragment of HIV-1 integrase: implications for domain organization in the intact protein. EMBO J. 20:7333-7343.
36. Yoder, K. E., and F. D. Bushman. 2000. Repair of gaps in retroviral DNA integration intermediates. J. Virol. 74:11191-11200.
37. Young, S. D. 2001. Inhibition of HIV-1 integrase by small molecules: the potential for a new class of AIDS chemotherapeutics. Curr. Opin. Drug Discov. Dev. 4:402-410.