Effects of Drug Resistance Mutations L100I and V106A on the Binding of Pyrrolobenzoxazepinone Nonnucleoside Inhibitors to the Human Immunodeficiency Virus Type 1 Reverse Transcriptase Catalytic Complex

Antimicrobial Agents and Chemotherapy

Volumn 48, Issue 5, 2004, Pages 1570-1580

  Locatelli, Giada A ^a   Campiani, Giuseppe ^b   Cancio, Reynel ^a   Morelli, Elena ^b   Ramunno, Anna ^b   Gemma, Sandra ^b   Hübscher, Ulrich ^c   Spadari, Silvio ^a   Maga, Giovanni ^a  

^a CNR   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOTIDE; PBO 269; PBO 354; PBO 355; PYRROLOBENZOXAZEPINONE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG EFFECT; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; ENERGY; ENZYME ACTIVITY; GENE MUTATION; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN INTERACTION; WILD TYPE;

ALGORITHMS; CATALYSIS; DNA, VIRAL; DNA-DIRECTED DNA POLYMERASE; DRUG RESISTANCE, VIRAL; HIV-1; HIV-1 REVERSE TRANSCRIPTASE; KINETICS; MUTATION; NUCLEIC ACIDS; REVERSE TRANSCRIPTASE INHIBITORS; RNA, VIRAL; THERMODYNAMICS;

EID: 2142827106     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.48.5.1570-1580.2004     Document Type: Article

References (37)

1. Archer, R. H., C. Dykes, P. Gerondelis, A. Lloyd, P. Fay, R. C. Reichman, R. A. Bambara, and L. M. Demeter. 2000. Mutants of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase resistant to nonnucleoside reverse transcriptase inhibitors demonstrate altered rates of RNase H cleavage that correlate with HIV-1 replication fitness in cell culture. J. Virol. 74:8390-8401.
2. Bacheler, L. T., E. D. Anton, P. Kudish, D. Baker, J. Bunville, K. Krakowski, L. Bolling, M. Aujay, X. V. Wang, D. Ellis, M. F. Becker, A. L. Lasut, H. J. George, D. R. Spalding, G. Hollis, and K. Abremski. 2000. Human immunodeficiency virus type 1 mutations selected in patients failing efavirenz combination therapy. Antimicrob. Agents Chemother. 44:2475-2484.
3. Bahar, I., B. Erman, R. L. Jernigan, A. R. Atilgan, and D. G. Covell. 1999. Collective motions in HIV-1 reverse transcriptase: examination of flexibility and enzyme function. J. Mol. Biol. 285:1023-1037.
4. Balzarini, J., A. Karlsson, C. Meichsner, A. Paessens, G. Riess, E. De Clercq, and J. P. Kleim. 1994. Resistance pattern of human immunodeficiency virus type 1 reverse transcriptase to quinoxaline S-2720. J. Virol. 68:7986-7992.
5. Boyer, P. L., J. Ding, E. Arnold, and S. H. Hughes. 1994. Drug resistance of human immunodeficiency virus type 1 reverse transcriptase: subunit specificity of mutations that confer resistance to nonnucleoside inhibitors in human immunodeficiency virus type 1 reverse transcriptase. Antimicrob. Agents Chemother. 38:1909-1914.
6. Boyer, P. L., A. L. Ferris, P. Clark, J. Whitmer, P. Frank, C. Tantillo, E. Arnold, and S. H. Hughes. 1994. Mutational analysis of the fingers and palm subdomains of human immunodeficiency virus type-1 (HIV-1) reverse transcriptase. J. Mol. Biol. 243:472-483.
7. Campiani, G., E. Morelli, M. Fabbrini, V. Nacci, G. Greco, E. Novellino, A. Ramunno, G. Maga, S. Spadari, G. Caliendo, A. Bergamini, E. Faggioli, I. Uccella, F. Bolacchi, S. Marini, M. Coletta, A. Nacca, and S. Caccia. 1999. Pyrrolobenzoxazepinone derivatives as non-nucleoside HIV-1 RT inhibitors: further structure-activity relationship studies and identification of more potent broad-spectrum HIV-1 RT inhibitors with antiviral activity. J. Med. Chem. 42:4462-4470.
8. Campiani, G., A. Ramunno, G. Maga, V. Nacci, C. Fattorusso, B. Catalanotti, E. Morelli, and E. Novellino. 2002. Non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors: past, present, and future perspectives. Curr. Pharm. Des. 8:615-657.
9. Crowe, S. 1999. New reverse transcriptase inhibitors. Adv. Exp. Med. Biol. 458:183-197.
10. De Clercq, E. 1994. New developments in the chemotherapy of lentivirus (human immunodeficiency virus) infections: sensitivity/resistance of HIV-1 to non-nucleoside HIV-1-specific inhibitors. Ann. N. Y. Acad. Sci. 724:438-456.
11. DeClercq, E. 1993. HIV-1-specific reverse transcriptase inhibitors: highly selective inhibitors of human immunodeficiency virus type 1 that are specifically targeted at the viral reverse transcriptase. Medicinal Res. Rev. 13:229-258.
12. Esnouf, R., J. Ren, C. Ross, Y. Jones, D. Stammers, and D. Stuart. 1995. Mechanism of inhibition of HIV-1 reverse transcriptase by non-nucleoside inhibitors. Nat. Struct. Biol. 2:303-308.
13. Fletcher, R. S., K. Syed, S. Mithani, G. I. Dmitrienko, and M. A. Parniak. 1995. Carboxanilide derivative non-nucleoside inhibitors of HIV-1 reverse transcriptase interact with different mechanistic forms of the enzyme. Biochemistry 34:4346-4353.
14. Harrington, M., and C. C. Carpenter. 2000. Hit HIV-1 hard, but only when necessary. Lancet 355:2147-2152.
15. Hsiou, Y., J. Ding, K. Das, A. D. Clark, Jr., S. H. Hughes, and E. Arnold. 1996. Structure of unliganded HIV-1 reverse transcriptase at 2.7 Å resolution: implications of conformational changes for polymerization and inhibition mechanisms. Structure 4:853-860.
16. Huang, H., R. Chopra, G. L. Verdine, and S. C. Harrison. 1998. Structure of a covalently trapped catalytic complex of HIV-1 reverse transcriptase: implications for drug resistance. Science 282:1669-1675.
17. Huang, H., S. C. Harrison, and G. L. Verdine. 2000. Trapping of a catalytic HIV reverse transcriptase template-primer complex through a disulfide bond. Chem. Biol. 7:355-364.
18. Hübscher, U., and S. Spadari. 1994. DNA replication and chemotherapy. Physiol. Rev. 74:259-304.
19. Jacobo-Molina, A., J. Ding, R. G. Nanni, A. D. Clark, Jr., X. Lu, C. Tantillo, R. L. Williams, G. Kamer, A. L. Ferris, P. Clark, et al. 1993. Crystal structure of human immunodeficiency virus type 1 reverse transcriptase complexed with double-stranded DNA at 3.0 Å resolution shows bent DNA. Proc. Natl. Acad. Sci. USA 90:6320-6324.
20. Jonckheere, H., J. Anne, and E. De Clercq. 2000. The HIV-1 reverse transcription (RT) process as target for RT inhibitors. Med. Res. Rev. 20:129-154.
21. Kati, W. M., K. A. Johnson, L. F. Jerva, and K. S. Anderson. 1992. Mechanism and fidelity of HIV reverse transcriptase. J. Biol. Chem. 267:25988-25997.
22. Kaufmann, G. R., and D. A. Cooper. 2000. Antiretroviral therapy of HIV-1 infection: established treatment strategies and new therapeutic options. Curr. Opin. Microbiol. 3:508-514.
23. Kohlstaedt, L. A. J. Wang, J. M. Friedman, P. A. Rice, and T. A. Steitz. 1992. Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed with an inhibitor. Science 256:1783-1790.
24. Maga, G., N. M. Amacker, Ruel, U. Hubscher, and S. Spadari. 1997. Resistance to nevirapine of HIV-1 reverse transcriptase mutants: loss of stabilizing interactions and thermodynamic or steric barriers are induced by different single amino acid substitutions. J. Mol. Biol. 274:738-747.
25. Maga, G., A. Ramunno, V. Nacci, G. A. Locatelli, S. Spadari, I. Fiorini, F. Baldanti, S. Paolucci, M. Zavattoni, A. Bergamini, B. Galletti, S. Muck, U. Hubscher, G. Giorgi, G. Guiso, S. Caccia, and G. Campiani. 2001. The stereoselective targeting of a specific enzyme-substrate complex is the molecular mechanism for the synergic inhibition of HIV-1 reverse transcriptase by (R)-(-)-PPO464: a novel generation of nonnucleoside inhibitors. J. Biol. Chem. 276:44653-44662.
26. Maga, G., and S. Spadari. 2002. Combinations against combinations: associations of anti-HIV 1 reverse transcriptase drugs challenged by constellations of drug resistance mutations. Curr. Drug Metab. 3:73-95.
27. Maga, G., D. Ubiali, R. Salvetti, M. Pregnolato, and S. Spadari. 2000. Selective interaction of the human immunodeficiency virus type 1 reverse transcriptase nonnucleoside inhibitor efavirenz and its thio-substituted analog with different enzyme-substrate complexes. Antimicrob. Agents Chemother. 44:1186-1194.
28. Moyle, G. 2001. The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy. Drugs 61:19-26.
29. O'Brien, W. A. 2000. Resistance against reverse transcriptase inhibitors. Clin. Infect. Dis. 30(Suppl. 2):S185-S192.
30. Ohtaka, H., A. Velazquez-Campoy, D. Xie, and E. Freire. 2002. Overcoming drug resistance in HIV-1 chemotherapy: the binding thermodynamics of amprenavir and TMC-126 to wild-type and drug-resistant mutants of the HIV-1 protease. Protein Sci. 11:1908-1916.
31. Rayner, M. M., B. Cordova, and D. A. Jackson. 1997. Population dynamics studies of wild-type and drug-resistant mutant HIV in mixed infections. Virology 236:85-94.
32. Ren, J., R. Esnouf, E. Garman, D. Somers, C. Ross, I. Kirby, J. Keeling, G. Darby, Y. Jones, D. Stuart, and D. Stammers. 1995. High resolution structures of HIV-1 RT from four RT-inhibitor complexes. Nat. Struct. Biol. 2:293-302.
33. Rodgers, D. W., S. J. Gamblin, B. A. Harris, S. Ray, J. S. Culp, B. Hellmig, D. J. Woolf, C. Debouck, and S. C. Harrison. 1995. The structure of unliganded reverse transcriptase from the human immunodeficiency virus type 1. Proc. Natl. Acad. Sci. USA 92:1222-1226.
34. Temiz, N. A., and I. Bahar. 2002. Inhibitor binding alters the directions of domain motions in HIV-1 reverse transcriptase. Proteins 49:61-70.
35. Vella, S., and L. Palmisano. 2000. Antiretroviral therapy: state of the HAART. Antivir. Res. 45:1-7.
36. Wang, D. P., R. C. Rizzo, J. Tirado-Rives, and W. L. Jorgensen. 2001. Antiviral drug design: computational analyses of the effects of the L100I mutation for HIV-RT on the binding of NNRTIs. Bioorg. Med. Chem. Lett. 11:2799-2802.
37. Weiser, T., M. Gassmann, P. Thommes, E. Ferrari, P. Hafkemeyer, and U. Hubscher. 1991. Biochemical and functional comparison of DNA polymerases alpha, delta, and epsilon from calf thymus. J. Biol. Chem. 266: 10420-10428.