Novel HIV-1 protease inhibitors (PIs) containing a bicyclic P2 functional moiety, tetrahydropyrano-tetrahydrofuran, that are potent against multi-PI-resistant HIV-1 variants

Antimicrobial Agents and Chemotherapy

Volumn 55, Issue 4, 2011, Pages 1717-1727

  Ide, Kazuhiko ^a   Aoki, Manabu ^a,b   Amano, Masayuki ^a   Koh, Yasuhiro ^a   Yedidi, Ravikiran S ^c   Das, Debananda ^c   Leschenko, Sofiya ^d   Chapsal, Bruno ^d   Ghosh, Arun K ^d   Mitsuya, Hiroaki ^a,c  

^a KUMAMOTO UNIVERSITY   (Japan)

^b KUMAMOTO HEALTH SCIENCE UNIVERSITY   (Japan)

^c NATIONAL CANCER INSTITUTE   (United States)

^d PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPRENAVIR; DARUNAVIR; GRL 1398; GRL 388; LEUCINE; PHENYLALANINE; PROTEINASE; PROTEINASE INHIBITOR; TETRAHYDROFURAN; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANTIVIRAL ACTIVITY; ANTIVIRAL SUSCEPTIBILITY; ARTICLE; CONCENTRATION (PARAMETERS); DRUG POTENCY; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; IN VITRO STUDY; MULTIDRUG RESISTANCE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION; VIRUS RESISTANCE; VIRUS STRAIN;

ANIMALS; CARBAMATES; CELL LINE; CERCOPITHECUS AETHIOPS; COS CELLS; DRUG RESISTANCE, VIRAL; FURANS; HIV PROTEASE INHIBITORS; HIV-1; HUMANS; PYRANS; SULFONAMIDES;

EID: 79953204965     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.01540-10     Document Type: Article

References (37)

1. Amano, M., et al. 2007. A novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI), GRL-98065, is potent against multiple-PI-resistant human immunodeficiency virus in vitro. Antimicrob. Agents Chemother. 51:2143-2155.
2. Bastiaens, P. I., and T. M. Jovin. 1996. Microspectroscopic imaging tracks the intracellular processing of a signal transduction protein: fluorescent-labeled protein kinase C beta I. Proc. Natl. Acad. Sci. U. S. A. 93:8407-8412.
3. Bastiaens, P. I., I. V. Majoul, P. J. Verveer, H. D. Soling, and T. M. Jovin. 1996. Imaging the intracellular trafficking and state of the AB5 quaternary structure of cholera toxin. EMBO J. 15:4246-4253.
4. Collaborative Computational Project, Number 4. 1994. The CCP4 suite: programs for protein crystallography. Acta Crystallogr. D50:760-763.
5. De Meyer, S., et al. 2005. TMC114, a novel human immunodeficiency virus type 1 protease inhibitor active against protease inhibitor-resistant viruses, including a broad range of clinical isolates. Antimicrob. Agents Chemother. 49:2314-2321.
6. De Meyer, S., et al. 2008. Resistance profile of darunavir: combined 24-week results from the POWER trials. AIDS Res. Hum. Retrovir. 24:379-388.
7. Fang, G., B. Weiser, A. Visosky, T. Moran, and H. Burger. 1999. PCR-mediated recombination: a general method applied to construct chimeric infectious molecular clones of plasma-derived HIV-1 RNA. Nat. Med. 5:239-242.
8. Friesner, R. A., et al. 2004. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J. Med. Chem. 47:1739-1749.
9. Friesner, R. A., et al. 2006. Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. J. Med. Chem. 49:6177-6196.
10. Gatanaga, H., et al. 2002. Amino acid substitutions in Gag protein at noncleavage sites are indispensable for the development of a high multitude of HIV-1 resistance against protease inhibitors. J. Biol. Chem. 277:5952-5961.
11. Ghosh, A. K., et al. 2008. Design and synthesis of stereochemically defined novel spirocyclic P2-ligands for HIV-1 protease inhibitors. Org. Lett. 10: 5135-5138.
12. Ghosh, A. K., et al. 2008. Flexible cyclic ethers/polyethers as novel P2-ligands for HIV-1 protease inhibitors: design, synthesis, biological evaluation, and protein-ligand X-ray studies. J. Med. Chem. 51:6021-6033.
13. Ghosh, A. K., et al. 2010. Synthesis and biological evaluation of novel allophenylnorstatine-based HIV-1 protease inhibitors incorporating high-affinity P2-ligands. Bioorg. Med. Chem. Lett. 20:1241-1246.
14. Ghosh, A. K., et al. 2008. Potent HIV-1 protease inhibitors incorporating meso-bicyclic urethanes as P2-ligands: structure-based design, synthesis, biological evaluation and protein-ligand X-ray studies. Org. Biomol. Chem. 6:3703-3713.
15. Ghosh, A. K., et al. 1998. Potent HIV protease inhibitors incorporating high-affinity P2-ligands and (R)-(hydroxyethylamino)sulfonamide isostere. Bioorg. Med. Chem. Lett. 8:687-690.
16. Ghosh, A. K., S. Leshchenko, and M. Noetzel. 2004. Stereoselective photochemical 1,3-dioxolane addition to 5-alkoxymethyl-2(5H)-furanone: synthesis of bis-tetrahydrofuranyl ligand for HIV protease inhibitor UIC-94017 (TMC-114). J. Org. Chem. 69:7822-7829. (Pubitemid 39507385)
17. Koh, Y., et al. 2010. In vitro selection of highly darunavir-resistant and replication-competent HIV-1 variants by using a mixture of clinical HIV-1 isolates resistant to multiple conventional protease inhibitors. J. Virol. 84:11961-11969.
18. Koh, Y., et al. 2007. Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization. J. Biol. Chem. 282:28709-28720.
19. Koh, Y., et al. 2003. Novel bis-tetrahydrofuranylurethane-containing non-peptidic protease inhibitor (PI) UIC-94017 (TMC114) with potent activity against multi-PI-resistant human immunodeficiency virus in vitro. Antimicrob. Agents Chemother. 47:3123-3129.
20. Lohse, N., et al. 2007. Survival of persons with or without HIV infection in Denmark, 1995-2005. Ann. Intern. Med. 146:87-95.
21. Madruga, J. V., et al. 2007. Efficacy and safety of darunavir-ritonavir compared with that of lopinavir-ritonavir at 48 weeks in treatment-experienced, HIV-infected patients in TITAN: a randomised controlled phase III trial. Lancet 370:49-58. (Pubitemid 47023100)
22. Maeda, K., et al. 2001. Novel low-molecular-weight spirodiketopiperazine derivatives potently inhibit R5 HIV-1 infection through their antagonistic effects on CCR5. J. Biol. Chem. 276:35194-35200.
23. Miller, J. F., et al. 2006. Ultra-potent P1 modified arylsulfonamide HIV protease inhibitors: the discovery of GW0385. Bioorg. Med. Chem. Lett. 16:1788-1794.
24. Mitsuya, Y., T. F. Liu, S. Y. Rhee, W. J. Fessel, and R. W. Shafer. 2007. Prevalence of darunavir resistance-associated mutations: patterns of occurrence and association with past treatment. J. Infect. Dis. 196:1177-1179.
25. Ortiz, R., et al. 2008. Efficacy and safety of once-daily darunavir/ritonavir versus lopinavir/ritonavir in treatment-naive HIV-1-infected patients at week 48. AIDS 22:1389-1397.
26. Reference deleted.
27. Sekar, R. B., and A. Periasamy. 2003. Fluorescence resonance energy transfer (FRET) microscopy imaging of live cell protein localizations. J. Cell Biol. 160:629-633. (Pubitemid 36298259)
28. Shirasaka, T., et al. 1995. Emergence of human immunodeficiency virus type 1 variants with resistance to multiple dideoxynucleosides in patients receiving therapy with dideoxynucleosides. Proc. Natl. Acad. Sci. U. S. A. 92:2398-2402.
29. Szczesna-Skorupa, E., B. Mallah, and B. Kemper. 2003. Fluorescence resonance energy transfer analysis of cytochromes P450 2C2 and 2E1 molecular interactions in living cells. J. Biol. Chem. 278:31269-31276.
30. Tamiya, S., S. Mardy, M. F. Kavlick, K. Yoshimura, and H. Mistuya. 2004. Amino acid insertions near Gag cleavage sites restore the otherwise compromised replication of human immunodeficiency virus type 1 variants resistant to protease inhibitors. J. Virol. 78:12030-12040. (Pubitemid 39390787)
31. Tie, Y., et al. 2004. High resolution crystal structures of HIV-1 protease with a potent non-peptide inhibitor (UIC-94017) active against multidrug-resistant clinical strains. J. Mol. Biol. 338:341-352.
32. Tojo, Y., et al. 2010. Novel protease inhibitors (PIs) containing macrocyclic components and 3(R),3a(S),6a(R)-bis-tetrahydrofuranylurethane that are potent against multi-PI-resistant HIV-1 variants in vitro. Antimicrob. Agents Chemother. 54:3460-3470.
33. Walensky, R. P., et al. 2006. The survival benefits of AIDS treatment in the United States. J. Infect. Dis. 194:11-19.
34. Watkins, T., W. Resch, D. Irlbeck, and R. Swanstrom. 2003. Selection of high-level resistance to human immunodeficiency virus type 1 protease inhibitors. Antimicrob. Agents Chemother. 47:759-769.
35. Yates, P. J., et al. 2006. In vitro development of resistance to human immunodeficiency virus protease inhibitor GW640385. Antimicrob. Agents Chemother. 50:1092-1095.
36. Yoshimura, K., et al. 2002. A potent human immunodeficiency virus type 1 protease inhibitor, UIC-94003 (TMC-126), and selection of a novel (A28S) mutation in the protease active site. J. Virol. 76:1349-1358. (Pubitemid 34066437)
37. Yoshimura, K., et al. 1999. JE-2147: a dipeptide protease inhibitor (PI) that potently inhibits multi-PI-resistant HIV-1. Proc. Natl. Acad. Sci. U. S. A. 96:8675-8680.