Antiviral properties of palinavir, a potent inhibitor of the human immunodeficiency virus type 1 protease

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 5, 1997, Pages 965-971

  Lamarre, D ^a,b,d   Croteau, G ^a   Wardrop, E ^a   Bourgon, L ^a   Thibeault, D ^a   Clouette, C ^a   Vaillancourt, M ^b   Cohen, E ^b   Pargellis, C ^c   Yoakim, C ^d   Anderson, P C ^d  

^a Department of Biochemistry ^*  (Canada)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

^c BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^d BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DIDANOSINE; NEVIRAPINE; PALINAVIR; PROTEINASE INHIBITOR; ZIDOVUDINE;

ANTIBIOTIC RESISTANCE; ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENTIATION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; PRIORITY JOURNAL; VIRUS INHIBITION;

EID: 0030902238     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.5.965     Document Type: Article

References (52)

1. Aldovini, A., and B. D. Walker. 1990. Virus production in stable cell lines, quantitative assays for virus infectivity, p. 66-69 and 71-76. In A. Aldovini and B. D. Walker (ed.), Techniques in HIV research. Stockton Press, New York, N.Y.
2. Anderson, P. C., and C. Yoakim. Unpublished data.
3. Bechtold, C. M., A. K. Patick, M. Alam, J. Greytok, J. A. Tino, P. Chen, E. Gordon, S. Ahmad, J. C. Barrish, R. Zahler, P.-F. Lin, and R. Colonno. 1995. Antiviral properties of aminodiol inhibitors against human immunodeficiency virus and protease. Antimicrob. Agents Chemother. 39:374-379.
4. Betageri, R., J. L. Hopkins, D. Thibeault, M. J. Emmanuel, G. C. Chow, M. T. Skoog, P. deDreu, and K. A. Cohen. 1993. Rapid, sensitive and efficient HPLC assays for HIV-1 proteinase. Biochem. Biophys. Methods 27:191-197.
5. 1 acid glycoprotein reduces uptake, intracellular concentration, and antiviral activity of A-80987, an inhibitor of the human immunodeficiency virus type 1 protease. Antimicrob. Agents Chemother. 40:1491-1497.
6. Bilello, J. A., P. A. Bilello, M. Prichard, T. Robins, and G. L. Drusano. 1995. Reduction of the in vitro activity of A77003, an inhibitor of human immunodeficiency virus protease, by human serum α1 acid glycoprotein. J. Infect. Dis. 171:546-551.
7. Billich, A., G. Fricker, I. Müller, P. Donatsch, P. Ettmayer, H. Gstach, P. Lehr, P. Peichl, D. Scholz, and B. Rosenwirth. 1995. SDZ PRI 053, an orally bioavailable human immunodeficiency virus type 1 proteinase inhibitor containing the 2-aminobenzylstatine moiety. Antimicrob. Agents Chemother. 39:1406-1413.
8. Bryant, M., D. Getman, M. Smidt, J. Marr, M. Clare, R. Dillard, D. Lansky, G. DeCrescenzo, R. Heintz, K. Houseman, K. Reed, J. Stolzenbach, J. Talley, M. Vazquez, and R. Mueller. 1995. SC-52151, a novel inhibitor of the human immunodeficiency virus protease. Antimicrob. Agents Chemother. 39:2229-2234.
9. Chokekijchai, S., T. Shirasaka, J. N. Weinstein, and H. Mitsuya. 1995. In vitro anti-HIV-1 activity of HIV protease inhibitor KNI-272 in resting and activated cells: implications for its combined use with AZT or ddI. Antivir. Res. 28:25-38.
10. Chou, T. C., and P. Talalay. 1984. Quantitative analysis of dose-effect relationships: the combined effect of multiple drugs or enzyme inhibitors. Adv. Enzyme Regul. 22:27-55.
11. Condra, J. H., W. A. Schleif, O. M. Blahy, L. J. Gabryelski, D. J. Graham, J. C. Quintero, A. Rhodes, H. L. Robbins, E. Roth, M. Shivaprakash, D. Titus, T. Yang, H. Teppler, K. E. Squires, P. J. Deutsch, and E. A. Emini. 1995. In vivo emergence of HIV-1 variants resistant to multiple protease inhibitors. Nature 374:569-571.
12. Croteau, G., L. Doyon, D. Thibeault, G. McKercher, L. Pilote, and D. Lamarre. 1997. Impaired fitness of human immunodeficiency virus type 1 variants with high-level resistance to protease inhibitors. J. Virol. 71:1089-1096.
13. Daniel, M. D., N. L. Letvin, N. W. King, M. Kannagi, P. K Sehgal, R. D. Hunt, P. J. Kanki, M. Essex, and R. C. Desrosiers. 1985. Isolation of T-cell tropic HTLF-III-like retrovirus from macaques. Science 228:1201-1204.
14. Danner, S. A., A. Carr, J. M. Leonard, L. M. Lehman, F. Gudiol, J. Gonzales, A. Raventos, R. Rubio, E. Bouza, V. Pintado, A. Gil Aguado, J. Garcia de Lomas, R. Delgado, J. C. C. Borleffs, A. Hsu, J. M. Valdes, C. A. B. Boucher, and D. A. Cooper. 1995. A short-term study of the safety, pharmacokinetics, and efficacy of Ritonavir, an inhibitor of HIV-1 protease. N. Engl. J. Med. 333:1528-1533.
15. Darke, P. A., and J. R. Huff. 1994. HIV protease as an inhibitor target for the treatment of AIDS. Adv. Pharmacol. 25:399-454.
16. Debouck, C. 1992. The HIV-1 protease as a therapeutic target for AIDS. AIDS Res. Hum. Retroviruses 8:153-164.
17. Doyon, L., G. Croteau, D. Thibeault, F. Poulin, L. Pilote, and D. Lamarre. 1996. Second locus involved in human immunodeficiency virus type 1 resistance to protease inhibitors. J. Virol. 70:3763-3769.
18. Folks, T. M., J. Justement, A. Kinter, C. A. Dinarello, and A. S. Fauci. 1987. Cytokine-induced expression of HIV-1 in a chronically infected promonocyte cell line. Science 238:800-802.
19. Galpin, S., N. A. Roberts, T. O'Connor, D. J. Jeffries, and D. Kinchington. 1994. Antiviral properties of the HIV-1 proteinase inhibitor Ro 31-8959.
20. Geleziunas, R., E. J. Arts, F. Boulerice, H. Goldman, and M. A. Wainberg. 1993. Effect of 3′-azido-3′-deoxythymidine on human immunodeficiency virus type 1 replication in human fetal brain macrophages. Antimicrob. Agents Chemother. 37:1305-1312.
21. Gendelman, H. E., J. M. Orenstein, L. M. Baca, B. Weiser, H. Burger, D. C. Kalter, and M. S. Meltzer. 1989. The macrophage in the persistence and pathogenesis of HIV infection. AIDS 3:475-495.
22. Gendelman, H. E., J. M. Orenstein, M. A. Martin, C. Ferrua, R. Mitra, T. Phipps, L. A. Wahl, H. C. Lane, A. S. Fauci, D. S. Burke, D. Skillman, and M. S. Meltzer. 1988. Efficient isolation and propagation of human immunodeficiency virus on recombinant colony-stimulating factor 1-treated monocytes J. Exp. Med. 167:1428-1441.
23. Hirsch, M. S., and R. T. D'Aquila. 1993. Therapy for human immunodeficiency virus infection. N. Engl. J. Med. 328:1686-1695.
24. 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.
25. Jacobsen, H. 1995. Resistance to protease inhibitors in vivo. Int. Antivir. News 3:S9.
26. Keirns, J., J. Jaramillo, and P. C. Anderson. Unpublished data.
27. Kempf, D. J., K. C. Marsh, E. Mcdonald, S. Vasavanonda, C. A. Flentge, B. E. Green, L. Fino, C. H. Park, X. P. Kong, N. E. Wideburg, A. Saldivar, L. Ruiz, W. M. Kati, H. L. Sham, T. Robins, K. D. Stewart, A. Hsu, J. J. Plattner, J. M. Leonard, and D. W. Norbeck. 1995. ABT-538 is a potent inhibitor of human immunodeficiency virus protease and has high oral bioavailability in humans. Proc. Natl. Acad. Sci. USA 92:2484-2488.
28. Kitchen, V. S., C. Skinner, K. Ariyoshi, E. A. Lane, I. B. Duncan, J. Burckhardt, H. U. Burger, K. Bragman, A. J. Pinching, and J. N. Weber. 1995. Safety and activity of suquinavir in HIV infection. Lancet 345:952-955.
29. Kohl, N. E., E. A. Emini, W. A. Schleiff, L. J. Davis, J. C. Heimbach, R. A. F. Dixon, E. M. Scolnick, and I. S. Sigal. 1988. Active human immunodeficiency virus protease is required for viral infectivity. Proc. Natl. Acad. Sci. USA 85:4686-4690.
30. Lam, P. Y. S., P. K. Jadhav, C. J. Eyeremann, C. N. Hodge, Y. Ru, L. T. Bacheler, J. L. Meek, M. J. Otto, M. M. Rayner, Y. N. Wong, C. H. Chang, P. C. Weber, D. A. Jackson, T. R. Sharpe, and S. Erickson-Viitanen. 1994. Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors. Science 263:380-384.
31. Lamarre, D., D. Doyon, G. Croteau, E. Wardrop, L. Pilote, G. McKercher, and D. Thibeault. 1995. Molecular basis of HIV-1 resistance to protease inhibitors. Structural flexibility of the prolease and second-site compensatory mutations in cleavage sites, abstr. 62. In Fourth International Workshop on HIV Drug Resistance, Sardinia, Italy, 6 to 9 July.
32. Larder, B. A., G. Darby, and D. D. Richman. 1989. HIV with reduced sensitivity to zidovudine (AZT) isolated during prolonged therapy. Science 243:1731-1734.
33. Markowitz, M., M. Saag, W. G. Powderly, A. M. Hurley, A. Hsu, J. M. Valdes, D. Henry, F. Sattler, A. La Marca, J. M. Leonard, and D. D. Ho. 1995. A preliminary study of Ritonavir, an inhibitor of HIV-1 protease, to treat HIV-1 infection. N. Engl. J. Med. 333:1534-1539.
34. Molla, A., M. Korneyeva, Q. Gao, S. Vasavanonda, P. J. Schipper, H.-M. Mo, M. Markowitz, T. Chernyavskiy, P. Niu, N. Lyons, A. Hsu, G. R. Granncman, D. D. Ho, C. A. B. Boucher, J. M. Leonard, D. W. Norbeck, and D. J. Kempf. 1996. Ordered accumulation of mutations in HIV protease confers resistance to ritonavir. Nature Med. 2:760-766.
35. Morrison, J. F., and C. T. Walsh. 1988. The behavior and significance of slow-binding enzyme inhibitors. Adv. Enzymol. 61:201-301.
36. Morrison, J. F., and S. R. Stone. 1985. Approaches to the study and analysis of the inhibition of enzymes by slow- and tight-binding inhibitors. Comments Mol. Cell. Biophys. 2:347-368.
37. Mosmann, T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65:55-63.
38. Moyle, G., and B. Gazzard. 1996. Current knowledge and future prospects for the use of HIV protease inhibitors. Drugs 51:701-712.
39. mac. J. Virol. 62:4691-4696.
40. Noble, S., and D. Faulds. 1996. Saquinavir: a review of its pharmacology and clinical potential in the management of HIV infection. Drugs 52:93-112.
41. Pargellis, C. A., M. M. Morelock, E. T. Graham, P. Kinkade, S. Pav, K. Lubbe, D. Lamarre, and P. C. Anderson. 1994. Determination of kinetic rate constants for the binding of inhibitors to HIV-1 protease and for the association and dissociation of active homodimer. Biochemistry 33:12527-12534.
42. Pav, S., K. Lubbe, F. Dô, D. Lamarre, C. A. Pargellis, and L. Tong. 1994. Microtube batch protein crystallization: applications to human immunodeficiency virus type 2 (HIV-2) protease and human renin. Proteins Struct. Funct. Genet. 20:98-102.
43. 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.
44. Popovic, M., E. Read-Connole, and R. C. Gallo. 1984. T4 positive human neoplastic cell lines susceptible to and permissive for HTLV-III. Lancet ii:1472-1473.
45. Ratner, L., W. Haseltine, R. Patarca, K. J. Livak, B. Starcich, S. F. Josephs, E. R. Doran, J. A. Rafalski, E. A. Whitehorn, K. Baumeister, L. Ivanoff, S. R. Petteway, Jr., M. L. Pearson, J. A. Lautenberger, T. S. Papas, J. Ghrayeb, N. T. Chang, R. C. Gallo, and F. Wong-Staal. 1985. Complete nucleotide sequence of the AIDS virus, HTLV-III. Nature 313:277-284.
46. Richman, D., C.-K. Shih, I. Lowy, J. Rose, P. Prodanovich, S. Goff, and J. Griffin. 1991. Human immunodeficiency virus type 1 mutants resistant to nonnucleoside inhibitors of reverse transcriptase arise in tissue culture. Proc. Natl. Acad. Sci. USA 88:11241-11245.
47. Roberts, N. A., J. A. Martin, D. Kinchington, A. V. Broadhurst, J. C. Craig, I. B. Duncan, S. A. Galpin, B. K. Handa, J. Kay, A. Krohn, R. W. Lambert, J. H. Merrett, J. S. Mills, K. E. B. Parks, S. Redshaw, A. J. Ritchie, D. L. Taylor, G. J. Thomas, and P. Machin. 1990. Rational design of peptide-based HIV protcinasc inhibitors. Science 248:358-361.
48. Shaw, G. M., B. H. Hahn, S. K. Arya, J. E. Groopman, R. C. Gallo, and F. Wong-Staal. 1984. Molecular characterization of human T-cell leukemia (lymphotropic) virus type III in the acquired immune deficiency syndrome. Science 226:1165-1170.
49. Tong, L. S. Pav, S. Mui, D. Lamarre, C. Yoakim, P. Beaulieu, and P. C. Anderson. 1995. Crystal structures of HIV-2 protease in complex with inhibitors containing the hydroxyethylamine dipeptide isostere. Structure 3:33-40.
50. Vacca, J. P., B. D. Dorsey, W. A. Schleif, R. B. Levin, S. L. McDaniel, P. L. Darke, J. Zugay, J. C. Quintero, O. M. Blahy, E. Roth, V. V. Sardana, A. J. Schlabach, P. I. Graham, J. H. Condra, L. Gotlib, M. K. Holloway, J. Lin, I.-W. Chen, K. Vastag, D. Ostovic, P. S. Anderson, E. A. Emini, and J. R. Huff. 1994. L-735,524: an orally bioavailable human immunodeficiency virus type 1 protease inhibitor. Proc. Natl. Acad. Sci. USA 91:4096-4100.
51. 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.
52. Wlodawer, A., and J. Erickson. 1993. Structure-based inhibitors of HIV-1 protease. Annu. Rev. Biochem. 62:543-585.