In vitro resistance to the human immunodeficiency virus type 1 maturation inhibitor PA-457 (Beviriniat)

Journal of Virology

Volumn 80, Issue 22, 2006, Pages 10957-10971

  Adamson, Catherine S ^a   Ablan, Sherimay D ^a   Boeras, Ioana ^b   Goila Gaur, Ritu ^a   Soheilian, Ferri ^c   Nagashima, Kunio ^c   Li, Feng ^d   Salzwedel, Karl ^d   Sakalian, Michael ^b   Wild, Carl T ^d   Freed, Eric O ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b UNIVERSITY OF OKLAHOMA COLLEGE OF MEDICINE   (United States)

^c SAIC FREDERICK INC   (United States)

^d Panacos Pharmaceuticals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 O (3,3 DIMETHYLSUCCINYL)BETULIC ACID; AMINO ACID; BETULIC ACID; BEVIRIMAT; GAG PROTEIN; HISTIDINE; LEUCINE; METHIONINE; PHENYLALANINE; SPACER PEPTIDE 1; TYROSINE; UNCLASSIFIED DRUG; VIRUS PROTEIN;

AMINO ACID SUBSTITUTION; ARTICLE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; DOSE RESPONSE; DRUG MECHANISM; EVOLUTION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IN VITRO STUDY; NONHUMAN; PHENOTYPE; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN PROCESSING; VIRION; VIROGENESIS; VIRUS CAPSID; VIRUS CULTURE; VIRUS MUTANT; VIRUS MUTATION; VIRUS REPLICATION; VIRUS RESISTANCE;

AMINO ACID SUBSTITUTION; ANTI-HIV AGENTS; CAPSID PROTEINS; DNA MUTATIONAL ANALYSIS; DRUG RESISTANCE, VIRAL; HIV-1; HUMANS; JURKAT CELLS; MICROSCOPY, ELECTRON, TRANSMISSION; MUTATION, MISSENSE; SUCCINATES; SUPPRESSION, GENETIC; TRITERPENES; VIRAL PROTEINS; VIRION; VIRUS ASSEMBLY; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1; MIRIDAE;

EID: 33750695698     PISSN: 0022538X     EISSN: None     Source Type: Journal    
DOI: 10.1128/JVI.01369-06     Document Type: Article

References (48)

1. Abdurahman, S., S. Hoglund, L. Goobar-Larsson, and A. Vahlne. 2004. Selected amino acid substitutions in the C-terminal region of human immunodeficiency virus type 1 capsid protein affect virus assembly and release. J Gen. Virol. 85:2903-2913.
2. Aberham, C., S. Weber, and W. Phares. 1996. Spontaneous mutations in the human immunodeficiency virus type 1 gag gene that affect viral replication in the presence of cyclosporins. J. Virol. 70:3536-3544.
3. Accola, M. A., S. Hoglund, and H. G. Gottlinger. 1998. A putative alpha-helical structure which overlaps the capsid-p2 boundary in the human immunodeficiency virus type 1 Gag precursor is crucial for viral particle assembly. J. Virol. 72:2072-2078.
4. 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.
5. Adamson, C. S., and I. M. Jones. 2004. The molecular basis of HIV capsid assembly-five years of progress. Rev. Med. Virol. 14:107-121.
6. Baldwin, C. E., R. W. Sanders, Y. Deng, S. Jurriaans, J. M. Lange, M. Lu, and B. Berkhout. 2004. Emergence of a drug-dependent human immunodeficiency virus type 1 variant during therapy with the T20 fusion inhibitor. J. Virol. 78:12428-12437.
7. Erickson-Viitanen, S., J. Manfredi, P. Viitanen, D. E. Tribe, R. Tritch, C. A. Hutchison III, D. D. Loeb, and R. Swanstrom. 1989. Cleavage of HIV-1 gag polyprotein synthesized in vitro: sequential cleavage by the viral protease. AIDS Res. Hum. Retroviruses 5:577-591.
8. Freed, E. O. 1998. HIV-1 Gag proteins: diverse functions in the virus life cycle. Virology 251:1-15.
9. Freed, E. O., and M. A. Martin. 1994. Evidence for a functional interaction between the V1/V2 and C4 domains of human immunodeficiency virus type 1 envelope glycoprotein gp120. J. Virol. 68:2503-2512.
10. Freed, E. O., J. M. Orenstein, A. J. Buckler-White, and M. A. Martin. 1994. Single amino acid changes in the human immunodeficiency virus type 1 matrix protein block virus particle production. J. Virol. 68:5311-5320.
11. Fujioka, T., Y. Kashiwada, R. E. Kilkuskie, L. M. Cosentino, L. M. Ballas, J. B. Jiang, W. P. Janzen, I. S. Chen, and K. H. Lee. 1994. Anti-AIDS agents, 11-betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids. J. Nat. Prod. 57:243-247.
12. Gamble, T. R., F. F. Vajdos, S. Yoo, D. K. Worthylake, M. Houseweart, W. I. Sundquist, and C. P. Hill. 1996. Crystal structure of human cyclophilin A bound to the amino-terminal domain of HIV-1 capsid. Cell 87:1285-1294.
13. Gamble, T. R., S. Yoo, F. F. Vajdos, U. K. von Schwedler, D. K. Worthylake, H. Wang, J. P. McCutcheon, W. I. Sundquist, and C. P. Hill. 1997. Structure of the carboxyl-terminal dimerization domain of the HIV-1 capsid protein. Science 278:849-853.
14. Guo, X., and C. Liang. 2005. Opposing effects of the M368A point mutation and deletion of the SP1 region on membrane binding of human immunodeficiency virus type 1 Gag. Virology 335:232-241.
15. Guo, X., A. Roldan, J. Hu, M. A. Wainberg, and C. Liang. 2005. Mutation of the SP1 sequence impairs both multimerization and membrane-binding activities of human immunodeficiency virus type 1 Gag. J. Virol. 79:1803-1812.
16. Joshi, A., K. Nagashima, and E. O. Freed. 2006. Mutation of dileucine-like motifs in the human immunodeficiency virus type 1 capsid disrupts virus assembly, Gag-Gag interactions, Gag-membrane binding, and virion maturation. J. Virol. 80:7939-7951.
17. Kanamoto, T., Y. Kashiwada, K. Kanbara, K. Gotoh, M. Yoshimori, T. Goto, K. Sano, and H. Nakashima. 2001. Anti-human immunodeficiency virus activity of YK-FH312 (a betulinic acid derivative), a novel compound blocking viral maturation. Antimicrob. Agents Chemother. 45:1225-1230.
18. Kaplan, A. H., J. A. Zack, M. Knigge, D. A. Paul, D. J. Kempf, D. W. Norbeck, and R. Swanstrom. 1993. Partial inhibition of the human immunodeficiency virus type 1 protease results in abberant virus assembly and the formation of noninfectious particles. J. Virol. 67:4050-4055.
19. Kiernan, R. E., A. Ono, G. Englund, and E. O. Freed. 1998. Role of matrix in an early postentry step in the human immunodeficiency virus type 1 life cycle. J. Virol. 72:4116-4126.
20. Krausslich, H. G., M. Facke, A. M. Heuser, J. Konvalinka, and H. Zentgraf. 1995. The spacer peptide between human immunodeficiency virus capsid and nucleocapsid proteins is essential for ordered assembly and viral infectivity. J. Virol. 69:3407-3419.
21. Krausslich, H. G., H. Schneider, G. Zybarth, C. A. Carter, and E. Wimmer. 1988. Processing of in vitro-synthesized Gag precursor proteins of human immunodeficiency virus (HIV) type 1 by HIV proteinase generated in Escherichia coli. J. Virol. 62:4393-4397.
22. Leitner, T., B. Foley, B. Hahn, P. Marx, F. McCutchan, J. Mellors, S. Wolinsky, and B. Korber. 2005. HIV sequence compendium. LA-UR 06-0680. Theoretical Biology and Biophysics Group, Los Alamos National Laboratory, Los Alamos, N.Mex.
23. Li, F., R. Goila-Gaur, K. Salzwedel, N. R. Kilgore, M. Reddick, C. Matallana, A. Castillo, D. Zoumplis, D. E. Martin, J. M. Orenstein, G. P. Allaway, E. O. Freed, and C. T. Wild. 2003. PA-457: a potent HIV inhibitor that disrupts cote condensation by targeting a late step in Gag processing. Proc. Natl. Acad. Sci. USA 100:13555-13560.
24. Liang, C., J. Hu, R. S. Russell, A. Roldan, L. Kleiman, and M. A. Wainberg. 2002. Characterization of a putative alpha-helix across the capsid-SP1 boundary that is critical for the multimerization of human immunodeficiency virus type 1 Gag. J. Virol. 76:11729-11737.
25. Liang, C., J. Hu, J. B. Whitney, L. Kleiman, and M. A. Wainberg. 2003. A structurally disordered region at the C terminus of capsid plays essential roles in multimerization and membrane binding of the Gag protein of human immunodeficiency virus type 1. J. Virol. 77:1772-1783.
26. Louis, J. M., I. T. Weber, J. Tozser, G. M. Clore, and A. M. Gronenborn. 2000. HIV-1 protease: maturation, enzyme specificity, and drug resistance. Adv. Pharmacol. 49:111-146.
27. Melamed, D., M. Mark-Danieli, M. Kenan-Eichler, O. Kraus, A. Castiel, N. Laham, T. Pupko, F. Glaser, N. Ben-Tal, and E. Bacharach. 2004. The conserved carboxy terminus of the capsid domain of human immunodeficiency virus type 1 Gag protein is important for virion assembly and release. J. Virol. 78:9675-9688.
28. Menzo, S., A. Monachetti, C. Balotta, S. Corvasce, S. Rusconi, S. Paolucci, F. Baldanti, P. Bagnarelli, and M. Clementi. 2003. Processivity and drug-dependence of HIV-1 protease: determinants of viral fitness in variants resistant to protease inhibitors. AIDS 17:663-671.
29. Mervis, R. J., N. Ahmad, E. P. Lillehoj, M. G. Raum, F. H. Salazar, H. W. Chan, and S. Venkatesan. 1988. The gag gene products of human immunodeficiency virus type 1: alignment within the gag open reading frame, identification of posttranslational modifications, and evidence for alternative gag precursors. J. Virol. 62:3993-4002.
30. Morellet, N., S. Druillennec, C. Lenoir, S. Bouaziz, and B. P. Roques. 2005. Helical structure determined by NMR of the HIV-1 (345-392)Gag sequence, surrounding p2: implications for particle assembly and RNA packaging. Protein Sci. 14:375-386.
31. Morikawa, Y., D. J. Hockley, M. V. Nermut, and I. M. Jones. 2000. Roles of matrix, p2, and N-terminal myristoylation in human immunodeficiency virus type 1 Gag assembly. J. Virol. 74:16-23.
32. Newman, J. L., E. W. Butcher, D. T. Patel, Y. Mikhaylenko, and M. F. Summers. 2004. Flexibility in the P2 domain of the HIV-1 Gag polyprotein. Protein Sci. 13:2101-2107.
33. Ono, A., and E. O. Freed. 1999. Binding of human immunodeficiency virus type 1 Gag to membrane: role of the matrix amino terminus. J. Virol. 73:4136-4144.
34. Ono, A., A. A. Waheed, A. Joshi, and E. O. Freed. 2005. Association of human immunodeficiency virus type 1 Gag with membrane does not require highly basic sequences in the nucleocapsid: use of a novel Gag multimerization assay. J. Virol. 79:14131-14140.
35. Pettit, S. C., G. J. Henderson, C. A. Schiffer, and R. Swanstrom. 2002. Replacement of the P1 amino acid of human immunodeficiency virus type 1 Gag processing sites can inhibit or enhance the rate of cleavage by the viral protease. J. Virol. 76:10226-10233.
36. Pettit, S. C., M. D. Moody, R. S. Wehbie, A. H. Kaplan, P. V. Nantermet, C. A. Klein, and R. Swanstrom. 1994. The p2 domain of human immunodeficiency virus type 1 Gag regulates sequential proteolytic processing and is required to produce fully infectious viiions. J. Virol. 68:8017-8027.
37. Sakalian, M., S. S. Dittmer, A. D. Gandy, N. D. Rapp, A. Zabransky, and E. Hunter. 2002. The Mason-Pfizer monkey virus internal scaffold domain enables in vitro assembly of human immunodeficiency virus type 1 Gag. J. Virol. 76:10811-10820.
38. Sakalian, M., C. P. McMurtrey, F. J. Deeg, C. W. Maloy, F. Li, C. T. Wild, and K. Salzwedel. 2006. 3-O-(3′,3′-Dimethysuccinyl)betulinic acid inhibits maturation of the human immunodeficiency virus type 1 Gag precursor assembled in vitro. J. Virol. 80:5716-5722.
39. Swanstrom, R., and J. W. Wills. 1997. Synthesis, assembly, and processing of viral proteins, p. 263-334. In J. M. Coffin, S. H. Hughes, and H. E. Varmus (ed.), Retroviruses. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
40. Tang, C., E. Loeliger, P. Luncsford, I. Kinde, D. Beckett, and M. F. Summers. 2004. Entropic switch regulates myristate exposure in the HIV-1 matrix protein. Proc. Natl. Acad. Sci. USA 101:517-522.
41. Tritch, R. J., Y. E. Cheng, F. H. Yin, and S. Erickson-Viitanen. 1991. Mutagenesis of protease cleavage sites in the human immunodeficiency virus type 1 Gag polyprotein. J. Virol. 65:922-930.
42. Vogt, V. M. 1996. Proteolytic processing and particle maturation. Curr. Top Microbiol. Immunol. 214:95-131.
43. Wiegers, K., G. Rutter, H. Kottler, U. Tessmer, H. Hohenberg, and H. G. Krausslich. 1998. Sequential steps in human immunodeficiency virus particle maturation revealed by alterations of individual Gag polyprotein cleavage sites. J. Virol. 72:2846-2854.
44. Willey, R. L., J. S. Bonifacino, B. J. Potts, M. A. Martin, and R. D. Klausner. 1988. Biosynthesis, cleavage, and degradation of the human immunodeficiency virus 1 envelope glycoprotein gp160. Proc. Natl. Acad. Sci. USA 85:9580-9584.
45. Worthylake, D. K., H. Wang, S. Yoo, W. I. Sundquist, and C. P. Hill. 1999. Structures of the HIV-1 capsid protein dimerization domain at 2.6 A resolution. Acta. Crystallogr. D 55:85-92.
46. Zhou, J., C. H. Chen, and C. Aiken. 2004. The sequence of the CA-SP1 junction accounts for the differential sensitivity of HIV-1 and SIV to the small molecule maturation inhibitor 3-O-{3′,3′-dimethylsuccinyl}- betulinic acid. Retrovirology 1:15.
47. Zhou, J., L. Huang, D. L. Hachey, C. H. Chen, and C. Aiken. 2005. Inhibition of HIV-1 maturation via drug association with the viral Gag protein in immature HIV-1 particles. J. Biol. Chem. 280:42149-42155.
48. Zhou, J., X. Yuan, D. Dismuke, B, M. Forshey, C. Lundquist, K. H. Lee, C. Aiken, and C. H. Chen. 2004. Small-molecule inhibition of human immunodeficiency virus type 1 replication by specific targeting of the final step of virion maturation. J. Virol. 78:922-929.