HIV fusion inhibitors

Reviews in Medical Virology

Volumn 20, Issue 1, 2010, Pages 23-33

  Qadir, M I ^a   Malik, S A ^b  

^a GC UNIVERSITY   (Pakistan)

^b QUAID I AZAM UNIVERSITY   (Pakistan)

Author keywords

[No Author keywords available]

Indexed keywords

ENFUVIRTIDE; FORMAZAN; GLYCOPROTEIN GP 41; HUMAN IMMUNODEFICIENCY VIRUS FUSION INHIBITOR; PEPTIDE FRAGMENT C34; T 21; TIFUVIRTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; DRUG PROTEIN BINDING; DRUG STRUCTURE; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; REVIEW; VIRUS CELL INTERACTION;

AMINO ACID SEQUENCE; DRUG RESISTANCE, VIRAL; HIV; HIV ENVELOPE PROTEIN GP41; HIV FUSION INHIBITORS; HIV INFECTIONS; HUMANS; MEMBRANE FUSION; MOLECULAR SEQUENCE DATA;

EID: 75749113640     PISSN: 10529276     EISSN: 10991654     Source Type: Journal    
DOI: 10.1002/rmv.631     Document Type: Review

References (92)

1. Huang JH, Qi Z, Wu F, Kotula L, Jiang S, Chen YH. Interaction of HIV-1 gp41 core with NPF motif in epsin: implication in endocytosis of HIV. J Biol Chem 2008; 283(22): 14994-15002.
2. Chien MP, Lin CH, Chang DK. Recruitment of HIV-1 envelope occurs subsequent to lipid mixing: a fluorescence microscopic evidence. Retroviro 2009; 6(1): 20.
3. Ji J, Cloyd MW. HIV-1 binding to CD4 on CD4+ CD25+ regulatory T cells enhances their suppressive function and induces them to home to, and accumulate in, peripheral and mucosal lymphoid tissues: an additional mechanism of immunosuppression. Int Immunol 2009; 21(3): 283-94.
4. Clapham PR, McKnight A. Cell surface receptors, virus entry and tropism of primate lentiviruses. J Genl Viro 2002; 83: 1809-1829.
5. Deng H, Liu R, Ellmei er W, et al. Identification of a major co-receptor for primary isolates of HIV-1. Nature 1996; 381: 661-666.
6. Lu M, Blacklow SC, Kim PS. A trimeric structural domain of the HIV-1 transmembrane glycoprotein. Nat Struct Biol 1995; 2: 1075-1082.
7. Weissenhorn W, Dessen A, Harrison SC, Skehel JJ, Wiley DC. Atomic structure of the ectodomain from HIV-1 gp41. Nature 1997; 387: 426-430.
8. Earl PL, Doms RW, Moss B. Oligomeric structure of the human immunodeficiency virus type 1 envelope glycoprotein. Proc Natl Acad Sci USA 1990; 87: 648-652.
9. Pinter A, Honnen WJ, Tilley SA, et al. Oligomeric structure of gp41, the transmembrane protein of human immunodeficiency virus type 1. J Virol 1989; 63: 2674-2679.
10. Einfeld D, Hunter E. Oligomeric structure of a prototype retrovirus glycoprotein. Proc Natl Acad Sci USA 1988; 85: 8688-8692.
11. Delwart EJ, Mosialos G, Gilmore T. Retroviral envelope glycoproteins contain a leucine zipper like repeat. AIDS Res Hum Retroviruses 1990; 6: 703-706.
12. Gallaher WR, Ball JM, Garry RF, Griffin MC, Montelaro RC. A general model for the transmembrane proteins of HIV and other retroviruses. AIDS Res Hum Retrovir 1989; 5:431-440.
13. Buckland R, Wild F. Leucine zipper motif extends. Nature 1989; 338: 547.
14. Chan DC, Fass D, Berger JM, Kim PS. Core structure of gp41 from the HIV envelope glycoprotein. Cell 1997; 89: 263-273.
15. Chambers P, Pringle CR, Easton AJ. Heptad repeat sequences are located adjacent to hydrophobic regions in several types of virus fusion glycoproteins. J Gen Virol 1990; 71(12): 3075-3080.
16. Rasmussen R, Benvegnu D, O'Shea EK, Kim PS, Abler T. X-ray scattering indicates that the leucine zipper is a coiled coil. Proc Natl Acad Sci USA 1991; 88: 561-564.
17. Wild CT, Oas T, McDanal CB, Bolognesi D, Matthews TJ. A synthetic peptide inhibitor of human immunodeficiency virus replication: correlation between solution structure and viral inhibition. Proc Natl Acad Sci USA 1992; 89: 10537-10541.
18. Harbury PB, Zhang T, Kim PS, Alber T. A switch between two-, three-, and four-stranded coiled coils in GCN4 leucine zipper mutants. Science 1993; 262: 1401-1407.
19. Kazmierski WM, McDermed J. A new method for defining dimerization interfaces in proteins. In Pept: Chem, Struct Biol, Proc Am Pept Symp, 13th, Hodges, Robert S, Smith, John A (eds). ESCOM: Leiden, Neth., 1994; pp. 1045-1047.
20. Kazmierski WM, McDermed J. Disruption of helix-helix interactions in biologically relevant proteins: HIV-1 inhibition by gp41 fragments. In Peptides 1994, Proc Europ Pept Symp, 23rd, Maia, Hernani LS (eds). Braga: Port., 1995; pp. 52-53.
21. Kazmierski WM, McDermed J, Aulabaugh A. A new experimental method to determine the mutual orientation of helixes in coiled-coil proteins: structural information about the dimeric interface of cJun, cFos, GCN4, and gp41. Chemistry-A Europ J 1996; 2: 403-411.
22. Chan DC, Chutkowski CT, Kim PS. Evidence that a prominent cavity in the coiled coil of HIV type 1 gp41 is an attractive drug target. Proc Natl Acad Sci USA 1998; 95: 15613-15617.
23. Liu S, Lu H, Niu J, Xu Y, Wu S, Jiang S. Different from the HIV fusion inhibitor C34, the anti-HIV drug fuzeon (T-20) inhibits HIV-1 entry by targeting multiple sites in gp41 and gp120. J Biol Chem 2005; 280: 11259-11273.
24. Briz V, Poveda E, Soriano V. HIV entry inhibitors: mechanisms of action and resistance pathways. J Antimicrob Chemother 2006; 57: 619-627.
25. McLachlan AD, Stewart M. Tropomyosin coiled-coil interactions: evidence for an unstaggered structure. J Mol Biol 1975; 98: 293-304.
26. Wild C, Greenwell T, Shugars D, Rimsky-Clarke L, Matthews T. The inhibitory activity of an HIV type 1 peptide correlates with its ability to interact with a leucine zipper structure. AIDS Res Hum Retrovir 1995; 11: 323-325.
27. Greenberg M, Cammack N, Salgo M, Smiley L. HIV fusion and its inhibition in antiretroviral therapy. Rev Med Virol 2004; 14: 321-337.
28. Jiang S, Lin K, Strick N, Neurath AR. HIV-1 inhibition by a peptide. Nature 1993; 365: 113.
29. Wild CT, Shugars DC, Greenwell TK, McDanal CB, Matthews TJ. Peptides corresponding to a predictive α-helical domain of human immunodeficiency virus type 1 gp41. Proc Natl Acad Sci USA 1994; 91: 9770-9774.
30. Chen SS. Functional role of the zipper motif region of human immunodeficiency virus type 1 transmembrane protein gp41. J Virol 1994; 68: 2002-2010.
31. Chen BK, Gandhi RT, Baltimore D. CD4 down-modulation during infection of human T cells with human immunodeficiency virus type 1 involves independent activities of vpu, env, and nef. J Virol 1996; 70(9): 6044-6053.
32. Kilgore NR, Salzwedel K, Reddick M, Allaway GP, Wild CT. Direct evidence that C-peptide inhibitors of human immunodeficiency virus type 1 entry bind to the gp41 N-helical domain in receptor-activated viral envelope. J Virol 2003; 77: 7669-7672.
33. Lazzarin A, Clotet B, Cooper D, et al. Efficacy of enfuvirtide in patients infected with drug-resistant HIV-1 in Europe and Australia. N Engl J Med 2003; 348: 2186-2195.
34. Lalezari JP, Henry K, O'Hearn M, et al. Enfuvirtide, an HIV-1 fusion inhibitor, for drug-resistant HIV infection in North and South America. N Engl J Med 2003; 348: 2175-2185.
35. Robertson D. US FDA approves new class of HIV therapeutics. Nat Biotechnol 2003; 21: 470-471.
36. Ji H, Shu W, Burling FT, Jiang S, Lu M. Inhibition of human immunodeficiency virus type 1 infectivity by the gp41 core: role of a conserved hydrophobic cavity in membrane fusion. J Virol 1999; 73: 8578-8586.
37. Kazmierski WM, McDermed J. Synthesis of the carbonic acid benzotriazol-1-yl-ester-(2-biotinylamino)-9H-fluoren-9-ylmethyl ester: a convenient transient-biotinylation reagent for use in affinity chromatography. Tetrahedron Lett 1995; 36: 9097-9100.
38. Jiang S, Lu H, Liu S, Zhao Q, He Y, Debnath AK. N-substituted pyrrole derivatives as novel human immunodeficiency virus type 1 entry inhibitors that interfere with the gp41 6-helix bundle formation and block virus fusion. Antimicrob Agents Chemother 2004; 48: 4349-4359.
39. Samson M, Libert F, Doranz BJ, et al. Resistance to HIV-1 infection in Caucasian individuals bearing mutant alleles of the CCR-5 chemokine receptor gene. Nature 1996; 382: 722-725.
40. Blanpain CC, Doranz BJ, Vaklil J, et al. Multiple charged and arpomatic residues in CCR5 aminoterminal domain are involved in high affinity binding of both chemokines and HIV-1 Env protein. J Biol Chem 1999; 274: 34719-34727.
41. Liu R, Paxton WA, Choe S, et al. Homozygous defect HIV-1 coreceptor accounts for resistance of some multiply exposed individuals to HIV-1 infection. Cell 1996; 86: 367-377.
42. Nishiyama Y, Murakami T, Kurita K, Yamamoto N. Low-molecular-weight anti-HIV-1 peptides from the amino-terminal sequence of RANTES: possible lead compounds for coreceptor-directed anti-HIV-1 compounds. Bioorg Med Chem Lett 1999; 9: 1357-1360.
43. Dwyer JJ, Hasan A, Wilson KL, White JM, Matthews TJ, Delmedico MK. The hydrophobic pocket contributes to the structural stability of the N-terminal coiled coil of HIV gp41 but is not required for sixhelix bundle formation. Biochem 2003; 42: 4945-4953.
44. Kashiwada Y, Hashimoto F, Cosentino LM, Chen CH, Garrett PE, Lee KH. Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J Med Chem 1996; 39: 1016-1017.
45. Kazmierski WM, Peckham JP, Duan M, et al. Recent progress in the discovery of new CCR5 and CXCR4 chemokine receptor antagonists as inhibitors of HIV-1 entry. Part 2. Curr Med Chem: Anti-Infective Agents 2005; 4: 133-152.
46. De Clercq, Eik. New anti-HIV agents in preclinical or clinical development Front Med Chem Online 2004; 1(1): 543-579.
47. Lapham CK, Zaitseva MB, Lee S, Romanstseva T, Golding H. Fusion of monocytes and macrophages with HIV-1 correlates with biochemical properties of CXCR4 and CCR5. Nature Med 1999; 5: 303-308.
48. Kazmierski WM, Kenakin TP, Gudmundsson KS. Peptide, peptidomimetic and small-molecule drug discovery targeting HIV-1 host-cell attachment and entry through gp120, gp41, CCR5 and CXCR4. Chem Biol Drug 2006; 67: 13-26.
49. Kilby JM, Hopkins S, Venetta TM, et al. Potent suppression of HIV-1 replication in humans by T-20, a peptide inhibitor of gp41-mediated virus entry. Nat Med 1998; 4: 1302-1307.
50. Yang X, Florin L, Farzan M. Modifications that stabilize human immunodeficiency virus envelope glycoprotein trimers in solution. J Virol 2005; 74: 4746-4754.
51. Vladimir N. Malashkevich, David C. Chan, Christine T. Chutkowski, Peter S. Kim. Crystal structure of the simian immunodeficiency virus (SIV) gp41 core: Conserved helical interactions underlie the broad inhibitory activity of gp41 peptides. PNAS 1998; 95(16): 9134-9139.
52. Frey G, Rits-Volloch S, Zhang XQ, Schooley RT, Chen B and Harrison ST. Small molecules that bind the inner core of gp41 and inhibit HIV envelope-mediated fusion. PNAS 2006; 103(38): 13938-13943
53. Bewley CA, Louis JM, Ghirlando R, Clore GM. Design of a novel peptide inhibitor of HIV fusion that disrupts the internal trimeric coiled-coil of gp41. J Biol Chem2002; 277(16): 14238-14245.
54. Jiang S. Development of HIV entry inhibitors targeted to the coiled-coil regions of gp41. Biochem Biophys Res Commun 2000; 269(3): 641-646.
55. Eckert DM, Kim PS. Mechanisms of viral membrane fusion and its inhibition. Annu Rev Biochem 2001; 70: 777-810.
56. Root MJ, Kay MS, Kim PS. Protein design of an HIV-1 entry inhibitor. Science2001; 291: 884-888.
57. Zhao Q, Ernst JT, Hamilton AD, Debnath AK, Jiang S. XTT formazan widely used to detect cell viability inhibits HIV type 1 infection in vitro by targeting gp41. AIDS Res Hum Retroviruses 2002; 18: 989-997.
58. Durant J, Clevenbergh P, Halfon P, et al. Drug-resistance genotyping in HIV-1 therapy: the VIRADAPT randomised controlled trial. Lancet 1999; 353: 2195-2199.
59. Baxter JD, Mayers DL, Wentworth DN, et al. A randomized study of antiretroviral management based on plasma genotypic antiretroviral resistance testing in patients failing therapy. CPCRA 046 Study Team for the Terry Beirn Community Programs for Clinical Research on AIDS. AIDS 2000; 14: F83-F93.
60. Cingolani A, Antinori A, Rizzo MG, et al. Usefulness of monitoring HIV drug resistance and adherence in individuals failing highly active antiretroviral therapy: a randomized study (ARGENTA). AIDS 2002; 16(3): 369-379.
61. Meynard JL, Vray M, Morand-Joubert L. Phenotypic or genotypic resistance testing for choosing antiretroviral therapy after treatment failure: a randomized trial. AIDS 2002; 16: 727-736.
62. Tural C, Ruiz L, Holtzer C, et al. Clinical utility of HIV-1 genotyping and expert advice: the Havana trial. AIDS 2002; 16(2): 209-218.
63. Young L, Jernigan RL, Covell DG. A role for surface hydrophobicity in protein-protein recognition. Protein Sci 1994; 3: 717-729.
64. Jones S, Thornton JM. Principles of protein-protein interactions. Proc Natl Acad Sci USA 1996; 93: 13-20.
65. Melikyan GB, Markosyan RM, Hemmati H, Delmedico MK, Lambert DM, Cohen FS. Evidence that the transition of HIV-1 gp41 into a six-helix bundle, not the bundle configuration, induces membrane fusion. J Cell Biol 2000; 151: 413-423.
66. Baldwin CE, Sanders RW, Berkhout B. Inhibiting HIV-1 entry with fusion inhibitors. Curr Med Chem 2003; 10: 1633-1642.
67. Greenberg ML, Davison D, Jin L. In vitro antiviral activity of T-1249, a second generation fusion inhibitor. Antivir Ther 2002; 7(1): S10.
68. Eron JJ, Gulick RM, Bartlett JA, Merigan T, Arduino R, Kilby JM. Short-term safety and antiviral activity of T-1249, a second generation fusion inhibitor. J Infect Dis 2004; 189:1075-1083.
69. Lalezari JP, Bellos NC, Sathasivam K, Richmond GJ, Cohen CJ, Myers RA. T-1249 retains potent antiretroviral activity in patients who had experienced virological failure while on an enfuvirtide-containing treatment regimen. J Infect Dis 2005; 191: 1155-1163.
70. Chinnadurai R, Rajan D, Mü nch J, Kirchhoff F. Human immunodeficiency virus Type 1 variants resistant to first- and second-version fusion inhibitors and cytopathic in ex vivo human lymphoid tissue. J Virol 2007; 81(12): 6563-6572.
71. Descamps D, Assoumou L, Masquelier B, et al. HIV-1-infected patients from the French National Observatory experiencing virological failure while receiving enfuvirtide. J Antimicrob Chemother 2008; 62(3): 451-455.
72. Greenberg ML, Melby T, Sista P, DeMasi R, Cammack N, Salgo M (2003). Baseline and on-treatment susceptibility to enfuvirtide seen in TORO 1 and TORO 2 to 24 weeks. Abstr 10th Conf Retrovir Opportun Infect 141.
73. Pilcher CD, Eron JJ, Ngo L. Prolonged therapy with the fusion inhibitor T-20 in conjunction with oral antiretroviral agents in an HIV-infected individual. AIDS 1999; 13: 2171-2173.
74. Sista PR, Melby T, Davison D, et al. Characterization of determinants of genotypic and phenotypic resistance to enfuvirtide in baseline and on-treatment HIV-1 isolates. AIDS 18: 1787-1794.
75. Xu L, Pozniak A, Wildfire A, et al. Emergence and evolution of enfuvirtide resistance following longterm therapy involves heptad repeat 2 mutations within gp41. Antimicrob Agents Chemother 2005; 49(3): 1113-1119.
76. Wei X, Decker JM, Liu H. Emergence of resistant human immunodeficiency virus type 1 in patients receiving fusion inhibitor (T-20) monotherapy. Antimicrob Agents Chemother 2002; 46: 1896-1905.
77. Marconi V, Bonhoeffer S, Paredes R, et al. Viral dynamics and in vivo fitness of HIV-1 in the presence and absence of enfuvirtide. J Acquir Immune Defic Syndr 2008; 48(5): 572-576.
78. Eggink D, Baldwin CE, Deng Y, et al. Selection of T1249-resistant human immunodeficiency virus type 1 variants. J Virol 2008; 82(13): 6678-6688.
79. Covens K, Kabeya K, Schrooten Y, et al. Evolution of genotypic resistance to enfuvirtide in HIV-1 isolates from different group M subtypes. J Clin Virol 2009; 44(4): 325-328.
80. Roman F, Gonzalez D, Lambert C, et al. Uncommon mutations at residue positions critical for enfuvirtide (T-20) resistance in enfuvirtide-naive patients infected with subtype B and non-B HIV-1 strains. J Acquir Immune Defic Syndr 2003; 33: 134-139.
81. Xu L, Hue S, Taylor S, et al. Minimal variation in T-20 binding domain of different HIV-1 subtypes from antiretroviral-naive and -experienced patients. AIDS 2002; 16: 1684-1686.
82. Zollner B, Feucht HH, Schroter M, et al. Primary genotypic resistance of HIV-1 to the fusion inhibitor T-20 in long-term infected patients. AIDS 2001; 15: 935-936.
83. Hanna SL, Yang C, Owen SM, Lai RB. Resistance mutation in HIV entry inhibitors. AIDS 2002; 16:1603-1608.
84. Oliveira AC, Martins AN, Pires AF, et al. Enfuvirtide (T-20) resistance-related mutations in HIV type 1 subtypes B, C, and F isolates from Brazilian patients failing HAART. AIDS Res Hum Retroviruses 2009; 25(2): 193-198.
85. Pillay D, Cane PA, Shirley J, Porter K. Detection of drug resistance associated mutations in HIV primary infection within the UK. AIDS 2000; 14: 906-908.
86. Dorn J, Masciotra S, Yang C, et al. Analysis of genetic variability within the immunodominant epitopes of envelope gp41 from human immunodeficiency virus type 1 (HIV-1) group M and its impact on HIV-1 antibody detection. J Clin Microbiol 2000; 38: 773-780.
87. Izumi K, Kodama E, Shimura K, et al. Design of peptide-based inhibitors for human immunodeficiency Virus Type 1 strains resistant to T-20. J Biol Chem 2009; 284(8): 4914-4920.
88. Wolf E (2005) HIV Drug Resistance. http://www.hivmedicine.com/textbook/ rt.html retrived on 11-09-08
89. Wolf E. HIV Resistance Testing. In HIV Medicine, Hoffmann C, Rockstroh JK, Kamps BS (eds). Flying Publisher: Paris, 2006; pp. 331-356.
90. Louwagie J, Janssens W, Mascola J, et al. Genetic diversity of the envelope glycoprotein from human immunodeficiency virus type 1 isolates of African origin. J Virol 1995; 69(1): 263-271.
91. Dong X, Ying J, Wu Y, Chen Y-H. Genetic variability of principal neutralizing determinants on HIV-1 gp41 and its correlation with subtypes. Immunol Letters 2005; 101(1): 104-107.
92. He Y, Liu S, Jing W, et al. Conserved residue lys574 in the cavity of HIV-1 Gp41 coiled-coil domain is critical for 6-helix bundle stability and virus entry. J Biol Chem 2007; 282(35): 25631-25639.