HIV-1 ENV gp120 structural determinants for peptide triazole dual receptor site antagonism

Proteins: Structure, Function and Bioinformatics

Volumn 81, Issue 2, 2013, Pages 271-290

  Tuzer, Ferit ^a   Madani, Navid ^b   Kamanna, Kantharaju ^a   Zentner, Isaac ^a   Lalonde, Judith ^c   Holmes, Andrew ^a   Upton, Elizabeth ^a   Rajagopal, Srivats ^d   McFadden, Karyn ^e   Contarino, Mark ^a   Sodroski, Joseph ^b   Chaiken, Irwin ^a  

^a DREXEL UNIVERSITY COLLEGE OF MEDICINE   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

^c BRYN MAWR COLLEGE   (United States)

^d SYNGENE INTERNATIONAL LTD   (India)

^e DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

Binding site; Dual antagonism; Entry inhibitor; KR21

Indexed keywords

EPITOPE; GLYCOPROTEIN GP 120; KR21 PROTEIN; MONOCLONAL ANTIBODY; TRIAZOLE; UNCLASSIFIED DRUG; VIRUS PROTEIN;

ARTICLE; BINDING AFFINITY; BINDING SITE; CD4+ T LYMPHOCYTE; CONTROLLED STUDY; ENZYME LINKED IMMUNOSORBENT ASSAY; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN STRUCTURE; SURFACE PLASMON RESONANCE; VIRUS ENVELOPE; VIRUS INHIBITION; VIRUS MUTANT; VIRUS MUTATION; VIRUS NEUTRALIZATION; VIRUS SPIKE;

ANTI-HIV AGENTS; ANTIGENS, CD4; HIV ENVELOPE PROTEIN GP120; HUMANS; KINETICS; MODELS, MOLECULAR; MUTATION; PEPTIDES; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 84872611358     PISSN: 08873585     EISSN: 10970134     Source Type: Journal    
DOI: 10.1002/prot.24184     Document Type: Article

References (36)

1. Joint United Nations Programme on HIV/AIDS (UNAIDS). World AIDS day report. Published online: 2011.
2. Lucas GM, Chaisson RE, Moore RD. Highly active antiretroviral therapy in a large urban clinic: risk factors for virologic failure and adverse drug reactions. Ann Intern Med 1999; 131: 81-87.
3. Yerly S, Kaiser L, Race E, Bru JP, Clavel F, Perrin L. Transmission of antiretroviral-drug-resistant HIV-1 variants. Lancet 1999; 354: 729-733.
4. Yost R, Pasquale TR, Sahloff EG. Maraviroc: a coreceptor CCR5 antagonist for management of HIV infection. Am J Health Syst Pharm 2009; 66: 715-726.
5. Lalezari JP, Bellos NC, Sathasivam K, Richmond GJ, Cohen CJ, Myers RAJr., Henry DH, Raskino C, Melby T, Murchison H, Zhang Y, Spence R, Greenberg ML, Demasi RA, Miralles GD. 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.
6. Merck. ISENTRESS (raltegravir) in Combination Therapy Demonstrated Long-Term Efficacy, Safety and Tolerability in Previously Untreated Adult Patients with HIV-1 for up to 240 Weeks. Press release. July 22, 2012.
7. Gallien S, Delaugerre C, Charreau I, Braun J, Boulet T, Barrail-Tran A, de Castro N, Molina JM, Kuritzkes DR. Emerging integrase inhibitor resistance mutations in raltegravir-treated HIV-1-infected patients with low-level viremia. AIDS 2011; 25: 665-669.
8. Ferrer M, Harrison SC. Peptide ligands to human immunodeficiency virus type 1 gp120 identified from phage display libraries. J Virol 1999; 73: 5795-5802.
9. Gopi HN, Tirupula KC, Baxter S, Ajith S, Chaiken IM. Click chemistry on azidoproline: high-affinity dual antagonist for HIV-1 envelope glycoprotein gp120. ChemMedChem 2006; 1: 54-57.
10. Umashankara M, McFadden, K, Zentner I, Schon A, Rajagopal S, Tuzer F, Kuriakose SA, Contarino, M, Lalonde J, Freire E, Chaiken I. The active core in a triazole peptide dual-site antagonist of HIV-1 gp120. ChemMedChem 2010; 5: 1871-1879.
11. McFadden K, Fletcher P, Rossi F, Kantharaju, Umashankara M, Pirrone V, Rajagopal S, Gopi H, Krebs FC, Martin-Garcia J, Shattock RJ, Chaiken I. Antiviral breadth and combination potential of peptide triazole HIV-1 entry inhibitors. Antimicrob Agents Chemother 2012; 56: 1073-1080.
12. Bastian AR, Kantharaju, McFadden K, Duffy C, Rajagopal S, Contarino MR, Papazoglou E, Chaiken I. Cell-free HIV-1 virucidal action by modified peptide triazole inhibitors of Env gp120. ChemMedChem 2011; 6: 1335-1339, 1318.
13. Biorn AC, Cocklin S, Madani N, Si Z, Ivanovic T, Samanen J, Van Ryk DI, Pantophlet R, Burton DR, Freire E, Sodroski J, Chaiken IM. Mode of action for linear peptide inhibitors of HIV-1 gp120 interactions. Biochemistry 2004; 43: 1928-1938.
14. Gopi H, Cocklin S, Pirrone V, McFadden K, Tuzer F, Zentner I, Ajith S, Baxter S, Jawanda N, Krebs FC, Chaiken IM. Introducing metallocene into a triazole peptide conjugate reduces its off-rate and enhances its affinity and antiviral potency for HIV-1 gp120. J Mol Recognit 2009; 22: 169-174.
15. Ishino T, Harrington AE, Zaks-Zilberman M, Scibek JJ, Chaiken I. Slow-dissociation effect of common signaling subunit beta c on IL5 and GM-CSF receptor assembly. Cytokine 2008; 42: 179-190.
16. Karlsson R, Michaelsson A, Mattsson L. Kinetic analysis of monoclonal antibody-antigen interactions with a new biosensor based analytical system. J Immunol Methods 1991; 145: 229-240.
17. Morton TA, Bennett DB, Appelbaum ER, Cusimano DM, Johanson KO, Matico RE, Young PR, Doyle M, Chaiken IM. Analysis of the interaction between human interleukin-5 and the soluble domain of its receptor using a surface plasmon resonance biosensor. J Mol Recognit 1994; 7: 47-55.
18. LaLonde JM, Kwon YD, Jones DM, Sun AW, Courter JR, Soeta T, Kobayashi T, Princiotto AM, Wu X, Schon A, Freire E, Kwong PD, Mascola JR, Sodroski J, Madani N, Smith AB 3rd. Structure-based design, synthesis, and characterization of dual hotspot small-molecule HIV-1 entry inhibitors. J Med Chem 2012; 55: 4382-4396.
19. Xiang SH, Kwong PD, Gupta R, Rizzuto CD, Casper DJ, Wyatt R, Wang L, Hendrickson WA, Doyle ML, Sodroski J. Mutagenic stabilization and/or disruption of a CD4-bound state reveals distinct conformations of the human immunodeficiency virus type 1 gp120 envelope glycoprotein. J Virol 2002; 76: 9888-9899.
20. Kwong PD, Wyatt R, Robinson J, Sweet RW, Sodroski J, Hendrickson WA. Structure of an HIV gp120 envelope glycoprotein in complex with the CD4 receptor and a neutralizing human antibody. Nature 1998; 393: 648-659.
21. Potapov V. CMA: contact map analysis. Online resource available from: http://ligin.weizmann.ac.il/cma/. Analysis done May 2012 for PDB ID 1RZK.
22. Culp JS, Johansen H, Hellmig B, Beck J, Matthews TJ, Delers A, Rosenberg M. Regulated expression allows high level production and secretion of HIV-1 gp120 envelope glycoprotein in Drosophila Schneider cells. Biotechnology (NY) 1991; 9: 173-177.
23. Pancera M, Lebowitz J, Schon A, Zhu P, Freire E, Kwong PD, Roux KH, Sodroski J, Wyatt R. Soluble mimetics of human immunodeficiency virus type 1 viral spikes produced by replacement of the native trimerization domain with a heterologous trimerization motif: characterization and ligand binding analysis. J Virol 2005; 79: 9954-9969.
24. Gopi H, Umashankara M, Pirrone V, LaLonde J, Madani N, Tuzer F, Baxter S, Zentner I, Cocklin S, Jawanda N, Miller SR, Schon A, Klein JC, Freire E, Krebs FC, Smith AB, Sodroski J, Chaiken I. Structural determinants for affinity enhancement of a dual antagonist peptide entry inhibitor of human immunodeficiency virus type-1. J Med Chem 2008; 51: 2638-2647.
25. Grupping K, Selhorst P, Michiels J, Vereecken K, Heyndrickx L, Kessler P, Vanham G, Martin L, Arien KK. MiniCD4 protein resistance mutations affect binding to the HIV-1 gp120 CD4 binding site and decrease entry efficiency. Retrovirology 2012; 9: 36.
26. Gift SK, Zentner IJ, Schon A, McFadden K, Umashankara M, Rajagopal S, Contarino M, Duffy C, Courter JR, Zhang MY, Gershoni JM, Cocklin S, Dimitrov DS, Smith AB 3rd, Freire E, Chaiken IM. Conformational and structural features of HIV-1 gp120 underlying the dual receptor antagonism by cross-reactive neutralizing antibody m18. Biochemistry 2011; 50: 2756-2768.
27. Huang CC, Lam SN, Acharya P, Tang M, Xiang SH, Hussan SS, Stanfield RL, Robinson J, Sodroski J, Wilson IA, Wyatt R, Bewley CA, Kwong PD. Structures of the CCR5 N terminus and of a tyrosine-sulfated antibody with HIV-1 gp120 and CD4. Science 2007; 317: 1930-1934.
28. Chen L, Kwon YD, Zhou T, Wu X, O'Dell S, Cavacini L, Hessell AJ, Pancera M, Tang M, Xu L, Yang ZY, Zhang MY, Arthos J, Burton DR, Dimitrov DS, Nabel GJ, Posner MR, Sodroski J, Wyatt R, Mascola JR, Kwong PD. Structural basis of immune evasion at the site of CD4 attachment on HIV-1 gp120. Science 2009; 326: 1123-1127.
29. Kwon YD, Finzi A, Wu X, Dogo-Isonagie C, Lee LK, Moore LR, Schmidt SD, Stuckey J, Yang Y, Zhou T, Zhu J, Vicic DA, Debnath AK, Shapiro L, Bewley CA, Mascola JR, Sodroski JG, Kwong PD. Unliganded HIV-1 gp120 core structures assume the CD4-bound conformation with regulation by quaternary interactions and variable loops. Proc Natl Acad Sci USA 2012; 109: 5663-5668.
30. Cocklin S, Gopi H, Querido B, Nimmagadda M, Kuriakose S, Cicala C, Ajith S, Baxter S, Arthos J, Martin-Garcia J, Chaiken IM. Broad-spectrum anti-human immunodeficiency virus (HIV) potential of a peptide HIV type 1 entry inhibitor. J Virol 2007; 81: 3645-3648.
31. Acharya P, Dogo-Isonagie C, LaLonde JM, Lam SN, Leslie GJ, Louder MK, Frye LL, Debnath AK, Greenwood JR, Luongo TS, Martin L, Watts KS, Hoxie JA, Mascola JR, Bewley CA, Kwong PD. Structure-based identification and neutralization mechanism of tyrosine sulfate mimetics that inhibit HIV-1 entry. ACS Chem Biol 2011; 6: 1069-1077.
32. LaLonde JM, Elban MA, Courter JR, Sugawara A, Soeta T, Madani N, Princiotto AM, Kwon YD, Kwong PD, Schon A, Freire E, Sodroski J, Smith AB 3rd. Design, synthesis and biological evaluation of small molecule inhibitors of CD4-gp120 binding based on virtual screening. Bioorg Med Chem 2011; 19: 91-101.
33. Si Z, Madani N, Cox JM, Chruma JJ, Klein JC, Schon A, Phan N, Wang L, Biorn AC, Cocklin S, Chaiken I, Freire E, Smith AB 3rd, Sodroski JG. Small-molecule inhibitors of HIV-1 entry block receptor-induced conformational changes in the viral envelope glycoproteins. Proc Natl Acad Sci USA 2004; 101: 5036-5041.
34. Rits-Volloch S, Frey G, Harrison SC, Chen B. Restraining the conformation of HIV-1 gp120 by removing a flexible loo EMBO J 2006; 25: 5026-5035.
35. Gift SK, Zentner IJ, Schon A, McFadden K, Umashankara M, Rajagopal S, Contarino M, Duffy C, Courter JR, Zhang MY, Gershoni JM, Cocklin S, Dimitrov DS, Smith AB, Freire E, Chaiken IM. Conformational and structural features of HIV-1 gp120 underlying the dual receptor antagonism by cross-reactive neutralizing antibody m18. Biochemistry 2011; 50: 2756-2768.
36. McKeating JA, Moore JP, Ferguson M, Marsden HS, Graham S, Almond JW, Evans DJ, Weiss RA. Monoclonal antibodies to the C4 region of human immunodeficiency virus type 1 gp120: use in topological analysis of a CD4 binding site. AIDS Res Hum Retroviruses 1992; 8: 451-459.