Rigid amphipathic fusion inhibitors, small molecule antiviral compounds against enveloped viruses

Proceedings of the National Academy of Sciences of the United States of America

Volumn 107, Issue 40, 2010, Pages 17339-17344

  St Vincent, Mireille R ^a   Colpitts, Che C ^a,b   Ustinov, Alexey V ^c   Muqadas, Muhammad ^a   Joyce, Michael A ^a,b   Barsby, Nicola L ^a,b   Epand, Raquel F ^d   Epand, Richard M ^d   Khramyshev, Stanislav A ^c   Valueva, Olga A ^c   Korshun, Vladimir A ^c   Tyrrell, D Lorne J ^a,b   Schang, Luis M ^a,b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

^c SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^d MCMASTER UNIVERSITY MEDICAL CENTRE   (Canada)

Author keywords

DNA virus; Lipid bilayer fusion; Nucleosides; RNA virus; Sindbis virus

Indexed keywords

AMPHOPHILE; PHOSPHOLIPID; RIGID AMPHIPATHIC FUSION INHIBITOR; UNCLASSIFIED DRUG; VIRUS PROTEIN;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; HEPATITIS C VIRUS; MEMBRANE FUSION; NONHUMAN; PRIORITY JOURNAL; VIRUS CELL INTERACTION; VIRUS ENVELOPE; VIRUS INFECTIVITY;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; CELL MEMBRANE; HERPESVIRUS 1, HUMAN; HUMANS; LIPID BILAYERS; MEMBRANE LIPIDS; MOLECULAR STRUCTURE; VIRAL PROTEINS; VIRION; VIRUS INTERNALIZATION; VIRUSES;

DNA VIRUSES; HEPATITIS C VIRUS; HUMAN HERPESVIRUS 1; RNA VIRUSES; SINDBIS VIRUS;

EID: 78049306063     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1010026107     Document Type: Article

References (49)

1. Pillay D (2007) The priorities for antiviral drug resistance surveillance and research. J Antimicrob Chemother 60(Suppl 1):i57-i58.
2. Phillips AN, et al.; UK Collaborative HIV Cohort (CHIC) Study (2007) Risk of extensive virological failure to the three original antiretroviral drug classes over long-term follow-up from the start of therapy in patients with HIV infection: An observational cohort study. Lancet 370:1923-1928.
3. De Clercq E, Brancale A, Hodge AV, Field HJ (2006) Antiviral chemistry and chemotherapy's current antiviral agents FactFile 2006 (1st edition). Antivir Chem Chemother 17:113-166. (Pubitemid 44369534)
4. De Clercq E (2007) Three decades of antiviral drugs. Nat Rev Drug Discov 6:941.
5. Gao M, et al. (2010) Chemical genetics strategy identifies an HCV NS5A inhibitor with a potent clinical effect. Nature 465:96-100.
6. Schinazi RF, Bassit L, Gavegnano C (2010) HCV drug discovery aimed at viral eradication. J Viral Hepat 17:77-90.
7. Soares MM, King SW, Thorpe PE (2008) Targeting inside-out phosphatidylserine as a therapeutic strategy for viral diseases. Nat Med 14:1357-1362.
8. Dwyer JJ, et al. (2007) Design of helical, oligomeric HIV-1 fusion inhibitor peptides with potentactivity against enfuvirtide-resistant virus. Proc Natl Acad Sci USA 104:12772-12777.
9. Münch J, et al. (2007) Discovery and optimization of a natural HIV-1 entry inhibitor targeting the gp41 fusion peptide. Cell 129:263-275.
10. Tan S-L, Ganji G, Paeper B, Proll S, Katze MG (2007) Systems biology and the host response to viral infection. Nat Biotechnol 25:1383-1389.
11. Schang LM, St Vincent MR, Lacasse JJ (2006) Five years of progress on cyclin-dependent kinases and other cellular proteins as potential targets for antiviral drugs. Antivir Chem Chemother 17:293-320.
12. Pérez-Alvarez L, et al. (2006) Long-term monitoring of genotypic and phenotypic resistance to T20 in treated patients infected with HIV-1. J Med Virol 78:141-147.
13. Baba M, Miyake H, Wang X, Okamoto M, Takashima K (2007) Isolation and characterization of human immunodeficiency virus type 1 resistant to the smallmolecule CCR5 antagonist TAK-652. Antimicrob Agents Chemother 51:707-715.
14. Schang LM (2006) Herpes simplex viruses in antiviral drug discovery. Curr Pharm Des 12:1357-1370.
15. Hao L, et al. (2008) Drosophila RNAi screen identifies host genes important for influenza virus replication. Nature 454:890-893.
16. Kozlov MM, Leikin SL, Chernomordik LV, Markin VS, Chizmadzhev YA (1989) Stalk mechanism of vesicle fusion. Intermixing of aqueous contents. Eur Biophys J 17:121-129.
17. Cooke IR, Deserno M (2006) Coupling between lipid shape and membrane curvature. Biophys J 91:487-495.
18. Markin VS, Albanesi JP (2002) Membrane fusion: Stalk model revisited. Biophys J 82:693-712.
19. Chernomordik LV, Kozlov MM (2005) Membrane hemifusion: Crossing a chasm in two leaps. Cell 123:375-382.
20. Yang L, Huang HW (2002) Observation of a membrane fusion intermediate structure. Science 297:1877-1879.
21. Epand RM (2003) Fusion peptides and the mechanism of viral fusion. Biochim Biophys Acta 1614:116-121.
22. Chizmadzhev YA (2004) The mechanisms of lipid-protein rearrangements during viral infection. Bioelectrochemistry 63:129-136.
23. Rothman JE, Lenard J (1977) Membrane asymmetry. Science 195:743-753.
24. Chan R, et al. (2008) Retroviruses human immunodeficiency virus and murine leukemia virus are enriched in phosphoinositides. J Virol 82:11228-11238.
25. van Til NP, et al. (2008) Alteration of viral lipid composition by expression of the phospholipid floppase ABCB4 reduces HIV vector infectivity. Retrovirology 5:14.
26. Teissier É, Pécheur E-I (2007) Lipids as modulators of membrane fusion mediated by viral fusion proteins. Eur Biophys J 36:887-899.
27. Cheetham JJ, Nir S, Johnson E, Flanagan TD, Epand RM (1994) The effects of membrane physical properties on the fusion of Sendai virus with human erythrocyte ghosts and liposomes. Analysis of kinetics and extent of fusion. J Biol Chem 269:5467-5472.
28. Yeagle PL, Young J, Hui SW, Epand RM (1992) On the mechanism of inhibition of viral and vesicle membrane fusion by carbobenzoxy-D-phenylalanyl- L-phenylalanylglycine. Biochemistry 31:3177-3183.
29. Miao L, et al. (1995) Potent inhibition of viral fusion by the lipophosphoglycan of Leishmania donovani. Biochemistry 34:4676-4683.
30. Kooijman EE, Chupin V, de Kruijff B, Burger KN (2003) Modulation of membrane curvature by phosphatidic acid and lysophosphatidic acid. Traffic 4:162-174.
31. Gaudin Y (2000) Rabies virus-induced membrane fusion pathway. J Cell Biol 150:601-612.
32. Chernomordik LV, Leikina E, Kozlov MM, Frolov VA, Zimmerberg J (1999) Structural intermediates in influenza haemagglutinin-mediated fusion. Mol Membr Biol 16:33-42.
33. WuDunn D, Spear PG (1989) Initial interaction of herpes simplex virus with cells is binding to heparan sulfate. J Virol 63:52-58.
34. Skorobogatyi MV, et al. (2006) 5-Arylethynyl-2′-deoxyuridines, compounds active against HSV-1. Org Biomol Chem 4:1091-1096.
35. Diwan P, Lacasse JJ, Schang LM (2004) Roscovitine inhibits activation of promoters in herpes simplex virus type 1 genomes independently of promoter-specific factors. J Virol 78:9352-9365.
36. Brandenburg B, et al. (2007) Imaging poliovirus entry in live cells. PLoS Biol 5:e183.
37. Skorobogatyi MV, et al. (2006) Fluorescent 5-alkynyl-2′- deoxyuridines: High emission efficiency of a conjugated perylene nucleoside in a DNA duplex. Chem Bio Chem 7:810-816.
38. Polozov IV, Bezrukov L, Gawrisch K, Zimmerberg J (2008) Progressive ordering with decreasing temperature of the phospholipids of influenza virus. Nat Chem Biol 4:248-255.
39. Mattila PK, et al. (2007) Missing-in-metastasis and IRSp53 deform PI(4,5)P2-rich membranes by an inverse BAR domain-like mechanism. J Cell Biol 176:953-964.
40. Peter BJ, et al. (2004) BAR domains as sensors of membrane curvature: The amphiphysin BAR structure. Science 303:495-499.
41. Hu J, et al. (2008) Membrane proteins of the endoplasmic reticulum induce high-curvature tubules. Science 319:1247-1250.
42. McMahon HT, Gallop JL (2005) Membrane curvature and mechanisms of dynamic cell membrane remodelling. Nature 438:590-596.
43. Zimmerberg J, Kozlov MM (2006) How proteins produce cellular membrane curvature. Nat Rev Mol Cell Biol 7:9-19.
44. Andronova VL, et al. (2003) Antiviral activity of some 5-arylethynyl 2′-deoxyuridine derivatives. Bioorg Chem 29:290-295. (Translated from Russian).
45. Balzarini J (2007) Targeting the glycans of glycoproteins: A novel paradigm for antiviral therapy. Nat Rev Microbiol 5:583-597.
46. Harada S (2005) The broad anti-viral agent glycyrrhizin directly modulates the fluidity of plasma membrane and HIV-1 envelope. Biochem J 392:191-199.
47. Nabatov AA, Pollakis G, Linnemann T, Paxton WA, de Baar MP (2007) Statins disrupt CCR5 and RANTES expression levels in CD4(+) T lymphocytes in vitro and preferentially decrease infection of R5 versus X4 HIV-1. PLoS ONE 2:e470.
48. Wolf MC, et al. (2010) A broad-spectrum antiviral targeting entry of enveloped viruses. Proc Natl Acad Sci USA 107:3157-3162.
49. Skorobogatyi MV, et al. (2006) 5-Alkynyl-2′-deoxyuridines, containing bulky aryl groups: Evaluation of structure-anti-HSV-1 activity relationship. Tetrahedron 62:1279-1287.