DC-SIGN antagonists, a potential new class of anti-infectives

Current Medicinal Chemistry

Volumn 19, Issue 7, 2012, Pages 992-1007

  Anderluh, M ^a   Jug, G ^a   Svajger U ^b   Obermajer, N ^a,c  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b BLOOD TRANSFUSION CENTRE OF SLOVENIA   (Slovenia)

^c JO EF STEFAN INSTITUTE   (Slovenia)

Author keywords

Anti infectives; C type lectin; DC SIGN; DC SIGN antagonists; Dendrimers; Dendritic cells; Dendrons; Glycomimetics; HIV 1; Pathogenrecognition receptor

Indexed keywords

ANTIINFECTIVE AGENT; CD209 ANTIGEN; CD209 ANTIGEN ANTAGONIST; FUCOSE; LANGERIN; MANNOSE OLIGOSACCHARIDE; POLYSACCHARIDE; UNCLASSIFIED DRUG;

ANTIGEN BINDING; ANTIGEN STRUCTURE; BINDING AFFINITY; BINDING SITE; CD4+ T LYMPHOCYTE; EBOLA VIRUS; HOST PATHOGEN INTERACTION; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; NONHUMAN; REVIEW;

EID: 84858256290     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986712799320664     Document Type: Review

References (88)

1. Banchereau, J.; Briere, F.; Caux, C.; Davoust, J.; Lebecque, S.; Liu, Y. T.; Pulendran, B.; Palucka, K. Immunobiology of dendritic cells. Ann. Rev. Immunol., 2000, 18, 767-811. (Pubitemid 30365397)
2. Svajger, U.; Anderluh, M.; Jeras, M.; Obermajer, N. C-type lectin DC-SIGN: An adhesion, signaling and antigen-uptake molecule that guides dendritic cells in immunity. Cell. Signal., 2010, 22 (10), 1397-1405.
3. Kwon, D.S.; Gregorio, G.; Bitton, N.; Hendrickson, W.A.; Littman, D.R. DC-SIGN-mediated internalisation of HIV is required for trans-enhancement of T cell infection. Immunity, 2002, 16 (1), 135-44. (Pubitemid 34143223)
4. van Kooyk, Y.; Geijtenbeek, T.B. DC-SIGN: escape mechanism for pathogens. Nat. Rev. Immunol. 2003, 3 (9), 697-709. (Pubitemid 41070811)
5. Khoo, U.S.; Chan, K.Y.; Chan, V.S.; Lin, C.L. DC-SIGN and L-SIGN: the SIGNs for infection. J. Mol. Med., 2008, 86 (8), 861-874.
6. Banchereau, J.; Steinman, R.M. Dendritic cells and the control of immunity. Nature, 1998, 392 (6673), 245-252. (Pubitemid 28155090)
7. Janeway, C.A.; Medzhitov, R., Innate immune recognition. Ann. Rev. Immunol., 2002, 20, 197-216. (Pubitemid 34293424)
8. Geijtenbeek, T.B.H.; Torensma, R.; van Vliet, S.J.; van Duijnhoven, G.C.F.; Adema, G.J.; van Kooyk, Y.; Figdor, C.G. Identification of DC-SIGN, a novel dendritic cell-specific ICAM-3 receptor that supports primary immune responses. Cell, 2000, 100 (5), 575-585.
9. Geijtenbeek, T.B.; Krooshoop, D.J.; Bleijs, D.A.; van Vliet, S.J.; van Duijnhoven, G.C.; Grabovsky, V.; Alon, R.; Figdor, C.G.; van Kooyk, Y. DC-SIGN-ICAM-2 interaction mediates dendritic cell trafficking. Nat. Immunol. 2000, 1 (4), 353-357.
10. van Kooyk, Y. C-type lectins on dendritic cells: key modulators for the induction of immune responses. Biochem. Soc. Trans., 2008, 36, 1478-1481.
11. Geijtenbeek, T.B.H.; Torensma, R.; van Vliet, S.J.; van Duijnhoven, G.C.F.; Middel, J.; Cornelissen, I. L.M.H.A.; Adema, G.J.; Nottet, H.S.L.M.; Figdor, C.G.; van Kooyk, Y. DC-sign, a novel dendritic cell-specific adhesion receptor for ICAM-3 mediates DC-T cell interactions and HIV-1 infection of DC. Blood, 1999, 94 (10), 434a-434a.
12. Feinberg, H.; Mitchell, D.A.; Drickamer, K.; Weis, W.I. Structural basis for selective recognition of oligosaccharides by DC-SIGN and DC-SIGNR. Science, 2001, 294 (5549), 2163-6. (Pubitemid 33150672)
13. Geijtenbeek, T.B.; van Duijnhoven, G.C.; van Vliet, S.J.; Krieger, E.; Vriend, G.; Figdor, C.G.; van Kooyk, Y. Identification of different binding sites in the dendritic cell-specific receptor DC-SIGN for intercellular adhesion molecule 3 and HIV-1. J. Biol. Chem., 2002, 277 (13), 11314-11320.
14. Guo, Y.; Feinberg, H.; Conroy, E.; Mitchell, D.A.; Alvarez, R.; Blixt, O.; Taylor, M.E.; Weis, W.I.; Drickamer, K. Structural basis for distinct ligand-binding and targeting properties of the receptors DC-SIGN and DC-SIGNR. Nat. Struct. Mol. Biol., 2004, 11 (7), 591-598. (Pubitemid 38823524)
15. Mitchell, D.A.; Fadden, A.J.; Drickamer, K. A novel mechanism of carbohydrate recognition by the C-type lectins DC-SIGN and DC-SIGNR. Subunit organisation and binding to multivalent ligands. J. Biol. Chem., 2001, 276 (31), 28939-28945.
16. Feinberg, H.; Guo, Y.; Mitchell, D.A.; Drickamer, K.; Weis, W.I. Extended neck regions stabilize tetramers of the receptors DC-SIGN and DC-SIGNR. J. Biol. Chem., 2005, 280 (2), 1327-1335.
17. Tabarani, G.; Thepaut, M.; Stroebel, D.; Ebel, C.; Vives, C.; Vachette, P.; Durand, D.; Fieschi, F. DC-SIGN Neck Domain Is a pH-sensor Controlling Oligomerisation SAXS and Hydrodynamic Studies of Extracellular Domain. J. Biol. Chem., 2009, 284 (32), 21229-21240.
18. Cambi, A.; Koopman, M.; Figdor, C.G. How C-type lectins detect pathogens. Cell. Microbiol., 2005, 7 (4), 481-488. (Pubitemid 40439447)
19. Menon, S.; Rosenberg, K.; Graham, S.A.; Ward, E. M.; Taylor, M.E.; Drickamer, K.; Leckband, D.E. Binding-site geometry and flexibility in DCSIGN demonstrated with surface force measurements. Proc. Natl. Acad. Sci. U S A, 2009, 106 (28), 11524-11529.
20. Cambi, A.; de Lange, F.; van Maarseveen, N.M.; Nijhuis, M.; Joosten, B.; van Dijk, E.M.; de Bakker, B.I.; Fransen, J.A.; Bovee-Geurts, P.H.; van Leeuwen, F.N.; Van Hulst, N.F.; Figdor, C.G. Microdomains of the C-type lectin DC-SIGN are portals for virus entry into dendritic cells. J. Cell. Biol., 2004, 164 (1), 145-155. (Pubitemid 38082465)
21. Appelmelk, B.J.; van Die, I.; van Vliet, S.J.; Vandenbroucke-Grauls, C.M.; Geijtenbeek, T.B.; van Kooyk, Y. Cutting edge: carbohydrate profiling identifies new pathogens that interact with dendritic cell-specific ICAM-3-grabbing nonintegrin on dendritic cells. J. Immunol., 2003, 170 (4), 1635-1639.
22. Tailleux, L.; Schwartz, O.; Herrmann, J.L.; Pivert, E.; Jackson, M.; Amara, A.; Legres, L.; Dreher, D.; Nicod, L.P.; Gluckman, J.C.; Lagrange, P.H.; Gicquel, B.; Neyrolles, O. DC-SIGN is the major Mycobacterium tuberculosis receptor on human dendritic cells. J. Exp. Med. 2003, 197 (1), 121-127. (Pubitemid 36110263)
23. Holt, P.G. Antigen presentation in the lung. Am. J. Resp. Crit. Care Med., 2000, 162 (4), S151-S156.
24. a) Schorey, J.S.; Carroll, M.C.; Brown, E.J. A macrophage invasion mechanism of pathogenic mycobacteria. Science, 1997, 277 (5329), 1091-1093;
25. b) Ernst, J.D. Macrophage receptors for Mycobacterium tuberculosis. Inf. Immun., 1998, 66 (4), 1277-1281. (Pubitemid 128471479)
26. Geijtenbeek, T.B.; Van Vliet, S.J.; Koppel, E.A.; Sanchez-Hernandez, M.; Vandenbroucke-Grauls, C.M.; Appelmelk, B.; Van Kooyk, Y. Mycobacteria target DC-SIGN to suppress dendritic cell function. J. Exp. Med., 2003, 197 (1), 7-17. (Pubitemid 36110253)
27. a) Maeda, N.; Nigou, J.; Herrmann, J.L.; Jackson, M.; Amara, A.; Lagrange, P.H.; Puzo, G.; Gicquel, B.; Neyrolles, O. The cell surface receptor DC-SIGN discriminates between Mycobacterium species through selective recognition of the mannose caps on lipoarabinomannan. J. Biol. Chem., 2003, 278 (8), 5513-5516;
28. b) Pitarque, S.; Herrmann, J.L.; Duteyrat, J.L.; Jackson, M.; Stewart, G.R.; Lecointe, F.; Payre, B.; Schwartz, O.; Young, D.B.; Marchal, G.; Lagrange, P.H.; Puzo, G.; Gicquel, B.; Nigou, J.; Neyrolles, O. Deciphering the molecular bases of Mycobacterium tuberculosis binding to the lectin DC-SIGN reveals an underestimated complexity. Biochem. J., 2005, 392 (Pt 3), 615-624;
29. c) Tailleux, L.; Gicquel, B.; Neyrolles, O. DC-SIGN, a key receptor of Mycobacterium tuberculosis? M S-Med. Sci., 2003, 19 (6-7), 658-660.
30. Tailleux, L.; Pham-Thi, N.; Bergeron-Lafaurie, A.; Herrmann, J.L.; Charles, P.; Schwartz, O.; Scheinmann, P.; Lagrange, P.H.; de Blic, J.; Tazi, A.; Gicquel, B.; Neyrolles, O. DC-SIGN induction in alveolar macrophages defines privileged target host cells for mycobacteria in patients with tuberculosis. Plos Medicine, 2005, 2 (12), 1269-1279. (Pubitemid 43020986)
31. Geijtenbeek, T.B.H.; van Kooyk, Y. Pathogens target DC-SIGN to influence their fate - DC-SIGN functions as a pathogen receptor with broad specificity. APMIS, 2003, 111 (7-8), 698-714.
32. Gringhuis, S.I.; den Dunnen, J.; Litjens, M.; van der Vlist, M.; Geijtenbeek, T.B. Carbohydrate-specific signaling through the DC-SIGN signalosome tailors immunity to Mycobacterium tuberculosis, HIV-1 and Helicobacter pylori. Nat. Immunol., 2009, 10 (10), 1081-1088.
33. Tsegaye, T.S.; Pohlmann, S. The multiple facets of HIV attachment to dendritic cell lectins. Cell. Microbiol., 2010, 12 (11), 1553-1561.
34. Cambi, A.; Beeren, I.; Joosten, B.; Fransen, J.A.; Figdor, C.G. The C-type lectin DC-SIGN internalizes soluble antigens and HIV-1 virions via a clathrin-dependent mechanism. Eur. J. Immunol., 2009, 39 (7), 1923-1928.
35. Trumpfheller, C.; Park, C.G.; Finke, J.; Steinman, R.M.; Granelli-Piperno, A. Cell type-dependent retention and transmission of HIV-1 by DC-SIGN. Int. Immunol., 2003, 15 (2), 289-298. (Pubitemid 36267121)
36. van Montfort, T.; Eggink, D.; Boot, M.; Tuen, M.; Hioe, C.E.; Berkhout, B.; Sanders, R.W. HIV-1 N-Glycan Composition Governs a Balance between Dendritic Cell-Mediated Viral Transmission and Antigen Presentation. J. Immunol., 2011, 187 (9), 4676-4685.
37. Sodhi, A.; Montaner, S.; Gutkind, J.S. Viral hijacking of G-protein-coupledreceptor signaling networks. Nat. Rev. Mol. Cell Biol., 2004, 5 (12), 998-1012. (Pubitemid 39611536)
38. van Kooyk, Y.; Appelmelk, B.; Geijtenbeek, T.B., A fatal attraction: Mycobacterium tuberculosis and HIV-1 target DC-SIGN to escape immune surveillance. Trends Mol. Med., 2003, 9 (4), 153-159. (Pubitemid 36626704)
39. Hatch, S.C.; Archer, J.; Gummuluru, S. Glycosphingolipid Composition of Human Immunodeficiency Virus Type 1 (HIV-1) Particles Is a Crucial Determinant for Dendritic Cell-Mediated HIV-1 trans-Infection. J. Virol., 2009, 83 (8), 3496-3506.
40. Sattin, S.; Daghetti, A.; Thepaut, M.; Berzi, A.; Sanchez-Navarro, M.; Tabarani, G.; Rojo, J.; Fieschi, F.; Clerici, M.; Bernardi, A. Inhibition of DC-SIGN- mediated HIV infection by a linear trimannoside mimic in a tetravalent presentation. ACS Chem. Biol., 2010, 5 (3), 301-312.
41. Requena, M.; Bouhlal, H.; Nasreddine, N.; Saidi, H.; Gody, J. C.; Aubry, S.; Gresenguet, G.; Kazatchkine, M.D.; Sekaly, R.P.; Belec, L.; Hocini, H. Inhibition of HIV-1 transmission in trans from dendritic cells to CD4(+) T lymphocytes by natural antibodies to the CRD domain of DC-SIGN purified from breast milk and intravenous immunoglobulins. Immunology, 2008, 123 (4), 508-518. (Pubitemid 351280964)
42. Alen, M.M.F.; Kaptein, S.J.F.; De Burghgraeve, T.; Balzarini, J.; Neyts, J.; Schols, D.,Antiviral activity of carbohydrate-binding agents and the role of DC-SIGN in dengue virus infection. Virology, 2009, 387 (1), 67-75.
43. a) Dai, B.; Yang, L.; Yang, H.; Hu, B.; Baltimore, D.; Wang, P. HIV-1 Gagspecific immunity induced by a lentivector-based vaccine directed to dendritic cells. Proc. Natl. Acad. Sci. U S A, 2009, 106 (48), 20382-20387;
44. b) Yang, L.; Yang, H.; Rideout, K.; Cho, T.; Il Joo, K.; Ziegler, L.; Elliot, A.; Walls, A.; Yu, D.; Baltimore, D.; Wang, P. Engineered lentivector targeting of dendritic cells for in vivo immunisation. Nat. Biotechnol., 2008, 26 (3), 326-334. (Pubitemid 351355129)
45. Cunningham, A.L.; Turville, S.; Wilkinson, J.; Cameron, P.; Dable, J., The role of dendritic cell C-type lectin receptors in HIV pathogenesis. J. Leukoc. Biol., 2003, 74 (5), 710-718. (Pubitemid 38040347)
46. Valladeau, J.; Ravel, O.; Dezutter-Dambuyant, C.; Moore, K.; Kleijmeer, M.; Liu, Y.; Duvert-Frances, V.; Vincent, C.; Schmitt, D.; Davoust, J.; Caux, C.; Lebecque, S.; Saeland, S. Langerin, a novel C-type lectin specific to Langerhans cells, is an endocytic receptor that induces the formation of Birbeck granules. Immunity, 2000, 12 (1), 71-81. (Pubitemid 30069216)
47. de Witte, L.; Nabatov, A.; Pion, M.; Fluitsma, D.; de Jong, M.; de Gruijl, T.; Piguet, V.; van Kooyk, Y.; Geijtenbeek, T.B.H. Langerin is a natural barrier to HIV-1 transmission by Langerhans cells. Nat. Med., 2007, 13 (3), 367-371. (Pubitemid 46376681)
48. Turville, S.G.; Cameron, P.U.; Handley, A.; Lin, G.; Pohlmann, S.; Doms, R.W.; Cunningham, A.L. Diversity of receptors binding HIV on dendritic cell subsets. Nat. Immunol., 2002, 3 (10), 975-983. (Pubitemid 35154012)
49. Fahrbach, K.M.; Barry, S.M.; Ayehunie, S.; Lamore, S.; Klausner, M.; Hope, T J. Activated CD34-derived langerhans cells mediate transinfection with human immunodeficiency virus. J. Virol., 2007, 81 (13), 6858-6868. (Pubitemid 46986622)
50. Chatwell, L.; Holla, A.; Kaufer, B.B.; Skerra, A. The caxbohydrate recognition domain of Langerin reveals high structural similarity with the one of DC-SIGN but an additional, calcium-independent sugar-binding site. Mol. Immunol., 2008, 45 (7), 1981-1994. (Pubitemid 351226273)
51. Andreini, M.; Doknic, D.; Sutkeviciute, I.; Reina, J.J.; Duan, J. X.; Chabrol, E.; Thepaut, M.; Moroni, E.; Doro, F.; Belvisi, L.; Weiser, J.; Rojo, J.; Fieschi, F.; Bernardi, A. Second generation of fucose-based DC-SIGN ligands: affinity improvement and specificity versus Langerin. Org. Biomol. Chem., 2011, 9 (16), 5778-5786.
52. Harding, M.M. Small revisions to predicted distances around metal sites in proteins. Acta Crystallogr. D Biol. Crystallogr., 2006, 62, 678-682. (Pubitemid 43806647)
53. Weis, W.I.; Drickamer, K.; Hendrickson, W.A., Structure of a C-Type Mannose-Binding Protein Complexed with an Oligosaccharide. Nature, 1992, 360 (6400), 127-134.
54. Feinberg, H.; Castelli, R.; Drickamer, K.; Seeberger, P.H.; Weis, W.I. Multiple modes of binding enhance the affinity of DC-SIGN for high mannose N-linked glycans found on viral glycoproteins. J. Biol. Chem., 2007, 282 (6), 4202-4209. (Pubitemid 47084456)
55. a) Hodges, A.; Sharrocks, K.; Edelmann, M.; Baban, D.; Moris, A.; Schwartz, O.; Drakesmith, H.; Davies, K.; Kessler, B.; McMichael, A.; Simmons, A. Activation of the lectin DC-SIGN induces an immature dendritic cell phenotype triggering Rho-GTPase activity required for HIV-1 replication. Nat. Immunol., 2007, 8 (6), 569-577;
56. b) Koopman, M.; Cambi, A.; de Bakker, B.I.; Joosten, B.; Figdor, C.G.; van Hulst, N.F.; Garcia- Parajo, M.F., Near-field scanning optical microscopy in liquid for high resolution single molecule detection on dendritic cells. FEBS Lett., 2004, 573 (1-3), 6-10.
57. Balzarini, J.; Van Herrewege, Y.; Vermeire, K.; Vanham, G.; Schols, D. Carbohydrate-binding agents efficiently prevent dendritic cell-specific intercellular adhesion molecule-3-grabbing nonintegrin (DC-SIGN)-directed HIV-1 transmission to T lymphocytes. Mol. Pharmacol., 2007, 71 (1), 3-11. (Pubitemid 46020972)
58. Lederman, M.M.; Offord, R.E.; Hartley, O. Microbicides and other topical strategies to prevent vaginal transmission of HIV. Nat. Rev. Immunol., 2006, 6 (5), 371-382.
59. Ernst, B.; Magnani, J.L. From carbohydrate leads to glycomimetic drugs. Nat. Rev. Drug. Discover., 2009, 8 (8), 661-677.
60. Timpano, G.; Tabarani, G.; Anderluh, M.; Invernizzi, D.; Vasile, F.; Potenza, D.; Nieto, P. M.; Rojo, J.; Fieschi, F.; Bernardi, A. Synthesis of novel DCSIGN ligands with an alpha-fucosylamide anchor. Chembiochem, 2008, 9 (12), 1921-1930.
61. Mitchell, D.A.; Jones, N.A.; Hunter, S.J.; Cook, J.M.D.; Jenkinson, S.F.; Wormald, M.R.; Dwek, R.A.; Fleet, G.W.J. Synthesis of 2-C-branched derivatives of D-mannose: 2-C-aminomethyl-D-mannose binds to the human C-type lectin DC-SIGN with affinity greater than an order of magnitude compared to that of D-mannose. Tetrahedron Asymm., 2007, 18 (12), 1502-1510. (Pubitemid 47069922)
62. Reina, J.J.; Sattin, S.; Invernizzi, D.; Mari, S.; Martinez-Prats, L.; Tabarani, G.; Fieschi, F.; Delgado, R.; Nieto, P. M.; Rojo, J.; Bernardi, A. 1,2- Mannobioside mimic: synthesis, DC-SIGN interaction by NMR and docking, and antiviral activity. ChemMedChem, 2007, 2 (7), 1030-1036.
63. Reina, J.J.; Maldonado, O.S.; Tabarani, G.; Fieschi, F.; Rojo, J. Mannose glycoconjugates functionalized at positions 1 and 6. Binding analysis to DC-SIGN using biosensors. Bioconj. Chem., 2007, 18 (3), 963-969. (Pubitemid 47010820)
64. Mari, S.; Sanchez-Medina, I.; Mereghetti, P.; Belvisi, L.; Jimenez-Barbero, J.; Bernardi, A. Synthesis and conformational analysis of an alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl- (1-->6)-alpha-D- mann opyranose mimic. Carbohydr. res., 2007, 342 (12-13), 1859-1868. (Pubitemid 47058050)
65. Garber, K.C.A.; Wangkanont, K.; Carlson, E.E.; Kiessling, L.L. A general glycomimetic strategy yields non-carbohydrate inhibitors of DC-SIGN. Chem. Commun. 2010, 46 (36), 6747-6749.
66. Turner, M.W. Mannose-binding lectin: The pluripotent molecule of the innate immune system. Immunol. Today, 1996, 17 (11), 532-540. (Pubitemid 26373253)
67. Obermajer, N.; Sattin, S.; Colombo, C.; Bruno, M.; Svajger, U.; Anderluh, M.; Bernardi, A. Design, synthesis and activity evaluation of mannose-based DC-SIGN antagonists. Mol. Divers., 2011, 15 (2), 347-360.
68. Obermajer, N.; Svajger, U.; Jeras, M.; Sattin, S.; Bernardi, A.; Anderluh, M. An assay for functional dendritic cell-specific ICAM-3-grabbing nonintegrin (DC-SIGN) inhibitors of human dendritic cell adhesion. Anal. Biochem., 2010, 406 (2), 222-229.
69. Tateno, H.; Ohnishi, K.; Yabe, R.; Hayatsu, N.; Sato, T.; Takeya, M.; Narimatsu, H.; Hirabayashi, J. Dual Specificity of Langerin to Sulfated and Mannosylated Glycans via a Single C-type Carbohydrate Recognition Domain. J. Biol. Chem., 2010, 285 (9), 6390-6400.
70. Holla, A.; Skerra, A. Comparative analysis reveals selective recognition of glycans by the dendritic cell receptors DC-SIGN and Langerin. PEDS, 2011, 24 (9), 659-669.
71. Naarding, M.A.; Ludwig, I.S.; Groot, F.; Berkhout, B.; Geijtenbeek, T.B.; Pollakis, G.; Paxton, W.A. Lewis X component in human milk binds DC-SIGN and inhibits HIV-1 transfer to CD4+ T lymphocytes. J. Clin. Invest., 2005, 115 (11), 3256-3264. (Pubitemid 41567590)
72. Hong, P.; Ninonuevo, M.R.; Lee, B.; Lebrilla, C.; Bode, L. Human milk oligosaccharides reduce HIV-1-gp120 binding to dendritic cell-specific ICAM3-grabbing non-integrin (DC-SIGN). Brit. J. Nutr., 2009, 101 (4), 482-486.
73. Rojo, J.; Delgado, R. Glycodendritic structures: promising new antiviral drugs. J. Antimicrob. Chemother., 2004, 54 (3), 579-581. (Pubitemid 39263896)
74. Reuter, J.D.; Myc, A.; Hayes, M.M.; Gan, Z.H.; Roy, R.; Qin, D.J.; Yin, R.; Piehler, L.T.; Esfand, R.; Tomalia, D.A.; Baker, J.R. Inhibition of viral adhesion and infection by sialic-acid-conjugated dendritic polymers. Bioconj. Chem.,1999, 10 (2), 271-278.
75. Lasala, F.; Arce, E.; Otero, J. R.; Rojo, J.; Delgado, R. Mannosyl glycodendritic structure inhibits DC-SIGN-mediated Ebola virus infection in cis and in trans. Antimicrob. Agents Chemother., 2003, 47 (12), 3970-3972. (Pubitemid 37485018)
76. Tabarani, G.; Reina, J.J.; Ebel, C.; Vives, C.; Lortat-Jacob, H.; Rojo, J.; Fieschi, F. Mannose hyperbranched dendritic polymers interact with clustered organisation of DC-SIGN and inhibit gp120 binding. FEBS Lett., 2006, 580 (10), 2402-2408. (Pubitemid 44389366)
77. Bernardi, A.; Cheshev, P. Interfering with the sugar code: Design and synthesis of oligosaccharide mimics. Chem. Eur J., 2008, 14 (25), 7434-7441.
78. Luczkowiak, J.; Sattin, S.; Sutkeviciute, I.; Reina, J.J.; Sanchez-Navarro, M.; Thepaut, M.; Martinez-Prats, L.; Daghetti, A.; Fieschi, F.; Delgado, R.; Bernardi, A.; Rojo, J. Pseudosaccharide Functionalized Dendrimers as Potent Inhibitors of DC-SIGN Dependent Ebola Pseudotyped Viral Infection. Bioconj.Chem., 2011, 22 (7), 1354-1365.
79. Wang, S.K.; Liang, P.H.; Astronomo, R.D.; Hsu, T.L.; Hsieh, S.L.; Burton, D.R.; Wong, C.H. Targeting the carbohydrates on HIV-1: Interaction of oligomannose dendrons with human monoclonal antibody 2G12 and DC-SIGN. Proc. Natl. Acad. Sci. USA, 2008, 105 (10), 3690-3695.
80. Becer, C.R.; Gibson, M.I.; Geng, J.; Ilyas, R.; Wallis, R.; Mitchell, D.A.; Haddleton, D.M. High-Affinity Glycopolymer Binding to Human DC-SIGN and Disruption of DC-SIGN Interactions with HIV Envelope Glycoprotein. J. Am. Chem. Soc., 2010, 132 (43), 15130-15132.
81. Martinez-Avila, O.; Hijazi, K.; Marradi, M.; Clavel, C.; Campion, C.; Kelly, C.; Penades, S. Gold Manno-Glyconanoparticies: Multivalent Systems to Block HIV-1 gp120 Binding to the Lectin DC-SIGN. Chem. Eur. J., 2009, 15 (38), 9874-9888.
82. Martinez-Avila, O.; Bedoya, L.M.; Marradi, M.; Clavel, C.; Alcami, J.; Penades, S. Multivalent Manno-Glyconanoparticles Inhibit DC-SIGN-Mediated HIV-1 Trans-infection of Human T Cells. Chembiochem, 2009, 10 (11), 1806-1809.
83. Borrok, M.J.; Kiessling, L.L., Non-carbohydrate inhibitors of the lectin DC-SIGN. J. Am. Chem. Soc., 2007, 129 (42), 12780-12785.
84. Wang, J.; Zhang, Y.; Wei, J.; Zhang, X.; Zhang, B.; Zhu, Z.; Zou, W.; Wang, Y.; Mou, Z.; Ni, B.; Wu, Y. Lewis X oligosaccharides targeting to DC-SIGN enhanced antigen-specific immune response. Immunology, 2007, 121 (2), 174-182. (Pubitemid 46663085)
85. Gringhuis, S.I.; den Dunnen, J.; Litjens, M.; van Het Hof, B.; van Kooyk, Y.; Geijtenbeek, T.B. C-type lectin DC-SIGN modulates Toll-like receptor signaling via Raf-1 kinase-dependent acetylation of transcription factor NF-kappaB. Immunity, 2007, 26 (5), 605-616.
86. Singh, S.K.; Stephani, J.; Schaefer, M.; Kalay, H.; Garcia-Vallejo, J.J.; den Haan, J.; Saeland, E.; Sparwasser, T.; van Kooyk, Y. Targeting glycan modified OVA to murine DC-SIGN transgenic dendritic cells enhances MHC class I and II presentation. Mol. Immunol. 2009, 47 (2-3), 164-174.
87. Finkelstein, J. Insight - Glycochemistry & glycobiology. Nature, 2007, 446 (7139), 999.
88. Cutler, B.; Justman, J. Vaginal microbicides and the prevention of HIV transmission. Lancet Infect. Dis., 2008, 8 (11), 685-697.