The Library

High-affinity glycopolymer binding to human DC-SIGN and disruption of DC-SIGN interactions with HIV envelope glycoprotein

Tools

Becer, C. Remzi, Gibson, Matthew I., Geng, Jin, Ilyas, Rebecca, Wallis, Russell, Mitchell, Daniel Anthony and Haddleton, David M.. (2010) High-affinity glycopolymer binding to human DC-SIGN and disruption of DC-SIGN interactions with HIV envelope glycoprotein. Journal of the American Chemical Society, Vol.132 (No.43). pp. 15130-15132. ISSN 0002-7863

Full text not available from this repository.

Official URL: http://dx.doi.org/10.1021/ja1056714

Abstract

Noncovalent interactions between complex carbohydrates and proteins drive many fundamental processes within biological systems, including human immunity. In this report we aimed to investigate the potential of mannose-containing glycopolymers to interact with human DC-SIGN and the ability of these glycopolymers to inhibit the interactions between DC-SIGN and the HIV envelope glycoprotein gp120. We used a library of glycopolymers that are prepared via combination of copper-mediated living radical polymerization and azide alkyne-alkyne [3+2] Huisgen cycloaddition reaction. We demonstrate that a relatively simple glycopolymer can effectively prevent the interactions between a human dendritic cell associated lectin (DC-SIGN) and the viral envelope glycoprotein gp120. This approach may give rise to novel insights into the mechanisms of HIV infection and provide potential new therapeutics.

Item Type:

Journal Article

Subjects:

Q Science > QD Chemistry

Divisions:

Faculty of Science > Chemistry

Library of Congress Subject Headings (LCSH):

Polymerization, Glycoproteins, Glycomics, Viral envelopes

Journal or Publication Title:

Journal of the American Chemical Society

Publisher:

American Chemical Society

ISSN:

0002-7863

Official Date:

3 November 2010

Dates:

Date	Event
3 November 2010	Published

Volume:

Vol.132

Number:

No.43

Number of Pages:

Page Range:

pp. 15130-15132

Identification Number:

10.1021/ja1056714

Status:

Peer Reviewed

Publication Status:

Published

Funder:

European Union (EU), University of Warwick, Wellcome Trust (London, England)

Grant number:

235999 (EU), 077400 (WT)

References:

(1) Sharon, N. Biochim. Biophys. Acta-Gen. Subjects 2006, 1760, 527.
(2) Haltiwanger, R. S.; Lowe, J. B. Annu. ReV. Biochem. 2004, 73, 491.
(3) Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357.
(4) Kiessling, L. L.; Gestwicki, J. E.; Strong, L. E. Curr. Opin. Chem. Biol.
2000, 4, 696.
(5) Geijtenbeek, T. B.; Kwon, D. S.; Torensma, R.; van Vliet, S. J.; van
Duijnhoven, G. C.; Middel, J.; Cornelissen, I. L.; Nottet, H. S.; Kewal-
Ramani, V. N.; Littman, D. R.; Figdor, C. G.; van Kooyk, Y. Cell 2000,
100, 587.
(6) Geijtenbeek, T. B.; Torensma, R.; van Vliet, S. J.; van Duijnhoven, G. C.;
Adema, G. J.; van Kooyk, Y.; Figdor, C. G. Cell 2000, 100, 575.
(7) van Liempt, E.; Bank, C. M. C.; Mehta, P.; Garcı´a-Vallejo, J. J.; Kawar,
Z. S.; Geyer, R.; Alvarez, R. A.; Cummings, R. D.; Kooyk, Y. v.; van Die,
I. FEBS Lett. 2006, 580, 6123.
(8) 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. J. Exp. Med. 2003, 197, 121.
(9) Mitchell, D. A.; Fadden, A. J.; Drickamer, K. J. Biol. Chem. 2001, 276,
28939.
(10) Feinberg, H.; Mitchell, D. A.; Drickamer, K.; Weis, W. I. Science 2001,
294, 2163.
(11) Feinberg, H.; Guo, Y.; Mitchell, D. A.; Drickamer, K.; Weis, W. I. J. Biol.
Chem. 2005, 280, 1327.
(12) Spain, S. G.; Gibson, M. I.; Cameron, N. R. J. Polym. Sci., Part A: Polym.
Chem. 2007, 45, 2059.
(13) Miura, Y.; Yasuda, K.; Yamamoto, K.; Koike, M.; Nishida, Y.; Kobayashi,
K. Biomacromolecules 2007, 8, 2129.
(14) Gibson, M. I.; Barker, C. A.; Spain, S. G.; Albertin, L.; Cameron, N. R.
Biomacromolecules 2009, 10, 328.
(15) Kiessling, L. L.; Strong, L. E.; Gestwicki, J. E. Annual Reports in Medicinal
Chemistry; Academic Press Inc.: San Diego, CA, 2000; Vol. 35, p 321.
(16) Ambrosi, M.; Cameron, N. R.; Davis, B. G. Org. Biomol. Chem. 2005, 3,
1593.
(17) Kiessling, L. L.; Gestwicki, J. E.; Strong, L. E. Angew. Chem., Int. Ed.
2006, 45, 2348.
(18) Pukin, A. V.; Branderhorst, H. M.; Sisu, C.; Weijers, C.; Gilbert, M.;
Liskamp, R. M. J.; Visser, G. M.; Zuilhof, H.; Pieters, R. J. Chembiochem
2007, 8, 1500.
(19) Gestwicki, J. E.; Cairo, C. W.; Strong, L. E.; Oetjen, K. A.; Kiessling,
L. L. J. Am. Chem. Soc. 2002, 124, 14922.
(20) Smith, E. A.; Thomas, W. D.; Kiessling, L. L.; Corn, R. M. J. Am. Chem.
Soc. 2003, 125, 6140.
(21) Ambrosi, M.; Cameron, N. R.; Davis, B. G.; Stolnik, S. Org. Biomol. Chem.
2005, 3, 1476.
(22) Joshi, A.; Vance, D.; Rai, P.; Thiyagarajan, A.; Kane, R. S. Chem.sEur.
J. 2006, 14, 7738.
(23) Pieters, R. J. Med. Res. ReV. 2007, 27, 796.
(24) Geng, J.; Mantovani, G.; Tao, L.; Nicolas, J.; Chen, G. J.; Wallis, R.;
Mitchell, D. A.; Johnson, B. R. G.; Evans, S. D.; Haddleton, D. M. J. Am.
Chem. Soc. 2007, 129, 15156.
(25) Schaefer, M.; Reiling, N.; Fessler, C.; Stephani, J.; Taniuchi, I.; Hatam,
F.; Yildirim, A. O.; Fehrenbach, H.; Walter, K.; Ruland, J.; Wagner, H.;
Ehlers, S.; Sparwasser, T. J. Immunol. 2008, 180, 6836.
(26) Gauthier, M. A.; Gibson, M. I.; Klok, H.-A. Angew. Chem., Int. Ed. 2009,
48, 48.
(27) Becer, C. R.; Hoogenboom, R.; Schubert, U. S. Angew. Chem., Int. Ed.
2009, 48, 4900.
(28) Klob, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001,
40, 2004.
(29) Nurmi, L.; Lindqvist, J.; Randev, R.; Syrett, J.; Haddleton, D. M. Chem.
Commun. 2009, 2727.
(30) Geng, J.; Lindqvist, J.; Mantovani, G.; Chen, G.; Sayers, C. T.; Clarkson,
G. J.; Haddleton, D. M. QSAR Comb. Sci. 2007, 26, 1220.
(31) Chen, G. J.; Tao, L.; Mantovani, G.; Geng, J.; Nystrom, D.; Haddleton,
D. M. Macromolecules 2007, 40, 7513.
(32) Becer, C. R.; Babiuch, K.; Pilz, D.; Hornig, S.; Heinze, T.; Gottschaldt,
M.; Schubert, U. S. Macromolecules 2009, 42, 2387.
(33) Ladmiral, V.; Mantovani, G.; Clarkson, G. J.; Cauet, S.; Irwin, J. L.;
Haddleton, D. M. J. Am. Chem. Soc. 2006, 128, 4823.
(34) Su, S. V.; Hong, P.; Baik, S.; Negrete, O. A.; Gurney, K. B.; Lee, B. J. Biol.
Chem. 2004, 279, 19122–19132.
(35) Lozach, P.-Y.; Lortat-Jacob, H.; De Lacroix De Lavalette, A.; Staropoli,
I.; Foung, S.; Amara, A.; Houle`s, C.; Fieschi, F.; Schwartz, O.; Virelizier,
J.-L.; Arenzana-Seisdedos, F.; Altmeyer, R. J. Biol. Chem. 2003, 278,
20358.
(36) Alvarez, C. P.; Lasala, F.; Carrillo, J.; Muniz, O.; Corbi, A. L.; Delgado,
R. J. Virol. 2002, 76, 6841.