Tunable heparan sulfate mimetics for modulating chemokine activity

Journal of the American Chemical Society

Volumn 135, Issue 30, 2013, Pages 10898-10901

  Sheng, Gloria J ^a   Oh, Young In ^a   Chang, Shuh Kuen ^b   Hsieh Wilson, Linda C ^a  

^a HOWARD HUGHES MEDICAL INSTITUTE   (United States)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PROCESS; CHEMOTACTIC ACTIVITY; DIVERGENT SYNTHESIS; GLYCOSAMINOGLYCANS; PLEIOTROPIC FUNCTIONS; POLYMERIC SCAFFOLD; PROTEIN BINDING PARTNERS; STRUCTURE AND ACTIVITIES;

AMINO ACIDS; BIOCHEMISTRY; SCAFFOLDS (BIOLOGY);

HYDRAULIC STRUCTURES;

BINDING PROTEIN; HEPARAN SULFATE; HEPARIN; POLYMER; RANTES; SERINE PROTEINASE;

ARTICLE; BINDING AFFINITY; BINDING SITE; BLOOD CLOTTING; IMMUNOCOMPETENT CELL; LYMPHOCYTE MIGRATION; PLEIOTROPY; PROTEIN BINDING; RING OPENING METATHESIS POLYMERIZATION; SULFATION; SYNTHESIS;

EID: 84881081059     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4027727     Document Type: Article

References (35)

1. Bishop, J. R.; Schuksz, M.; Esko, J. D. Nature 2007, 446, 1030
2. Ori, A.; Wilkinson, M. C.; Fernig, D. G. J. Biol. Chem. 2011, 286, 19892
3. Lortat-Jacob, H.; Grosdidier, A.; Imberty, A. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 1229
4. Gerard, C.; Rollins, B. J. Nature Immunol. 2001, 2, 108
5. Proudfoot, A. E.; Handel, T. M.; Johnson, Z.; Lau, E. K.; LiWang, P.; Clark-Lewis, I.; Borlat, F.; Wells, T. N.; Kosco-Vilbois, M. H. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 1885
6. Mackman, N. Nature 2008, 451, 914
7. Petitou, M.; Hérault, J. P.; Bernat, A.; Driguez, P. A.; Duchaussoy, P.; Lormeau, J. C.; Herbert, J. M. Nature 1999, 398, 417
8. Choay, J.; Petitou, M.; Lormeau, J. C.; Sinay, P.; Casu, B.; Gatti, G. Biochem. Biophys. Res. Commun. 1983, 116, 492
9. Xu, Y.; Masuko, S.; Takieddin, M.; Xu, H.; Liu, R.; Jing, J.; Mousa, S. A.; Linhardt, R. J.; Liu, J. Science 2011, 334, 498
10. Young, E. Thromb. Res. 2008, 122, 743
11. Wang, L. C.; Brown, J. R.; Varki, A.; Esko, J. D. J. Clin. Invest. 2002, 110, 127
12. Wang, J.-G.; Mu, J.-S.; Zhu, H.-S.; Geng, J.-G. Inflamm. Res. 2002, 51, 435
13. Alban, S.; Ludwig, R. J.; Bendas, G.; Schön, M. P.; Oostingh, G. J.; Radeke, H. H.; Fritzsche, J.; Pfeilschifter, J.; Kaufmann, R.; Boehncke, W.-H. J. Invest. Derm. 2009, 129, 1192
14. Powell, A. L.; Ahmed, Y. A.; Yates, E. A.; Turnbull, J. E. Nat. Protoc. 2010, 5, 821
15. de Paz, J. L.; Moseman, E. A.; Noti, C.; Polito, L.; von Andrian, U. H.; Seeberger, P. H. ACS Chem. Biol. 2007, 2, 735
16. Hu, Y.-P.; Zhong, Y.-Q.; Chen, Z.-G.; Chen, C.-Y.; Shi, Z.; Zulueta, M. M.; Ku, C.-C.; Lee, P.-Y.; Wang, C.-C.; Hung, S.-C. J. Am. Chem. Soc. 2012, 134, 20722
17. Fan, R.-H.; Achkar, J.; Hernández-Torres, J. M.; Wei, A. Org. Lett. 2005, 7, 5095
18. Arungundram, S.; Al-Mafraji, K.; Asong, J.; Leach, F. E., III; Amster, I. J.; Venot, A.; Turnbull, J. E.; Boons, G.-J. J. Am. Chem. Soc. 2009, 131, 17394
19. Goger, B.; Halden, Y.; Rek, A.; Mösl, R.; Pye, D.; Gallagher, J.; Kungl, A. J. Biochemistry 2002, 41, 1640
20. Shaw, J. P.; Johnson, Z.; Borlat, F.; Zwahlen, C.; Kungl, A.; Roulin, K.; Harrenga, A.; Wells, T. N.; Proudfoot, A. E. Structure 2004, 12, 2081
21. Rawat, M.; Gama, C. I.; Matson, J. B.; Hsieh-Wilson, L. C. J. Am. Chem. Soc. 2008, 130, 2959
22. Grubbs, R. H. Handbook of Metathesis, 1 st ed.; Wiley-VCH: Weinheim, Germany, 2003.
23. Kanai, M.; Mortell, K. H.; Kiessling, L. L. J. Am. Chem. Soc. 1997, 119, 9931
24. Lee, S.-G.; Brown, J. M.; Rogers, C. J.; Matson, J. B.; Krishnamurthy, C.; Rawat, M.; Hsieh-Wilson, L. C. Chem. Sci. 2010, 1, 322
25. Canales, A.; Angulo, J.; Ojeda, R.; Bruix, M.; Fayos, R.; Lozano, R.; Giménez-Gallego, G.; Martín-Lomas, M.; Nieto, P. M.; Jiménez-Barbero, J. J. Am. Chem. Soc. 2005, 127, 5778
26. Orgueira, H. A.; Bartolozzi, A.; Schell, P.; Litjens, R. E.; Palmacci, E. R.; Seeberger, P. H. Chem.-Eur. J. 2003, 9, 140
27. Lohman, G. J; Hunt, D. K.; Högermeier, J. A.; Seeberger, P. H. J. Org. Chem. 2003, 68, 7559
28. Gavard, O.; Hersant, Y.; Alais, J.; Duverger, V.; Dilhas, A.; Bascou, A.; Bonnaffé, D. Eur. J. Org. Chem. 2003, 2003, 3603
29. Dilhas, A.; Bonnaffé, D. Carbohydr. Res. 2003, 338, 681
30. Ravidà, A.; Liu, X.; Kovacs, L.; Seeberger, P. H. Org. Lett. 2006, 8, 1815
31. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953
32. Qin, S.; Rottman, J. B.; Myers, P.; Kassam, N.; Weinblatt, M.; Loetscher, M.; Koch, A. E.; Moser, B.; Mackay, C. R. J. Clin. Invest. 1998, 101, 746
33. Martin, L.; Blanpain, C.; Garnier, P.; Wittamer, V.; Parmentier, M.; Vita, C. Biochemistry 2001, 40, 6303
34. Kitaura, M.; Nakajima, T.; Imai, T.; Harada, S.; Combadiere, C.; Tiffany, H. L.; Murphy, P. M.; Yoshie, O. J. Biol. Chem. 1996, 271, 7725
35. Borish, L. C.; Steinke, J. W. J. Allergy Clin. Immunol. 2003, 111, S460