Sialic acids in biological and therapeutic processes: opportunities and challenges

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1. Marth JD, Grewal PK. Mammalian glycosylation in immunity. Nature Reviews Immunology 8(11), 874-887 (2008). 2. Ohtsubo K, Marth JD. Glycosylation in cellular mechanisms of health and disease. Cell 126(5), 855-867 (2006). 3. Dube DH, Bertozzi CR. Glycans in cancer and inflammation. Potential for therapeutics and diagnostics. Nature Reviews Drug Discovery 4(6), 477-488 (2005). 4. Fuster MM, Esko JD. The sweet and sour of cancer: Glycans as novel therapeutic targets. Nature Reviews Cancer 5, 526-542 (2005). 5. Galan MC, Benito-Alifonso D, Watt GM. Carbohydrate chemistry in drug discovery. Organic & Biomolecular Chemistry 9(10), 3598-3610 (2011). 6. Bernardes GJL, Castagner B, Seeberger PH. Combined approaches to the synthesis and study of glycoproteins. ACS Chemical Biology 4(9), 703-713 (2009). 7. Chen X, Varki A. Advances in the biology and chemistry of sialic acids. ACS Chemical Biology 5(2), 163-176 (2010). 8. Schauer R. Achievements and challenges of sialic acid research. Glycoconjugate Journal 17(7-9), 485-499 (2000). 9. Schauer R. Sialic acids: Chemistry, metabolism and function. Springer Verlag, (1982). 10. Varki A. Sialic acids in human health and disease. Trends in Molecular Medicine 14(8), 351-360 (2008). 11. Hudak JE, Canham SM, Bertozzi CR. Glycocalyx engineering reveals a siglec-based mechanism for nk cell immunoevasion. Nature Chemical Biology 10, 69-77 (2014). **A comprehensive study on the role of sialosides on Siglec function and NK cell cytotoxicity. 12. Chokhawala HA, Huang SS, Lau K et al. Combinatorial chemoenzymatic synthesis and high-through put screening of sialosides. Acs Chemical Biology 3(9), 567-576 (2008). 13. Crocker PR, Varki A. Siglecs in the immune system. Immunology 103(2), 137-145 (2001). 14. Stevens J, Blixt O, Paulson JC, Wilson IA. Glycan microarray technologies: Tools to survey host specificity of influenza viruses. Nature Reviews Microbiology 4(11), 857-864 (2006). 15. Varki A, Cummings, R.D., Esko, J.D., Freeze, H.H., Stanley, P., Bertozzi, C.R., Hart, G.W., Etzler, M.W. Essentials of glycobiology. (2). Cold Spring Harbour Press, (2008). 16. Rao FV, Rich JR, Rakic B et al. Structural insight into mammalian sialyltransferases. Nature Structural & Molecular Biology 16(11), 1186-1188 (2009). 17. Rillahan C, Schwartz E, Rademacher C et al. On-chip synthesis and screening of a sialoside library yields a high affinity ligand for siglec-7. ACS Chemical Biology 8, 1417-1422 (2013). 18. Macauley MS, Crocker PR, Paulson JC. Siglec-mediated regulation of immune cell function in disease. Nature Reviews Immunology 14, 653-666 (2014). 19. Cazet A, Julien S, Bobowski M, Burchell J, Delannoy P. Tumour-associated carbohydrate antigens in breast cancer. Breast Cancer Research 12(3), (2010). 20. Cazet A, Julien S, Bobowski M et al. Consequences of the expression of sialylated antigens in breast cancer. Carbohydrate Research 345(10), 1377-1383 (2010). 21. Ernst B, Magnani JL. From carbohydrate leads to glycomimetic drugs. Nature Reviews Drug Discovery 8(8), 661-677 (2009). 22. Lowe JB, Marth JD. A genetic approach to mammalian glycan function. Annu. Rev. Biochem. 72, 643-691 (2003). 23. Filser C, Kowalczyk D, Jones C et al. Synthetic glycopeptides from the e-selectin ligand 1 with varied sialyl lewis(x) structure as cell-adhesion inhibitors of e-selectin. Angewandte Chemie-International Edition 46(12), 2108-2111 (2007). 24. Anonymous. Deal watch: Pfizer deal for selectin inhibitor highlights potential of glycomimetic drugs. Nature reviews. Drug discovery 10(12), 890-890 (2011). 25. http://www.clinicaltrials.gov/. 26. Watz H, Bock D, Meyer M et al. Inhaled pan-selectin antagonist bimosiamose attenuates airway inflammation in copd. Pulmonary pharmacology & therapeutics 26(2), 265-270 (2013). 27. Mesch S, Moser D, Strasser DS et al. Low molecular weight antagonists of the myelin-associated glycoprotein: Synthesis, docking, and biological evaluation. Journal of Medicinal Chemistry 53(4), 1597-1615 (2010). 28. Magano J. Synthetic approaches to the neuraminidase inhibitors zanamivir (Relenza) and oseltamivir phosphate (Tamiflu) for the treatment of influenza. Chemical Reviews 109(9), 4398-4438 (2009). 29. Pera NP, Branderhorst HM, Kooij R et al. Rapid screening of lectins for multivalency effects with a glycodendrimer microarray. Chembiochem 11(13), 1896-1904 (2010). 30. Chen WC, Sigal DS, Saven A, Paulson JC. Targeting b lymphoma with nanoparticles bearing glycan ligands of cd22. Leukemia & Lymphoma 53(2), 208-210 (2012). 31. Chen WC, Kawasaki N, Nycholat CM et al. Antigen delivery to macrophages using liposomal nanoparticles targeting sialoadhesin/cd169. Plos One 7(6), (2012). 32. Blixt O, Han SF, Liao L et al. Sialoside analogue arrays for rapid identification of high affinity siglec ligands. Journal of the American Chemical Society 130(21), 6680-6681 (2008). 33. Rillahan CD, Macauley MS, Schwartz E et al. Disubstituted sialic acid ligands targeting siglecs CD33 and CD22 associated with myeloid leukaemias and b cell lymphomas. Chemical Science 5, 2398-2406 (2014). ** Reveals novel stratgies for cell directed therapies. 34. Jandus C, Simon H-U, Von Gunten S. Targeting siglecs-a novel pharmacological strategy for immuno- and glycotherapy. Biochemical Pharmacology 82(4), 323-332 (2011). 35. O'Reilly MK, Paulson JC. Siglecs as targets for therapy in immune-cell-mediated disease. Trends in Pharmacological Sciences 30(5), 240-248 (2009). 36. http://www.fda.gov/. 37. Zhu J, Wan Q, Ragupathi G, George CM, Livingston PO, Danishefsky SJ. Biologics through chemistry: Total synthesis of a proposed dual-acting vaccine targeting ovarian cancer orchestration of oligosaccharide and polypeptide domains. Journal of the American Chemical Society 131(11), 4151-4158 (2009). 38. Zhu J, Warren JD, Danishefsky SJ. Synthetic carbohydrate-based anticancer vaccines: The memorial sloan-kettering experience. Expert Review of Vaccines 8(10), 1399-1413 (2009). 39. Astronomo RD, Burton DR. Carbohydrate vaccines: Developing sweet solutions to sticky situations? Nature Reviews Drug Discovery 9(4), 308-324 (2010). 40. Zeichner SB. The failed theratope vaccine: 10 years later. The Journal of the American Osteopathic Association 112(8), 482-483 (2012). 41. Wilson RM, Danishefsky SJ. A vision for vaccines built from fully synthetic tumor-associated antigens: From the laboratory to the clinic. Journal of the American Chemical Society 135, 14462-14472 (2013). 42. Danishefsky SJ, Shue Y-K, Chang C-H. Development of Globo-H cancer vaccine. Accounts of Chemical Research 48, 643-652 (2015). **An impressive example of the path of development of an anticancer vaccine. 43. Byrne B, Donohoe GG, O'Kennedy R. Sialic acids: Carbohydrate moieties that influence the biological and physical properties of biopharmaceutical proteins and living cells. Drug Discovery Today 12(7-8), 319-326 (2007).