30. Turnbull WB, Stoddart JF (2002) Design and synthesis of glycodendrimers. Rev Mol
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31. Li Y, Cheng Y, Xu T (2007) Design, synthesis and potent pharmaceutical applications of
glycodendrimers: a mini review. Curr Drug Discov Technol 4:246–254
32. Tanaka K, Siwu ERO, Minami K et al (2010) Noninvasive imaging of dendrimer-type
N-glycan clusters: in vivo dynamics dependence on oligosaccharide structure. Angew Chem Int
Ed 49:8195–8200
33. Kamerling JP, Boons GJ, Lee YC, Suzuki A, Taniguchi N, Voragen AGJ (eds) (2007)
Analysis of glycans, polysaccharide functional properties & biochemistry of glycoconjugate
glycans, carbohydrate-mediated interactions: comprehensive glycoscience: From Chemistry
to Systems Biology, vol. II and III. Elsevier, Amsterdam
34. Kaneko Y, Nimmerjahn F, Ravetch JV (2006) Anti-inflammatory activity of immunoglobulin
G resulting from Fc sialylation. Science 313:670–673
35. Crocker PR, Paulson JC, Varki A (2007) Siglecs and their roles in the immune system.
Nat Rev Immunol 7:255–266
36. Shiao TC, Roy R (2012) Glycodendrimers as functional antigens and antitumor vaccines.
New J Chem 36:324–339
37. Toyokuni T, Singhal AK (1995) Synthetic carbohydrate vaccines based on tumour-associated
antigens. Chem Soc Rev 24:231–242
38. Toyokuni T, Dean B, Cai S et al (1994) Synthetic vaccines: synthesis of a dimeric Tn antigenlipopeptide conjugate that elicits immune responses against Tn-expressing glycoproteins.
J Am Chem Soc 116:395–396
39. Kaiser A, Gaidzik N, Becker T et al (2010) Fully synthetic vaccines consisting of
tumor-associated MUC1 glycopeptides and a lipopeptide ligand of the toll-like receptor 2.
Angew Chem Int Ed 49:3688–3692
40. Kudryashov V, Glunz PW, Williams LJ et al (2001) Toward optimized carbohydrate-based
anticancer vaccines: epitope clustering, carrier structure, and adjuvant all influence antibody
response to LewisY conjugates in mice. Proc Natl Acad Sci USA 98:3264–3269
41. Dumy P, Eggleston IM, Cervigni S et al (1995) A convenient synthesis of cyclic peptides as
regioselectively addressable functionalized templates (RAFT). Tetrahedron Lett 36:
1255–1258
42. Renaudet O, BenMohamed L, Dasgupta G et al (2008) Towards a self-adjuvanting multivalent B and T cell epitope containing synthetic glycolipopeptide cancer vaccine.
ChemMedChem 3:737–741
43. Bettahi I, Dasgupta G, Renaudet O et al (2009) Antitumor activity of a self-adjuvanting
glycol-lipopeptide vaccine bearing B cell, CD4+ and CD8+ T cell epitopes. Cancer Immunol
Immunother 58:187–200
44. Renaudet O, Dasgupta G, Bettahi I et al (2010) Linear and branched glyco-lipopeptide
vaccines follow distinct cross-presentation pathways and generate different magnitudes of
antitumor immunity. PLoS One 5:e11216
45. Jeon I, Lee D, Krauss IJ et al (2009) A new model for the presentation of tumor-associated
antigens and the quest for an anticancer vaccine: a solution to the synthesis challenge via ringclosing metathesis. J Am Chem Soc 131:14337–14344
46. Fiore M, Thomas B, Dule ´ry V et al (2012) Synthesis of multi-antigenic platforms as vaccine
candidates against cancers. New J Chem. doi:10.1039/C2NJ40972K
47. Bossu I, S ˇ ulc M, Kr ˇenek K et al (2011) Dendri-RAFTs: a second generation of cyclopeptidebased glycoclusters. Org Biomol Chem 9:1948–1959
48. Andre ´ S, Renaudet O, Bossu I et al (2011) Cyclic neoglycodecapeptides: how to increase
their inhibitory activity and selectivity on lectin/toxin binding to a glycoprotein and cells.
J Pept Sci 17:427–437
49. Kroto HW, Heath JR, O’ Brien SCO et al (1985) C60: buckminsterfullerene. Nature 318:
162–163
Applications of Glyconanoparticles as “Sweet” Glycobiological. . .
337
Biotechnol 90:231–255
31. Li Y, Cheng Y, Xu T (2007) Design, synthesis and potent pharmaceutical applications of
glycodendrimers: a mini review. Curr Drug Discov Technol 4:246–254
32. Tanaka K, Siwu ERO, Minami K et al (2010) Noninvasive imaging of dendrimer-type
N-glycan clusters: in vivo dynamics dependence on oligosaccharide structure. Angew Chem Int
Ed 49:8195–8200
33. Kamerling JP, Boons GJ, Lee YC, Suzuki A, Taniguchi N, Voragen AGJ (eds) (2007)
Analysis of glycans, polysaccharide functional properties & biochemistry of glycoconjugate
glycans, carbohydrate-mediated interactions: comprehensive glycoscience: From Chemistry
to Systems Biology, vol. II and III. Elsevier, Amsterdam
34. Kaneko Y, Nimmerjahn F, Ravetch JV (2006) Anti-inflammatory activity of immunoglobulin
G resulting from Fc sialylation. Science 313:670–673
35. Crocker PR, Paulson JC, Varki A (2007) Siglecs and their roles in the immune system.
Nat Rev Immunol 7:255–266
36. Shiao TC, Roy R (2012) Glycodendrimers as functional antigens and antitumor vaccines.
New J Chem 36:324–339
37. Toyokuni T, Singhal AK (1995) Synthetic carbohydrate vaccines based on tumour-associated
antigens. Chem Soc Rev 24:231–242
38. Toyokuni T, Dean B, Cai S et al (1994) Synthetic vaccines: synthesis of a dimeric Tn antigenlipopeptide conjugate that elicits immune responses against Tn-expressing glycoproteins.
J Am Chem Soc 116:395–396
39. Kaiser A, Gaidzik N, Becker T et al (2010) Fully synthetic vaccines consisting of
tumor-associated MUC1 glycopeptides and a lipopeptide ligand of the toll-like receptor 2.
Angew Chem Int Ed 49:3688–3692
40. Kudryashov V, Glunz PW, Williams LJ et al (2001) Toward optimized carbohydrate-based
anticancer vaccines: epitope clustering, carrier structure, and adjuvant all influence antibody
response to LewisY conjugates in mice. Proc Natl Acad Sci USA 98:3264–3269
41. Dumy P, Eggleston IM, Cervigni S et al (1995) A convenient synthesis of cyclic peptides as
regioselectively addressable functionalized templates (RAFT). Tetrahedron Lett 36:
1255–1258
42. Renaudet O, BenMohamed L, Dasgupta G et al (2008) Towards a self-adjuvanting multivalent B and T cell epitope containing synthetic glycolipopeptide cancer vaccine.
ChemMedChem 3:737–741
43. Bettahi I, Dasgupta G, Renaudet O et al (2009) Antitumor activity of a self-adjuvanting
glycol-lipopeptide vaccine bearing B cell, CD4+ and CD8+ T cell epitopes. Cancer Immunol
Immunother 58:187–200
44. Renaudet O, Dasgupta G, Bettahi I et al (2010) Linear and branched glyco-lipopeptide
vaccines follow distinct cross-presentation pathways and generate different magnitudes of
antitumor immunity. PLoS One 5:e11216
45. Jeon I, Lee D, Krauss IJ et al (2009) A new model for the presentation of tumor-associated
antigens and the quest for an anticancer vaccine: a solution to the synthesis challenge via ringclosing metathesis. J Am Chem Soc 131:14337–14344
46. Fiore M, Thomas B, Dule ´ry V et al (2012) Synthesis of multi-antigenic platforms as vaccine
candidates against cancers. New J Chem. doi:10.1039/C2NJ40972K
47. Bossu I, S ˇ ulc M, Kr ˇenek K et al (2011) Dendri-RAFTs: a second generation of cyclopeptidebased glycoclusters. Org Biomol Chem 9:1948–1959
48. Andre ´ S, Renaudet O, Bossu I et al (2011) Cyclic neoglycodecapeptides: how to increase
their inhibitory activity and selectivity on lectin/toxin binding to a glycoprotein and cells.
J Pept Sci 17:427–437
49. Kroto HW, Heath JR, O’ Brien SCO et al (1985) C60: buckminsterfullerene. Nature 318:
162–163
Applications of Glyconanoparticles as “Sweet” Glycobiological. . .
337