394
Views
20
CrossRef citations to date
0
Altmetric
Original Articles

Recent Advances in the Synthesis and Biomedical Applications of Chain-End Functionalized Glycopolymers

, , &
Pages 67-92 | Received 31 Dec 2011, Accepted 01 Jan 2012, Published online: 07 Feb 2012

REFERENCES

  • Lis , H. and Sharon , N. 1998 . Lectins: carbohydrate-specific proteins that mediate cellular recognition . Chem. Rev. , 98 : 637 – 674 .
  • Flistsch , S. L. and Ulijn , R. V. 2003 . Sugar tied to the spot . Nature , 421 : 219 – 220 .
  • Sodetz , J. M. , Paulson , J. C. and McKee , P. A. 1979 . Carbohydrate composition and identification of blood group A, B, and H oligosaccharide structures on human factor VIII/von Willebrand factor . J. Biol. Chem. , 254 : 10754 – 10760 .
  • Karlsson , K. A. 1995 . Microbial recognition of target-cell glycoconjugates . Curr. Opin. Struct. Biol. , 5 : 622 – 635 .
  • Lee , K. J. , Mao , S. , Sun , C. , Gao , C. , Blixt , O. , Arrues , S. , Hom , L. G. , Kaufmann , G. F. , Hoffman , T. Z. , Coyle , A. R. , Paulson , J. , Felding-Habermann , B. and Janda , K. D. 2002 . Phage-display selection of a human single-chain Fv antibody highly specific for melanoma and breast cancer cells using a chemoenzymatically synthesized GM3–carbohydrate antigen . J. Am. Chem. Soc. , 124 : 12439 – 12446 .
  • Varki , A. 1993 . Biological roles of oligosaccharides: all of the theories are correct . Glycobiology , 3 : 97 – 130 .
  • Ritter , T. K. and Wong , C. H. 2003 . “ Carbohydrate-based drug discovery in the battle against bacterial infections: new opportunities arising from programmable one-pot oligosaccharide synthesis ” . In Carbohydrate-Based Drug Discovery , 899 – 932 . Wiley-VCH Verlag GmbH & Co: Malden, MA .
  • Fenselau , C. and Bundy , J. 2001 . Lectin and carbohydrate affinity capture surfaces . Anal. Chem. , 73 : 751 – 757 .
  • Zhang , H. , Ma , Y. and Sun , X-L. 2010 . Recent developments in carbohydrate-decorated targeted drug/gene delivery . Med. Res. Rev. , 30 : 270 – 289 .
  • Lee , Y. C. and Lee , R. T. 1995 . Carbohydrate-protein interactions: basis of glycobiology . Acc. Chem. Res. , 28 : 321 – 327 .
  • Zhang , H. , Ma , Y. and Sun , X-L. 2011 . Chemically selective liposome surface glyco-functionalization . Methods Mol. Biol. , 751 : 269 – 280 .
  • Kheireddine El-Boubbou , H. and Huang , X. 2011 . Glyco-nanomaterials: translating insights from the “sugar-code” to biomedical . Curr. Med. Chem. , 18 : 2060 – 2078 .
  • Branerhorst , H. M. , Ruijtenbeek , R. , Liskamp , R. M.J. and Piters , R. J. 2008 . Multivalent carbohydrate recognition on a glycodendrimer-functionalized flow-though chip . ChemBiochem. , 9 : 1836 – 1844 .
  • Ting , S. S.R. , Chen , G. and Stenzel , M. H. 2010 . Synthesis of glycopolymers and their multivalent recognitions with lectins . Polym. Chem. , 1 : 1392 – 1412 .
  • Strong , L. E. and Kiessling , L. L. 1999 . A general synthetic route to defined, biologically active multivalent array . J. Am. Chem. Soc. , 121 : 6193
  • Lundquist , J. J. and Toone , E. J. 2002 . The cluster glycoside effect . Chem. Rev. , 102 : 555 – 578 .
  • Armes , R. N. and Steven , P. 2003 . Synthesis and aqueous solution properties of novel sugar methacylate-based homopolymers and block polymers . Biomacromolecules , 4 : 1746 – 1758 .
  • Wulff , G. , Schmid , J. and Venhoff , T. 1996 . The synthesis of polymerizable vinyl sugars . Macromol. Chem. Phys. , 197 : 259 – 274 .
  • Okada , M. 2001 . Molecular design and syntheses of glycopolymers . Prog. Polym. Sci. , 26 : 67 – 104 .
  • Narian , R. , Jhurry , D. and Wulff , G. 2002 . Synthesis and characterization of polymers containing linear sugar moieties as side groups . Eur. Polym. J. , 38 : 273 – 280 .
  • Ohno , K. , Izu , Y. , Yamamoto , S. , Miyamoto , T. and Fukuda , T. 1999 . Nitroxide-controlled free radical polymerization of a sugar-carrying acryloyl monomer . Macromol. Chem. Phys. , 200 : 1619 – 1625 .
  • Strong , L. E. and Kiessling , L. L. 1999 . A general synthetic route to defined, biologically active multivalent arrays . J. Am. Chem. Soc. , 121 : 6193 – 6196 .
  • Roy , R. , Laferrière , C. A. , Pon , R. A. and Gamian , A. 1994 . Induction of rabbit immunoglobulin G antibodies against synthetic sialylated neoglycoproteins . Methods Enzymol. , 247 : 351 – 361 .
  • Ambrosi , M. , Cameron , N. R. and Davis , B. G. 2005 . Lectins: tools for the molecular understanding of the glycocode . Org. Biomol. Chem. , 3 : 1593 – 1608 .
  • Voit , B. and Appelhans , D. 2010 . Glycopolymers of various architectures—more than mimicking nature . Macromol. Chem. Phys. , 211 : 727 – 735 .
  • Boyer , C. , Bulmus , V. , Liu , J. , Davis , T. P. , Stenzel , M. H. and Barner-Kowollik , C. 2007 . Well-defined protein−polymer conjugates via in situ RAFT polymerization . J. Am. Chem. Soc. , 129 : 7145 – 7154 .
  • Roth , P. J. , Jochum , F. D. , Zentel , R. and Theato , P. 2010 . Synthesis of hetero-telechelic α,ω bio-functionalized polymers . Biomacromolecules , 11 : 238 – 244 .
  • Narla , S. N. and Sun , X-L. 2011 . Orientated glyco-macroligand formationbased on site-specific immobilization of O-cyanate chain-end functionalized glycoolymer . Org. Biomol. Chem. , 9 : 845 – 850 .
  • Tugulu , S. , Silacci , P. , Stergiopulos , N. and Klok , H-A. 2007 . RGD-functionalized polymer brushes as substrates for the integrin specific adhesion of human umbilical vein endothelial cells . Biomaterials , 28 : 2536 – 2546 .
  • Spain , S. G. , Gibson , M. I. and Cameron , N. R. 2007 . Recent advances in the synthesis of well-defined glycopolymers . J. Polym. Sci. Part A: Polym. Chem. , 45 : 2059 – 2072 .
  • Sato , H. , Miura , Y. , Saito , N. , Kobayashi , K. and Takai , O. 2007 . A micropatterned multifunctional carbohydrate display by an orthogonal self-assembling strategy . Biomacromolecules , 8 : 753 – 756 .
  • Loykulnant , S. and Hirao , A. 2000 . Protection and polymerization of functional monomers. 30. Anionic living polymerization of 4-alkylstyrenescontaining acetal-protected monosaccharide residues . Macromolecules , 33 : 4757 – 4764 .
  • Tsutsumiuchi , K. , Aoi , K. and Okada , M. 1997 . Synthesis of polyoxazoline-(glyco)peptide block copolymers by ring-opening polymerization of(sugar-substituted) alpha-amino acid N-carboxyanhydrides with polyoxazoline macroinitiators . Macromolecules , 30 : 4013 – 4017 .
  • Mortell , K. H. , Gingras , M. and Kiessling , L. L. 1994 . Synthesis of cell agglutination inhibitors by aqueous ring-opening metathesis polymerization . J. Am. Chem. Soc. , 116 : 12053 – 12054 .
  • Grande , D. , Baskaran , S. , Baskaran , C. , Gnanou , Y. and Chaikof , E. L. 2000 . Glycosaminoglycan-mimetic biomaterials. 1. Nonsulfated and sulfated glycopolymers by cyanoxyl-mediated free-radical polymerization . Macromolecules , 33 : 1123 – 1125 .
  • Ohno , K. , Tsujii , Y. , Miyamoto , T. , Fukuda , T. , Goto , M. , Kobayashi , K. and Akaike , T. 1998 . Synthesis of a well defined glycopolymer by nitroxide-controlled free radical polymerization . Macromolecules , 31 : 1064 – 1069 .
  • Muthukrishnan , S. , Jutz , G. , Andre , A. , Mori , H. and Muller , A. H.E. 2005 . Synthesis of hyperbranched glycopolymers via self-condensing atom transfer radical copolymerization of a sugar-carrying acrylate . Macromolecules , 38 : 9 – 18 .
  • Albertin , L. , Stenzel , M. H. , Barner-Kowollik , C. , Foster , L. J.R. and Davis , T. P. 2005 . Well-defined diblock glycopolymers from RAFT polymerization in homogeneous aqueous medium . Macromolecules , 38 : 9075 – 9084 .
  • Gordon , E. J. , Gestwicki , J. E. , Strong , L. E. and Kiessling , L. J. 2000 . Synthesis of end-labelled multivalent ligands for exploring cell-surface-receptor-ligand interactions . Chem. Biol. , 7 : 9 – 16 .
  • Gestwicki , J. E. , Cairo , C. W. , Mann , D. A. , Owen , R. M. and Kiessling , L. L. 2002 . Selective immobilization of multivalent ligands For surface plasmon resonance and fluorescence microscopy . Anal. Biochem. , 305 : 149 – 155 .
  • Brown , J. M. , Rogers , C. J. , Matson , J. B. , Krishnamurthy , C. , Rawat , M. , Hsiesh-Wilson , L. C. and Lee , S. G. 2010 . End-functionalized glycopolymers as mimetics of chondroitin sulfate proteoglycans . Chem. Sci. , 1 : 322 – 325 .
  • Sun , X-L. , Houston , K. M.F. , Grande , D. and Chaikof , E. L. 2002 . Design and synthesis of biotin terminated glycopolymers for surface glycoengineering . J. Am. Chem. Soc. , 124 : 7258 – 7259 .
  • Hou , S. , Sun , X-L. , Dong , C-M. and Chaik , E. L. 2004 . Facile synthesis of chain-end functionalized glycopolymer for site specific bioconjugation . Bioconjugate Chem. , 15 : 954 – 959 .
  • Gupta , S. S. , Raja , K. S. , Kaltgrad , E. , Dtrable , E. and Finn , M. G. 2005 . Virus-glycopolymer conjugates by copper(I) catalysis of atom transfer radical polymerization and azide-alkyne cycloaddition . Chem. Commun. , : 4315 – 4317 .
  • Maynard , H. D. and Vazquez-Dorbatt , V. 2006 . Biotinylated glycopolymers synthesized by atom transfer radical polymerization . Biomacromolecules , 7 : 2297 – 2302 .
  • Geng , J. , Mantovani , G. , Tao , L. , Nicholas , J. , Chen , G. , Wallis , R. , Mitchell , D. A. , Johnson , B. R.G. , Evans , S. D. and Haddleton , D. M. 2007 . Site-directed conjugation of “clicked” glycopolymers to form glycoprotein mimics: binding to mammalian lectin and introduction of immunological function . J. Am. Chem. Soc. , 129 : 15156 – 15163 .
  • Vazruez-Dorbatt , V. , Tolstyka , Z. P. , Chang , C-W. and Maynard , H. D. 2009 . Synthesis of a pyridyl disulfide end-functionalized glycopolymer for conjugation to biomolecules and patterning on gold surfaces . Biomacromolecules , 10 : 2207 – 2212 .
  • Bathfield , M. , D’Agosto , F. , Spitz , R. , Charreyre , M-T. and Delair , T. 2006 . Versatile precursors of functional RAFT agents. application to the synthesis of bio-related end-functionalized polymers . J. Am. Chem. Soc. , 128 : 2546 – 2547 .
  • Housni , A. , Cai , H. , Liu , S. , Pun , S. H. and Nirvan , R. 2007 . Facile preparation of glyconanoparticles and their bioconjugation to streptavidin . Langmuir , 23 : 5056 – 5061 .
  • Godula , K. , Rabuka , D. , Nam , K. T. and Betrozi , C. R. 2009 . Synthesis and microcontact printing of dual end-functionalized mucin-like glycopolymers for microarray applications . Angew. Chem. Int. Ed. , 48 : 4973 – 4976 .
  • Jiang , X. , Housni , A. , Gody , G. , Boullanger , P. , Charreyre , M-T. , Delair , T. and Narain , R. 2010 . Synthesis of biotinylated alfa-D-mannoside or N-Acetyl -beta-D-glucosaminoside decorated gold nanoparticles: study of their biomolecular recognition with Con A and WGA lectins . Bioconjugate Chem. , 21 : 521 – 530 .
  • Godula , K. and Betrozzi , C. R. 2010 . Synthesis of glycopolymers for microarray applications via ligation of reducing sugars to a poly(acrolyl hydrazide) scaffold . J. Am. Chem. Soc. , 132 : 9963 – 9996 .
  • Godula , K. , Umbel , M. L. , Rabuka , D. , Botyanszki , Z. , Bertozzi , C. R. and Parthasarathy , R. 2009 . Control of the molecular orientation of membrane-anchored biomimetic glycopolymers . J. Am. Chem. Soc. , 131 : 10263 – 10268 .
  • Grande , D. , Guerrero , R. and Gnanou , Y. 2005 . Cyanoxyl-mediated free-radical polymerization of acrylic acid: its scope and limitations . J. Polym. Sci. Part A: Polym. Chem. , 43 : 519 – 533 .
  • Rye , P. D. and Bovin , N. V. 1997 . Selection of carbohydrate-binding cell phenotypes using oligosaccharide-coated magnetic particles . Glycobiology , 7 : 179 – 182 .
  • Fenselau , C. and Bundy , J. 2001 . Lectin and carbohydrate affinity capture surfaces . Anal. Chem. , 73 : 751 – 757 .
  • Sun , X.-L. , Cui , W. , Haller , C. and Chaikof , E. L. 2004 . Site-specific multivalent carbohydrate-labeled quantum dots and magnetic beads . Chem. Bio. Chem. , 5 : 1593 – 1596 .
  • Chen , G. , Tao , L. , Mantovani , G. , Geng , J. , Nystroem , D. and Haddleton , D. M. 2007 . A modular click approach to glycosylated polymeric beads: design, synthesis and preliminary lectin recognition studies . Macromolecules , 40 : 7513 – 7520 .
  • Oyelaran , O. and Gildersleeve , J. C. 2009 . Glycan arrays: recent advances and future challenges . Curr. Opin. Chem. Biol. , 13 : 406 – 413 .
  • Oyelaran , O. , Li , Q. , Farnsworth , D. and Gildersleeve , J. C. 2009 . Microarrays with varying carbohydrate density reveal distinct subpopulations of serum antibodies . J. Proteome Res. , 8 : 3529 – 3538 .
  • Manimala , J. , Li , Z. , Jain , A. , VedBrat , S. and Gildersleeve , J. C. 2005 . Array analysis of anti-Tn antibodies and lectins reveals unexpected specificities: implications for diagnostic and vaccine development . Chem. Bio. Chem. , 6 : 2229 – 2241 .
  • Qiu , Y. , Patwa , T. , Xu , L. , Shedden , K. , Misek , D. E. , Tuck , M. , Jin , G. , Ruffin , M. T. , Turgeon , D. K. , Synal , S. , Bresalier , R. , Marcon , N. , Brenner , D. E. and Lubman , D. M. 2008 . Plasma glycoprotein profiling for colorectal cancer biomarker identification by lectin glycoarray and lectin blot . J. Proteome Res. , 7 : 1693 – 1703 .
  • Zhang , Y. , Li , Q. , Rodriguez , L. G. and Gildersleeve , J. C. 2010 . An array-based method to identify multivalent inhibitors . J. Am. Chem. Soc. , 132 : 9653 – 9662 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.