Metabolic Delivery of Methacryloyl Groups on Living Cells and Cell Surface Modification via Thiol-Ene "Click" Reaction

Macromolecular Bioscience

Volumn 11, Issue 11, 2011, Pages 1478-1483

  Iwasaki, Yasuhiko ^a   Matsuno, Hiroshi ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

Bioconjugation; Glycosylation; Imaging; Modifications; Thiol ene reaction

Indexed keywords

BIO-CONJUGATION; BIOLOGICAL APPLICATIONS; BIOTINYLATIONS; CELL SURFACES; CELL VIABILITY; CELL-BASED; CULTURE MEDIUM; HELA CELL; LIVING CELL; MANNOSAMINE; METHACRYLOYL GROUPS; MODIFICATIONS; PEGYLATION; PHOTO-INITIATOR; THIOL-ENE REACTIONS; THIOL-ENES; UV-LIGHT;

CELL MEMBRANES; CYTOLOGY; DRUG DELIVERY; ESTERIFICATION; FLUORESCENCE MICROSCOPY; GLYCOSYLATION;

CELL IMMOBILIZATION;

MANNOSAMINE; METHACRYLIC ACID DERIVATIVE; PHOTOINITIATOR; SIALIC ACID; THIOL GROUP; VINYL DERIVATIVE;

ARTICLE; BIOTINYLATION; CELL SURFACE; CELL VIABILITY; CULTURE MEDIUM; FLUORESCENCE MICROSCOPY; GLYCOSYLATION; HELA CELL; HUMAN; HUMAN CELL; IMMOBILIZATION; SYNTHESIS; ULTRAVIOLET RADIATION;

BIOTINYLATION; CELL MEMBRANE; CELL SURVIVAL; CLICK CHEMISTRY; DRUG DELIVERY SYSTEMS; GLYCOSYLATION; HELA CELLS; HEXOSAMINES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALEIMIDES; METHACRYLATES; MICROSCOPY, FLUORESCENCE; POLYETHYLENE GLYCOLS; SULFHYDRYL COMPOUNDS; SURFACE PROPERTIES;

EID: 80355135332     PISSN: 16165187     EISSN: 16165195     Source Type: Journal    
DOI: 10.1002/mabi.201100242     Document Type: Article

References (36)

1. S. Boonyarattanakalin, S. E. Martin, Q. Sun, B. R. Peterson, J. Am. Chem. Soc. 2006, 128, 11463.
2. I. Chen, M. Howarth, W. Lin, A. Y. Ting, Nat. Meth. 2005, 2, 99.
3. J. H. Lee, T. J. Baker, L. K. Mahal, J. Zabner, C. R. Bertozzi, D. F. Wiemer, M. J. Welsh, J. Biol. Chem. 1999, 274, 21878.
4. K. Kato, K. Umezawa, D. P. Funeriu, M. Miyake, J. Miyake, T. Nagamune, Biotechniques 2003, 35, 1014.
5. D. Rabuka, M. B. Forstner, J. T. Groves, C. R. Bertozzi, J. Am. Chem. Soc. 2008, 130, 5947.
6. Y. Teramura, H. Chen, T. Kawamoto, H. Iwata, Biomaterials 2007, 28, 4818.
7. C. L. Stabler, X. L. Sun, W. Cui, J. T. Wilson, C. A. Haller, E. L. Chaikof, Bioconjugate Chem. 2007, 18, 1713.
8. J. K. Armstrong, H. J. Meiselman, T. C. Fisher, Am. J. Hematol. 1997, 56, 26.
9. J. L. Panza, W. R. Wagner, H. L. Rilo, R. H. Rao, E. J. Beckman, A. J. Russell, Biomaterials 2000, 21, 1155.
10. R. A. Dwek, Chem. Rev. 1996, 96, 683.
11. H. Kayser, R. Zeitler, C. Kannicht, D. Grunow, R. Nuck, W. Reutter, J. Biol. Chem. 1992, 267, 16934.
12. L. K. Mahal, K. J. Yarema, C. R. Bertozzi, Science 1997, 276, 1125.
13. K. J. Yarema, L. K. Mahal, R. E. Bruehl, E. C. Rodriguez, C. R. Bertozzi, J. Biol. Chem. 1998, 273, 31168.
14. E. Saxon, C. R. Bertozzi, Science 2000, 287, 2007.
15. K. J. Yarema, C. R. Bertozzi, Genome Biol. 2001, 2, 1.
16. S.-G. Sampathkumar, A. V. Li, M. B. Jones, Z. Sun, K. J. Yarema, Nat. Chem. Biol. 2006, 2, 149.
17. Y. Tanaka, J. J. Kohler, J. Am. Chem. Soc. 2008, 130, 3278.
18. G. A. Lemieux, K. J. Yarema, C. L. Jacobs, C. R. Bertozzi, J. Am. Chem. Soc. 1999, 121, 4278.
19. Y. Iwasaki, H. Maie, K. Akiyoshi, Biomacromolecules 2007, 8, 3162.
20. O. T. Keppler, R. Horstkorte, M. Pawlita, C. Schmidt, W. Reutter, Glycobiology 2001, 11, 11R.
21. J. A. Prescher, D. H. Duhe, C. R. Bertozzi, Nature 2004, 430, 873.
22. D. S. Del Amo, W. Wang, H. Jiang, C. Besanceney, Y. Amos, M. Levy, Y. Liu, F. L. Marlow, P. Wu, J. Am. Chem. Soc. 2010, 132, 16893.
23. S.-H. Jung, H.-Y. Son, J. S. Yuk, J.-W. Jung, K. H. Kim, C.-H. Lee, H. Hwang, K.-S. Ha, Colloids Surf. B: Biointerfaces 2006, 47, 107.
24. S. J. Bryant, C. R. Nuttelman, K. S. Anseth, J. Biomater. Sci., Polym. Ed. 2000, 11, 439.
25. J. A. Prescher, C. R. Bertozzi, Nat. Chem. Biol. 2005, 1, 13.
26. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed. 2001, 40, 2004.
27. H. C. Kolb, K. B. Sharpless, Drug Discov. Today 2003, 8, 1128.
28. C. E. Hoyle, A. B. Lowe, C. N. Bowman, Chem. Soc. Rev. 2010, 39, 1355.
29. A. B. Lowe, Polym. Chem. 2010, 1, 17.
30. R. K. Iha, K. L. Wooley, A. M. Nyström, D. J. Burke, M. J. Kade, C. J. Hawker, Chem. Rev. 2009, 109, 5620.
31. C. E. Hoyle, T. Y. Lee, T. Roper, J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 5301.
32. F. M. Veronese, G. Pasut, Drug Discov. Today 2005, 10, 1451.
33. M. J. Joralemon, S. McRae, T. Emrick, Chem. Commun. 2010, 46, 1377.
34. J. L. Contreras, D. Xie, J. Mays, C. A. Smyth, C. Eckstein, F. G. Rahemtulla, C. J. Young, J. T. Anthony, G. Bilbao, D. T. Curiel, D. E. Eckhoff, Surgery 2004, 136, 537.
35. S. I. Gundersen, M. S. Kennedy, A. F. Palmer, Biotechnol. Bioeng. 2008, 101, 337.
36. J. Du, M. A. Meledeo, Z. Wang, H. S. Khanna, V. D. Paruchuri, K. J. Yarema, Glycobiology 2009, 19, 1382.