Copper-catalyzed azide-alkyne cycloaddition in the synthesis of polydiacetylene: "click glycoliposome" as biosensors for the specific detection of lectins

Chemistry - A European Journal

Volumn 17, Issue 6, 2011, Pages 1828-1836

  Leal, Manuel Pernía ^a   Assali, Mohyeddin ^a   Fernández, Inmaculada ^a   Khiar, Noureddine ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

biosensors; carbohydrates; click chemistry; lectins; polydiacetylene

Indexed keywords

AQUEOUS SOLUTIONS; AZIDE-ALKYNE CYCLOADDITION; BIOLOGICAL ANALYTES; BIOLOGICAL TARGETS; CLICK CHEMISTRY; COLORIMETRIC BIOSENSORS; COLORIMETRIC DETECTION; ELECTRONIC MICROSCOPY; ENE-YNE; FUNCTIONAL LIPOSOME; HEAD GROUPS; HYDROPHILIC SPACERS; LECTINS; MATRIX; MOLECULAR RECOGNITION ELEMENT; NANO-ASSEMBLIES; POLYDIACETYLENES; RAPID OPTIMIZATION; RECOGNITION ELEMENT; REGIO-SELECTIVE; SPECIFIC BINDING; SPECIFIC DETECTION; SPECIFIC INTERACTION; SUPRAMOLECULAR SELF-ASSEMBLIES; TEM; TETHERED LIGAND; UV/ VIS SPECTROSCOPY;

ACETYLENE; CATALYSIS; COLOR; COLORIMETRY; DYNAMIC LIGHT SCATTERING; LIPOSOMES; MOLECULAR RECOGNITION; MONOMERS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; PHOSPHOLIPIDS; SUGARS;

BIOSENSORS;

ALKYNE; AZIDE; CONCANAVALIN A; COPPER; GLYCOLIPID; LIPOSOME; POLYACETYLENE DERIVATIVE; POLYDIACETYLENE; POLYMER; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CLICK CHEMISTRY; COLORIMETRY; GENETIC PROCEDURES; SYNTHESIS; ULTRASTRUCTURE;

ALKYNES; AZIDES; BIOSENSING TECHNIQUES; CATALYSIS; CLICK CHEMISTRY; COLORIMETRY; CONCANAVALIN A; COPPER; GLYCOLIPIDS; LIPOSOMES; MOLECULAR STRUCTURE; POLYACETYLENES; POLYMERS; TRIAZOLES;

EID: 79551493498     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002236     Document Type: Article

References (86)

1. S. J. Singer and G. L. Nicolson, Science 1972, 175, 720
2. B. Alberts, A. Johnson, J. Lewis, M. Raff, K. Roberts, P. Walter, Molecular Biology of the Cell, 4 th ed., Garland Science, New York, 2002.
3. Essentials of Glycobiology (Eds.:, A. Varki, R. Cummings, J. Esko, H. Freeze, G. Hart., J. Marth,), Cold Spring Harbor Laboratory Press, New York, 1999
4. N. Sharon, Biochim. Biophys. Acta 2006, 1760, 527
5. C. R. Bertozzi, L. L. Kiessling, Science 2001, 291, 2357
6. H. D. Dube, C. R. Bertozzi, Nat. Rev. Drug Discovery 2005, 4, 477.
7. Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321
8. M. Mammen, S.-k Choi, G. M. Whitesides, Angew. Chem. Int. Ed. 1998, 37, 2754
9. J. J. Lundquist, E. J. Toone, Chem. Rev. 2002, 102, 555.
10. S.-K Choi, Synthetic Multivalent Molecules: Concepts and biomedical Applications, Wiley Interscience, Hoboken, 2004
11. N. Jayaraman, Chem. Soc. Rev. 2009, 38, 3463.
12. J. H. Fendler, Membrane Mimetic Chemistry, Wiley, New York, 1982
13. G. B. Thomas, L. H. Rader, J. Park, L. Abezgauz, D. Danino, P. DeShong, D. S. English, J. Am. Chem. Soc. 2009, 131, 5471
14. J. Voskuhl, M. C. A. Stuart, B. J. Ravoo, Chem. Eur. J. 2010, 16, 2790.
15. S. Okada, S. Peng, W. Spevak, D. Charych, Acc. Chem. Res. 1998, 31, 229
16. D. J. Ahn, J. -M Kim, Acc. Chem. Res. 2008, 41, 805.
17. D. W. Britt, U. G. Hofmann, D. MÌbius, S. W. Hell, Langmuir 2001, 17, 3757
18. K. Morigaki, T. Baumgart, A. Offenhäusser, W. Knoll, Angew. Chem. 2001, 113, 184
19. ngew. Chem. Int. Ed. 2001, 40, 172
20. R. B. M. Koehorst, R. G. Fokkink, M. C. Stuart, H. Zuilhof, E. J. R. Studhöler, Macromolecules 2002, 35, 4226
21. J. M. Kim, E. K. Ji, S. M. Woo, H. Lee, D. J. Ahn, Adv. Mater. 2003, 15, 1118
22. J. M. Kim, J. S. Lee, H. Coi, D. Sohn, D. J. Ahn, Macromolecules 2005, 38, 9366.
23. A. Singh, R. B. Thompson, J. M. Schnur, J. Am. Chem. Soc. 1986, 108, 2785
24. Z. Yuan, C.-W. Lee, S.-H. Lee, Angew. Chem. 2004, 116, 4293
25. Angew. Chem. Int. Ed. 2004, 43, 4197.
26. R. R. Chance, Macromolecules 1980, 13, 396-398.
27. R. A. Nallicheri, M. F. Rubner, Macromolecules 1991, 24, 517.
28. S. Kolusheva, R. Kafri, M. Katz, R. Jelinek, J. Am. Chem. Soc. 2001, 123, 417
29. S. Okada, R. Jelinek, D. Charych, Angew. Chem. 1999, 111, 678
30. Angew. Chem. Int. Ed. 1999, 38, 655
31. Q. Cheng, R. C. Stevens, Adv. Mater. 1997, 9, 481.
32. D. H. Charych, J. O. Nagy, W. Spevak, M. D. Bednarski, Science 1993, 261, 585
33. A. Reichert, J. O. Nagy, D. Charych, J. Am. Chem. Soc. 1995, 117, 829
34. J. Deng, Z. Sheng, K. Zhou, M. Duan, C. Y. Yu, L. Jiang, Bioconjugate Chem. 2009, 20, 533.
35. J. J. Pan, D. Charych, Langmuir 1997, 13, 1365.
36. Z. Ma, J. Li, M. Liu, J. Cao, Z. Zou, J. Tu, L. Jiang, J. Am. Chem. Soc. 1998, 120, 12678
37. M. Rangin, A. Basu, J. Am. Chem. Soc. 2004, 126, 5038.
38. S. Kolusheva, L. Boyer, R. Jelinek, Nat. Biotechnol. 2000, 18, 225.
39. C. Sun, Y. Zhang, Y. Fan, Y. Li, J. Li, J. Inorg. Biochem. 2004, 98, 925
40. C. Wang, Z. Ma, Anal. Bioanal. Chem. 2005, 382, 1708-1710.
41. R. Jelinek, S. Kolusheva, Chem. Rev. 2004, 104, 5987
42. M. Reppy, B. A. Pindzola, Chem. Commun. 2007, 4317
43. P. Boullanger, D. Lafont, M.-N. Bouchou, L. Jiang, T. Liu, W. Lu, C. X. Guo, J. Li, C. R. Chim. 2008, 11, 43
44. B. Yoon, S. Lee, J. M. Kim, Chem. Soc. Rev. 2009, 38, 1958.
45. J. O. Nagy, M. D. Bednarski, Tetrahedron Lett. 1991, 32, 3953
46. A. Lio, A. Reichert, D. J. Ahn, J. O. Nagy, M. Salmeron, D. H. Charych, Langmuir 1997, 13, 6524
47. Q. Cheng, R. C. Stebvens, Chem. Phys. Lipids 1997, 87, 41
48. H. Bader, R. Vana Wagenen, J. D. Andrade, H. Ringsdorf, J. Colloid Interface Sci. 1984, 101, 246
49. H. Bader, H. Ringsdorf, J. Skura, Angew. Chem. 1981, 93, 109
50. Angew. Chem. Int. Ed. Engl. 1981, 20, 91.
51. R. Jelinek, S. Y. Okada, S. Norvez, D. H. Charych, Chem. Biol. 1998, 5, 619
52. S. Y. Okada, R. Jelinek, D. H. Charych, Angew. Chem. 1999, 111, 678
53. Angew. Chem. Int. Ed. 1999, 38, 655.
54. H. C. Kolb, H. K. B. Sharpless, Drug Discovery Today 2003, 8, 1128
55. F. Saida Hassane, B. Frisch, F. Schuber, Bioconjugate Chem. 2006, 17, 849
56. S. Cavalli, A. R. Tipton, M. Overhand, A. Kros, Chem. Commun. 2006, 3193
57. J.-Y. Namgung, B.-H. Jun, Y.-S. Lee, Synlett 2010, 449.
58. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Chem. Soc. 2003, 125, 3192
59. B. Parrish, R. B. Breitenkamp, T. Emrick, J. Am. Chem. Soc. 2005, 127, 7404
60. M. Sawa, T. L. Hsu, T. Itoh, M. Sugiyama, S. R. Hanson, P. K. Vogt, C. H. Wong, Proc. Natl. Acad. Sci. USA 2006, 103, 12371.
61. Z. Ma, J. Li, L. Jiang, Langmuir 2000, 16, 7801
62. M. Gelhausen, F. Besson, S. Chierici, D. Lafont, P. Boulanger, B. Roux, Coll. Surf. B: Biointerfaces 1998, 10, 395.
63. N. Sharon, H. Lis, Science 1972, 177, 949
64. H. Lis, N. Sharon, Chem. Rev. 1998, 98, 637
65. E. E. Simanek, G. J. McGarvey, J. A. Jablonski, C. H. Wong, Chem. Rev. 1998, 98, 833.
66. A. K. Deisingh, M. Thompson, Analyst 2002, 127, 567
67. I.-B. Kim, J. N. Wilson, U. H. F. Bunz, Chem. Commun. 2005, 1273.
68. I. Baussanne, J. M. Benito, C. Ortiz Mellet, J. M. GarcIa Fernández, H. Law, J. Defaye, Chem. Commun. 2000, 1489
69. M. Köhn, J. M. Benito, C. Ortiza Mellet, T. K. Linhorst, J. M. García Fernández, ChemBioChem 2004, 5, 771.
70. F. Fazio, M. C. Bryan, O. Blixt, J. C. Paulson, C. H. Wong, J. Am. Chem. Soc. 2002, 124, 14397.
71. N. Khiar, M. Pernía Leal, R. Baati, C. Ruhlmann, C. Mioskowski, P. Schultz, I. Fernández, Chem. Commun. 2009, 4121
72. M. Assali, M. P. Pernía Leal, I. Fernández, R. Baati, C. Mioskowski, N. Khiar, Soft Matter 2009, 5, 948.
73. W. Spevak, C. Foxall, D. H. Charych, F. Dasgupta, J. O. Nagy, J. Med. Chem. 1996, 39, 1018
74. R. Bruehl, F. Dsgupta, T. R. Katsumoto, J. H. Tan, C. R. Bertozzi, W. Spevak, D. J. Ahn, S. D. Rosen, J. O. Nagy, Biochemistry 2001, 40, 5964.
75. R. R. C. New, in Liposome: A Practical Approach (Ed.:, R.A R.A C. New,), Oxford University Press, Oxford, 1990, pp.A 33-104.
76. C. X. Guo, P. Boulanger, T. Liu, L. Jiang, J. Phys. Chem. B 2005, 109, 18765.
77. Polydiacetylenes: Synthesis Structure and Electronic Properties, Vol.A 102, (Ed.:, D. Bloor, R.A R. Chance,), Martinus Nijhoff Publishers, Boston, 1985
78. S. R. Sheth, D. E. Leckband, Langmuir 1997, 13, 5652
79. H. Eckhardt, D. S. Boudreaux, R. R. Chance, J. Chem. Phys. 1986, 85, 4116
80. V. Dobrosavljevic, R. M. Stratt, Phys. Rev. B 1987, 35, 2781
81. K. Kuriyama, H. Kikuchi, T. Kajiyama, Lamgmuir 1998, 14, 1130.
82. S. Segota, D. Tezak, Adv. Coll. Int. Sci. 2006, 121, 51
83. C. Lohr, A. H. Kundig, V. K. Bhatia, D. Stamouu, Methods Enzymol. 2009, 465, 143.
84. R. Jelinek, S. Kolusheva, Biotechnol. Adv. 2001, 19, 109.
85. M. Dela Carmena Luzardo, M. E. Lanio, C. Alvarez, I. F. Pazos, S. Figueroa, V. Verez, E. A. Disalvo, Colloids Surf. B 2002, 26, 281
86. I. J. Goldstein, C. E. Hollerman, E. E. Smith, Biochemistry 1965, 4, 876.