Simple biosensor with high selectivity and sensitivity: Thiol-specific biomolecular probing and intracellular imaging by AIE fluorogen on a TLC plate through a thiol-ene click mechanism

Chemistry - A European Journal

Volumn 16, Issue 28, 2010, Pages 8433-8438

  Liu, Yang ^a   Yu, Yong ^a   Lam, Jacky W Y ^a   Hong, Yuning ^a   Faisal, Mahtab ^a   Yuan, Wang Zhang ^a   Tang, Ben Zhong ^a,b  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

Aggregation induced emissions; Biological activity; Biosensors; Tetraphenylethene; Thiols

Indexed keywords

AGGREGATION-INDUCED EMISSIONS; ANALYTE CONCENTRATION; BIO-MOLECULAR; BIOLOGICAL ACTIVITIES; BIOLOGICAL ACTIVITY; BIOPROBE; CELLULAR SYSTEM; CLICK REACTION; FLUORESCENCE IMAGE; FUNCTIONALIZED; GLUTATHIONES; HIGH SELECTIVITY; INTRACELLULAR IMAGING; L-CYSTEINE; LIVING CELL; MALEIMIDES; NAKED-EYE; THIOL GROUPS; THIOL SPECIES; THIOL-ENES;

AMINO ACIDS; BIOACTIVITY; FLUORESCENCE; ORGANIC ACIDS; VISUALIZATION;

BIOSENSORS;

COLORING AGENT; ETHYLENE DERIVATIVE; MALEIMIDE; MALEIMIDE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DIAGNOSTIC IMAGING; FLUORESCENCE; GENETIC PROCEDURES; METHODOLOGY; STAINING; THIN LAYER CHROMATOGRAPHY;

BIOSENSING TECHNIQUES; CHROMATOGRAPHY, THIN LAYER; COLORING AGENTS; DIAGNOSTIC IMAGING; ETHYLENES; FLUORESCENCE; MALEIMIDES; MOLECULAR STRUCTURE; STAINING AND LABELING; SULFHYDRYL COMPOUNDS;

EID: 77954856417     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902505     Document Type: Article

References (75)

1. a) M. Sameiro T. Goncalves, Chem. Rev. 2009, 709, 190;
2. b) I. L. Medintz, H. T. Uyeda, E. R. Goldman, H. Mattoussi, Nat. Mater. 2005, 4, 435.
3. a) A. P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515;
4. b) W. P. Ambrose, P.M. Goodwin, J. H. Jett, A. Van Orden, J. H. Werner, R. A. Keller, Chem. Rev. 1999, 99, 2929;
5. c) W. F. Patton, Biotechniques 2000, 28, 944.
6. T. Terail, T. Nagano, Curr. Opin. Chem. Biol. 2008, 72, 515.
7. a) Z. A. Wood, E. Schröder, J. R. Harris, L. B. Poole, Trends Biochem. Sci. 2003, 28, 32;
8. b) S. Shahrokhian, Anal. Chem. 2001, 73, 5972;
9. c) Homocysteine in Health and Disease (Eds.: R. Carmel, D. W. Jacobsen), Cambridge University Press, Cambridge, 2001.
10. a) R. H. Schirmer, J. G. Müller, R. L. Krauth-Siegel, Angew. Chem. 1995, 107, 153;
11. Angew. Chem. Int. Ed. Engl. 1995, 34, 141;
12. b) R. L. Krauth-Siegel, H. Bauer, R. H. Schirmer, Angew. Chem. 2005, 117, 698;
13. Angew. Chem. Int. Ed. 2005, 44, 690;
14. c) T. P. Dalton, H. G. Shertzer, A. Puga, Annu. Rev. Pharmacol. Toxicol. 1999, 39, 67;
15. d) S. M. Kanzok, R. H. Schirmer, I. Türbachova, R. Iozef, K. Becker, J. Biol. Chem. 2000, 275, 40180;
16. e) R. Hong, G. Han, J. M. Fernández, B.-J. Kim, N. S. Forbes, V. M. Rotello, J. Am. Chem. Soc. 2006, 128, 1078.
17. a) H. Refsum, P. M. Ueland, O. Nygard, S. E. Vollset, Annu. Rev. Med. 1989, 40, 31;
18. b) S. Seshadri, A. Beiser, J. Selhub, P. F. Jacques, I. H. Rosenberg, R. B. D'Agostino, P. W. F. Wilson, New Engl. J. Med. 2002, 346, 476;
19. c) D. M. Townsend, K. D. Tew, H. Tapiero, Biomed. Pharmacother. 2003, 57, 145;
20. d) R. Njålsson, S. Norgren, Acta Paediatr. 2005, 94, 132;
21. e) L. A. Herzenberg, S. C. De Rosa, J. G. Dubs, M. Roederer, M. T. Anderson, S. W. Ela, S. C. Deresinski, L. A. Herzenberg, Proc. Natl. Acad. Sci. USA 1997, 94, 1967.
22. a) H. Maeda, H. Matsuno, M. Ushida, K. Katayama, K. Saeki, N. Itoh, Angew. Chem. 2005, 117, 2982;
23. Angew. Chem. Int. Ed. 2005, 44, 2922;
24. b) J. Guy, K. Caron, S. Dufresne, S.W. Michnick, W. G. Skene, J. W. Keillor, J. Am. Chem. Soc. 2007, 129, 11969;
25. c) T. Matsumoto, Y. Urano, T. Shoda, H. Kojima, T. Nagano, Org. Lett. 2007, 9, 3375;
26. d) S. Mare, S. Penugonda, N. Ercal, Biomed. Chromatogr. 2005, 19, 80;
27. e) A. M. Piggott, P. Karuso, Anal. Chem. 2007, 79, 8769;
28. f) P. K. Pullela, T. Chiku, M. J. Carvan III, D.S. Sem, Anal. Biochem. 2006, 352, 265;
29. g)W. Jiang, Q. Fu, H. Fan, J. Ho, W. Wang, Angew. Chem. 2007, 119, 8597;
30. Angew. Chem. Int. Ed. 2007, 46, 8445;
31. h) J. Bouffard, Y. Kim, T. M. Swager, R. Weissleder, S. A. Hilderbrand, Org. Lett. 2008, 10, 37;
32. i) A. Shibata, K. Furukawa, H. Abe, S. Tsuneda, Y. Ito, Bioorg. Med. Chem. Lett. 2008, 18, 2246;
33. j) H. Maeda, K. Katayama, H. Matsuno, T. Uno, Angew. Chem. 2006, 118, 1842;
34. Angew. Chem. Int. Ed. 2006, 45, 1810;
35. k)Y. H. Ahn, J. S. Lee, Y. T. Chang, J. Am. Chem. Soc. 2007, 129, 4510;
36. P. Root, B. Mutus, Anal. Biochem. 2003, 320, 299;
37. m) Y. Fu, H. Li, W. Hu, D. Zhu, Chem. Commun. 2005, 3189;
38. n) M. Zhang, M. Yu, F. Li, M. Zhu, M. Li, Y. Gao, L. Li, Z. Liu, J. Zhang, D. Zhang, T. Yi, C. Huang, J. Am. Chem. Soc. 2007, 129, 10322;
39. o) L. Yi, H. Li, L. Sun, L. Liu, C. Zhang, Z. Xi, Angew. Chem. 2009, 121, 4094;
40. Angew. Chem. Int. Ed. 2009, 48, 4034.
41. a) A. Leino, B. M. Loo, Ann. Clin. Biochem. 2007, 44, 563;
42. b) W. Putalun, H. Tanaka, Y. Shoyama, Phytochem. Anal. 2005, 16, 370.
43. a) J. Luo, Z. Xie, J. W. Y. Lam, L. Cheng, H. Chen, C. Qiu, H. S. Kwok, X. Zhan, Y. Liu, D. Zhu, B. Z. Tang, Chem. Commun. 2001, 1740;
44. b) Y. Liu, X. Tao, F. Wang, X. Dang, D. Zou, Y. Ren, M. Jiang, J. Phys. Chem. C 2008, 112, 3975;
45. c) B. K. An, S. K. Kwon, S. D. Jung, S. Y. Park, J. Am. Chem. Soc. 2002, 124, 14410;
46. d) H. C. Yeh, S. J. Yeh, C. T. Chen, Chem. Commun. 2003, 2632;
47. e) Z. Zhao, Z. Wang, P. Lu, C. Y. K. Chan, D. Liu, J. W. Y. Lam, H. H. Y. Sung, I. D. Williams, Y. Ma, B. Z. Tang, Angew. Chem. 2009, 121, 7744;
48. Angew. Chem. Int. Ed. 2009, 48, 7608;
49. f) W. Z. Yuan, P. Lu, S. Chen, J. W. Y. Lam, Z. Wang, Y. Liu, H. S. Kowk, Y. Ma, B. Z. Tang, Adv. Mater. 2010, 22, 2159.
50. For reviews, see: a) H. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Commun. 2009, 4332;
51. b)J. Liu, J. W. Y. Lam, B. Z. Tang, J. Inorg. Organomet. Polym. Mater. 2009, 19, 249;
52. c) J. Liu, J. W. Y. Lam, B. Z. Tang, Chem. Rev. 2009, 109, 5799;
53. d) M. Wang, G. Zhang, D. Zhang, D. Zhu, B. Z. Tang, J. Mater. Chem. 2010, 20, 1858.
54. a) H. Tong, Y. Hong, Y. Dong, M. Häußler, Z. Li, J. W. Y. Lam, Z. Li, Y. Dong, H. H. Y. Sung, I. D. Williams, B. Z. Tang, J. Phys. Chem. B 2007, 111, 11817;
55. b) Y. Hong, M. Haussler, J. W. Y. Lam, Z. Li, K. Sin, Y. Dong, H. Tong, J. Liu, A. Qin, R. Renneberg, B. Z. Tang, Chem. Eur. J. 2008, 14, 6428;
56. c) H. Tong, Y. Hong, Y. Dong, M. Haussier, J. W. Y. Lam, Z. Li, Z. Guo, Z. Guo, B. Z. Tang, Chem. Commun. 2006, 3705;
57. d) L. Liu, G. Zhang, J. Xiang, D. Zhang, D. Zhu, Org. Lett. 2008, 10, 4581;
58. e) Y. Hong, H. Xiong, J. W. Y. Lam, M. Häußler, J. Liu, Y. Yu, Y. Zhong, H. H. Y. Sung, I. D. Williams, K. S. Wong, B. Z. Tang, Chem. Eur. J. 2010, 16, 1232;
59. f) M. Faisal, Y. Hong, J. Liu, Y. Yu, J. W. Y. Lam, A. Qin, P. Lu, B. Z. Tang, Chem. Eur. J. 2010, 16, 4266.
60. a) R. K. Iha, K. L. Wooley, A. M. Nystrom, D. J. Burke, M. J. Kade, C. J. Hawker, Chem. Rev. 2009, 109, 5620;
61. b) A. Qin, J. W. Y. Lam, B. Z. Tang, Chem. Soc. Rev. 2010, 39, DOI:10.1039/b909064a;
62. c) C. K. W. Jim, A. Qin, J. W. Y. Lam, F. Mahtab, Y. Yu, B. Z. Tang, Adv. Funct. Mater. 2010, 20, 1319;
63. d) B. S. Sumerlin, A. P. Vogt, Macromolecules 2010, 43, 1.
64. a) J. E. McMurry, Chem. Rev. 1989, 89, 1513;
65. b) B. E. Kahn, R. D. Rieke, Chem. Rev. 1988, 88, 733;
66. c) X. F. Duan, J. Zeng, J. W. Lu, Z. B. Zhang, J. Org. Chem. 2006, 71, 9873.
67. a) M. E. Langmuir, J.-R. Yang, A. M. Moussa, R. Laura, K. A. LeCompte, Tetrahedron Lett. 1995, 36, 3989;
68. b) J.-R. Yang, M. E. Langmuir, J. Heterocycl. Chem. 1991, 28, 1177;
69. c) S. Girouard, M. H. Houle, A. Grandbois, J. W. Keillor, S. W. Michnick, J. Am. Chem. Soc. 2005, 127, 559.
70. a) T. Lee, R. L. Heintz, Eur. J. Biochem. 2001, 268, 3793;
71. b) K. Tyagarajan, E. Pretzer, J. E. Wiktorowicz, Electrophoresis 2003, 24, 2348;
72. c) N. Venkatesan, B. H. Kim, Chem. Rev. 2006, 106, 3712.
73. a) J. Sherma, Rev. Anal. Chem. 1995, 14, 75;
74. b) G. W. Somsen, W. Morden, I. D. Wilson, J. Chromatogr. A 1995, 703, 613.
75. J. Chen, C. C. W. Law, J. W. Y. Lam, Y. Dong, S. M. F. Lo, I. D. Williams, D. Zhu, B. Z. Tang, Chem. Mater. 2003, 15, 1 535.