Tetraphenylethylene conjugated with a specific peptide as a fluorescence turn-on bioprobe for the highly specific detection and tracing of tumor markers in live cancer cells

Chemistry - A European Journal

Volumn 20, Issue 1, 2014, Pages 158-164

  Huang, Yanyan ^a   Hu, Fang ^a   Zhao, Rui ^a   Zhang, Guanxin ^a   Yang, Hua ^b   Zhang, Deqing ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

aggregation induced emission; cancer; fluorescent probes; peptides; tetraphenylethylene

Indexed keywords

AGGREGATION-INDUCED EMISSIONS; CANCER; CHEMICAL EVENTS; FLUORESCENT PROBES; LIVE CANCER CELLS; MOLECULAR PROBES; SPECIFIC DETECTION; TETRAPHENYLETHYLENE;

DISEASES; FLUORESCENCE; PEPTIDES; PROBES;

CELLS;

ETHYLENE DERIVATIVE; FLUORESCENT DYE; LAPTM4B PROTEIN, HUMAN; MEMBRANE PROTEIN; ONCOPROTEIN; PEPTIDE; TUMOR MARKER;

AMINO ACID SEQUENCE; ARTICLE; CELL SURVIVAL; CHEMISTRY; CONFOCAL MICROSCOPY; DRUG EFFECT; GENETIC PROCEDURES; HEPG2 CELL LINE; HUMAN; METABOLISM; NEOPLASM; PATHOLOGY; PH; SYNTHESIS;

AMINO ACID SEQUENCE; BIOSENSING TECHNIQUES; CELL SURVIVAL; ETHYLENES; FLUORESCENT DYES; HEP G2 CELLS; HUMANS; HYDROGEN-ION CONCENTRATION; MEMBRANE PROTEINS; MICROSCOPY, CONFOCAL; NEOPLASMS; ONCOGENE PROTEINS; PEPTIDES; TUMOR MARKERS, BIOLOGICAL;

EID: 84891486779     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303679     Document Type: Article

References (68)

1. a) C. Burd, J. Sorrentino, K. Clark, D. Darr, J. Krishnamurthy, A. Deal, N. Bardeesy, D. Castrillon, D. Beach, N. Sharpless, Cell 2013, 152, 340-351
2. b) Z. Yu, R. M. Schmaltz, T. C. Bozeman, R. Paul, M. J. Rishel, K. S. Tsosie, S. M. Hecht, J. Am. Chem. Soc. 2013, 135, 2883-2886
3. c) K. K. Palaniap-pan, R. M. Ramirez, V. S. Bajaj, D. E. Wemmer, A. Pines, M. B. Francis, Angew. Chem. 2013, 125, 4949-4953
4. Angew. Chem. Int. Ed. 2013, 52, 4849-4853.
5. a) W. Silvers, B. Prasai, D. Burk, M. Brown, R. McCarley, J. Am. Chem. Soc. 2013, 135, 309-314
6. b) N. Li, C. Chang, W. Pan, B. Tang, Angew. Chem. 2012, 124, 7544-7548
7. Angew. Chem. Int. Ed. 2012, 51, 7426-7430
8. c) L. E. Edgington, M. Verdoes, A. Ortega, N. P. Withana, J. Lee, S. Syed, M. H. Bachmann, G. Blum, M. Bogyo, J. Am. Chem. Soc. 2013, 135, 174-182.
9. A. LeBeau, M. Lee, S. T. Murphy, B. C. Hann, R. S. Warren, R. D. Santos, J. Kurhanewicz, S. M. Hanash, H. F. VanBrocklin, C. S. Craik, Proc. Natl. Acad. Sci. USA 2013, 110, 93-98.
10. B. A. Smith, B. D. Smith, Bioconjugate Chem. 2012, 23, 1989-2006.
11. S. L. Deutscher, Chem. Rev. 2010, 110, 3196-3211.
12. a) H. Kobayashi, M. Ogawa, R. Alford, P. L. Choyke, Y. Urano, Chem. Rev. 2010, 110, 2620-2640
13. b) S. Watanabe, S. Mizukami, Y. Akimoto, Y. Hori, K. Kikuchi, Chem. Eur. J. 2011, 17, 8342-8349
14. c) H. Zhong, Q. Zhang, S. Zhang, Chem. Eur. J. 2011, 17, 8388-8394
15. d) G. Wang, X. Zhang, J. Geng, K. Li, D. Ding, K. Pu, L. Cai, Y. Lai, B. Liu, Chem. Eur. J. 2012, 18, 9705-9713.
16. Y. Hong, J. Lam, B. Tang, Chem. Commun. 2009, 4332-4353.
17. a) J. Luo, Z. Xie, J. Lam, L. Cheng, H. Chen, C. Qiu, H. Kwok, X. Zhan, Y. Liu, D. Zhu, B. Tang, Chem. Commun. 2001, 1740-1741
18. b) M. Wang, G. Zhang, D. Zhang, D. Zhang, D. Zhu, B. Tang, J. Mater. Chem. 2010, 20, 1858-1867
19. c) Y. Hong, J. Lam, B. Tang, Chem. Soc. Rev. 2011, 40, 5361-5388
20. d) N. Shustova, B. McCarthy, M. Dincǎ, J. Am. Chem. Soc. 2011, 133, 20126-20129
21. e) N. Shustova, T. Ong, A. Cozzolino, V. Michaelis, R. Griffin, M. Dincǎ, J. Am. Chem. Soc. 2012, 134, 15061-15070
22. f) N. Shus-tova, A. Cozzolino, M. Dincǎ, J. Am. Chem. Soc. 2012, 134, 19596-19599.
23. a) Y. Wu, M. Kuo, Y. Chang, C. Shin, T. Wu, C. Tai, T. Cheng, W. Liu, Angew. Chem. 2008, 120, 10039-10042
24. Angew. Chem. Int. Ed. 2008, 47, 9891-9894
25. b)T. Mutai, H. Tomoda, T. Ohkawa, Y. Yabe, K. Araki, Angew. Chem. 2008, 120, 9664-9666
26. Angew. Chem. Int. Ed. 2008, 47, 9522-9524
27. c) P. Kapadia, L. Ditzler, J. Baltrusaitis, D. Swenson, A. Tivanski, F. Pigge, J. Am. Chem. Soc. 2011, 133, 8490-8493
28. d)G. Huang, B. Ma, J. Chen, Q. Peng, G. Zhang, Q. Fan, D. Zhang, Chem. Eur. J. 2012, 18, 3886-3892
29. e) B. An, J. Gierschner, S. Park, Acc. Chem. Res. 2012, 45, 544-554.
30. a) H. Sohn, R. Calhoun, M. Sailor, W. Trogler, Angew. Chem. 2001, 113, 2162-2163
31. Angew. Chem. Int. Ed. 2001, 40, 2104-2105
32. b)H. Sohn, M. Sailor, W. Trogler, J. Am. Chem. Soc. 2003, 125, 3821-3830
33. c) Z. Ning, Z. Chen, Q. Zhang, Y. Yan, S. Qian, Y. Cao, H. Tian, Adv. Funct. Mater. 2007, 17, 3799-3807.
34. a) L. Liu, G. Zhang, J. Xiang, G. Zhang, D. Zhang, D. Zhu, Org. Lett. 2008, 10, 4581-4584
35. b) G. Huang, G. Zhang, D. Zhang, Chem. Commun. 2012, 48, 7504-7506
36. c) F. Sun, G. Zhang, D. Zhang, L. Xue, H. Jiang, Org. Lett. 2011, 13, 6378-6381
37. d) S. Toal, K. Jones, D. Magde, W. Trogler, J. Am. Chem. Soc. 2005, 127, 11661-11665
38. e) L. Peng, M. Wang, G. Zhang, D. Zhang, D. Zhu, Org. Lett. 2009, 11, 1943-1946
39. f) X. Huang, X. Gu, G. Zhang, D. Zhang, Chem. Commun. 2012, 48, 12915-12197.
40. a) H. Tong, Y. Hong, Y. Dong, M. Häußler, J. Lam, Z. Li, Z. Guo, B. Tang, Chem. Commun. 2006, 3705-3707
41. b) M. Wang, D. Zhang, G. Zhang, Y. Tang, S. Wang, D. Zhu, Anal. Chem. 2008, 80, 6443-6448.
42. a)X. Gu, G. Zhang, D. Zhang, Analyst 2012, 137, 365-369
43. b)X. Hu, Q. Chen, J. Wang, Q. Cheng, C. Yan, J. Cao, Y. He, B. Han, Chem. Asian J. 2011, 6, 2376-2381.
44. a) M. Wang, X. Gu, G. Zhang, D. Zhang, D. Zhu, Anal. Chem. 2009, 81, 4444-4449
45. b) X. Gu, G. Zhang, Z. Wang, W. Liu, L. Xiao, D. Zhang, Analyst 2013, 138, 2427-2431
46. c)W. Xue, G. Zhang, D. Zhang, D. Zhu, Org. Lett. 2010, 12, 2274-2277.
47. a) Y. Liu, C. Deng, L. Tang, A. Qin, R. Hu, J. Z. Sun, B. Z. Tang, J. Am. Chem. Soc. 2011, 133, 660-663
48. b) X. Shen, G. Zhang, D. Zhang, Org. Lett. 2012, 14, 1744-1747.
49. a) S. Chen, Y. Hong, Y. Liu, J. Lui, C. W. T. Leung, M. Li, R. T. K. Kwok, E. Zhao, J. W. Y. Lam, Y. Yu, B. Z. Tang, J. Am. Chem. Soc. 2013, 135, 4926-4929
50. b) C. W. T. Leung, Y. Hong, S. Chen, E. Zhao, J. W. Y. Lam, B. Z. Tang, J. Am. Chem. Soc. 2013, 135, 62-65.
51. a) H. Shi, J. Liu, J. Geng, B. Tang, B. Liu, J. Am. Chem. Soc. 2012, 134, 9569-9572
52. b) Z. Wang, S. Chen, J. Lam, W. Qin, R. Kwok, N. Xie, Q. Hu, B. Tang, J. Am. Chem. Soc. 2013, 135, 8238-8245
53. c) Y. Liu, Y. Yu, J. Lam, Y. Hong, M. Faisal, W. Yuan, B. Tang, Chem. Eur. J. 2010, 16, 8433-8438
54. d) D. Ding, K. Li, B. Liu, B. Z. Tang, Acc. Chem. Res. 2013; DOI: 10.1021/ar3003464.
55. Y. Huang, R. Zhao, Y. Fu, Q. Zhang, S. Xiong, L. Li, R. Zhou, G. Liu, Y. Chen, ChemBioChem 2011, 12, 1209-1215.
56. a) G. Shao, R. Zhou, Q. Zhang, Y. Zhang, J. J. Liu, J. Rui, X. Wei, D. Ye, Oncogene 2003, 22, 5060-5069
57. b) G. Kasper, A. Vogel, I. Klaman, J. Grçne, I. Petersend, B. Weber, E. CastaÇos-Vélez, E. Staub, D. Mennerich, Cancer Lett. 2005, 224, 93-103.
58. a) Y. Li, L. Zou, Q. Li, B. Haibe-Kains, R. Tian, Y. Li, C. Desmedt, C. Sotiriou, Z. Szallasi, J. D. Iglehart, A. L. Richardson, Z.C. Wang, Nat. Med. 2010, 16, 214-218
59. b)Y Li, Q. Zhang, R. Tian, Q. Wang, J. J. Zhao, J. D. Iglehart, Z. C. Wang, A. L. Richardson, Cancer Res. 2011, 71, 7481-7489
60. c)S. Wang, Q. Zhang, R. Zhou, Ann. Oncol. 2012, 23, 1864-1869.
61. a) D. Fukumura, L. Xu, Y. Chen, T. Gohongi, B. Seed, R. K. Jain, Cancer Res. 2001, 61, 6020-6024
62. b) D. Weerakkody, A. Moshnikova, M.S. Thakur, V. Moshnikova, J. Daniels, D. M. Engelman, O. A. Andreev, Y. K. Reshetnyak, Proc. Natl. Acad. Sci. USA 2013, 110, 5834-5839
63. c) L. Yao, J. Daniels, A. Moshnikova, S. Kuznetsov, A. Ahmed, D. M. Engelman, Y. K. Reshetnyak, O.A. Andreev, Proc. Natl. Acad. Sci. USA 2013, 110, 465-470.
64. K. Na, E. S. Lee, Y. H. Bae, Bioconjugate Chem. 2007, 18, 1568-1574.
65. a)C. Peng, R. L. Zhou, G. Z. Shao, J. A. Rui, S. B. Wang, M. Lin, S. Zhang, Z. F. Gao, World J. Gastroenterol. 2005, 11, 2704-2708
66. b) R. Milkereit, D. Rotin, PLoS One 2011, 6, e27478.
67. a)X. Duan, J. Zeng, J. Lu, Z. Zhang, J. Org. Chem. 2006, 71, 9873-9876
68. b) J. Park, M. Hesse, J. Org. Chem. 1998, 63, 8200-8204.