Fluorimetric and colorimetric detection of nitric oxide in living cells by rhodamine derivatives assisted by Cu2+

Tetrahedron

Volumn 69, Issue 2, 2013, Pages 636-641

  Meng, Qingtao ^a,b   Zhang, Yixin ^a   Hou, Dongyan ^a   Xin, Guang ^a   Li, Tiechun ^a   He, Cheng ^b   Duan, Chunying ^b  

^a ANSHAN NORMAL UNIVERSITY   (China)

^b DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Fluorescence imaging; Nitric oxide; Rhodamine

Indexed keywords

COPPER; NITRIC OXIDE; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE; RHODAMINE; RHODAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL LEVEL; CHEMICAL ANALYSIS; COLORIMETRY; FLUORESCENCE; FLUOROMETRY; LIMIT OF DETECTION; PRIORITY JOURNAL; SPECTROSCOPY; SYNTHESIS;

EID: 84878857418     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.11.010     Document Type: Article

References (52)

1. Ignarro, L. J. Nitric Oxide Biology and Pathobiology, 1st ed.; Academic: San Diego, CA, 2000.
2. (a) King, S. B. Curr. Top. Med. Chem. 2005, 5, 665-673;
3. (b) Maragos, C. M.; Morley, D.; Wink, D. A.; Dunams, T.; Saavedra, J. E.; Hoffman, A.; Bove, A. A.; Isaac, L.; Hrabie, J. A.; Keefer, L. K. J. Med. Chem. 1991, 34, 3242-3247;
4. (c) Culotta, E.; Koshland, D. E. Science 1992, 258, 1862-1865;
5. (d) Murad, F. Angew. Chem., Int. Ed. 1999, 38, 1856-1868;
6. (e) Furchgott, R. F. Angew. Chem., Int. Ed. 1999, 38, 1870-1880.
7. Hummel, G.; Fisher, A. J.; Martin, S.; Schafer, F. Q.; Buettner, G. R. Free Radical Biol. Med. 2006, 40, 501-506.
8. (a) Xu, W.; Liu, L. Z.; Loizidou, M.; Ahmed, M.; Charles, I. G. Cell Res. 2002, 12, 311-320;
9. (b) Mitrovic, B.; Ignarro, L. J.; Vinters, H. V.; Akerms, M. A.; Schmid, I.;Uittenbogaart, C. Neuroscience 1995, 65, 531-538;
10. (c) Hou, Y.; Wang, J.; Andreana, P. R.; Cantauria, G.; Tarasia, S.; Sharp, L.; Braunschweiger, P. G.; Wang, P. G. Bioorg. Med. Chem. Lett. 1999, 9, 2255-2258.
11. (a) Nagano, T.; Yoshimura, T. Chem. Rev. 2002, 102, 1235-1269;
12. (b) Kobayashi, H.; Ogawa, M.; Alford, R.; Choyke, P. L.; Urano, Y. Chem. Rev. 2010, 110, 2620-2640.
13. (a) Leone, A. M.; Furst, V. W.; Foxwell, N. A.; Cellek, S.; Moncada, S. Biochem. Biophys. Res. Commun. 1996, 221, 37-41;
14. (b) Hampl, V.; Walters, C. L.; Archer, S. L. In Methods in Nitric Oxide Research; Feelisch, M., Stamler, J. S., Eds.; John Wiley & Sons: New York, NY, 1996; pp 309-318.
15. (a) Yoshimura, T.; Yokoyama, H.; Fujii, S.; Takayama, F.; Oikawa, K.; Kamada, H. Nat. Biotechnol. 1996, 14, 992-994;
16. (b) Kotake, Y.; Tanigawa, T.; Tanigawa, M.; Ueno, I.; Allen, D. R.; Lai C-, S. Biochim. Biophys. Acta 1996, 1289, 362-368;
17. (c) Yoshimura, T.; Fujii, S.; Yokoyama, H.; Kamada, H. Chem. Lett. 1995, 309-310;
18. (d) Komarov, A. M.; Lai C-, S. Biochim. Biophys. Acta 1995, 1272, 29-36.
19. (a) Malinski, T.; Mesaros, S.; Tomboulian, P. Methods Enzymol. 1996, 268, 58-69;
20. (b) Mao, L.; Tian, Y.; Shi, G.; Liu, H.; Jin, L.; Yamamoto, K.; Tao, S.; Jin, J. Anal. Lett. 1998, 31, 1991-2007.
21. (a) Lim, M. H.; Lippard, S. J. J. Am. Chem. Soc. 2005, 127, 12170-12171;
22. (b) Hilderbrand, S. A.; Lippard, S. J. Inorg. Chem. 2004, 43, 5294-5301;
23. (c) Lim, M. H.; Lippard, S. J. Inorg. Chem. 2006, 45, 8980-8989;
24. (d) Franz, K. J.; Singh, N.; Spingler, B.; Lippard, S. J. Inorg. Chem. 2000, 39, 4081-4092.
25. (a) Lim, M. H. Nat. Protoc. 2007, 2, 408-415;
26. (b) Lim, M. H.; Xu, D.; Lippard, S. J. Nat. Chem. Biol. 2006, 2, 375-380;
27. (c) Lim, M. H.;Wong, B. A.; Pitcock,W. H., Jr.; Mokshagundam, D.; Baik, M.-H.; Lippard, S. J. J. Am. Chem. Soc. 2006, 128, 14364-14373;
28. (d) Pluth, M. D.; McQuade, L. E.; Lippard, S. J. Org. Lett. 2010, 12, 2318-2321.
29. (a) Wang, J.; He, C.; Wu, P. Y.; Wang, J.; Duan, C. Y. J. Am. Chem. Soc. 2011, 133, 12402-12405;
30. (b) Wang, S. H.; Han, M. Y.; Huang, D. J. J. Am. Chem. Soc. 2009, 131, 11692-11694;
31. (c) Sarma, M.; Mondal, B. Inorg. Chem. 2011, 50, 3206-3212;
32. (d) Zhang, R.; Ye, Z. Q.; Wang, G. L.; Zhang, W. Z.; Yuan, J. L. Chem.-Eur. J. 2010, 16, 6884-6891.
33. (a) Batista, R. M. F.; Oliveira, E.; Costa, S. P. G.; Lodeiro, C.; Raposo, M. M. M. Org. Lett. 2007, 9, 3201-3204;
34. (b) Qu, Y.; Hua, J.; Tian, H. Org. Lett. 2010, 12, 3320-3323.
35. Zheng, H.; Shang, G. Q.; Yang, S. Y.; Gao, X.; Xu, J. G. Org. Lett. 2008, 10, 2357-2360.
36. (a) Yang, Y. K.; Yook, K. J.; Tae, J. J. Am. Chem. Soc. 2005, 127, 16760-16761;
37. (b) Xiang, Y.; Tong, A. J.; Jin, P. Y.; Ju, Y. Org. Lett. 2006, 8, 2863-2866.
38. Hu, X. Y.; Wang, J.; Zhu, X.; Dong, D. P.; Zhang, X. L.; Wu, S.; Duan, C. Y. Chem. Commun. 2011, 11507-11509.
39. Weerasinghe, A. J.; Schmiesing, C.; Sinn, E. Tetrahedron Lett. 2009, 50, 6407-6410.
40. Wu, D. Y.; Huang, W.; Duan, C. Y.; Lin, Z. H.; Meng, Q. J. Inorg. Chem. 2007, 46, 1538-1540.
41. (a) Kim, H. N.; Lee, M. H.; Kim, H. J.; Kim, J. S.; Yoon, J. Y. Chem. Soc. Rev. 2008, 37, 1465-1472;
42. (b) McQuade, L. E.; Pluth, M. D.; Lippard, S. J. Inorg. Chem. 2010, 49, 8025-8033.
43. Nagano, T.; Yoshimura, T. Chem. Rev. 2002, 102, 1235-1270.
44. Miyamoto, S.; Martinez, G. R.; Martins, A. P. B.; Medeiros, M. H. G.; Mascio, P. D. J. Am. Chem. Soc. 2003, 125, 4510-4517.
45. Aubry, J. M. J. Am. Chem. Soc. 1985, 107, 5844-5849.
46. (a) Huang, K. W.; Yang, H.; Zhou, Z. G.; Yu, M. X.; Li, F. Y.; Gao, X.; Yi, T.; Huang, C. H. Org. Lett. 2008, 10, 2557-2560;
47. (b) Mao, J.; Wang, L.; Dou, W.; Tang, X.; Yan, Y.; Liu, W. Org. Lett. 2007, 9, 4567-4570.
48. Ko, S.-K.; Yang, Y.-K.; Tae, J.; Shin, I. J. Am. Chem. Soc. 2006, 128, 14150-14155.
49. Zhou, Y.; Wang, F.; Kim, Y.; Kim, S. J.; Yoon, J. Org. Lett. 2009, 11, 4442-4445.
50. Wu, D. Y.; Huang,W.; Hua,W. J.; Song, Y.; Duan, C. Y.; Li, S. H.; Meng, Q. J. Dalton Trans. 2007, 18, 1838-1845.
51. (a) Ford, P. C.; Lorkovic, I. M. Chem. Rev. 2002, 102, 993-1017.
52. Sarkar, K.; Dhara, K.; Nandi, M.; Roy, P.; Bhaumik, A.; Banerjee, P. Adv. Funct. Mater. 2009, 19, 223-234.