A near-IR reversible fluorescent probe modulated by selenium for monitoring peroxynitrite and imaging in living cells

Journal of the American Chemical Society

Volumn 133, Issue 29, 2011, Pages 11030-11033

  Yu, Fabiao ^a   Li, Peng ^a   Li, Guangyue ^a   Zhao, Guangjiu ^a   Chu, Tianshu ^a   Han, Keli ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AUTOFLUORESCENCE; FLUORESCENT PROBES; HIGHLY SENSITIVE; LIVING CELL; NEAR-IR; ORGANOSELENIUM; OXIDATION AND REDUCTION; PEROXYNITRITES; PHYSIOLOGICAL CONDITION; REAL-TIME IMAGES;

FLUORESCENCE; FUNCTIONAL GROUPS; SELENIUM; SELENIUM COMPOUNDS;

PROBES;

FLUORESCENT DYE; NEAR IR REVERSIBLE FLUORESCENT PROBE; ORGANOSELENIUM DERIVATIVE; PEROXYNITRITE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; AUTOFLUORESCENCE; CONTROLLED STUDY; FLUORESCENCE IMAGING; OXIDATION;

ANIMALS; BIOSENSING TECHNIQUES; CELL LINE; FLUORESCENT DYES; MACROPHAGES; MICE; MICROSCOPY, CONFOCAL; ORGANOSELENIUM COMPOUNDS; OXIDATION-REDUCTION; OXIDATIVE STRESS; PEROXYNITROUS ACID; SENSITIVITY AND SPECIFICITY;

EID: 79960586391     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja202582x     Document Type: Article

References (42)

1. Ferrer-Sueta, G.; Radi, R. ACS Chem. Biol. 2009, 4, 161
2. Pacher, P.; Beckman, J. S.; Liaudet, L. Physiol. Rev. 2007, 87, 315
3. Szabó, C.; Ischiropoulos, H.; Radi, R. Nat. Rev. Drug Discovery 2007, 6, 662
4. Beckman, J. S. The Physiological and Pathophysiological Chemistry of Nitric Oxide. In Nitric Oxide: Principles and Actions; Lancaster, J., Ed.; Academic Press: San Diego, CA, 1996.
5. Nagano, T. J. Clin. Biochem. Nutr. 2009, 45, 111
6. Ashki, N.; Hayes, K. C.; Bao, F. Neuroscience 2008, 156, 107
7. Ducrocq, C.; Blanchard, B.; Pignatelli, B.; Ohshima, H. Cell. Mol. Life Sci. 1999, 55, 1068
8. Masumoto, H.; Kissner, R.; Koppenol, W. H.; Sies, H. FEBS Lett. 1996, 398, 179
9. Wiseman, H.; Halliwell, B. Biochem. J. 1996, 313, 17
10. Pacher, P.; Beckman, J. S.; Liaudet, L. Physiol. Rev. 2007, 87, 315
11. Beckman, J. S.; Carson, M.; Smith, C. D.; Koppenol, W. H. Nature 1993, 364, 584
12. Estevez, A. G.; Crow, J. P.; Sampson, J. B.; Reiter, C.; Zhuang, Y.; Richardson, G. J.; Tarpey, M. M.; Barbeito, L.; Beckman, J. S. Science 1999, 286, 2498
13. Schieke, S. M.; Briviba, K.; Klotz, L.-O.; Sies, H. FEBS Lett. 1999, 448, 301
14. Kermis, H. R.; Kostov, Y.; Harms, P.; Rao, G. Biotechnol. Prog. 2002, 18, 1047
15. Ueno, T.; Urano, Y.; Setsukinai, K.; Takakusa, H.; Kojima, H.; Kikuchi, K.; Ohkubo, K.; Fukuzumi, S.; Nagano, T. J. Am. Chem. Soc. 2004, 126, 14079
16. Ueno, T.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2006, 128, 10640
17. Yang, D.; Wang, H.-L.; Sun, Z.-N.; Chung, N.-W.; Shen, J.-G. J. Am. Chem. Soc. 2006, 128, 6004
18. Sun, Z.-N.; Wang, H.-L.; Liu, F.-Q.; Chen, Y.; Tam, P. K. H.; Yang, D. Org. Lett. 2009, 11, 1887
19. Hempel, S. L.; Buettner, G. R.; O'Malley, Y. Q.; Wessels, D. A.; Flaherty, D. M. Free Radical Biol. Med. 1999, 27, 146
20. Miyasaka, N.; Hirata, Y. Life Sci. 1997, 61, 2073
21. Oushiki, D.; Kojima, H.; Terai, T.; Arita, M.; Hanaoka, K.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2010, 132, 2795
22. Peng, T.; Yang, D. Org. Lett. 2010, 12, 4932
23. Miller, E. W.; Bian, S. X.; Chang, C. J. J. Am. Chem. Soc. 2007, 129, 3458
24. Winterbourn, C. C. Nat. Chem. Biol. 2008, 4, 278
25. Rotruck, J. T.; Pope, A. L.; Ganther, H. E.; Swanson, A. B.; Hafeman, D. G.; Hoekstra, W. G. Science 1973, 179, 588
26. Flohé, L. In Glutathione: Chemical, Biochemical, and Medical Aspects; Dolphin, D.; Poulson, R.; Avramovic, O., Eds.; Wiley: New York, 1989.
27. Wendel, A.; Pilz, W.; Ladenstein, R.; Sawatzki, G.; Weser, U. Biochim. Biophys. Acta 1975, 377, 211
28. Masumoto, H.; Kissner, R.; Koppenol, W. H.; Sies, H. FEBS Lett. 1996, 398, 179
29. Tang, B.; Yu, F.; Li, P.; Tong, L.; Duan, X.; Xie, T.; Wang, X. J. Am. Chem. Soc. 2009, 131, 3016
30. Nogueira, C. W.; Zeni, G.; Rocha, J. B. Chem. Rev. 2004, 104, 6255
31. Mugesh, G.; du Mont, W.-W.; Sies, H. Chem. Rev. 2001, 101, 2125
32. Sasaki, E.; Kojima, H.; Nishimatsu, H.; Urano, Y.; Kikuchi, K.; Hirata, Y.; Nagano, T. J. Am. Chem. Soc. 2005, 127, 3684
33. Becke, A. D. Phys. Rev. A 1988, 38, 3098
34. Friesner, R. A.; Murphy, R. B.; Beachy, M. D.; Ringnalda, M. N.; Pollard, W. T.; Dunietz, B. D.; Cao, Y. X. J. Phys. Chem. A 1999, 103, 1913
35. Frisch, M. J.; Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
36. de Silva, A. P.; Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A. J.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515
37. DiCesare, N.; Lakowicz, J. R. J. Phys. Chem. A 2001, 105, 6834
38. Pastore, A.; Piemonte, F.; Locatelli, M.; Lo Russo, A.; Gaeta, L. M.; Tozzi, G.; Federici, G. Clin. Chem. 2001, 47, 1467
39. Iovine, N. M.; Pursnani, S.; Voldman, A.; Wasserman, G.; Blaser, M. J.; Weinrauch, Y. Infect. Immun. 2008, 76, 986
40. Salonen, T.; Sareila, O.; Jalonen, U.; Kankaanranta, H.; Tuominen, R.; Moilanen, E. Br. J. Pharmacol. 2006, 147, 790
41. Muijsers, R. B.; Van Den Worm, E.; Folkerts, G.; Beukelman, C. J.; Koster, A. S.; Postma, D. S.; Nijkamp, F. P. Br. J. Pharmacol. 2000, 130, 932
42. Bunting, J. R.; Phan, T. V.; Kamali, E.; Dowben, R. M. Biophys. J. 1989, 56, 979