The rational design of a highly sensitive and selective fluorogenic probe for detecting nitric oxide

Chemical Communications

Volumn 50, Issue 49, 2014, Pages 6475-6478

  Ma, Sufang ^a   Fang, De Cai ^a   Ning, Baoming ^b   Li, Minfeng ^a   He, Lan ^a,b   Gong, Bing ^a,c  

^a BEIJING NORMAL UNIVERSITY   (China)

^b NATIONAL INSTITUTES FOR FOOD AND DRUG CONTROL   (China)

^c UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID; COUMARIN DERIVATIVE; DIHYDROPYRIDINE; DIHYDROPYRIDINE DERIVATIVE; HERNIARIN; NITRIC OXIDE; NITROGEN; OXYGEN; PYRIDINE; RESORCINOL; 1,4-DIHYDROPYRIDINE; FLUORESCENT DYE; NICOTINIC ACID; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE;

ABSORPTION; ANIMAL CELL; AROMATIZATION; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; FLUORESCENCE; FLUOROGENIC PROBE; HUMAN; HUMAN CELL; LIMIT OF DETECTION; MASS SPECTROMETRY; MOLECULAR PROBE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; QUANTUM YIELD; X RAY CRYSTALLOGRAPHY; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; FLUORESCENCE MICROSCOPY; MOUSE; SPECTROFLUOROMETRY; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; CELL LINE, TUMOR; COUMARINS; DIHYDROPYRIDINES; ELECTRON TRANSPORT; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; MICE; MICROSCOPY, FLUORESCENCE; NIACIN; NITRIC OXIDE; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN SPECIES; SPECTROMETRY, FLUORESCENCE;

EID: 84901344046     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc01142b     Document Type: Article

References (55)

1. R. M. Rapoport, M. B. Draznin, F. Murad, Nature, 1983, 306:174
2. L. J. Ignarro, G. M. Buga, K. S. Wood, R. E. Byrns, G. Chaudhuri, Proc. Natl. Acad. Sci. U. S. A., 1987, 84:9265
3. R. F. Furchgott, P. M. Vanhoutte, FASEB J., 1989, 3:2007
4. D. S. Bredt, Free Radical Res., 1999, 31:577
5. L. J. Ignarro, Nitric Oxide: Biology and Pathobiology, Academic Press, San Diego, CA, 2000
6. B. G. Hill, B. P. Dranka, S. M. Bailey, J. R. Lancaster Jr., V. M. Darley-Usmar, J. Biol. Chem., 2010, 285:19699
7. C. Bogdan, Nat. Immunol., 2001, 2:907
8. F. C. Fang, Nat. Rev. Microbiol., 2004, 2:820
9. J. F. Brien, B. E. McLaughlin, K. Nakatsu, G. S. Marks, Methods Enzymol., 1996, 268:83
10. L. C. Green, D. A. Wagner, J. Glogowski, P. L. Skipper, J. S. Wishnok, S. R. Tannenbaum, Anal. Biochem., 1982, 126:131
11. F. Brown, N. J. Finnerty, F. B. Bolger, J. Millar, J. P. Lowry, Anal. Bioanal. Chem., 2005, 381:964
12. H. Kosaka, M. Watanabe, H. Yoshihara, N. Harada, T. Shiga, Biochem. Biophys. Res. Commun., 1992, 184:1119
13. Y. Katayama, N. Soh, M. Maeda, ChemPhysChem, 2001, 2:655
14. T. Malinski, Z. Taha, Nature, 1992, 358:676
15. F. Bedioui, N. Villeneuve, Electroanalysis, 2003, 15:5
16. P. Meineke, U. Rauen, H. de Groot, H.-G. Korth, R. Sustmann, Chem. Eur. J., 1999, 5:1738
17. H. Yu, Y. Xiao, L. Jin, J. Am. Chem. Soc., 2012, 134:17486
18. H. Zheng, G. Q. Shang, S. Y. Yang, X. Gao, J. G. Xu, Org. Lett., 2008, 10:2357
19. C. Sun, W. Shi, Y. Song, W. Chen, H. Ma, Chem. Commun., 2011, 47:8638
20. M. H. Lim, D. Xu, S. J. Lippard, Nat. Chem. Biol., 2006, 2:375
21. M. H. Lim, B. A. Wong, W. H. Pitcock Jr., D. Mokshagundam, M.-H. Baik, S. J. Lippard, J. Am. Chem. Soc., 2006, 128:14364
22. J. Ouyang, H. Hong, C. Shen, Y. Zhao, C. Ouyang, L. Dong, J. Zhu, Z. Guo, K. Zeng, J. Chen, J. Zhang, C. Zhang, Free Radical Biol. Med., 2008, 45:1426
23. M. D. Pluth, M. R. Chan, L. E. McQuade, S. J. Lippard, Inorg. Chem., 2011, 50:9385
24. Y. G. Chen, W. H. Guo, Z. Q. Ye, G. L. Wang, J. L. Yuan, Chem. Commun., 2011, 47:6266
25. H. Kojima, N. Nakatsubo, K. Kikuchi, S. Kawahara, Y. Kirino, H. Nagoshi, Y. Hirata, T. Nagano, Anal. Chem., 1998, 70:2446
26. P. Heiduschka, S. Thanos, NeuroReport, 1998, 9:4051
27. H. Kojima, M. Hirotani, N. Nakatsubo, K. Kikuchi, Y. Urano, T. Higuchi, Y. Hirata, T. Nagano, Anal. Chem., 2001, 73:1967
28. Y. Gabe, Y. Urano, K. Kikuchi, H. Kojima, T. Nagano, J. Am. Chem. Soc., 2004, 126:3357
29. E. Sasaki, H. Kojima, H. Nishimatsu, Y. Urano, K. Kikuchi, Y. Hirata, T. Nagano, J. Am. Chem. Soc., 2005, 127:3684
30. F. Galindo, N. Kabir, J. Gavrilovic, D. A. Russell, Photochem. Photobiol. Sci., 2007, 7:126
31. T. W. Shiue, Y. H. Chen, C. M. Wu, G. Singh, H. Y. Chen, C. H. Hung, W. F. Liaw, Y. M. Wang, Inorg. Chem., 2012, 51:5400
32. Y. Yang, S. K. Seidlits, M. M. Adams, V. M. Lynch, C. E. Schmidt, E. V. Anslyn, J. B. Shear, J. Am. Chem. Soc., 2010, 132:13114
33. T. Nagano, T. Yoshimura, Chem. Rev., 2002, 102:1235
34. T. Nagano, H. Takizawa, M. Hirobe, Tetrahedron Lett., 1995, 36:8239
35. D. Jourd’heuil, Free Radical Biol. Med., 2002, 33:676
36. A. Balcerczyka, M. Soszynskia, G. Bartosz, Free Radical Biol. Med., 2005, 39:327
37. P. Wardman, Free Radical Biol. Med., 2007, 43:995
38. T. Itoh, K. Nagata, M. Okada, A. Ohsawa, Tetrahedron Lett., 1995, 36:2269
39. T. Itoh, K. Nagata, Y. Matsuya, M. Miyazaki, A. Ohsawa, J. Org. Chem., 1997, 62:3582
40. Y. Urano, M. Kamiya, K. Kanda, T. Ueno, K. Hirose, T. Nagano, J. Am. Chem. Soc., 2005, 127:4888
41. T. Miura, Y. Urano, K. Tanaka, T. Nagano, K. Ohkubo, S. Fukuzumi, J. Am. Chem. Soc., 2003, 125:8666
42. K. Tanaka, T. Miura, N. Umezawa, Y. Urano, K. Kikuchi, T. Higuchi, T. Nagano, J. Am. Chem. Soc., 2001, 123:2530
43. Y. Gabe, Y. Urano, K. Kikuchi, H. Kojima, T. Nagano, J. Am. Chem. Soc., 2004, 126:3357
44. T. Ueno, Y. Urano, K. Setsukinai, H. Takakusa, H. Kojima, K. Kikuchi, K. Ohkubo, S. Fukuzumi, T. Nagano, J. Am. Chem. Soc., 2004, 126:14079
45. P. Shieh, M. J. Hangauer, C. R. Bertozzi, J. Am. Chem. Soc., 2012, 134:17428
46. A. D. Becke, J. Chem. Phys., 1993, 98:5648
47. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Gaussian, Inc., Wallingford, CT, 2010
48. M. Cossi, V. Barone, R. Cammi, J. Tomasi, Chem. Phys. Lett., 1996, 255:327
49. G. Scalmani, M. J. Frisch, J. Chem. Phys., 2010, 132:114110
50. D. J. Yee, V. Balsanek, D. Sames, J. Am. Chem. Soc., 2004, 126:2282
51. S. R. Trenor, A. R. Shultz, B. J. Love, T. E. Long, Chem. Rev., 2004, 104:3059
52. R. M. Uppu, W. A. Pryor, Anal. Biochem., 1996, 236:242
53. J. Hartung, Chem. Rev., 2009, 109:4500
54. B. Zhu, C. Gao, Y. Zhao, C. Liu, Y. Li, Q. Wei, Z. Ma, B. Du, X. Zhang, Chem. Commun., 2011, 47:8656
55. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Kluwer Academic/Plenum Publishers, New York, 2nd edn, 1999