A fluorescent and colorimetric chemosensor for nitric oxide based on 1,8-naphthalimide

Dyes and Pigments

Volumn 96, Issue 2, 2013, Pages 333-337

  Wang, Min ^a,b   Xu, Zhaochao ^b   Wang, Xu ^a,b   Cui, Jingnan ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

1,8 Naphthalimide; Bioimaging; Colorimetric; Fluorescent chemosensor; Nitric oxide; o phenylenediamine

Indexed keywords

1 ,8-NAPHTHALIMIDE; BIO-IMAGING; CHEMOSENSOR; COLORIMETRIC; O-PHENYLENEDIAMINE;

CHARGE TRANSFER; COLOR; COLORIMETRY; FLUORESCENCE; NITRIC OXIDE;

PHYSIOLOGY;

EID: 84867422725     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.08.024     Document Type: Article

References (37)

1. I.M. Goldstein, P. Ostwald, and S. Roth Nitric oxide: a review of its role in retinal function and disease Vision Res 36 1996 2979 2994
2. M. Tare, H.C. Parkington, H.A. Coleman, T.O. Neild, and G.J. Dusting Hyperpolarization and relaxation of arterial smooth muscle caused by nitric oxide derived from the endothelium Nature 346 1990 69 71
3. H. Bult, G.E. Boeckxstaens, P.A. Pelckmans, F.H. Jordaens, Y.M. Van Maercke, and A.G. Herman Nitric oxide as an inhibitory non-Adrenergic non-cholinergic neurotransmitter Nature 345 1990 346 347
4. C. Bogdan Nitric oxide and the immune response Nat Immunol 2 2001 907 916
5. J.L. Balligand, R.A. Kelly, P.A. Marsden, T.W. Smith, and T. Michel Control of cardiac muscle cell function by an endogenous nitric oxide signaling system Proc Natl Acad Sci U S A 90 1993 347 351
6. M.D. Pluth, E. Tomat, and S.J. Lippard Biochemistry of mobile zinc and nitric oxide revealed by fluorescent sensors Annu Rev Biochem 80 2011 333 355
7. V.J. Thannickal, and B.L. Fanburg Reactive oxygen species in cell signaling Am J Physiol - Lung Cell Mol Physiol 279 2000 L1005 L1028
8. Fl.M. Ricciardolo, P.J. Sterk, B. Gaston, and G. Folkerts Reference values for exhaled nitric oxide (reveno) study Physiol Rev 84 2004 731 765
9. C.E. Thomas, and V. Darley-Usmar Forum on therapeutic applications of reactive oxygen and nitrogen species in human disease Free Radic Biol Med 28 2000 1449 1450
10. X. Zhang Real time and in vivo monitoring of nitric oxide by electrocehmical sensors-from dream to reality Front Biosci 9 2004 3434 3446
11. F. Bedioui, and N. Villeneuve Electrochemical nitric oxide sensors for biological samples-principle, selected examples and applications Electroanalysis 15 2003 5 18
12. X. Chen, Y. Zhou, X. Peng, and J. Yoon Fluorescent and colorimetric probes for detection of thiols J Chem Soc Rev 39 2010 2120 2135
13. X. Chen, X. Tian, I. Shin, and J. Yoon Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species Chem Soc Rev 40 2011 4783 4804
14. H. Kojima, M. Hirotani, Y. Urano, K. Kikuchi, T. Higuchi, and T. Nagano Fluorescent indicators for nitric oxide based on rhodamine chromophore Tetrahedron Lett 41 2000 69 72
15. N. Suzuki, H. Kojima, Y. Urano, K. Kikuchi, Y. Hirata, and T. Nagano Orthogonality of calcium concentration and ability of 4,5-diaminofluorescein to detect NO J Biol Chem 277 2002 47 49
16. H. Kojima, N. Nakatsubo, K. Kikuchi, S. Kawahara, Y. Kirino, and H. Nagoshi Detection and imaging of nitric oxide with novel fluorescent indicators: diaminofluoresceins Anal Chem 70 1998 2446 2453
17. E. Sasaki, H. Kojima, H. Nishimatsu, Y. Urano, K. Kikuchi, and Y. Hirata Highly sensitive near-infrared fluorescent probes for nitric oxide and their application to isolated organs J Am Chem Soc 127 2005 3684 3685
18. T. Nagano Bioimaging probes for reactive oxygen species and reactive nitrogen species J Clin Biochem Nutr 45 2009 111 124
19. T. Nagano Development of fluorescent probes for bioimaging applications Proc Jpn Acad Ser B Phys Biol Sci 86 2010 837 847
20. M.H. Lim, and S.J. Lippard Metal-based turn-on fluorescent probes for sensing nitric oxide Acc Chem Res 40 2007 41 51
21. R.M. Duke, E.B. Veale, F.M. Pfeffer, P.E. Kruger, and T. Gunnlaugsson Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors Chem Soc Rev 39 2010 3936 3953
22. A. Coskun, and E.U. Akkaya Ion sensing coupled to resonance energy transfer: a highly selective and sensitive ratiometric fluorescent chemosensor for Ag(I) by a modular approach J Am Chem Soc 127 2005 10464 10465
23. II based on internal charge transfer (ICT) Org Lett 7 2005 889 892
24. Z. Xu, X. Qian, and J. Cui Colorimetric and ratiometric fluorescent chemosensor with a large red-shift in emission: Cu(II)-only sensing by deprotonation of secondary amines as receptor Org Lett 7 2005 3029 3032
25. Z. Xu, S.J. Han, C. Lee, J. Yoon, and D.R. Spring Development of off-on fluorescent probes for heavy and transition metal ions Chem Commun 46 2010 1679 1681
26. 2+ fluorescent probe based on naphthalimide excimer-monomer switching Chem Commun 46 2010 2563 2565
27. 2+ displacement approach Tetrahedron 66 2010 1678 1683
28. ii fluorescent probe based on internal charge transfer (ICT) Tetrahedron 67 2011 4869 4873
29. 2+ fluorescent chemosensor with a large red-shift in emission Tetrahedron 62 2006 10117 10122
30. 2+ Chem Soc Rev 39 2010 1996 2006
31. 2+-selective, cell-permeable, and ratiometric fluorescent sensor J Am Chem Soc 132 2009 601 610
32. 2+ and its use for detection of intracellular zinc ions Tetrahedron 65 2009 2307 2312
33. C. Lu, Z. Xu, J. Cui, R. Zhang, and X. Qian Ratiometric and highly selective fluorescent sensor for cadmium under physiological pH range: a new strategy to discriminate cadmium from zinc J Org Chem 72 2007 3554 3557
34. + Analyst 135 2010 2554 2559
35. J.A. Hrabie, J.R. Klose, D.A. Wink, and L.K. Keefer New nitric oxide-releasing zwitterions derived from polyamines J Org Chem 58 1993 1472 1476
36. F. Li, J. Cui, L. Guo, X. Qian, W. Ren, and K. Wang Molecular design, chemical synthesis, and biological evaluation of '4-1' pentacyclic aryl/heteroaryl-imidazonaphthalimides Bioorg Med Chem 15 2007 5114 5121
37. Y. Gabe, Y. Urano, K. Kikuchi, H. Kojima, and T. Nagano Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe J Am Chem Soc 126 2004 3357 3367