A BODIPY fluorescence probe modulated by selenoxide spirocyclization reaction for peroxynitrite detection and imaging in living cells

Dyes and Pigments

Volumn 96, Issue 2, 2013, Pages 383-390

  Wang, Bingshuai ^a   Yu, Fabiao ^a   Li, Peng ^a   Sun, Xiaofei ^a   Han, Keli ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

BODIPY; Fluorescence imaging; Fluorescent probes; Peroxynitrite; Redox chemistry; Selenium

Indexed keywords

BODIPY; FLUORESCENCE IMAGING; FLUORESCENT PROBES; PEROXYNITRITES; REDOX CHEMISTRY;

CELL CULTURE; CHARGE TRANSFER; CONFOCAL MICROSCOPY; FLUORESCENCE; FUNCTIONAL GROUPS; SELENIUM; SELENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

PROBES;

EID: 84867421133     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.09.006     Document Type: Article

References (43)

1. C. Ducrocq, B. Blanchard, B. Pignatelli, and H. Ohshima Peroxynitrite: an endogenous oxidizing and nitrating agent Cell Mol Life Sci 55 1999 1068 1077
2. R. Radi, A. Cassina, R. Hodara, C. Quijano, and L. Castro Peroxynitrite reactions and formation in mitochondria Free Radic Biol Med 33 2002 1451 1464
3. P. Pacher, J.S. Beckman, and L. Liaudet Nitric oxide and peroxynitrite in health and disease Physiol Rev 87 2007 315 424
4. G. Ferrer-Sueta, and R. Radi Chemical biology of peroxynitrite: kinetics, diffusion, and radicals ACS Chem Biol 4 2009 161 177
5. C. Szabó, H. Ischiropoulos, and R. Radi Peroxynitrite: biochemistry, pathophysiology and development of therapeutics Nat Rev Drug Discov 6 2007 662 680
6. L. Liaudet, G. Vassalli, and P. Pacher Role of peroxynitrite in the redox regulation of cell signal transduction pathways Front Biosci 14 2009 4809 4814
7. S.L. Chen, L. Jian, and H.Q. Lang Optimization of peroxynitrite- luminolchemiluminescence system for detecting peroxynitrite in cell culture solution exposed to carbon disulphide Luminescence 18 2003 249 253
8. Z.Y. Bian, X.Q. Guo, Y.B. Zhao, and J.O. Du Probing the hydroxyl radical-mediated reactivity of peroxynitrite by a spin-labeling fluorophore Anal Sci 21 2005 553 559
9. A. Daiber, M. Oelze, M. August, M. Wendt, K. Sydow, and H. Wieboldt Detection of superoxide and peroxynitrite in model systems and mitochondria by the luminol analogue L-012 Free Radic Res 38 2004 259 269
10. J. Xue, X.Y. Ying, J.S. Chen, Y.Z. Xian, L.T. Jin, and J.Y. Jin Amperometricultramicrosensors for peroxynitrite detection and its application toward single myocardial cells Anal Chem 72 2000 5313 5321
11. R. Wang, C.W. Yu, F.B. Yu, and L.X. Chen Molecular fluorescent probes for monitoring pH changes in living cells TrAC Trends Anal Chem vol. 29 2010 1004 1013
12. T. Ueno, and T. Nagano Fluorescent probes for sensing and imaging Nat Methods 8 2011 642 645
13. T. Ueno, Y. Urano, K. Setsukinai, H. Takakusa, H. Kojima, and K. Kikuchi Rational principles for modulating fluorescence properties of fluorescein J Am Chem Soc 126 2004 14079 14085
14. T. Ueno, Y. Urano, H. Kojima, and T. Nagano Mechanism-based molecular design of highly selective fluorescence probes for nitrative stress J Am Chem Soc 128 2006 10640 10641
15. D. Yang, H.L. Wang, Z.N. Sun, N.W. Chung, and J.G. Shen A highly selective fluorescent probe for the detection and imaging of peroxynitrite in living cells J Am Chem Soc 128 2006 6004 6005
16. Z.N. Sun, H.L. Wang, F.Q. Liu, Y. Chen, P.K. Tam, and D. Yang BODIPY-based fluorescent probe for peroxynitrite detection and imaging in living cells Org Lett 11 2009 1887 1890
17. D. Oushiki, H. Kojima, T. Terai, M. Arita, K. Hanaoka, and Y. Urano Development and application of a near-infrared fluorescence probe for oxidative stress based on differential reactivity of linked cyanine dyes J Am Chem Soc 132 2010 2795 2801
18. T. Peng, and D. Yang HKGreen-3: a rhodol-based fluorescent probe for peroxynitrite Org Lett 12 2010 4932 4935
19. K.H. Xu, H.C. Chen, J.W. Tian, B.Y. Ding, Y.X. Xie, and M.M. Qiang A near-infrared reversible fluorescent probe for peroxynitrite and imaging of redox cycles in living cells Chem Commun 47 2011 9468 9470
20. J. Zielonka, A. Sikora, J. Joseph, and B. Kalyanaraman Peroxynitrite is the major species formed from different flux ratios of co-generated nitric oxide and superoxide: direct reaction with boronate-based fluorescent probe J Biol Chem 285 2010 14210 14216
21. F.B. Yu, P. Song, P. Li, B.S. Wang, and K.L. Han A fluorescent probe directly detect peroxynitrite based on boronate oxidation and its applications for fluorescence imaging in living cells Analyst 137 2012 3740 3749
22. J.J. Ma, J.S. Wu, W.M. Liu, P.F. Wang, and Z.Y. Fan Ruthenium(II) complex-based fluorescent sensor for peroxynitrite Spectrochim Acta Part A 94 2012 340 345
23. Q.C. Wang, D.H. Qu, J. Ren, L.H. Xu, M.Y. Liu, and H. Tian New benzo[e]indolinium cyanine dyes with two different fluorescence wavelengths Dyes Pigments 59 2003 163 172
24. J. Jiao, X.R. Zhang, N.H. Chang, J. Wang, J.F. Wei, and X.Y. Shi A facile and practical copper powder-catalyzed, organic solvent- and ligand-free Ullmann amination of aryl halides J Org Chem 76 2011 1180 1183
25. 2+ in living cells J Am Chem Soc 129 2007 1500 1501
26. K. Rurack, M. Kollmannsberger, and J. Daub Molecular switching in the near infrared (NIR) with a functionalized boron-dipyrromethene dye Angew Chem Int Ed 40 2001 385 387
27. H.J. Reich, M.L. Cohen, and P.S. Clark Reagents for synthesis of organoselenium compounds: diphenyl diselenide and benzeneselenenyl chloride Org Synth 59 1979 141
28. L. Henriksen, and N. Stuhr-Hansen Rapid and precise preparation of reactive benzeneselenolate solutions by reduction of diphenyl diselenide with hydrazine-sodium methanolate J Chem Soc Perkin Trans 1 1999 1915 1916
29. F.B. Yu, P. Li, G.Y. Li, G.J. Zhao, T.S. Chu, and K.L. Han A near-IR reversible fluorescent probe modulated by selenium for monitoring peroxynitrite and imaging in living cells J Am Chem Soc 133 2011 11030 11033
30. A.J. Mukherjee, S.S. Zade, H.B. Singh, and R.B. Sunoj Organoselenium chemistry: role of intramolecular interactions Chem Rev 110 2010 4357 4416
31. B.K. Sarma, D. Manna, M. Minoura, and G. Mugesh Synthesis, structure, spirocyclization mechanism, and glutathione peroxidase-like antioxidant activity of stable spirodiazaselenurane and spirodiazatellurane J Am Chem Soc 132 2010 5364 5374
32. N. Boens, V. Leen, and W. Dehaen Fluorescent indicators based on BODIPY Chem Soc Rev 41 2012 1130 1172
33. G. Ulrich, R. Ziessel, and A. Harriman The chemistry of fluorescent bodipy dyes: versatility unsurpassed Angew Chem Int Ed 47 2008 1184 1201
34. H.M. Guo, Y.Y. Jing, X.L. Yuan, S.M. Ji, J.Z. Zhao, and X.H. Li Highly selective fluorescent OFF-ON thiol probes based on dyads of BODIPY and potent intramolecular electron sink 2,4-dinitrobenzenesulfonyl subunits Org Biomol Chem 9 2011 3844 3853
35. Y.H. Chen, J.Z. Zhao, H.M. Guo, and L.J. Xie Geometry relaxation-induced large stokes shift in red-emitting borondipyrromethenes (BODIPY) and applications in fluorescent thiol probes J Org Chem 77 2012 2192 2206
36. P. Pahari, and S. Chaturvedi Determination of best-fit potential parameters for a reactive force field using a genetic algorithm J Mol Model 18 2012 1049 1061
37. Z.Y. Zhang, B. Xu, J.H. Su, L.P. Shen, Y.S. Xie, and H. Tian Color-tunable solid-state emission of 2,2′-biindenyl-based fluorophores Angew Chem Int Ed 50 2011 11654 11657
38. A.P. de Silva, H.Q. Gunaratne, T. Gunnlaugsson, A.J. Huxley, C.P. McCoy, and J.T. Rademacher Signaling recognition events with fluorescent sensors and switches Chem Rev 97 1997 1515 1566
39. M. Baruah, W. Qin, C. Flors, J. Hofkens, R. Vallée, and D. Beljonne Solvent and pH dependent fluorescent properties of a dimethylaminostyryl borondipyrromethene dye in solution J Phys Chem A 110 2006 5998 6009
40. E. Bassenge, and W.R. Kukovetz Molsidomine Cardiovasc Drug Rev 2 1984 177 191
41. N.M. Iovine, S. Pursnani, A. Voldman, G. Wasserman, M.J. Blaser, and Y. Weinrauch Reactive nitrogen species contribute to innate host defense against campylobacter jejuni Infect Immun 76 2008 986 993
42. R.B. Muijsers, E. Van Den Worm, G. Folkerts, C.J. Beukelman, A.S. Koster, and D.S. Postma Apocynin inhibits peroxynitrite formation by murine macrophages Br J Pharmacol 130 2000 932 936
43. B.C. Dickinson, J. Peltier, D. Stone, D.V. Schaffer, and C.J. Chang Nox2 redox signaling maintains essential cell populations in the brain Nat Chem Biol 7 2011 106 112