A near-infrared phenoxazinium-based fluorescent probe for zinc ions and its imaging in living cells

Sensors and Actuators, B: Chemical

Volumn 171-172, Issue , 2012, Pages 1001-1006

  Zhang, Qian Qian ^a   Yang, Bai Xia ^b   Sun, Ru ^a   Ge, Jian Feng ^a   Xu, Yu Jie ^b   Li, Na Jun ^c   Lu, Jian Mei ^a,c  

^a SOOCHOW UNIVERSITY   (China)

^b MEDICAL COLLEGE OF SOOCHOW UNIVERSITY   (China)

^c Key Laboratory of Functional Materials for Environment Protection of Suzhou City   (China)

Author keywords

Biosensor; Phenoxazinium; Red emitting; Zinc

Indexed keywords

FLUORESCENCE IMAGING; FLUORESCENT PROBES; GOOD STABILITY; LIVING CELL; NEAR INFRA RED; PHENOXAZINIUM; PHYSIOLOGICAL PH; RED FLUORESCENCE; RED-EMITTING; SELECTIVE FLUORESCENCE; ZINC IONS;

BIOSENSORS; FLUORESCENCE; INFRARED DEVICES; PH;

ZINC;

EID: 84864289478     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2012.06.017     Document Type: Article

References (31)

1. B.L. Vallee, and K.H. Falchuk The biochemical basis of zinc physiology Physiological Reviews 73 1993 79 118
2. J.M. Berg, and Y. Shi The galvanization of biology: a growing appreciation for the roles of zinc Science 271 1996 1081 1085
3. P. Jiang, and Z. Guo Fluorescent detection of zinc in biological systems: recent development on the design of chemosensors and biosensors Coordination Chemistry Reviews 248 2004 205 229
4. M.P. Cuajungco, and G.J. Lees Zinc metabolism in the brain: relevance to human neurodegenerative disorders Neurobiology of Disease 4 1997 137 169
5. T. Hirano, K. Kikuchi, Y. Urano, T. Higuchi, and T. Nagano Highly zinc-selective fluorescent sensor molecules suitable for biological applications Journal of the American Chemical Society 122 2000 12399 12400
6. S. Maruyama, K. Kikuchi, T. Hirano, Y. Urano, and T. Nagano A novel, cell-permeable, fluorescent probe for ratiometric imaging of zinc ion Journal of the American Chemical Society 124 2002 10650 10651
7. M. Taki, J.L. Wolford, and T.V. O'Halloran Emission ratiometric imaging of intracellular zinc: design of a benzoxazole fluorescent sensor and its application in two-photon microscopy Journal of the American Chemical Society 126 2004 712 713
8. H.M. Kim, M.S.M. Seo, Jin. An, J.H. Hong, Y.S. Tian, J.H.O.K. Choi, K.J. Lee, and B.R. Cho Two-photon fluorescent probes for intracellular free zinc ions in living tissue Angewandte Chemie: International Edition 120 2008 5245 5248
9. X.-Y. Chen, J. Shi, Y.-M. Li, F.-L. Wang, X. Wu, Q.-X. Guo, and L. Liu Two-photon fluorescent probes of biological zn(II) derived from 7-hydroxyquinoline Organic Letters 11 2009 4426 4429
10. Y. Mikata, A. Yamashita, K. Kawata, H. Konno, S. Itami, K. Yasudad, and S. Tamotsud Methoxyquinoline-diethylenetriamine conjugate as a fluorescent zinc sensor Dalton Transactions 40 2011 4976 4981
11. 2+-triggered excited-state intramolecular proton transfer: a sensitive probe with near-infrared emission from bis(benzoxazole) derivative Dalton Transactions 40 2011 1503 1509
12. 2+ sensors based on di- and tripyrrins with readily modulated emission wavelengths Chemical Communications 47 2011 5431 5433
13. 2+ in water Journal of Organic Chemistry 77 2012 3670 3673
14. B. Tang, H. Huang, K. Xu, L. Tong, G. Yang, X. Liu, and L. An Highly sensitive and selective near-infrared fluorescent probe for zinc and its application to macrophage cells Chemical Communications 2006 3609 3611
15. K. Kiyose, H. Kojima, Y. Urano, and T. Nagano Development of a ratiometric fluorescent zinc ion probe in near-infrared region, based on tricarbocyanine chromophore Journal of the American Chemical Society 128 2006 6548 6549
16. S. Atilgan, T. Ozdemir, and E.U. Akkaya A sensitive and selective ratiometric near IR fluorescent probe for zinc ions based on the distyryl-bodipy fluorophore Organic Letters 10 2008 4065 4067
17. X. Lu, W. Zhu, Y. Xie, X. Li, Y. Gao, F. Li, and H. Tian Near-IR core-substituted naphthalenediimide fluorescent chemosensors for zinc ions: ligand effects on PET and ICT channels Chemistry: A European Journal 16 2010 8355 8364
18. X.-B. Yang, B.-X. Yang, J.-F. Ge, Y.-J. Xu, Q.-F. Xu, J. Liang, and J.-M. Lu Benzo[a]phenoxazinium-based red-emitting chemosensor for zinc ions in biological media Organic Letters 13 2011 2710 2713
19. B.-Q. Liu, R. Sun, J.-F. Ge, N.-J. Li, X.-L. Shi, L.-H. Qiu, and J.-M. Lu The synthesis and third-order nonlinear optical properties of resonance benzo[α]phenoxazinium salts Dyes and Pigments 88 2011 50 56
20. J.-F. Ge, C. Arai, and M. Ihara The convenient synthesis of zinc chloride-free 3,7-bis(dialkylamino)phenoxazinium salts Dyes and Pigments 79 2008 33 39
21. J.-F. Ge, C. Arai, M. Yang, A.B. Md, J. Lu, N.S.M. Ismail, S. Wittlin, M. Kaiser, R. Brun, S.A. Charman, T. Nguyen, J. Morizzi, I. Itoh, and M. Ihara Discovery of novel benzo[α]phenoxazine SSJ-183 as a drug candidate for malaria ACS Medicinal Chemistry Letters 1 2010 360 364
22. M. Ihara Discovery of new anti-protozoan agents having novel mode of action Heterocycles 83 2011 1727 1756
23. 2+ Journal of Luminescence 114 2005 125 130
24. T. Hirayama, S. Iyoshi, M. Taki, Y. Maeda, and Y. Yamamoto Synthesis of a new bifunctionalised fluorescent label and physical properties of the bound form on model peptide of troponin C Organic and Biomolecular Chemistry 5 2007 2040 2045
25. G.S. Poindexter, D.A. Owens, P.L. Dolan, and Edmund Woo The use of 2-oxazolidinones as latent aziridine equivalents. 2. Aminoethylation of aromatic amines, phenols, and thiophenols Journal of Organic Chemistry 57 1992 6257 6265
26. S. Fukuoka, T. Kida, Y. Nakajima, T. Tsumagari, W. Watanabe, Y. Inaba, A. Mori, T. Matsumura, Y. Nakano, and K. Takeshita Thermo-responsive extraction of cadmium(II) ion with TPEN-NIPA gel. Effect of the number of polymerizable double bond toward gel formation and the extracting behavior Tetrahedron 66 2010 1721 1727
27. T.Y. Cheng, T. Wang, W.P. Zhu, Y.Y. Yang, B.B. Zeng, Y.F. Xu, and X.H. Qian Modulating the selectivity of near-IR fluorescent probes toward various metal ions by judicious choice of aqueous buffer solutions Chemical Communications 47 2011 3915 3917
28. M.S. Moores, W.J. Balon, and C.W. Maynard The structure of basic blue 4. 3,7-Bis(diethylamino)phenazoxonium chloride Journal of Heterocyclic Chemistry 6 1969 755 757
29. X.-A. Zhang, D. Hayes, S.J. Smith, S. Friedle, and S.J. Lippard New strategy for quantifying biological zinc by a modified zinpyr fluorescence sensor Journal of the American Chemical Society 130 2008 15788 15789
30. K. Komatsu, Y. Urano, H. Kojima, and T. Nagano Development of an iminocoumarin-based zinc sensor suitable for ratiometric fluorescence imaging of neuronal zinc Journal of the American Chemical Society 129 2007 13447 13454
31. U.C. Saha, B. Chattopadhyay, K. Dhara, S.K. Mandal, S. Sarkar, A.R. Khuda-Bukhsh, M. Mukherjee, M. Helliwell, and P. Chattopadhyay A highly selective fluorescent chemosensor for zinc ion and imaging application in living cells Inorganic Chemistry 50 2011 1213 1219