Acylhydrazone based fluorescent chemosensor for zinc in aqueous solution with high selectivity and sensitivity

Sensors and Actuators, B: Chemical

Volumn 208, Issue , 2015, Pages 581-587

  Hu, Jing Han ^a   Li, Jian Bin ^a   Qi, Jing ^a   Sun, You ^a  

^a LANZHOU JIAOTONG UNIVERSITY   (China)

Author keywords

Acylhydrazone; Fluorescent sensors; Test strip; Zinc (Zn2+)

Indexed keywords

CADMIUM; CADMIUM COMPOUNDS; FLUORESCENCE; LEAD; NAPHTHALENE; PHYSIOLOGY; PROBES; SOLUTIONS; ZINC;

ACYLHYDRAZONE; DETECTION LIMITS; FLUORESCENCE SIGNALS; FLUORESCENT CHEMOSENSOR; FLUORESCENT SENSORS; HIGH SELECTIVITY; SPECIFIC SELECTIVITY; TEST STRIPS;

COPPER;

EID: 84912119565     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2014.11.066     Document Type: Article

References (51)

1. C.J. Frederickson, J.Y. Koh, A.I. Bush, The neurobiology of zinc in health and disease, Nat. Rev. Neurosci. 6 (2005) 449-462.
2. A.I. Bush, W.H. Pettingell, G. Multhaup, M.D. Paradis, J.P. Vonsattel, J.F. Gusella, K. Beyreuther, C.L. Masters, R.E. Tanzi, Rapid induction of Alzheimer a beta amyloid formation by zinc, Science 265 (1994) 1464-1467.
3. Q.P. Peterson, D.R. Goode, D.C. West, K.N. Ramsey, J.J.Y. Lee, P.J. Hergenrother, PAC-1 activates procaspase-3 in vitro through relief of zinc-mediated inhibition, J. Mol. Biol. 388 (2009) 144-158.
4. R. BarKalifa, M. Hershfinkel, J.E. Friedman, A. Kozak, I. Sekler, The lipophilic zinc chelator DP-b99 prevents zinc induced neuronal death, Eur. J. Pharmacol. 618 (2009) 15-21.
5. C.J. Frederickson, M.D. Hernandez, J.F. McGinty, Translocation of zinc may contribute to seizure-induced death of neurons, Brain Res. 480 (1989) 317-321.
6. (a) M.P. Cuajungco, G.J. Lees, Zinc metabolism in the brain: relevance to human neurodegenerative disorders, Neurobiol. Dis. 4 (1997) 137-169;
7. (b) C.F. Walker, R.E. Black, Zinc and the risk for infectious disease, Annu. Rev. Nutr. 24 (2004) 255-275.
8. Z. Yang, C. Yan, Y. Chen, C. Zhu, C. Zhang, X. Dong, W. Yang, Z. Guo, Y. Lu, W. He, A novel terpyridine/benzofurazan hybrid fluorophore: metal sensing behavior and application, Dalton Trans. 40 (2011) 2173-2176.
9. M.E. Moragues, R. Martinez-Manez, F. Sancenon, Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the year 2009, Chem. Soc. Rev. 40 (2011) 2593-2643.
10. (a) B.B. Shi, Y.M. Zhang, T.B. Wei, Q. Lin, H. Yao, P. Zhang, X.M. You, A fluorescent and colorimetric chemosensor for dihydrogenphosphate ions based on 2-pyridine-1H-imidazo[4,5-b]phenazine-zinc ensemble, Sens. Actuators B 190 (2014) 555-561;
11. (b) Y.M. Zhang, Q. Lin, T.B. Wei, X.P. Qin, Y. Li, A novel smart organogel which could allow a two channel anion response by proton controlled reversible sol-gel transition and color changes, Chem. Commun. 45 (2009) 6074-6083;
12. 3+ and resultant complex as a chemosensor for fluoride, Sens. Actuators B 186 (2013) 657-665.
13. W. Jiang, Q. Fu, H. Fan, W. Wang, An NBD fluorophore-based sensitive and selective fluorescent probe for zinc ion, Chem. Commun. (2008) 259-261.
14. (a) C.J. Chang, E.M. Nolan, J. Jaworski, S.C. Burdette, M. Sheng, S.J. Lippard, Bright fluorescent chemosensor platforms for imaging endogenous pools of neuronal zinc, Chem. Biol. 11 (2004) 203-210;
15. (b) E.M. Nolan, J.W. Ryu, J. Jaworski, R.P. Feazell, M. Sheng, S.J. Lippard, Zinspy sensors with enhanced dynamic range for imaging neuronal cell zinc uptake and mobilization, J. Am. Chem. Soc. 128 (2006) 15517-15528.
16. 2+ chemosensors, functional in aqueous solution under environmentally relevant conditions, Tetrahedron Lett. 51 (2010) 1161-1165.
17. 2+-selective, cell-permeable, and ratiometric fluorescent sensor, J. Am. Chem. Soc. 132 (2010) 601-610;
18. (b) C. Lu, Z. Xu, J. Cui, R. Zhang, 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.
19. 2+ probes for ratiometric fluorescence imaging, Inorg. Chem. 48 (2009) 7630-7638.
20. (a) Y. Mikata, A. Ugai, K. Yasuda, S. Itami, S. Tamotsu, H. Konno, S. Iwatsuki, Quinoline-based, glucose-pendant fluorescent zinc probes, Chem. Biodivers. 9 (2012) 2064-2075;
21. 2+ in aqueous solution and imaging in living neuron cells, Sens. Actuators B 186 (2013) 755-760.
22. (a) B. Tang, H. Huang, K. Xu, L. Tong, G. Yang, X. Liu, L. An, Highly sensitive and selective near-infrared fluorescent probe for zinc and its application to macrophage cells, Chem. Commun. 34 (2006) 3609-3611;
23. (b) K. Kiyose, H. Kojima, Y. Urano, T. Nagano, Development of a ratiometric fluorescent zinc ion probe in near-infrared region, based on tricarbocyanine chromophore, J. Am. Chem. Soc. 128 (2006) 6548-6549.
24. 2+ using a rhodamine spirolactam as a trigger, Anal. Chem. 82 (2010) 3108-3113;
25. 2+ based on the spirolactam ring-opening process of rhodamine derivatives, Bioorg. Med. Chem. 19 (2011) 1072-1078.
26. S. Atilgan, T. Ozdemir, E.U. Akkaya, A sensitive and selective ratiometric near IR fluorescent probe for zinc ions based on the distyryl-bodipy fluorophore, Org. Lett. 10 (2008) 4065-4067.
27. 2+ fluorescent sensor derived from an intramolecular charge transfer fluorophore and its in vitro and in vivo application, J. Am. Chem. Soc. 131 (2009) 1460-1468;
28. (b) E. Tomat, E.M. Nolan, J. Jaworski, S.J. Lippard, Organelle-specific zinc detection using zinpyr-labeled fusion proteins in live cells, J. Am. Chem. Soc. 130 (2008) 15776-15777.
29. (a) L. Xue, C. Liu, H. Jiang, A ratiometric fluorescent sensor with a large Stokes shift for imaging zinc ions in living cells, Chem. Commun. 9 (2009) 1061-1063;
30. 2+ with a tetraphenylethylene compound, Org. Lett. 13 (2011) 6378-6381.
31. 2+ release upon different stimulations, Chem. Commun. 48 (2012) 8365-8367.
32. M. Wolfgang, Redox biochemistry of mammalian metallothioneins, J. Biol. Inorg. Chem. (2011) 0949-8257.
33. 2+ ions: a molecular 'butterfly', Chem. Commun. 47 (2011) 8796-8798.
34. 2+ based on a 3,8-extended 1,10-phenanthroline derivative, Eur. J. Inorg. Chem. 24 (2012) 3844-3851;
35. 2+ chemosensor based on an easy to prepare C3-symmetric schiff-base derivative in 100% aqueous solution, Org. Lett. 14 (2012) 1214-1217.
36. A. Hartwig, Role of magnesium in genomic stability, Mutat. Res., Fundam. Mol. Mech. Mutagen. 475 (2001) 113-121.
37. 2+, Chem. Soc. Rev. 39 (2010) 1996-2006.
38. 2+ ions based on flavonol derivatives, Sens. Actuators B 202 (2014) 674-682;
39. 2+ using a single Schiff base, Inorg. Chem. Commun. 45 (2014) 15-19.
40. (a) H.H. Wang, Q. Gan, X.J. un Wang, L. Xue, S.H. Liu, H. Jiang, A water-soluble, small molecular fluorescent sensor with femtomolar sensitivity for zinc ion, Org. Lett. 9 (2007) 4995-4998;
41. 2+ in the endoplasmic reticulum with benzoresorufin-based fluorescent probes, J. Am. Chem. Soc. 135 (2013) 13512-13520.
42. 2+ in physiological medium and in HeLa cells, Org. Biomol. Chem. 12 (2014) 4975-4982;
43. 2+ ion, J. Fluoresc. 24 (2014) 827-834;
44. (c) J. Li, C.F. Zhang, Z.Z. Ming, G.F. Hao, W.C. Yang, Coumarin-based novel fluorescent zinc ion probe in aqueous solution, Tetrahedron 69 (2013) 4743-4748.
45. (a) Y.Y. Lv, M.D. Cao, J.K. Li, J.B. Wang, A sensitive ratiometric fluorescent sensor for zinc(II) with high selectivity, Sensors 13 (2013) 3131-3141;
46. 2+ probes, J. Org. Chem. 78 (2013) 5328-5340.
47. (a) J.H. Hu, N.P. Yan, J.J. Chen, Synthesis of 4-nitrophenylthiosemi-carbazone of salicylaldehyde and its colorimetric anion recognition properties, J. Chem. Res. 36 (2012) 619-622;
48. (b) J.H. Hu, N.P. Yan, J.J. Chen, J.B. Li, Synthesis of azosalicylic aldehyde of benzoyl hydrazone based sensor and it's colorimetric sensing properties for cyanide anions in aqueous solutions, Chem. J. Chin. Univ. 34 (2013) 1368-1373;
49. (c) J.B. Li, J.H. Hu, J.J. Chen, J. Qi, Cyanide detection using a benzimidazole derivative in aqueous media, Spectrochim. Acta A: Mol. Biomol. Spectrosc. 133 (2014) 773-777;
50. (d) J.H. Hu, J.B. Li, J. Qi, J.J. Chen, Highly selective and effective mercury(II) fluorescent sensors, N. J. Chem. (2014), http://dx.doi.org/10.1039/c4nj01147c.
51. Recommendations for the definition, estimation and use of the detection limit, Analytical Methods Committee, Analyst 112 (1987) 199-204.