The synthesis and study of the fl uorescent probe for sensing Cu<sub>2</sub> based on a novel coumarin Schiff-base

Citation: Yu-Wei Duan, Hao-Yang Tang, Yuan Guo, Zhan-Ke Song, Meng-Jiao Peng, Yong Yan. The synthesis and study of the fl uorescent probe for sensing Cu₂ based on a novel coumarin Schiff-base[J]. Chinese Chemical Letters, 2014, 25(7): 1082-1086. doi: 10.1016/j.cclet.2014.05.001 shu

The synthesis and study of the fl uorescent probe for sensing Cu₂ based on a novel coumarin Schiff-base

通讯作者: Yuan Guo,

基金项目:

the Natural Science Foundation of Shaanxi Province (No. 2012JM8022) (No. 2012JM8022)

the Special Foundation of the Education Committee of Shaanxi Province (No. 12JK0580) (No. 12JK0580)

Applications (FFSCA) (FFSCA)

the China Scholars Council (CSC). (CSC)

摘要: A novel, fluorescent probe was synthesized from 2,4-dihydroxybenzaldehyde and 8-hydroxyquinoline for sensing Cu²⁺ by the naked eye. The structure was confirmed by IR, MS, ¹H NMR, ¹³C NMR and the spectral properties of the probe were investigated. It exhibited strong fluorescence responses toward Cu²⁺ and high selectivity over other metal ions. The binding constant between the probe and Cu²⁺ was calculated using Benesi-Hildebrand equation.

关键词:

English

The synthesis and study of the fl uorescent probe for sensing Cu₂ based on a novel coumarin Schiff-base

1.
a Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710069, China;
2.
b School of Automation, Xi'an University of Posts and Telecommunications, Xi'an 710121, China

Corresponding author: Yuan Guo,

Received Date: 27 February 2014
Fund Project:

Abstract: A novel, fluorescent probe was synthesized from 2,4-dihydroxybenzaldehyde and 8-hydroxyquinoline for sensing Cu²⁺ by the naked eye. The structure was confirmed by IR, MS, ¹H NMR, ¹³C NMR and the spectral properties of the probe were investigated. It exhibited strong fluorescence responses toward Cu²⁺ and high selectivity over other metal ions. The binding constant between the probe and Cu²⁺ was calculated using Benesi-Hildebrand equation.

Key words:

1. [1] Y. Lin, W.Y. Lin, B. Chen, Y.A. Xie, Development of FRET-based ratiometric fluorescent Cu²⁺ chemodosimeters and the applications for living cell imaging, Org. Lett. 14 (2012) 432-435.[1] Y. Lin, W.Y. Lin, B. Chen, Y.A. Xie, Development of FRET-based ratiometric fluorescent Cu²⁺ chemodosimeters and the applications for living cell imaging, Org. Lett. 14 (2012) 432-435.
2. [2] J.L. Fan, P. Zhan, M.M. Hu, et al., A fluorescent ratiometric chemodosimeter for Cu²⁺ based on TBET and its application in living cells, Org. Lett. 12 (2013) 492-495.[2] J.L. Fan, P. Zhan, M.M. Hu, et al., A fluorescent ratiometric chemodosimeter for Cu²⁺ based on TBET and its application in living cells, Org. Lett. 12 (2013) 492-495.
3. [3] D.J. Waggoner, T.B. Bart, J.D. Gitlin, The role of copper in neurodegenerative disease, Neurobiol. Dis. 6 (1999) 221-230.[3] D.J. Waggoner, T.B. Bart, J.D. Gitlin, The role of copper in neurodegenerative disease, Neurobiol. Dis. 6 (1999) 221-230.
4. [4] C. Vulpe, B. Levinson, S. Whitney, S. Packman, J. Gitschier, Isolation of a candidate gene for Menkes disease and evidence that it encodes a copper-transporting ATPase, Nat. Genet. 3 (1993) 7-13.[4] C. Vulpe, B. Levinson, S. Whitney, S. Packman, J. Gitschier, Isolation of a candidate gene for Menkes disease and evidence that it encodes a copper-transporting ATPase, Nat. Genet. 3 (1993) 7-13.
5. [5] P.C. Bull, G.R. Thomas, J.M. Rommens, J.R. Forbes, D.W. Cox, The Wilson disease gene is a putative copper transporting P-type ATPase similar to the Menkes gene, Nat. Genet. 5 (1993) 327-337.[5] P.C. Bull, G.R. Thomas, J.M. Rommens, J.R. Forbes, D.W. Cox, The Wilson disease gene is a putative copper transporting P-type ATPase similar to the Menkes gene, Nat. Genet. 5 (1993) 327-337.
6. [6] J.S. Valentine, B.G. Hart, J.R. Winkler, Copper(II) binding to alpha-synuclein, the Parkinson's protein, Proc. Natl. Acad. Sci. U.S.A. 130 (2008) 6898-6899.[6] J.S. Valentine, B.G. Hart, J.R. Winkler, Copper(II) binding to alpha-synuclein, the Parkinson's protein, Proc. Natl. Acad. Sci. U.S.A. 130 (2008) 6898-6899.
7. [7] N. Shao, J.Y. Jin, H. Wang, et al., Tunable photochromism of spirobenzopyran via selective metal ion coordination: an efficient visual and ratioing fluorescent probe for divalent copper ion, Anal. Chem. 80 (2008) 3466-3475.[7] N. Shao, J.Y. Jin, H. Wang, et al., Tunable photochromism of spirobenzopyran via selective metal ion coordination: an efficient visual and ratioing fluorescent probe for divalent copper ion, Anal. Chem. 80 (2008) 3466-3475.
8. [8] G. Meloni, P. Faller, M. Vasak, Redox silencing of copper in metal-linked neurodegenerative disorders: reaction of Zn7metallothionein-3 with Cu²⁺, J. Biol. Chem. 282 (2007) 16068-16078.[8] G. Meloni, P. Faller, M. Vasak, Redox silencing of copper in metal-linked neurodegenerative disorders: reaction of Zn7metallothionein-3 with Cu²⁺, J. Biol. Chem. 282 (2007) 16068-16078.
9. [9] T.Y. Han, Y.F. Dong, Z.Y. Li, et al., Turn-on fluorescent detection of 2,5-di(4'-carboxylphenyl)-1-phenylpyrrole to amines, Acta Chem. Sin. 70 (2012) 1187-1192.[9] T.Y. Han, Y.F. Dong, Z.Y. Li, et al., Turn-on fluorescent detection of 2,5-di(4'-carboxylphenyl)-1-phenylpyrrole to amines, Acta Chem. Sin. 70 (2012) 1187-1192.
10. [10] X.B. Li, Z.G. Niu, L.L. Chang, M.X. Chen, E.J. Wang, Quinoline-based colorimetric chemosensor for Cu²⁺: Cu²⁺ induced deprotonation leading to color change, Chin. Chem. Lett. 25 (2014) 80-82.[10] X.B. Li, Z.G. Niu, L.L. Chang, M.X. Chen, E.J. Wang, Quinoline-based colorimetric chemosensor for Cu²⁺: Cu²⁺ induced deprotonation leading to color change, Chin. Chem. Lett. 25 (2014) 80-82.
11. [11] Z.C. Xu, X.H. Qian, J.N. Cui, Colorimetric and ratiometric fluorescent chemosensor with a large red-shift in emission: Cu(II)-only sensing by deprotonation of secondary amines as receptor conjugated to naphthalimide fluorophore, Org. Lett. 7 (2005) 3029-3032.[11] Z.C. Xu, X.H. Qian, J.N. Cui, Colorimetric and ratiometric fluorescent chemosensor with a large red-shift in emission: Cu(II)-only sensing by deprotonation of secondary amines as receptor conjugated to naphthalimide fluorophore, Org. Lett. 7 (2005) 3029-3032.
12. [12] Ulf-P. Apfel, D. Buccella, J.J. Wilson, S.J. Lippard, Detection of nitric oxide and nitroxyl with benzoresorufin-based fluorescent sensors, Inorg. Chem. 52 (2013) 3285-3294.[12] Ulf-P. Apfel, D. Buccella, J.J. Wilson, S.J. Lippard, Detection of nitric oxide and nitroxyl with benzoresorufin-based fluorescent sensors, Inorg. Chem. 52 (2013) 3285-3294.
13. [13] Y. Fu, C.Q. Ding, A.W. Zhu, et al., Two-photon ratiometric fluorescent sensor based on specific biomolecular recognition for selective and sensitive detection of copper ions in live cells, Anal. Chem. 85 (2013) 11936-11943.[13] Y. Fu, C.Q. Ding, A.W. Zhu, et al., Two-photon ratiometric fluorescent sensor based on specific biomolecular recognition for selective and sensitive detection of copper ions in live cells, Anal. Chem. 85 (2013) 11936-11943.
14. [14] Y. Zhao, X.B. Zhang, Z. Han, et al., Highly sensitive and selective colorimetric and off-on fluorescent chemosensor for Cu²⁺ in aqueous solution and living cells, Anal. Chem. 81 (2009) 7022-7030.[14] Y. Zhao, X.B. Zhang, Z. Han, et al., Highly sensitive and selective colorimetric and off-on fluorescent chemosensor for Cu²⁺ in aqueous solution and living cells, Anal. Chem. 81 (2009) 7022-7030.
15. [15] D.M. Pluth, L.E. McQuade, S.J. Lippard, Cell-trappable fluorescent probes for nitric oxide visualization in living cells, Org. Lett. 12 (2010) 2318-2321.[15] D.M. Pluth, L.E. McQuade, S.J. Lippard, Cell-trappable fluorescent probes for nitric oxide visualization in living cells, Org. Lett. 12 (2010) 2318-2321.
16. [16] J.Y. Jo, H.Y. Lee, W.J. Liu, et al., Reactivity-based detection of copper (II) ion in water: oxidative cyclization of azoaromatics as fluorescence turn-on signaling mechanism, J. Am. Chem. Soc. 134 (2012) 16000-16007.[16] J.Y. Jo, H.Y. Lee, W.J. Liu, et al., Reactivity-based detection of copper (II) ion in water: oxidative cyclization of azoaromatics as fluorescence turn-on signaling mechanism, J. Am. Chem. Soc. 134 (2012) 16000-16007.
17. [17] S.J. Hyo, H.H. Ji, H.K. Zee, H.K. Chul, S.K. Jong, Coumarin-Cu (II) ensemble-based cyanide sensing chemodosimeter, Org. Lett. 13 (2011) 5056-5059.[17] S.J. Hyo, H.H. Ji, H.K. Zee, H.K. Chul, S.K. Jong, Coumarin-Cu (II) ensemble-based cyanide sensing chemodosimeter, Org. Lett. 13 (2011) 5056-5059.
18. [18] C.J. Kirubaharan, D. Kalpana, Y.S. Lee, et al., Biomediated silver nanoparticles for the highly selective copper(II) ion sensor applications, Ind. Eng. Chem. Res. 51 (2012) 7441-7446.[18] C.J. Kirubaharan, D. Kalpana, Y.S. Lee, et al., Biomediated silver nanoparticles for the highly selective copper(II) ion sensor applications, Ind. Eng. Chem. Res. 51 (2012) 7441-7446.
19. [19] F.P. Hou, L. Huang, P.X. Xi, A retrievable and highly selective fluorescent probe for monitoring sulfide and imaging in living cells, Inorg. Chem. 51 (2012) 2454-2460.[19] F.P. Hou, L. Huang, P.X. Xi, A retrievable and highly selective fluorescent probe for monitoring sulfide and imaging in living cells, Inorg. Chem. 51 (2012) 2454-2460.
20. [20] A. Coskun, 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.[20] A. Coskun, 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.
21. [21] J.B. Wang, X.H. Qian, A series of polyamide receptor based PET fluorescent sensor molecules: positively cooperative Hg²⁺ ion binding with high sensitivity, Org. Lett. 8 (2006) 3721-3724.[21] J.B. Wang, X.H. Qian, A series of polyamide receptor based PET fluorescent sensor molecules: positively cooperative Hg²⁺ ion binding with high sensitivity, Org. Lett. 8 (2006) 3721-3724.
22. [22] A.P. de Silva, A.H.Q. Gun, L.T. Gunn, et al., Signaling recognition events with fluorescent sensors and switches, Chem. Rev. 97 (1997) 1515-1566.[22] A.P. de Silva, A.H.Q. Gun, L.T. Gunn, et al., Signaling recognition events with fluorescent sensors and switches, Chem. Rev. 97 (1997) 1515-1566.
23. [23] X. Zhao, M.X. Jia, X.K. Jiang, et al., Zipper-featured d-peptide foldamers driven by donor-acceptor interaction. Design, synthesis, and characterization, J. Org. Chem. 69 (2004) 270-279.[23] X. Zhao, M.X. Jia, X.K. Jiang, et al., Zipper-featured d-peptide foldamers driven by donor-acceptor interaction. Design, synthesis, and characterization, J. Org. Chem. 69 (2004) 270-279.
24. [24] H.A. Benesi, J.H. Hildebrand, A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons, J. Am. Chem. Soc. 71 (1947) 2703-2707.[24] H.A. Benesi, J.H. Hildebrand, A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons, J. Am. Chem. Soc. 71 (1947) 2703-2707.

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沈阳化工大学材料科学与工程学院沈阳 110142

The synthesis and study of the fl uorescent probe for sensing Cu₂ based on a novel coumarin Schiff-base

通讯作者: Yuan Guo,

English

The synthesis and study of the fl uorescent probe for sensing Cu₂ based on a novel coumarin Schiff-base

Corresponding author: Yuan Guo,

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

The synthesis and study of the fl uorescent probe for sensing Cu2 based on a novel coumarin Schiff-base

通讯作者: Yuan Guo,

English

The synthesis and study of the fl uorescent probe for sensing Cu2 based on a novel coumarin Schiff-base

Corresponding author: Yuan Guo,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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通讯作者: 陈斌, bchen63@163.com

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The synthesis and study of the fl uorescent probe for sensing Cu₂ based on a novel coumarin Schiff-base

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