Citation: Shuang Zhang, Ji-Ming Yan, An-Jun Qin, Jing-Zhi Sun, Ben-Zhong Tang. The specific detection of Cu(Ⅱ) using an AIE-active alanine ester[J]. Chinese Chemical Letters, ;2013, 24(8): 668-672. shu

The specific detection of Cu(Ⅱ) using an AIE-active alanine ester

1.
a MoE Key Laboratory of Macromolecule Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China;
2.
b Department of Chemistry, Institute of Molecular Functional Materials, the Institute for Advanced Study (IAS), The Hong Kong University of Science & Technology, Hong Kong, China

Corresponding author: Jing-Zhi Sun, Ben-Zhong Tang,
Received Date: 25 February 2013
Available Online: 17 April 2013

Cu(Ⅱ) detection is important because it plays crucial role in several biological processes and ecological systems. Fluorescent techniques have attracted more and more attention in Cu(Ⅱ) detection. In this report, we contribute a novel strategy to use fluorescence spectroscopy for Cu(Ⅱ) specific detection. The specificity relies on the fact that, of the many metal cations, only Cu(Ⅱ) can catalyze the hydrolyzation of a-amino acid ester. The novelty originates from the unique aggregation-induced emission (AIE) property of the fluorescent label. We designed a model a-amino acid ester (TPE-Ala) constructed with alanine and tetraphenylethene-functionalizedmethanol (TPE-methanol). In comparison with the precursor TPE-Ala, TPE-methanol has lower solubility and is easy to form aggregates in water, thereby displaying a higher fluorescent response. Thus, the Cu(Ⅱ) catalyzed hydrolyzation can be monitored by recording the fluorescence enhancement and fluorescent detection Cu(Ⅱ) is rationally achieved.
- Aggregation-induced emission,
- Fluorescence enhancement,
- Cu(Ⅱ) catalyzed
1. [1]
  [1] M.C. Linder, M. Hazegh-Azam, Copper biochemistry and molecular biology, Am. J. Clin. Nutr. 63 (1996) 797S-811S.
2. [2]
  [2] C. Vulpe, B. Levinson, S. Whitney, et al., Isolation of a candidate gene for Menkes disease and evidence that it encodes a copper-transporting ATPase, J. Gitschier Nat. Genet. 3 (1993) 7-13.
3. [3]
  [3] D.R. Brown, H. Kozlowski, Biological inorganic and bioinorganic chemistry of neurodegeneration based on Prion and Alzheimer diseases, Dalton. Trans. (2004) 1907-1917.
4. [4]
  [4] K.J. Barnham, C.L. Masters, A.I. Bush, Neurodegenerative diseases and oxidative stress, Nat. Rev. Drug Discov. 3 (2004) 205-214.
5. [5]
  [5] L.I. Bruijn, T.M. Miller, D.W. Cleveland, Unraveling the mechanisms involved in motor neuron degeneration in ALS, Annu. Rev. Neurosci. 27 (2004) 723-749.
6. [6]
  [6] S. Kaur, S. Kumar, Photoactive chemosensors: a unique case of lluorescence enhancement with Cu(Ⅱ), Chem. Commun. (2002) 2840-2841.
7. [7]
  [7] X. Qi, E.J. Jun, L. Xu, et al., New BODIPY derivatives as off-on fluorescent chemosensor and fluorescent chemodosimeter for Cu²⁺: cooperative selectivity enhancement toward Cu²⁺, J. Org. Chem. 71 (2006) 2881-2884.
8. [8]
  [8] X. Zhang, Y. Shiraishi, T. Hirai, Cu (Ⅱ)-selective green fluorescence of a rhodaminediacetic acid conjugate, Org. Lett. 9 (2007) 5039-5042.
9. [9]
  [9] M. Yu, M. Shi, Z. Chen, et al., Highly sensitive and fast responsive fluorescence turn-on chemodosimeter for Cu²⁺ and its application in live cell imaging, Chem. Eur. J. 14 (2008) 6892-6900.
10. [10]
  [10] Y. Zhao, X.B. Zhang, Z.X. Han, et al., Highly sensitive and selective colorimetric and off-on fluorescent chemosensor for Cu²⁺ in aqueous solution and lving cells, Anal. Chem. 81 (2009) 7022-7030.
11. [11]
  [11] K.L. Ciesienski, L.M. Hyman, S. Derisavifard, K.J. Franz, Toward the detection of cellular copper(Ⅱ) by a light-activated fluorescence increase, Inorg. Chem. 49 (2010) 6808-6810.
12. [12]
  [12] F.T. Lv, X.L. Feng, H.W. Tang, et al., Development of film sensors based on conjugated polymers for copper (Ⅱ) ion detection, Adv. Funct. Mater. 21 (2011) 845-850.
13. [13]
  [13] Y. Zhou, Y.W. Yao, J.Y. Li, et al., Nitroxyl induced fluorescence enhancement via reduction of a copper(Ⅱ) coumarin-ester complex: its application for bioimaging in vivo, Sens. Actuator B -Chem. 174 (2012) 414-420.
14. [14]
  [14] C.W. Yu, T. Wang, K. Xu, et al., Characterization of a highly Cu²⁺-selective fluorescent probe derived from rhodamine B, Dyes Pigments 96 (2013) 38-44.
15. [15]
  [15] J. Luo, Z. Xie, J.W.Y. Lam, et al., Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole, Chem. Commun. (2001) 1740-1741.
16. [16]
  [16] Y. Hong, J.W.Y. Lam, B.Z. Tang, Aggregation-induced emission, Chem. Soc. Rev. 40 (2011) 536-5388.
17. [17]
  [17] S. Zhang, A. Qin, J. Sun, B.Z. Tang, Mechanism study of aggregation-induced emission, Prog. Chem. 23 (2011) 623-636.
18. [18]
  [18] J. Yan, J. Sun, A. Qin, B.Z. Tang, Application of AIE-active molecules in biosensing, Chin. Sci. Bull. 55 (2010) 1206-1213.
19. [19]
  [19] Y. Hong, J.W.Y. Lam, B.Z. Tang, Aggregation-induced emission: phenomenon, mechanism and applications, Chem. Commun. (2009) 4332-4353.
20. [20]
  [20] J. Chen, C.C.W. Law, J.W.Y. Lam, et al., Synthesis, light emission, nanoaggregation and restricted intramolecular rotation of 1,1-substituted 2,3,4,5-tetraphenylsiloles, Chem. Mater. 15 (2003) 1535-1546.
21. [21]
  [21] J. Mei, Y. Wang, J.Q. Tong, et al., Discriminatory detection of cysteine and homocysteine based on dialdehyde-functionalized aggregation-induced emission fluorophores, Chem. Eur. J. 19 (2013) 613-620.
22. [22]
  [22] J. Mei, J.Q. Tong, J. Wang, et al., Discriminative fluorescence detection of cysteine, homocysteine and glutathione via reaction-dependent aggregation of fluorophore-analyte adducts, J. Mater. Chem. 22 (2012) 17063-17070.
23. [23]
  [23] Z. Yang, N. Zhao, Y.M. Sun, et al., Highly selective red-and green-emitting twophoton fluorescent probes for cysteine detection and their bio-imaging in living cells, Chem. Commun. 48 (2012) 3442-3444.
24. [24]
  [24] M.L. Bender, B.W. Turnquest, The kinetics and oxygen exchange of the cupric ioncatalyzed hydrolysis of a-amino esters, Org. Biol. Chem. 79 (1957) 1889-1893.
25. [25]
  [25] M.M. Shoukry, E.M. Khairy, R.G. Khalil, Binary and ternary complexes involving copper (Ⅱ), glycyl-DL-leucine and amino acids or amino acid esters: hydrolysis and equilibrium studies, Transit. Met. Chem. 22 (1997) 465-470.
26. [26]
  [26] J. Zhao, J.W.Y. Lam, B.Z. Tang, Aggregation-induced emission of tetraarylethene luminogens, Curr. Org. Chem. 14 (2010) 2109-2131.
27. [27]
  [27] X. Chen, X.Y. Shen, E. Guan, et al., A pyridinyl-functionalized tetraphenylethylene fluorogen for specific sensing of trivalent cations, Chem. Commun. 49 (2013) 1503-1505.
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