A pyridoxal-based chemosensor for visual detection of copper ion and its application in bioimaging

注册 English

A pyridoxal-based chemosensor for visual detection of copper ion and its application in bioimaging

Cai-Xia Yin , Li-Jun Qu , Fang-Jun Huo

Citation: Cai-Xia Yin, Li-Jun Qu, Fang-Jun Huo. A pyridoxal-based chemosensor for visual detection of copper ion and its application in bioimaging[J]. Chinese Chemical Letters, 2014, 25(9): 1230-1234. doi: 10.1016/j.cclet.2014.06.017 shu

shu

A pyridoxal-based chemosensor for visual detection of copper ion and its application in bioimaging

通讯作者: Fang-Jun Huo,

基金项目:
The work was supported by the National Natural Science Foundation of China (No. 21102086) (No. 21102086)

the Shanxi Province Foundation for Returnee (No. 2012-007) (No. 2012-007)

the Taiyuan Technology Star Special (No. 12024703) (No. 12024703)

Middle-aged Innovative Talents of Higher Learning Institutions of Shanxi (TYMIT, No. 2013802) (TYMIT, No. 2013802)

talents Support Program of Shanxi Province (No. 2014401) (No. 2014401)

CAS Key Laboratory of Analytical Chemistry for Living Biosystems Open Foundation (No. ACL201304). (No. ACL201304)

摘要: A pyridoxal-based chemosensor was synthesized by reacting hydrazine hydrate and pyridoxal hydrochloride in ethanol and characterized by NMR and ESI-MS. The optical properties of the compound were investigated in a methanol: HEPES solution. The compound displayed selectivity for Cu²⁺, as evidenced by a colorless to yellow color change, which was characterized using UV-vis spectroscopy. The fluorescence of the compound can be quenched only by Cu²⁺, accompanying by a color change from blue to colorless. Furthermore, it can be used in bioimaging.

关键词:

English

A pyridoxal-based chemosensor for visual detection of copper ion and its application in bioimaging

1.
a Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Shanxi University, Taiyuan 030006, China;
2.
b Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China

Corresponding author: Fang-Jun Huo,

Received Date: 31 March 2014
Fund Project:

Abstract: A pyridoxal-based chemosensor was synthesized by reacting hydrazine hydrate and pyridoxal hydrochloride in ethanol and characterized by NMR and ESI-MS. The optical properties of the compound were investigated in a methanol: HEPES solution. The compound displayed selectivity for Cu²⁺, as evidenced by a colorless to yellow color change, which was characterized using UV-vis spectroscopy. The fluorescence of the compound can be quenched only by Cu²⁺, accompanying by a color change from blue to colorless. Furthermore, it can be used in bioimaging.

Key words:

1. [1] V. Dujols, F. Ford, A.W. Czarnik, A long-wavelength fluorescent chemo-dosimeter selective for Cu (II) ion in water, J. Am. Chem. Soc. 119 (1997) 7386-7387.[1] V. Dujols, F. Ford, A.W. Czarnik, A long-wavelength fluorescent chemo-dosimeter selective for Cu (II) ion in water, J. Am. Chem. Soc. 119 (1997) 7386-7387.
2. [2] J. Tan, X.P. Yan, 2,1,3-Benzoxadiazole-based selective chromogenic chemosensor for rapid naked-eye detection of Hg²⁺ and Cu²⁺, Talanta 76 (2008) 9-14.[2] J. Tan, X.P. Yan, 2,1,3-Benzoxadiazole-based selective chromogenic chemosensor for rapid naked-eye detection of Hg²⁺ and Cu²⁺, Talanta 76 (2008) 9-14.
3. [3] L.P. Singh, J.M. Bhatnagar, Copper(II) selective electrochemical sensor based on Schiff base complexes, Talanta 64 (2004) 313-319.[3] L.P. Singh, J.M. Bhatnagar, Copper(II) selective electrochemical sensor based on Schiff base complexes, Talanta 64 (2004) 313-319.
4. [4] Y.S. Xie, Y.B. Ding, X. Li, et al., Selective, sensitive and reversible "turn-on" fluorescent cyanide probes based on 2,20-dipyridylaminoanthracene-Cu²⁺ ensembles, Chem. Commun. 48 (2012) 11513-11515.[4] Y.S. Xie, Y.B. Ding, X. Li, et al., Selective, sensitive and reversible "turn-on" fluorescent cyanide probes based on 2,20-dipyridylaminoanthracene-Cu²⁺ ensembles, Chem. Commun. 48 (2012) 11513-11515.
5. [5] F.J. Huo, C.X. Yin, Y.T. Yang, et al., Ultraviolet-visible light (UV-vis)-reversible but fluorescence irreversible chemosensor for copper in water and its application in living cells, Anal. Chem. 84 (2012) 2219-2223.[5] F.J. Huo, C.X. Yin, Y.T. Yang, et al., Ultraviolet-visible light (UV-vis)-reversible but fluorescence irreversible chemosensor for copper in water and its application in living cells, Anal. Chem. 84 (2012) 2219-2223.
6. [6] L.J. Qu, C.X. Yin, F.J. Huo, Y.B. Zhang, Y.Q. Li, A commercially available fluorescence chemosensor for copper ion and its application in bioimaging, Sens. Actuators B 183 (2013) 636-640.[6] L.J. Qu, C.X. Yin, F.J. Huo, Y.B. Zhang, Y.Q. Li, A commercially available fluorescence chemosensor for copper ion and its application in bioimaging, Sens. Actuators B 183 (2013) 636-640.
7. [7] Y.T. Yang, F.J. Huo, C.X. Yin, et al., Combined spectral experiment and theoretical calculation to study the chemosensors of copper and their applications in anion bioimaging, Sens. Actuators B 177 (2013) 1189-1197.[7] Y.T. Yang, F.J. Huo, C.X. Yin, et al., Combined spectral experiment and theoretical calculation to study the chemosensors of copper and their applications in anion bioimaging, Sens. Actuators B 177 (2013) 1189-1197.
8. [8] F.J. Huo, L. Wang, C.X. Yin, et al., The synthesis, characterization of three isomers of rhodamine derivative and their application in copper (II) ion recognition, Sens. Actuators B 188 (2013) 735-740.[8] F.J. Huo, L. Wang, C.X. Yin, et al., The synthesis, characterization of three isomers of rhodamine derivative and their application in copper (II) ion recognition, Sens. Actuators B 188 (2013) 735-740.
9. [9] L.J. Qu, C.X. Yin, F.J. Huo, et al., A pyridoxal-based dual chemosensor for visual detection of copper ion and ratiometric fluorescent detection of zinc ion, Sens. Actuators B 191 (2014) 158-164.[9] L.J. Qu, C.X. Yin, F.J. Huo, et al., A pyridoxal-based dual chemosensor for visual detection of copper ion and ratiometric fluorescent detection of zinc ion, Sens. Actuators B 191 (2014) 158-164.
10. [10] F.Y. Wu, S.G. Cao, C.X. Xie, A highly selective chemosensor for copper ion based on ICT fluorescence, Chin. Chem. Lett. 23 (2012) 607-610.[10] F.Y. Wu, S.G. Cao, C.X. Xie, A highly selective chemosensor for copper ion based on ICT fluorescence, Chin. Chem. Lett. 23 (2012) 607-610.
11. [11] 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] 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.
12. [12] K. Yoosaf, B.I. Ipe, C.H. Suresh, K.G. Thomas, In situ synthesis of metal nanoparticles and selective naked-eye detection of lead ions from aqueous media, J. Phys. Chem. C 111 (2007) 12839-12847.[12] K. Yoosaf, B.I. Ipe, C.H. Suresh, K.G. Thomas, In situ synthesis of metal nanoparticles and selective naked-eye detection of lead ions from aqueous media, J. Phys. Chem. C 111 (2007) 12839-12847.
13. [13] T. Gunnlaugsson, J.P. Leonard, N.S. Murray, Highly selective colorimetric nakedeye Cu(II) detection using an azobenzene chemosensor, Org. Lett. 6 (2004) 1557-1560.[13] T. Gunnlaugsson, J.P. Leonard, N.S. Murray, Highly selective colorimetric nakedeye Cu(II) detection using an azobenzene chemosensor, Org. Lett. 6 (2004) 1557-1560.
14. [14] M.H. Lee, B.K. Cho, J. Yoon, et al., Selectively chemodosimetric detection of Hg(II) in aqueous media, Org. Lett. 9 (2007) 4515-4518.[14] M.H. Lee, B.K. Cho, J. Yoon, et al., Selectively chemodosimetric detection of Hg(II) in aqueous media, Org. Lett. 9 (2007) 4515-4518.
15. [15] M. Zhu, M.G. Yuan, X.F. Liu, et al., Visible near-infrared chemosensor for mercury ion, Org. Lett. 10 (2008) 1481-1484.[15] M. Zhu, M.G. Yuan, X.F. Liu, et al., Visible near-infrared chemosensor for mercury ion, Org. Lett. 10 (2008) 1481-1484.
16. [16] S.J. Lee, S.S. Lee, I.Y. Jeong, et al., Azobenzene coupled chromogenic receptors for the selective detection of copper(II) and its application as a chemosensor kit, Tetrahedron Lett. 48 (2007) 393-396.[16] S.J. Lee, S.S. Lee, I.Y. Jeong, et al., Azobenzene coupled chromogenic receptors for the selective detection of copper(II) and its application as a chemosensor kit, Tetrahedron Lett. 48 (2007) 393-396.
17. [17] R.L. Sheng, P.F. Wang, W.M. Liu, et al., A new colorimetric chemosensor for Hg²⁺ based on coumarin azine derivative, Sens. Actuators B 128 (2008) 507-511.[17] R.L. Sheng, P.F. Wang, W.M. Liu, et al., A new colorimetric chemosensor for Hg²⁺ based on coumarin azine derivative, Sens. Actuators B 128 (2008) 507-511.
18. [18] H.L. Mu, R. Gong, Q. Ma, Y.M. Sun, E.Q. Fu, A novel colorimetric and fluorescent chemosensor: synthesis and selective detection for Cu²⁺ and Hg²⁺, Tetrahedron Lett. 48 (2007) 5525-5529.[18] H.L. Mu, R. Gong, Q. Ma, Y.M. Sun, E.Q. Fu, A novel colorimetric and fluorescent chemosensor: synthesis and selective detection for Cu²⁺ and Hg²⁺, Tetrahedron Lett. 48 (2007) 5525-5529.
19. [19] T. Elisa, M.N. Elizabeth, J. Jacek, S.J. Lippard, Organelle-specific zinc detection using zinpyr-labeled fusion proteins in live cells, J. Am. Chem. Soc. 130 (2008) 15776-15777.[19] T. Elisa, M.N. Elizabeth, J. Jacek, S.J. Lippard, Organelle-specific zinc detection using zinpyr-labeled fusion proteins in live cells, J. Am. Chem. Soc. 130 (2008) 15776-15777.
20. [20] B. Tang, H. Huang, K.H. Xu, et al., Highly sensitive and selective near-infrared fluorescent probe for zinc and its application to macrophage cells, Chem. Commun. 34 (2006) 3609-3611.[20] B. Tang, H. Huang, K.H. Xu, et al., Highly sensitive and selective near-infrared fluorescent probe for zinc and its application to macrophage cells, Chem. Commun. 34 (2006) 3609-3611.
21. [21] M.N. Elizabeth, J.L. Stephen, Turn-on and ratiometric mercury sensing in water with a red-emitting probe, J. Am. Chem. Soc. 129 (2007) 5910-5918.[21] M.N. Elizabeth, J.L. Stephen, Turn-on and ratiometric mercury sensing in water with a red-emitting probe, J. Am. Chem. Soc. 129 (2007) 5910-5918.
22. [22] P. Li, X. Duan, Z.Z. Chen, et al., A near-infrared fluorescent probe for detecting copper(II) with high selectivity and sensitivity and its biological imaging applications, Chem. Commun. 47 (2011) 7755-7757.[22] P. Li, X. Duan, Z.Z. Chen, et al., A near-infrared fluorescent probe for detecting copper(II) with high selectivity and sensitivity and its biological imaging applications, Chem. Commun. 47 (2011) 7755-7757.
23. [23] T.R. Li, Z.Y. Yang, Y. Li, et al., A novel fluorescein derivative as a colorimetric chemosensor for detecting copper(II) ion, Dyes Pigments 88 (2011) 103-108.[23] T.R. Li, Z.Y. Yang, Y. Li, et al., A novel fluorescein derivative as a colorimetric chemosensor for detecting copper(II) ion, Dyes Pigments 88 (2011) 103-108.
24. [24] R. Martínez, A. Espinosa, A. Tárraga, P. Molina, Bis(indolyl)methane derivatives as highly selective colourimetric and ratiometric fluorescent molecular chemosensors for Cu²⁺ cations, Tetrahedron 64 (2008) 2184-2191.[24] R. Martínez, A. Espinosa, A. Tárraga, P. Molina, Bis(indolyl)methane derivatives as highly selective colourimetric and ratiometric fluorescent molecular chemosensors for Cu²⁺ cations, Tetrahedron 64 (2008) 2184-2191.
25. [25] N. Aksuner, E. Henden, I. Yilmaz, A. Cukurovali, Selective optical sensing of copper(II) ions based on a novel cyclobutane-substituted Schiff base ligand embedded in polymer films, Sens. Actuators B 134 (2008) 510-515.[25] N. Aksuner, E. Henden, I. Yilmaz, A. Cukurovali, Selective optical sensing of copper(II) ions based on a novel cyclobutane-substituted Schiff base ligand embedded in polymer films, Sens. Actuators B 134 (2008) 510-515.
26. [26] J.W. Karr, V.A. Szalai, Role of aspartate-1 in Cu(II) binding to the amyloid-b peptide of alzheimer's disease, J. Am. Chem. Soc. 129 (2007) 3796-3797.[26] J.W. Karr, V.A. Szalai, Role of aspartate-1 in Cu(II) binding to the amyloid-b peptide of alzheimer's disease, J. Am. Chem. Soc. 129 (2007) 3796-3797.
27. [27] J. Li, V.N. Uversky, A.L. Fink, Effect of familial parkinson's disease point mutations A30P and A53T on the structural properties, aggregation, and fibrillation of humana-synuclein, Biochemistry 40 (2001) 11604-11613.[27] J. Li, V.N. Uversky, A.L. Fink, Effect of familial parkinson's disease point mutations A30P and A53T on the structural properties, aggregation, and fibrillation of humana-synuclein, Biochemistry 40 (2001) 11604-11613.
28. [28] B.B. Tewari, Studies on complexation in solution with a paper electrophoretic technique [the system copper(II)/cobalt(II) emethioninee penicillamine], J. Chem. Eng. Data 55 (2010) 1779-1783.[28] B.B. Tewari, Studies on complexation in solution with a paper electrophoretic technique [the system copper(II)/cobalt(II) emethioninee penicillamine], J. Chem. Eng. Data 55 (2010) 1779-1783.
29. [29] L.M. Zhang, J. Lichtmannegger, K.H. Summer, et al., Tracing copper-thiomolybdate complexes in a prospective treatment for Wilson's disease, Biochemistry 48 (2009) 891-897.[29] L.M. Zhang, J. Lichtmannegger, K.H. Summer, et al., Tracing copper-thiomolybdate complexes in a prospective treatment for Wilson's disease, Biochemistry 48 (2009) 891-897.
30. [30] C. Kar, M.D. Adhikari, B.K. Datta, et al., A CHEF-based biocompatible turn ON ratiometric sensor for sensitive and selective probing of Cu²⁺, Sens. Actuators B 188 (2013) 1132-1140.[30] C. Kar, M.D. Adhikari, B.K. Datta, et al., A CHEF-based biocompatible turn ON ratiometric sensor for sensitive and selective probing of Cu²⁺, Sens. Actuators B 188 (2013) 1132-1140.
31. [31] X.F. Yang, D.B. Wu, H. Li, Sensitive determination of cobalt(II) using a spiro fluorescein hydrazide as a chemiluminogenic reagent, Microchim. Acta 149 (2005) 123-129.[31] X.F. Yang, D.B. Wu, H. Li, Sensitive determination of cobalt(II) using a spiro fluorescein hydrazide as a chemiluminogenic reagent, Microchim. Acta 149 (2005) 123-129.
32. [32] H.A. Benesi, J.H. Hildebrand, A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons, J. Am. Chem. Soc. 71 (1949) 2703-2707.[32] H.A. Benesi, J.H. Hildebrand, A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons, J. Am. Chem. Soc. 71 (1949) 2703-2707.
33. [33] M. Barra, C. Bohne, J.C. Scaiano, Effect of cyclodextrin complexation on the photochemistry of xanthone. Absolute measurement of the kinetics for tripletstate exit, J. Am. Chem. Soc. 112 (1990) 8075-8079.[33] M. Barra, C. Bohne, J.C. Scaiano, Effect of cyclodextrin complexation on the photochemistry of xanthone. Absolute measurement of the kinetics for tripletstate exit, J. Am. Chem. Soc. 112 (1990) 8075-8079.
34. [34] S.Q. Cui, S.Z. Pu, W.J. Liu, G. Liu, Synthesis and photochromic properties of a multiple responsive diarylethene and its selective binding affinity for copper(II) ion, Dyes Pigments 91 (2011) 435-441.[34] S.Q. Cui, S.Z. Pu, W.J. Liu, G. Liu, Synthesis and photochromic properties of a multiple responsive diarylethene and its selective binding affinity for copper(II) ion, Dyes Pigments 91 (2011) 435-441.
35. [35] Y.B. Ding, X. Li, T. Li, W.H. Zhu, Y.S. Xie, α-Monoacylated and α,α'-and α,β'-diacylated dipyrrins as highly sensitive fluorescence "Turn-on" Zn²⁺ probes, J. Org. Chem. 78 (2013) 5328-5338.[35] Y.B. Ding, X. Li, T. Li, W.H. Zhu, Y.S. Xie, α-Monoacylated and α,α'-and α,β'-diacylated dipyrrins as highly sensitive fluorescence "Turn-on" Zn²⁺ probes, J. Org. Chem. 78 (2013) 5328-5338.
36. [36] B. Chen, Y.B. Ding, X. Li, et al., Steric hindrance-enforced distortion as a general strategy for the design of fluorescence "turn-on" cyanide probes, Chem. Commun. 49 (2013) 10136-10138.[36] B. Chen, Y.B. Ding, X. Li, et al., Steric hindrance-enforced distortion as a general strategy for the design of fluorescence "turn-on" cyanide probes, Chem. Commun. 49 (2013) 10136-10138.
37. [37] B.P. Joshi, J. Park, W.I. Lee, et al., Ratiometric and turn-on monitoring for heavy and transition metal ions in aqueous solution with a fluorescent peptide sensor, Talanta 78 (2009) 903-909.[37] B.P. Joshi, J. Park, W.I. Lee, et al., Ratiometric and turn-on monitoring for heavy and transition metal ions in aqueous solution with a fluorescent peptide sensor, Talanta 78 (2009) 903-909.
38. [38] M.J. Kim, K. Kaur, N. Singh, D.O. Jang, Benzim idazole-based receptor for Zn²⁺ recognition in a biological system: a chemosensor operated by retarding the excited state proton transfer, Tetrahedron 68 (2012) 5429-5433.[38] M.J. Kim, K. Kaur, N. Singh, D.O. Jang, Benzim idazole-based receptor for Zn²⁺ recognition in a biological system: a chemosensor operated by retarding the excited state proton transfer, Tetrahedron 68 (2012) 5429-5433.
39. [39] S.H. Mashraqui, R. Betkar, S. Ghorpade, et al., A new internal charge transfer probe for the highly selective detection of Zn(II) by means of dual colorimetric and fluorescent turn-on responses, Sens. Actuators B 174 (2012) 299-305.[39] S.H. Mashraqui, R. Betkar, S. Ghorpade, et al., A new internal charge transfer probe for the highly selective detection of Zn(II) by means of dual colorimetric and fluorescent turn-on responses, Sens. Actuators B 174 (2012) 299-305.
40. [40] C.J. Gao, X.J. Jin, X.H. Yan, et al., A small molecular fluorescent sensor for highly selectivity of zinc ion, Sens. Actuators B 176 (2013) 775-781.[40] C.J. Gao, X.J. Jin, X.H. Yan, et al., A small molecular fluorescent sensor for highly selectivity of zinc ion, Sens. Actuators B 176 (2013) 775-781.

WeChat

扫一扫看文章

计量

PDF下载量: 0
文章访问数: 1678
HTML全文浏览量: 30

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

/

下载: 全尺寸图片幻灯片

分享

用微信扫码二维码

分享至好友和朋友圈