A Novel Schiff-Base Fluorescent Probe for Cr3+ and Its Bioimaging in Cells

doi:10.6023/cjoc201809028

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1023-1028.DOI: 10.6023/cjoc201809028 Previous Articles Next Articles

Special Issue: 荧光探针-生物传感合辑；有机超分子化学合辑

Articles

新型席夫碱Cr³⁺荧光探针及其细胞成像研究

常永新^a, 李白^a, 高云帆^b, 徐括喜^a,b

a 河南大学化学化工学院功能有机分子研究中心河南省阻燃与功能材料工程实验室开封 475004;
b 河南大学民生学院开封 475004

收稿日期:2018-09-21 修回日期:2018-10-29 发布日期:2018-12-07
通讯作者: 徐括喜 E-mail:xukx@henu.edu.cn
基金资助:
国家自然科学基金（No.U1404207）资助项目.

A Novel Schiff-Base Fluorescent Probe for Cr³⁺ and Its Bioimaging in Cells

Chang Yongxina^a, Li Baia^a, Gao Yunfana^b, Xu Kuoxi^a,b

a Institute of Functional Organic Molecular Engineering, Engineering Laboratory for Flame Retardant and Functional Materials of Henan Province, College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004;
b Henan University Mingsheng College, Kaifeng, 475004

Received:2018-09-21 Revised:2018-10-29 Published:2018-12-07
Contact: 10.6023/cjoc201809028 E-mail:xukx@henu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No.U1404207).

1. A Novel Schiff-Base Fluorescent Probe for Cr³⁺ and Its Bioimaging in Cells.PDF(1336KB)

Abstract

Trivalent chromium (Cr³⁺) plays an important role in the metabolismof fats, nucleic acids, carbohydrates and proteins. Moreover, Cr³⁺ is considered to be a carcinogen and is extremely harmful to humans. Therefore, Cr³⁺ fluorescent probe L was synthesized by reaction of 8-hydroxyquinolinaldehyde with thiocarbazone. The probe L showed high selectivity towards Cr³⁺ ion through the color of solution changed from colorless to yellow for naked-eye detection and significant fluorescence intensity enhanced in CH₃CN/H₂O (V:V=1:2, Tris buffer 50 mmol/L, pH=7.3) solution. The 1:1 binding stoichiometry between probe and Cr³⁺ was determined from Job's plot, fluorescence titration, ESI-MS and density functional theory (DFT) calculations. The association constant (K_a) and the detection limit for Cr³⁺ were found to be to be 1.00×10⁵ and 2.85×10^-7 mol/L, respectively. Moreover, bioimaging experiments showed that L could sense Cr³⁺ ion in living cells with a fluorescence enhancement signal.

Key words: Cr³⁺, fluorescent probe, DFT, bioimaging

Cite this article

Chang Yongxina, Li Baia, Gao Yunfana, Xu Kuoxi. A Novel Schiff-Base Fluorescent Probe for Cr³⁺ and Its Bioimaging in Cells[J]. Chin. J. Org. Chem., 2019, 39(4): 1023-1028.

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References

[1] Vincent, J. B. Proc. Nutr. Soc. 2004, 63, 41.
[2] Filik, H.; Dondurmacioglu, F. J. Anal. Chem. 2009, 64, 455.
[3] Wang, Y. T. J. Ind. Microbiol. Biotechnol 1995, 14, 159.
[4] Filik, H.; Dondurmacioglu, F. J. Anal. Chem. 2009, 64, 455.
[5] Chalmardia, G. B.; Tajbakhsha, M. Tetrahedron 2018, 18, 40.
[6] Gou, C.; Qin, S. H.; Wang, Y.; Liu, X. Y. Inorg. Chem. Commun. 2011, 14, 1622.
[7] Azadbakht, R.; Keypour, H. Spectrochim. Acta, Part A 2012, 85, 293.
[8] Vincent, J, B. Nutr. Rev. 2000, 58, 67.
[9] Anderson, R. A. Regul. Toxicol. Pharmacol. 1997, 26, 35.
[10] Filik, H.; Dondurmacioglu, F. J. Anal. Chem. 2009, 64, 455.
[11] Gómez, V.; Callao, M. P. TrAC, Trends Anal. Chem. 2006, 25, 1006.
[12] Lu, J. S.; Tian, J. Y.; Wu, H. Chin. J. Anal. Chem. 2009, 37, 99.
[13] Xu, K. X.; Kong, H. J.; Li, Q.; Song, P.; Dai, Y. P.; Li, Y. Spectrochim. Acta, Part A 2015, 137, 957.
[14] Kamakura, N.; Inui, T.; Kitano, M.; Nakamura, T. Spectrochim. Acta, Part B 2014, 93, 28.
[15] Li, M.; Zhang, D.; Liu, Y.; Ding, P. J. Fluorescence 2014, 24, 119.
[16] Noorbasha, N. M.; Jiangb, S. J. Talanta 2009, 80, 173.
[17] Zhang, N.; Suleiman, J. S.; He, M. Talanta 2008, 75, 536.
[18] Aydan, F. A.; Soylak, M. J. Hazard. Mater. 2010, 173, 669.
[19] Xie, X.; Tang, F.; Shangguan, X.; Che, S.; Niu J.; Xiao, Y.; Wang, X.; Tang, B. Chem. Commun. 2017, 53, 6520.
[20] Dai, Y. P.; Fu, J. X.; Yao, K.; Song, Q. Q.; Xu, K. X. Spectrochim. Acta, Part A 2018, 192, 257.
[21] Dolaia, M.; Sahab, U.; Dasc, A. K.; Kumarb, G. S. Anal. Methods-UK 2018, 10, 4063.
[22] Liu, X. Y.; Wang, P.; Fu, J. X.; Yao, K.; Xue, K.; Xu, K. X. J. Lumin. 2017, 186, 16.
[23] Brewer, T. F.; Chang, C. J. J. Am. Chem. Soc. 2015, 137, 10886.
[24] Keck, J.; Kramer, H. E. A.; Port, H.; Hirsch, T.; Fischer, P.; Rytz, G. J. Phys. Chem. 1996, 100, 14468.
[25] Hou, S. H.; Qu, Z. G.; Zhong, K. H.; Bian, Y. J.; Tang, L. J. Chin. J. Org. Chem. 2016, 36, 768(in Chinese).(侯淑华, 曲忠国, 钟克利, 边延江, 汤立军, 有机化学, 2016, 36, 768.)
[26] Yao, K.; Fu, J. X.; Chang, Y. X.; Li, B.; Li, Y.; Xu, K. X. Spectrochim. Acta, Part A 2018, 205, 410.
[27] Zhang, P.; Wang, H.; Zhang, D.; Zeng, X.; Zeng, R.; Xiao, L.; Tao, H.; Long, Y.; Yi, P.; Chen, J. Sens. Actuators, B 2018, 255, 2223.
[28] Fu, Y. J.; Yao, H. W.; Zhu, X. Y.; Guo, X. F.; Wang, H. Anal. Chim. Acta 2017, 994, 1.
[29] Dai, Y. P.; Liu, X. Y.; Wang, P.; Fu, J. X.; Yao, K.; Xu, K. X. RSC Adv. 2016, 6, 99933.
[30] Wang, P.; Fu, J. X.; Yao, K. Chang, Y. X.; Xu, K. X. Sens. Actuators, B 2018, 273, 1070.
[31] Samir, M.; Milan, S.; Debasish, D.; Prativa, M.; Gobinda, P.; Sahoo, A. Sens. Actuators, B 2017, 248, 223.

新型席夫碱Cr³⁺荧光探针及其细胞成像研究

A Novel Schiff-Base Fluorescent Probe for Cr³⁺ and Its Bioimaging in Cells

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新型席夫碱Cr3+荧光探针及其细胞成像研究