Abstract
A novel coumarin-derived Schiff base fluorescent probe was reported to detect Cu2+ ions in human cells. It was synthesized by the reaction between 7-(diethylamino)coumarin-3-carbohydrazide and pyridoxal 5′-phosphate. The probe has good stability and it exhibited obviously decreasing fluorescent response at λ 490 nm upon addition of Cu(II) ions. The fluorescent probe showed high selectivity for Cu(II) ions compared to other metal ions. The probe has been successfully applied to detect Cu(II) ions in human cells.
REFERENCES
Li, M., Ge, H., Arrowsmith, R.L., Mirabello, V., Botchway, S.W., Zhu, W., Pascu, S.I., and James, T.D., Chem. Commun., 2014, vol. 50, p. 11806. https://doi.org/10.1039/c4cc03453h
Xiong, J.J., Huang, P.C., Zhou, X., and Wu, F.Y., Sens. Actuators, B, 2016, vol. 232, p. 673. https://doi.org/10.1016/j.snb.2016.04.004
Huang, H., Shi, F.P., Li, Y., Niu, L., Gao, Y., and Shah, S.M., Sens. Actuators, B, 2013, vol. 178, p. 532. https://doi.org/10.1016/j.snb.2013.01.003
Xie, X.L., Chen, X.P., Li, B., and Zhang, L.M., Dyes Pigm., 2013, vol. 98, p. 422. https://doi.org/10.1016/j.dyepig.2013.03.022
Pham, T.A., Horwood, C., Maiti, A., Peters, V., Bunn, T., and Stadermann, M., J. Phys. Chem. B, 2018, vol. 122, p. 12139. https://doi.org/10.1021/acs.jpcb.8b10559
Wang, L., Sun, Y.G., Hu, L.L., Piao, J.Y., Guo, J., Manthiram, A., Ma, J., and Cao, A.M., J. Mater. Chem. A, 2017, vol. 5, p. 8752. https://doi.org/10.1039/C7TA00880E
Qian, X.H. and Xu, Z.C., Chem. Soc. Rev., 2015, vol. 44, p. 4487. https://doi.org/10.1039/c4cs00292j
Zou, R.F., Wang, Q., Wu, J.C., Wu, J.X., Schmuck, C., and Tian, H., Chem. Soc. Rev., 2015, vol. 44, p. 5200. https://doi.org/10.1039/C5CS00234F
Cotruvo, J.A., Jr., Aron, A.T., Ramos-Torres, K.M., and Chang, C.J., Chem. Soc. Rev., vol. 44, p. 4400. https://doi.org/10.1039/c4cs00346b
Becker, J.S., Matusch, A., Depboylu, C., Dobrowolska, J., and Zoriy, M.V., Anal. Chem., 2007, vol. 79, p. 6074. https://doi.org/10.1021/ac0700528
Gonzáles, A.P.S., Firmino, M.A., Nomura, C.S., Rocha, F.R.P., Oliveira, P.V., and Gaubeur, I., Anal. Chim. Acta, 2009, vol. 636, p. 198. https://doi.org/10.1016/j.aca.2009.01.047
Manto, M., Toxics, 2014, vol. 2, p. 327. https://doi.org/10.3390/toxics2020327
Anbu, S., Paul, A., Surendranath, K., Sidali, A., and Pombeiro, A.J.L., J. Inorg. Biochem., 2021, vol. 220, article ID 111466. https://doi.org/10.1016/j.jinorgbio.2021.111466
Cho, S.W., Rao, A.S., Bhunia, S., Reo, Y.J., Singha, S., and Ahn, K.H, Sens. Actuators, B, 2019, vol. 279, p. 204. https://doi.org/10.1016/j.snb.2018.09.122
Li, M., Lv, H.S., Luo, J.Z., Miao, J.Y., and Zhao, B.X., Sens. Actuators, B, 2013, vol. 188, p. 1235. https://doi.org/10.1016/J.SNB.2013.08.030
Wang, Y., Zhu, Z., Fan, C., Liu, G., and Pu, S., Tetrahedron Lett., 2020, vol. 61, article ID 151427. https://doi.org/10.1016/j.tetlet.2019.151427
Xu, Z., Yoon, J., and Spring, D.R., Chem. Commun., 2010, vol. 46, p. 2563. https://doi.org/10.1039/c000441c
Sun, R., Wang, L., Jiang, C., Du, Z., Chen, S., and Wu, W., J. Fluoresc., 2020, vol. 30, p. 883. https://doi.org/10.1007/s10895-020-02544-9
Zhang, C., Zhang, Y., Li, M., Gong, S., Gao, Y., Yang, Y., Wang, Z., and Wang, S., New J. Chem., 2021, vol. 45, p. 15247. https://doi.org/10.1039/d1nj02662c
Li, M., Ruan, S., Yang, H., Zhang, Y., Yang, Y., Song, J., Xu, X., Wang, Z., and Wang, S., Dalton Trans., 2020, vol. 49, p. 15299. https://doi.org/10.1039/D0DT02888F
Kim, H.N., Ren, W.X., Kim, J.S., and Yoon, J., Chem. Soc. Rev., 2012, vol. 41, p. 3210. https://doi.org/10.1039/C1CS15245A
Qazi, M.A., Ocak, U., Ocak, M., and Memon, S., Anal. Chim. Acta, 2013, vol. 761, p. 157. https://doi.org/10.1016/j.aca.2012.11.026
Chawla, H.M. and Gupta, T., Tetrahedron Lett., 2013, vol. 54, p. 1794. https://doi.org/10.1016/j.tetlet.2013.01.038
Kar, C., Adhikari, M.D., Ramesh, A., and Das, G., Inorg. Chem., 2013, vol. 52, p. 743. https://doi.org/10.1021/ic301872q
Yang, Y., Huo, F., Yin, C., Chu, Y., Chao, J., Zhang, Y., Zhang, J., Li, S., Lv, H., Zheng, A., and Liu, D., Sens. Actuators, B, 2013, vol. 177, p. 1189. https://doi.org/10.1016/j.snb.2012.12.043
Rathinam, B., Chien, C.C., Chen, B.C., and Liu, J.H., Tetrahedron, 2013, vol. 69, p. 235. https://doi.org/10.1016/j.tet.2012.10.040
Jung, H.S., Kwon, P.S., Lee, J.W., Kim, J.I., Hong, C.S., Kim, J.W., Yan, S., Lee, J. Y., Lee, J.H., Joo, T., and Kim, J.S., J. Am. Chem. Soc., 2009, vol. 131, p. 2008. https://doi.org/10.1021/ja808611d
Zhou, Z.J., Li, N., and Tong, A.J., Anal. Chim. Acta, 2011, vol. 702, p. 81. https://doi.org/10.1016/j.aca.2011.06.041
Mani, K.S., Rajamanikandan, R., Murugesapandian, B., Shankar, R., Sivaraman, G., Ilanchelian, M., and Rajendran, S.P., Spectrochim. Acta, Part A, 2019, vol. 214, p. 170. https://doi.org/10.1016/j.saa.2019.02.020
Li, Q., Guo, Y., and Shao, S., Sens. Actuators, B, 2012, vol. 171, p. 872. https://doi.org/10.1016/j.snb.2012.05.086
Yin, S., Yuan, W., Huang, J., Xie, D., Liu, B., Jiang, K., and Qiu, H., Spectrochim. Acta, Part A, 2012, vol. 96, p. 82. https://doi.org/10.1016/j.saa.2012.04.091
Madhu, S., Basu, S.K., Jadhav, S., and Ravikanth, M., Analyst, 2013, vol. 138, p. 299. https://doi.org/10.1039/c2an36407g
Helal, A., Or Rashid, M.H.O., Choi, C.-H., and Kim, H.-S., Tetrahedron, 2011, vol. 67, p. 2794. https://doi.org/10.1016/j.tet.2011.01.093
Kim, M.H., Jang, H.H., Yi, S., Chang, S.K., and Han, M.S., Chem. Commun., 2009, vol. 32, p. 4838. https://doi.org/10.1039/b908638b
Chandrasekhar, V., Bag, P., and Pandey, M.D., Tetrahedron, 2009, vol. 65, p. 9876. https://doi.org/10.1016/j.tet.2009.09.040
Ma, Y., Luo, W., Quinn, P.J., Liu, Z., and Hider, R.C., J. Med. Chem., 2004, vol. 47, p. 6349. https://doi.org/10.1021/jm049751s
Takechi, H., Oda, Y., Nishizono, N., Oda, K., and Machida, M., Chem. Pharm. Bull., 2000, vol. 48, p. 1702. https://doi.org/10.1248/cpb.48.1702
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This work was financially supported by the National Natural Science Foundation of China.
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Gao, S., Wang, AL. & Wang, MZ. A Coumarin-Based Fluorescent Probe for Selective Detection of Cu(II) and Imaging in Human Cell. Russ J Org Chem 60, 467–471 (2024). https://doi.org/10.1134/S107042802403014X
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DOI: https://doi.org/10.1134/S107042802403014X