Chinese Journal of Organic Chemistry >
Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu2+ and Glyphosate
Received date: 2021-09-29
Revised date: 2021-10-28
Online published: 2021-11-25
Supported by
National Natural Science Foundation of China(21908034); Natural Science Foundation of Heilongjiang Province(LH2021H001)
A novel fluorescent probe L based on coumarin-derived acylhydrazone was designed and synthesized by using 7-(4-methoxyphenyl)ethynyl coumarin as report group. The probe L showed high selectivity and good anti-interference ability towards Cu2+ ion through the color of solution changed from light brown to yellow for naked-eye detection and significant fluorescence intensity quenched in the dimethyl sulfoxide (DMSO)/H2O [V:V=7:3, 2-[4-(2-hydroxyethyl)piperazin-1- yl]ethanesulfonic acid (HEPES) 10 mmol/L, pH=7.4] solution, and the detection limit of probe L to Cu2+ could reach 5.6×10–8 mol/L. Meanwhile, the L-Cu2+ system has high selectivity, good sensitivity, wide pH range (5~9) and low detection limit (11.3 ng/mL) for the detection of glyphosate by ligand replacement method. In addition, glyphosate detection was assessed within the actual water samples for testing the L-Cu2+actual application and the method was expected to the detection in environmental samples.
Mianyuan Wu , Yanchao Yu , Yang Liu , Jun You , Wenju Wu , Bo Liu . Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu2+ and Glyphosate[J]. Chinese Journal of Organic Chemistry, 2022 , 42(3) : 803 -811 . DOI: 10.6023/cjoc202109049
[1] | Elcin, S.; Deligoz, H.; Bhatti, A. A.; Oguz, M.; Karakurt, S.; Yilmaz, M. Sens. Actuators, B 2016, 234, 345. |
[2] | Sunnapu, O.; Kotla, N. G.; Maddiboyina, B.; Marepally, S.; Shanmugapriya, J.; Sekar, K.; Singaravadivel, S.; Sivaraman, G. Anal. Chem. 2017, 2, 7654. |
[3] | He, J. W.; Xie, Z. F.; Xue, S. S.; Liu, Y. C.; Shi, W.; Chen, X. Chin. J. Org. Chem. 2021, 41, 2839. (in Chinese) |
[3] | (何佳伟, 解正峰, 薛松松, 刘宇程, 石伟, 陈鑫, 有机化学, 2021, 41, 2839.) |
[4] | Viles, J. H. Coord. Chem. Rev. 2012, 256, 2271. |
[5] | Fasea, K. D.; Abolaji, A. O.; Faloye, T. R.; Odunsi, A. Y.; Oyetayo, B. O.; Enya, J. I.; Rotimi, J. A.; Akinyemi, R. O.; Whitworth, A. J.; Aschner, M. J. Trace Elem. Med. Biol. 2021, 67, 126779. |
[6] | Mezzaroba, L.; Alfieri, D. F.; Simao, A. C.; Reiche, E. M. Neurotoxichology 2019, 74, 230. |
[7] | Keep, K. P.; Squitti, R. Coord. Chem. Rev. 2019, 397, 168. |
[8] | Lei, M. M.; Zhou, Q. H.; Yang, L.; Xu, Z. H.; Yang, F. L. Chin. J. Org. Chem. 2020, 40, 2798. (in Chinese) |
[8] | (雷萌萌, 周起航, 杨莉, 许志红, 杨凤岭, 有机化学, 2020, 40, 2798.) |
[9] | Fang, R.; Ding, X.; Luo, W.; Hong, C. Chin. J. Org. Chem. 2020, 40, 2949. (in Chinese) |
[9] | (房茹, 丁旭, 罗稳, 洪琛, 有机化学, 2020, 40, 2949.) |
[10] | Beckie, H. J.; Flower, K. C.; Ashworth, M. B. Plants 2020, 9, 96. |
[11] | Heymann, A. K.; Schnabel, K.; Billenkamp, F.; Bühler, S.; Frahm, J.; Kersten, S.; Hüther, L.; Meyer, U.; Soosten, D. V.; Trakooljul, N.; Teifke, J. P.; Dänicke, S. Plos One 2021, 16, e0246679. |
[12] | Tu, Q.; Yang, T. X.; Qu, Y. Q.; Gao, S. Y.; Zhang, Z. Y.; Zhang, Q. M.; Wang, Y. L.; Wang, J. Y.; He, L. L. Analyst 2019, 144, 2017. |
[13] | Cao, Y.; Wang, L. N.; Shen, C.; Wang, C. Y.; Hu, X. Y.; Wang, G. X. Sens. Actuators, B 2019, 283, 487. |
[14] | Aguirre, M. C.; Urreta, S. E.; Gomez, C. G. Sens. Actuators, B 2019, 284, 675. |
[15] | Gandhi, K.; Khan, S.; Patrikar, M.; Markad, A.; Kumar, N.; Choudhari, A.; Sagar, P.; Indurkar, S. Environ. Challenges 2021, 4, 100149. |
[16] | Mesnage, R.; Defarge, N.; Vendomis, J. S.; Seralini, G. E. Food Chem. Toxicol. 2015, 84, 133. |
[17] | Benedetti, A. L.; Vituri, C. L.; Trentin, A. G.; Dominues, M. A.; Silva, M. A. Toxicol. Lett. 2004, 153, 227. |
[18] | Jasper, R.; Locatelli, G. O.; Pilati, C.; Locatelli, C. Interdiscip. Toxicol. 2012, 5, 133. |
[19] | Mesnage, R.; Biserni, M.; Wozniak, E.; Xenakis, T.; Mein, C. A.; Antoniou, M. N. Toxicol. Rep. 2018, 5, 819. |
[20] | Topal, A.; Atamanalp, M.; Ucar, A.; Oruc, E.; Kocaman, E. M.; Sulukan, E.; Akdemir, F.; Beydemir, S.; Kilinc, N.; Erdogan, O.; Ceyhun, S. B. Ecotoxicol. Environ. Saf. 2015, 111, 206. |
[21] | Schnabel, K.; Schmitz, R.; Frahm, J.; Meyer, U.; Breves, G.; Danicke, S. Arch. Anim. Nutr. 2020, 74, 1. |
[22] | Guyton, K. Z.; Loomis, D.; Grosse, Y.; Ghissassi, F. E.; Tallaa, L. B.; Guha, N.; Scoccianti, C.; Mattock, H.; Straif, K. Lancet Oncol. 2015, 16, 490. |
[23] | Tseng, S. H.; Lo, Y. W.; Chang, P. C.; Chou, S. S.; Chang, H. M. J. Agric. Food Chem. 2004, 52, 4057. |
[24] | Wang, S.; Liu, B. M.; Yuan, D. X.; Ma, J. Talanta 2016, 161, 700. |
[25] | Liao, Y.; Berthion, J. M.; Colet, I.; Merlo, M.; Nougadere, A.; Hu, R. J. Chromatogr. A 2018, 1549, 31. |
[26] | Wumbei, A.; Goeteyn, L.; Lopez, E.; Houbraken, M.; Spanoghe, P. Food Addit. Contam., art B 2019, 12, 231. |
[27] | Gendy, K. E.; Mosallam, E.; Ahmed, N.; Aly, N. Anal. Biochem. 2018, 557, 1. |
[28] | Wang, L.; Bi, Y. D.; Li, Y. J.; Ding, H.; Ding, L. RSC Adv. 2016, 6, 85820. |
[29] | Gui, M. F.; Jiang, J.; Wang, X.; Yan, Y. X.; Li, S. Q.; Xiao, X. L.; Liu, T. B.; Liu, T. G.; Feng, Y. Sens. Actuators, B 2017, 243, 696. |
[30] | Wang, X. F.; Sakinati, M.; Yang, Y. X.; Ma, Y.; Yang, M.; Luo, H. B.; Hou, C. J. Anal. Methods 2020, 12, 520. |
[31] | Gou, Z. N.; Zhao, S. S.; Zhang, P. Chin. J. Synth. Chem. 2019, 27, 673. (in Chinese) |
[31] | (苟珍妮, 赵顺省, 张盼, 合成化学, 2019, 27, 673.) |
[32] | Zhong, K. L.; Guo, B. F.; Sun, X. H.; Zhou, X.; Zhang, Q.; Tang, L. J.; Zhang, X. R. Chin. J. Org. Chem. 2017, 37, 2002. (in Chinese) |
[32] | (钟克利, 郭宝峰, 孙笑寒, 周雪, 张强, 汤立军, 张行荣, 有机化学, 2017, 37, 2002.) |
[33] | Shi, F.; Gui, S. Q.; Liu, H. L.; Pu, S. Z. Dyes Pigm. 2020, 173, 107914. |
[34] | Tang, Y.; Li, Y. Y.; Han, J.; Mao, Y. L.; Ni, L.; Wang, Y. Spectrochim. Acta, Part A 2019, 208, 299. |
[35] | He, G. J.; Liu, X. L.; Xu, J. H.; Yang, L. L.; Fan, A. Y.; Wang, S. J.; Wang, Q. Z. Spectrochim. Acta, Part A 2018, 190, 116. |
[36] | Paul, K.; Bindal, S.; Luxami, V. Bioorg. Med. Chem. Lett. 2013, 23, 3667. |
[37] | Yin, H. J.; Zhang, B. C.; Yu, H. Z.; Zhu, L.; Feng, Y.; Zhu, M. Z.; Guo, Q. X.; Meng, X. M. J. Org. Chem. 2015, 80, 4306. |
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