三唑基团功能化的三苯胺类Cu2+荧光探针的合成及在检测和HeLa细胞中的应用
收稿日期: 2021-11-15
修回日期: 2022-01-12
网络出版日期: 2022-01-27
基金资助
四川省青年科技创新研究团队(2020JDTD0018); 贵州省遵义市科学技术局及茅台学院市校联合科技合作资金(遵市科合HZ字[2021]333号资助项目)
Synthesis of Triazole Functionalized Triphenylamine Cu2+ Fluorescent Probe and Its Application in Detection and HeLa Cells
Received date: 2021-11-15
Revised date: 2022-01-12
Online published: 2022-01-27
Supported by
Sichuan Youth Science and Technology Innovation Research Team Project(2020JDTD0018); Zunyi Science and Technology Bureau of Guizhou Province and the Maotai Institute Joint Science and Technology Cooperation Fund Project(Zunyi Kehe HZ [2021]333)
以2-(4-溴苯基)-2H-1,2,3-三唑-4-甲醛、(4-(二苯基氨基)苯基)硼酸和氨基硫脲为原料, 设计合成了一种新型的可高选择性快速识别Cu2+的荧光探针分子N'-((2-(4'-(二苯胺基)-[1,1'-联苯]-4-基)-2H-1,2,3-三唑-4-基)亚甲基)肼-1-硫代酰胺(DBTMC). DBTMC展示出优异的溶剂效应和聚集态效应, 对Cu2+展现出高选择、高灵敏和快速响应性, 检测限为4.48×10–8 mol/L. 通过job’s曲线、1H NMR滴定、HRMS及密度泛函理论(DFT)计算对其可能的响应机理进行了探究. 用探针DBTMC制备的测试条, 可用于快速检测Cu2+. 将DBTMC应用于检测HeLa细胞中的Cu2+, 也取得了良好的效果, 具有潜在的应用价值.
文乙评 , 解正峰 , 史天柱 , 褚义成 , 周荣贵 , 陶奕杉 , 梁焕敏 , 邱海燕 , 赵云辉 . 三唑基团功能化的三苯胺类Cu2+荧光探针的合成及在检测和HeLa细胞中的应用[J]. 有机化学, 2022 , 42(5) : 1463 -1473 . DOI: 10.6023/cjoc202111013
A novel fluorescence probe N'-((2-(4'-(diphenyl)-[1,1'-biphenyl]-4-yl)-2H-1,2,3-triazole-4-yl)methylene) hydrazine- 1-thioamide (DBTMC) was designed and synthesized from (4-(diphenylamino)-phenyl)boronic acid, (4-bromophenyl)- 2H-[1,2,3]-triazole-4-carbaldehyde and thiosemicarbazide. DBTMC possessed excellent solvent effect and aggregation effect, and exhibited high selectivity, high sensitivity and rapid response to Cu2+ with detection limit of 4.48×10–8 mol/L. The possible response mechanism was explored through job’s curve, 1H NMR titration, HRMS and density functional theory (DFT) calculations. The test strip prepared with the probe DBTMC solution could be used for quick recognition of Cu2+. DBTMC was applied to HeLa cells to detect Cu2+ and excellent results were achieved, possessing potential application.
Key words： fluorescent probe; copper ion; solvent effect; aggregation effect; HeLa cells
| [1] | Hanif, M.; Rafiq, M.; Saleem, M.; Mustaqeem, M.; Jamil, S.; Janjua, M. J. Chin. Chem. Soc. 2018, 66, 500. |
| [2] | Li, Y.; Gu, Z.-Y.; He, T.; Yuan, X.-C.; Zhang, Y.-Y.; Xu, Z.; Qiu, H.-Y.; Zhang, Q.; Yin, S.-C. Dyes Pigm. 2020, 173, 107969. |
| [3] | Fu, Y.; Pang, X.-X.; Wang, Z.-Q.; Chai, Q.; Ye, F. Spectrochim. Acta, Part A 2019, 208, 198. |
| [4] | Qu, Q.; Zhu, A.-W.; Shao, X.-L.; Shi, G.-Y.; Tian, Y. Chem. Commun. 2012, 48, 5473. |
| [5] | Lei, M.-M.; Zhou, Q.-H.; Yang, L.; Xu, Z.-H.; Yang, F.-L. Chin. J. Org. Chem. 2020, 40, 2798. (in Chinese) |
| [5] | (雷萌萌, 周起航, 杨莉, 许志红, 杨风岭, 有机化学, 2020, 40, 2798.) |
| [6] | Ghule, N. V.; Bhosale, R. S.; Puyad, A. L.; Bhosale, S. V.; Bhosale, S. V. Sens. Actuators, B 2021, 338, 129734. |
| [7] | Wang, X.-Y.; Li, Z.; Nie, J.-J.; Wu, L.-Q.; Chen, W.-H.; Qi, S. L.; Xu, H.; Du, J. S.; Shan, Y. M.; Yang, Q. B. RSC Adv. 2021, 11, 10264. |
| [8] | Murakami, T. N.; Koumura, N. Adv. Energy Mater. 2019, 9, 1802967. |
| [9] | Zhang, C.-C.; Fan, C.-B.; Pu, S.-Z.; Liu, G. Chin. J. Chem. 2015, 33, 1310. |
| [10] | Zhang, Y.-Q.; Li, Y.; Zhang, L. Spectrochim. Acta, Part A 2021, 259, 119892. |
| [11] | Shen, P.; Hua, J.-Y.; Jin, H.-D.; Du, J.-Y.; Liu, C.-L.; Yang, W.; Gao, Q.-Y.; Luo, H.-J.; Liu, Y.; Yang, C.-Y. Sens. Actuators, B 2017, 247, 587. |
| [12] | Lal, S.; Prakash, K.; Hooda, S.; Kumar, V.; Kumar, P. J. Mol. Struct. 2020, 1199, 127003. |
| [13] | Singh, N.; Paknikar, K. M.; Rajwade, J. Environ. Res. 2019, 175, 367. |
| [14] | Chen, F.; Hao, Y.-Q.; Zhang, X.-F.; Shao, M.-L.; Cao, G.-X.; Zhai, B.; Zhang, C. Sens. Actuators, B 2021, 330, 129327. |
| [15] | Yang, Q.; Deng, S.; Jin, L.-Y.; Jiang, Y.-L.; Jin, C.; Wang, B.-X.; Shen, J. J. Photochem. Photobiol., 2021, 409, 113143. |
| [16] | Wei, M.-J.; Zhang, Y.-Y.; Li, H.-T.; Yao, S.-Z. Anal. Methods 2017, 9, 3956. |
| [17] | Rodriguez-Seco, C.; Mendez, M.; Roldan-Carmona, C.; Pudi, R.; Nazeeruddin, M. K.; Palomares, E. J. Angew. Chem., Int. Ed. 2020, 59, 5303. |
| [18] | Zhang, X.; Chen, Y.-A.; Cai, X.-Y.; Liu, C.-Y.; Jia, P.; Li, Z.-L.; Zhu, H.-C.; Yu, Y.-M.; Wang, K.; Li, X.-W.; Sheng, W.-L.; Zhu, B.-C. Dyes Pigm. 2020, 174, 108065. |
| [19] | Park, S. H.; Kwon, N.; Lee, J. H.; Yoon, J.; Shin, I. Chem. Soc. Rev. 2020, 49, 143. |
| [20] | Jiao, X.-J.; Liu, C.; He, S.; Zhao, L.-C.; Zeng, X.-H. Dyes Pigm. 2019, 160, 86. |
| [21] | Chowdhury, S.; Rooj, B.; Dutta, A.; Mandal, U. J. Fluoresc. 2018, 28, 999. |
| [22] | Wang, S.-J.; Li, C.-W.; Li, J.; Chen, B.; Guo, Y. Acta Chim. Sinica 2017, 75, 383. (in Chinese) |
| [22] | (王少静, 李长伟, 李锦, 陈邦, 郭媛, 化学学报, 2017, 75, 383.) |
| [23] | Mu, Y.-L.; Zhang, C.-J.; Gao, Z.-L.; Zhang, X.; Lu, Q.; Yao, J.-S.; Xing, S. Synth. Met. 2020, 262, 116334. |
| [24] | Shi, F.; Cui, S.-Q.; Liu, H.-L.; Pu, S.-Z. Dyes Pigm. 2020, 173, 107914. |
| [25] | Chen, H.; Yang, P.; Li, Y.-H.; Zhang, L.-L.; Ding, F.; He, X.-J.; Shen, J.-L. Spectrochim. Acta, Part A 2020, 224, 117384. |
| [26] | Zhang, Z.-X.; Li, F.; He, C.-Y.; Ma, H.-W.; Feng, Y.-T.; Zhang, Y.-N.; Zhang, M. Sens. Actuators, B 2018, 255, 1878. |
| [27] | Xiao, H.-B.; Zhang, Y.-Z.; Li, S.-Z.; Zhang, W.; Han, Z.-Y.; Tan, J.-J.; Zhang, S.-Y.; Du, J.-Y. Sens. Actuators, B 2016, 236, 233. |
| [28] | Abdurahman, A.; Wang, L.; Zhang, Z.-X.; Feng, Y.-T.; Zhao, Y.-H.; Zhang, M. Dyes Pigm. 2020, 174, 108050 |
| [29] | Cai, W.-N.; Xiao, T.-D.; Niu, H.-J.; Bai, X.-D.; Zhang, Y.-H.; Wang, C.; Wang, W.; Qi, H. Sens. Actuators, B 2017, 252, 330. |
| [30] | Liu, Y.-X.; Yan, W.-M; Chen, Y.-F.; Petersen, J. L.; Shi, X.-D. Org. Lett. 2008, 10, 5389. |
| [31] | Yan, W.-M.; Wang, Q.-Y.; Lin, Q.; Li, M.-Y.; Petersen, J. L.; Shi, X.-D. Chem.-Eur. J. 2011, 17, 5011. |
| [32] | Zhang, Y.-W.; Ye, X.-H.; Petersen, J. L.; Li, M.-Y.; Shi, X.-D. J. Org. Chem. 2015, 80, 3664. |
| [33] | Padalkar, V. S.; Chemate, S. B.; Lanke, S. K.; Sekar, N. J. Lumin. 2015, 168, 114. |
| [34] | Chu, Y.-C.; Xie, Z.-F.; Zhuang, D.-J.; Yue, Y.-S.; Yue, Y.-H.; Shi, W.; Feng, S. Chin. J. Chem. 2019, 37, 1216. |
| [35] | Chu, Y.-C.; Xie, Z.-F.; Yue, Y.-Y.; Yue, Y.-H.; Kong, X.-J.; Shi, W.; Feng, S. ACS Omega 2019, 4, 5367. |
| [36] | Xie, Z.-F.; Kong, X.-J.; Feng, L.; Ma, J.-C.; Li, Y.-Q., Wang, X.; Bao, W.-R.; Shi, W.; Hui, Y.-H. Sens. Actuators, B 2018, 257, 154. |
| [37] | Xue, S.-S.; Xie, Z.-F; Wen, Y.-P.; He, J.-W.; Liu, Y.-C.; Shi, W. ChemistrySelect 2021, 6, 7123. |
| [38] | 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) |
| [38] | (何佳伟, 解正峰, 薛松松, 刘宇程, 石伟, 陈鑫, 有机化学, 2021, 41, 2839.) |
| [39] | Xue, S.-S.; Xie, Z.-F.; Chu, Y.-C.; Yue, Y.-Y.; Shi, W.; Zhou, J.-B. Chin. J. Org. Chem. 2021, 41, 1138. (in Chinese) |
| [39] | (薛松松, 解正峰, 褚义成, 岳永双, 石伟, 周家斌, 有机化学, 2021, 41, 1138.) |
| [40] | Liu, C.-S.; Zou, G.-R.; Peng, S.; Wang, Y-F.; Yang, W.; Wu, F.; Jiang, Z-R.; Zhang, X.; Zhou, X. Angew. Chem.,Int. Ed. 2018, 57, 9689. |
| [41] | Zhang, Z.-Y.; Liu, Y.-P.; Wang, E.-J. Dyes Pigm. 2019, 163, 533. |
| [42] | Yin, J.; Wang, Z.-L.; Zhao, F.; Yang, H.-Y.; Li, M.-X.; Yang, Y.-Q. Spectrochim. Acta, Part A 2020, 239, 118470. |
| [43] | Jiang, N.; Gong, X.; Zhong, T.-Y.; Zheng, Y.; Wang, G. J. Mol. Struct. 2020, 1219, 128573. |
| [44] | Li, B.; Kou, J.-J.; Mei, H.-H.; Gu, X.; Wang, M.-H.; Xie, X.-M.; Xu, K.-X. Anal. Methods 2020, 12, 4181. |
| [45] | Wang, Y.-S.; Zhu, Z.-F.; Fan, C.-B.; Liu, G.; Pu, S.-Z. Tetrahedron Lett. 2020, 61, 151427. |
/
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〉 |
