Chinese Journal of Organic Chemistry >
A Flavone-Based Long-Wavelength Fluorescent Probe to Detect Biothiols in vitro and in vivo
Received date: 2022-06-11
Revised date: 2022-08-10
Online published: 2022-09-15
Supported by
Key Science and Technology Program of Henan Province(212102311030); Key Science and Technology Program of Henan Province(222102310671); Foundation of Henan Educational Committee(22A350012)
Biothiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play crucial roles in physiological and pathological processes. GSH, especially, is overexpressed in numerous types of tumor cells and could be considered as a biomarker. However, owing to the difficulty and challenge in sensing normal and cancer cells simultaneously, it is important to solve this problem in biological processes. Herein, a naked-eye visible, “off-on” long-wavelength fluorescent probe (4) based on N,N-(dimethylamino)naphthalenyl flavone (3) was designed and synthesized. This probe showed high selectivity for biothiols and low detection limits. The mechanism study revealed that biothiols catalyzed the cleavage of the ester bond, and strongly fluorescent flavone 3 was released. Probe 4 could be used for the imaging of biothiols in living cells and mice. In addition, the probe was optimized to achieve the selective imaging of normal hepatocyte HL-7702 and heptocarcinoma cell HepG2.
Key words： long-wavelength; fluorescence probe; flavone; biothiol
Siyi Zhou , Xu Ding , Yongmei Zhao , Jinghua Li , Wen Luo . A Flavone-Based Long-Wavelength Fluorescent Probe to Detect Biothiols in vitro and in vivo[J]. Chinese Journal of Organic Chemistry, 2023 , 43(1) : 178 -185 . DOI: 10.6023/cjoc202206016
| [1] | Dong, J.; Lu, G.; Tu, Y., Fan, C. New J. Chem. 2022, 46, 10995. |
| [2] | Dai, J.; Ma, C.; Zhang, P.; Fu, Y.; Shen, B. Dyes Pigm. 2020, 177, 108321. |
| [3] | Gao, J.; Tao, Y.; Wang, N.; He, J.; Zhang, J; Zhao, W. Spectrochim. Acta, Part A 2018, 203, 77. |
| [4] | Jung, H.; Chen, X.; Kim, J.; Yoon, J. Chem. Soc. Rev. 2013, 42, 6019. |
| [5] | Cui, L.; Baek, Y.; Lee, S.; Kwona, N.; Yoon, J. J. Mater. Chem. C 2016, 4, 2909. |
| [6] | Wang, Z.; Ding, X.; Huang, Y.; Yan, X.; Ding, B.; Li, Q.; Xie, C.; Xu, J. Dyes Pigm. 2020, 175, 108156. |
| [7] | Bansal, A.; Simon, M. J. Cell Biol. 2018, 217, 2291. |
| [8] | Carlucci, F.; Tabucchi, A. J. Chromatogr. B 2009, 877, 3347. |
| [9] | Suh, J.; Kim, R.; Yavuz, B.; Lee, D.; Lal, A.; Ames, B.; Shigenaga, M. J. Chromatogr. B 2009, 877, 3418. |
| [10] | Zhao, Y.; Li, H.; Chai, Z.; Shi, W.; Li, X.; Ma, H. Chem. Commun. 2020, 56, 6344. |
| [11] | Li, X.; Li, X.; Ma, H. Chem. Sci. 2020, 11, 1617. |
| [12] | Lu, H. X.; Tang, Y. H.; Zhou, H. M.; Lin, W. Y. Chin. J. Org. Chem. 2022, 42, 1163. (in Chinese) |
| [12] | (卢辉旭, 唐永和, 周红梅, 林伟英, 有机化学, 2022, 42, 1163.) |
| [13] | Wu, M. Y.; Yu, Y. C.; Liu, Y.; You, J.; Wu, W. J.; Liu, B. Chin. J. Org. Chem. 2022, 42, 803. (in Chinese) |
| [13] | (吴锦园, 喻艳超, 刘洋, 由君, 武文菊, 刘波, 有机化学, 2022, 42, 803.) |
| [14] | Cao, J.; Jiang, X.; Fu, N. Dyes Pigm. 2020, 174, 107978. |
| [15] | Liu, K.; Shang, H.; Kong, X.; Lin, W. J. Mater. Chem. B 2017, 5, 3836. |
| [16] | Ma, J.; Si, T.; Yan, C.; Li, Y.; Li, Q.; Lu, X.; Guo, Y. ACS Sens. 2020, 5, 83. |
| [17] | Tan, H.; Qiu, Y.; Sun, H.; Yan, J.; Zhang, L. Chem. Commun. 2019, 55, 2688. |
| [18] | Fu, H.; Cui, M. Curr. Med. Chem. 2018, 25, 2736. |
| [19] | Hong, J.; Zhou, E.; Gong, S.; Feng, G. ACS Sens. 2019, 160, 787. |
| [20] | Reis, J.; Gaspar, A.; Mihazes, N.; Borges, F. J. Med. Chem. 2017, 60, 7941. |
| [21] | Qin, T.; Liu, B.; Huang, Y.; Yang, K.; Zhu, K.; Luo, Z.; Pan, C.; Wang, L. Sens. Actuators, B 2018, 277, 484. |
| [22] | Zhu, K.; Lv, T.; Qin, T.; Huang, Y.; Wang, L.; Liu, B. Chem. Commun. 2019, 55, 13983. |
| [23] | Dai, F.; Li, Q.; Wang, Y.; Ge, C.; Feng, C.; Xie, S.; He, H.; Xu, X.; Wang, C. J. Med. Chem. 2017, 60, 2071. |
| [24] | Li, Q.; Zhai, Y.; Luo, W.; Zhu, Z.; Zhang, X.; Xie, S.; Hong, C.; Wang, Y.; Su, Y.; Zhao, J.; Wang, C. Eur. J. Med. Chem. 2016, 121, 110. |
| [25] | Luo, W.; Wang, T.; Hong, C.; Yang, Y.; Chen, Y.; Cen, J.; Xie, S.; Wang, C. Eur. J. Med. Chem. 2016, 122, 17. |
| [26] | Yang, Y.; Zhao, Y.; Wang, Q.; Ren, Q.; Shao, S.; Luo, W. Fine Chem. 2018, 35, 569. (in Chinese) |
| [26] | (杨亚成, 赵永梅, 王清照, 任倩蕾, 邵双宇, 罗稳, 精细化工, 2018, 35, 569.) |
| [27] | Yin, C.; Zhang, W.; Liu, T.; Chao, J.; Huo, F. Sens. Actuators, B 2017, 246, 988. |
| [28] | Zhang, W.; Wang, B.; Gu, W.; Cheng, T.; Jiang, Y.; Shen, J. Anal. Methods 2018, 10, 1039. |
| [29] | Cao, J.; Jiang, X.; Fu, N. Dyes Pigm. 2020, 174, 107978. |
| [30] | Dai, F.; Zhao, M.; Yang, F.; Wang, T.; Wang, C. Dyes Pigm. 2020, 183, 108627. |
| [31] | Chao, D.; Pan, Y.; Gao, X. Spectrochim. Acta, Part A 2020, 227, 117770. |
| [32] | Zhang, X.; Jin, X.; Zhang, C.; Zhong, H.; Zhu, H. Spectrochim. Acta, Part A 2021, 244, 118839. |
| [33] | Hou, J.; Cai, P.; Wang, C.; Shen, Y. Tetrahedron Lett. 2018, 59, 2581. |
| [34] | Cheng, X.; Xu, K.; Qu, S.; Ruan, Z. Chin. J. Org. Chem. 2019, 39, 2835. (in Chinese) |
| [34] | (程晓红, 徐可, 屈少华, 阮志军, 有机化学, 2019, 39, 2835.) |
| [35] | Xia, Y.; Jiang, B.; Wu, Q.; Hu, Q.; Yuan, Z. Chem. J. Chin. Univ. 2018, 39, 1647. (in Chinese) |
| [35] | (夏玉婷, 江波, 吴庆, 胡庆红, 袁泽利, 高等学校化学学报, 2019, 39, 1647.) |
| [36] | Zhao, H.; Wen, X.; Li, W.; Li, Y.; Yin, C. J. Mater. Chem. B 2019, 7, 2169. |
| [37] | Petri?, A.; Johnson, S.; Pham, H.; Li, Y.; ?eh, S.; Golobi?, A.; Agdeppa, E.; Timbol, G.; Liu, J.; Keum, G.; Satyamurthy, N.; Kepe, V.; Houk, K.; Barrio, J. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 16492. |
| [38] | Luo, W.; Chen, Y.; Wang, T.; Hong, C.; Chang, L.; Chang, C.; Yang, Y.; Xie, S.; Wang, C. Bioorg. Med. Chem. 2016, 24, 672. |
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