基于1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(DDAO)的近红外荧光探针研究进展
收稿日期: 2022-06-23
修回日期: 2022-07-01
网络出版日期: 2022-09-09
基金资助
2022年河北省在读研究生创新能力培养(CXZZSS2022101)
Research Progress of Near-Infrared Fluorescent Probes Based on 1,3-Dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO)
Received date: 2022-06-23
Revised date: 2022-07-01
Online published: 2022-09-09
Supported by
Graduate Student Innovation Ability Training Project of Hebei Province(CXZZSS2022101)
1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(DDAO)是一种优异的近红外荧光染料, 具有近红外发射、低pKa值(≈5.0)、高水溶性以及高量子产率(Φ=0.39), 近年来在荧光探针领域受到广泛关注. 研究证明, 以该染料设计合成的荧光探针可以在温和的水溶液中工作, 具有反应迅速、选择性和灵敏度高、检测限低以及比色信号变化明显等优异的传感性能. 此外, 该类探针的细胞毒性低, 对于活细胞和生物体的检测具有显著的应用价值. 综述了基于DDAO及其衍生物的荧光探针的研究进展, 主要包括探针在生物酶、活性氧、活性氮、蛋白质以及Pd0的识别检测中的分子设计、作用机理和应用, 并对该类荧光探针的发展前景进行了展望.
关键词： 1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(DDAO); 荧光探针; 近红外; 检测
马延慧 , 武宇乾 , 王晓旭 , 高贵 , 周欣 . 基于1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(DDAO)的近红外荧光探针研究进展[J]. 有机化学, 2023 , 43(1) : 94 -111 . DOI: 10.6023/cjoc202206044
1,3-Dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO) is an excellent near-infrared fluorescent dye with near-infrared emission, low pKa (≈5.0), high water solubility and high quantum yield (Φ=0.39), which has attracted much attention in recent years in the field of fluorescent probes. The researches prove that the fluorescent probes designed and synthesized based on this dye can work in mild aqueous solutions, and have excellent sensing performance, such as rapid reaction, high selectivity and sensitivity, low detection limit and obvious colorimetric signal change. In addition, the low cytotoxicity of this class of probes is of significant application for the detection of living cells and organisms. The research progress of fluorescent probes based on DDAO and its derivatives, mainly including the molecular design, action mechanism and application of probes in the recognition and detection of biological enzymes, reactive oxygen species, reactive nitrogen species, proteins and Pd0, is reviewed, and the development prospect of this type of fluorescent probes is prospected.
| [1] | Li, X. H.; Gao, X. H.; Shi, W.; Ma, H. M. Chem. Rev. 2014, 114, 590. |
| [2] | Lavis, L. D.; Raines, R. T. ACS Chem. Biol. 2014, 9, 855. |
| [3] | Cao, L. Y.; Zhang, R.; Zhang, W. Z.; Du, Z. B.; Liu, C. J.; Ye, Z. Q.; Song, B.; Yuan, J. L. Biomaterials 2015, 68, 21. |
| [4] | Ma, Z. W.; Wang, X.; Wang, C. C.; Chen, X. P.; Lv, Q. J. Spectrochim. Acta, Part A 2019, 213, 370. |
| [5] | Zhang, J.; Wang, X. L.; Yang, X. R. Analyst 2012, 137, 2806. |
| [6] | Ning, J.; Wang, W.; Ge, G. B.; Chu, P.; Long, F. D.; Yang, Y. L.; Peng, Y. L.; Feng, L.; Ma, X. C.; James, T. D. Angew. Chem., Int. Ed. 2019, 58, 9959. |
| [7] | Liu, H. W.; Chen, L. L.; Xu, C. Y.; Li, Z.; Zhang, H. Y.; Zhang, X. B.; Tan, W. H. Chem. Soc. Rev. 2018, 47, 7140. |
| [8] | Zhou, P. C.; She, M. Y.; Liu, P.; Zhang, S. Y.; Li, J. L. Sens. Actuators, B 2020, 318, 120035. |
| [9] | Wu, D.; Sedgwick, A. C.; Gunnlaugsson, T.; Akkaya, E. U.; Yoon, J.; James, T. D. Chem. Soc. Rev. 2017, 46, 7105. |
| [10] | Huang, M. M.; Ren, H. Y.; Shi, J. Z.; Chen, J. C.; Chi, X. W.; Lu, W. Guangzhou Chem. 2022, 47, 1. (in Chinese) |
| [10] | (黄萌萌, 任红宇, 史久州, 陈继超, 池杏微, 卢雯, 广州化学, 2022, 47, 1.) |
| [11] | Qian, X. H.; Xu, Z. C. Chem. Soc. Rev. 2015, 44, 4487. |
| [12] | Li, S. J.; Wu, Z. F.; Liu, W.; Li, L. H.; Lu, L.; Yu, Q.; Ma, S. F. Chin. J. Org. Chem. 2021, 41, 229. (in Chinese) |
| [12] | (李思进, 武志芳, 刘文, 李丽红, 陆利, 余强, 马素芳, 有机化学, 2021, 41, 229.) |
| [13] | Wang, B.; Deng, W. L.; Li, D. L. Light Text. Ind. Fujian 2022, 38. (in Chinese) |
| [13] | (王博, 邓威力, 李达谅, 福建轻纺, 2022, 38.) |
| [14] | Ren, C. P.; Nie, W.; Leng, J. Q.; Liu, Z. B. Prog. Chem. 2021, 33, 942. (in Chinese) |
| [14] | (任春平, 聂雯, 冷俊强, 刘振波, 化学进展, 2021, 33, 942.) |
| [15] | Tang, L. J.; Ban, L. F.; Li, J. J. Chin. J. Org. Chem. 2021, 41, 241. (in Chinese) |
| [15] | (汤立军, 班立夫, 李娇娇, 有机化学, 2021, 41, 241.) |
| [16] | She, M. Y.; Wang, Z. H.; Luo, T. Y.; Yin, B.; Liu, P.; Liu, J.; Chen, F. L.; Zhang, S. Y.; Li, J. L. Chem. Sci. 2018, 9, 8065. |
| [17] | Wen, Y.; Huo, F. J.; Yin, C. X. Chin. Chem. Lett. 2019, 30, 1834. |
| [18] | Wang, J. P.; Huo, F. J.; Yue, Y. K.; Yin, C. X. Luminescence 2020, 35, 1156. |
| [19] | Wang, X. P.; Li, Y. D.; Wang, J. G. Chin. J. Lumin. 2021, 42, 938. (in Chinese) |
| [19] | (王晓鹏, 李永东, 王建国, 发光学报, 2021, 42, 938.) |
| [20] | Huang, Y. R.; Chen, W. J.; Chung, J. W.; Yin, J.; Yoon, J. Y. Chem. Soc. Rev. 2021, 50, 7725. |
| [21] | Marshall, A. P.; Shirley, J. D.; Carlson, E. E. Curr. Opin. Chem. Biol. 2020, 57, 155. |
| [22] | Dong, L. L.; Shen, S. Q.; Lu, H. Z.; Jin, S. H.; Zhang, J. J. ACS Sens. 2019, 4, 1222. |
| [23] | Zhang, X.; Yin, J.; Yoon, J. Chem. Rev. 2014, 114, 4918. |
| [24] | Liu, Y. Y.; Guo, Y.; Luo, X. G.; Liu, G. Y.; Sun, Q. Prog. Chem. 2021, 33, 199. (in Chinese) |
| [24] | (刘园园, 郭芸, 罗晓刚, 刘根炎, 孙琦, 化学进展, 2021, 33, 199.) |
| [25] | Wang, Y.; Huang, C. S.; Jia, N. Q. Prog. Chem. 2020, 32, 204. (in Chinese) |
| [25] | (王阳, 黄楚森, 贾能勤, 化学进展, 2020, 32, 204.) |
| [26] | Hou, P.; Chen, S.; Wang, H. B.; Wang, J. X.; Voitchovsky, K.; Song, X. Z. Chem. Commun. 2014, 50, 320. |
| [27] | Yang, L.; Su, Y. A.; Sha, Z. K.; Geng, Y. N.; Qi, F. P.; Song, X. Z. Org. Biomol. Chem. 2018, 16, 1150. |
| [28] | Wang, J. M.; Zhang, L.; Qu, Y.; Yang, Y. X.; Cao, T.; Cao, Y. P.; Iqbal, A.; Qin, W. W.; Liu, Y. Anal. Chem. 2021, 93, 11461. |
| [29] | Xu, H.; Wu, S. L.; Lin, N. J.; Lu, Y.; Xiao, J.; Wang, Y. W.; Peng, Y. Sens. Actuators, B 2021, 346, 130484. |
| [30] | Ge, C. P.; Shen, F. G.; Yin, Y. Y.; Chang, K. W.; Zhang, X.; Zhou, P. X.; Li, J. M.; Liu, Y. X.; Lu, C. B. Talanta 2021, 223, 121758. |
| [31] | Wu, X. F.; Wang, R.; Qi, S. J.; Kwon, N.; Han, J. J.; Kim, H.; Li, H. D.; Yu, F. B.; Yoon, J. Y. Angew Chem., Int. Ed. 2021, 60, 15418. |
| [32] | Yang, Y.; Zhang, L. W.; Zhang, X.; Liu, S. D.; Wang, Y.; Zhang, L.; Ma, Z.; You, H. Y.; Chen, L. X. Chem. Commun. 2021, 57, 5810. |
| [33] | Jin, Y. L.; Liu, R.; Zhan, Z. X.; Lv, Y. Talanta 2019, 202, 159. |
| [34] | She, Z. P.; Wang, W. X.; Mao, G. J.; Jiang, W. L.; Wang, Z. Q.; Li, Y.; Li, C. Y. Chem. Commun. 2021, 57, 4811. |
| [35] | Palanisamy, S.; Chen, L. F.; Tzou, S. C.; Wang, Y. M. Sens. Actuators, B 2020, 310, 127839. |
| [36] | Lin, Q. S.; Huang, Y. L.; Fan, X. X.; Zheng, X. L.; Chen, X. L.; Zhan, X. Q.; Zheng, H. Talanta 2017, 170, 496. |
| [37] | Zhang, K. X.; Wang, H.; Cheng, S. Y.; Zhang, C.; Zhai, X. R.; Lin, X. P.; Chen, H.; Gao, R. R.; Dong, W. Analyst 2021, 146, 5658. |
| [38] | Liu, Q. C.; Li, J.; Liu, C.; He, S.; Zhao, L. C.; Zeng, X. S.; Wang, T. H. Dyes Pigm. 2021, 196, |
| [39] | Zha, J. Y.; Fu, B. Q.; Qin, C. Q.; Zeng, L. T.; Hu, X. C. RSC Adv. 2014, 4, 43110. |
| [40] | Jiao, X. J.; Xiao, Y. S.; Li, Y.; Liang, M. W.; Xie, X. L.; Wang, X.; Tang, B. Anal. Chem. 2018, 90, 7510. |
| [41] | Xia, Q. F.; Feng, S. M.; Hong, J. X.; Feng, G. Q. Sens. Actuators, B 2021, 337, 129732. |
| [42] | Zhao, X. J.; Jiang, Y. R.; Chen, Y. X.; Yang, B. Q.; Li, Y. T.; Liu, Z. H.; Liu, C. Spectrochim. Acta, Part A 2019, 219, 509. |
| [43] | Wu, P.; Zhu, Y.; Chen, L. L.; Tian, Y.; Xiong, H. Anal. Chem. 2021, 93, 13014. |
| [44] | Cheng, W.; Xue, X. Q.; Gan, L.; Jin, P.; Zhang, B. X.; Guo, M. H.; Si, J.; Du, H. Y.; Chen, H. L.; Fang, J. G. Anal. Chim. Acta 2021, 1156, 338362. |
| [45] | Rout, Y.; Montanari, C.; Pasciucco, E.; Misra, R.; Carlotti, B. J. Am. Chem. Soc. 2021, 143, 9933. |
| [46] | Chiorazzo, M. G.; Bloch, N. B.; Popov, A. V.; Delikatny, E. J. Bioconjugate Chem. 2015, 26, 2360. |
| [47] | Hu, Q.; Guan, X. Q.; Song, L. L.; Wang, H. N.; Xiong, Y.; Liu, J. L.; Yin, H.; Cao, Y. F.; Hou, J.; Yang, L.; Ge, G. B. Ecotoxicol. Environ. Saf. 2020, 192, 110305. |
| [48] | Chung, C.; Srikun, D.; Lim, C. S.; Chang, C. J.; Cho, B. R. Chem. Commun. 2011, 47, 9618. |
| [49] | Qiao, J.; Liu, Z.; Tian, Y.; Wu, M.; Niu, Z. W. Chem. Commun. 2015, 51, 3641. |
| [50] | Wu, G. F.; Zeng, F.; Yu, C. M.; Wu, S. Z.; Li, W. S. J. Mater. Chem. B 2014, 2, 8528. |
| [51] | Du, F. K.; Min, Y. H.; Zeng, F.; Yu, C. M.; Wu, S. Z. Small 2014, 10, 964. |
| [52] | Zinselmeyer, B. H.; Breggbie, N.; Uchegbu, I. F.; Schatzlein, A. G. J. Controlled Release 2003, 91, 201. |
| [53] | Tian, Z. H.; Feng, L.; Li, L.; Tian, X. G.; Cui, J. N.; Zhang, H. L.; Wang, C.; Huang, H. L.; Zhang, B. J.; Ma, X. C. Sens. Actuators, B 2020, 310, 127872. |
| [54] | Tian, Z. H.; Yan, F.; Tian, X. G.; Feng, L.; Cui, J. N.; Deng, S.; Zhang, B. J.; Xie, T.; Huang, S. S.; Ma, X. C. Acta Pharm. Sin. B 2022, 12, 316. |
| [55] | Tian, M. M.; Tian, Z. H.; Yao, D. H.; Ning, J.; Deng, S.; Feng, L.; Huo, X. K.; Tian, X. G.; Zhang, B. J.; Wang, C.; Yu, Z. L.; Ma, X. C. J. Mater. Chem. B 2021, 9, 6460. |
| [56] | Jin, Q.; Feng, L.; Wang, D. D.; Wu, J. J.; Hou, J.; Dai, Z. R.; Sun, S. G.; Wang, J. Y.; Ge, G. B.; Cui, J. N.; Yang, L. Biosens. Bioelectron. 2016, 83, 193. |
| [57] | Hu, Q.; Tian, Z. H.; Wang, H. N.; Huang, J.; Wang, F. Y.; Zhao, B.; He, R. J.; Jin, Q.; Hou, X. D.; Hou, J.; Fang, S. Q.; Wang, P.; Ge, G. B. Sens. Actuators, B 2021, 341, 130033. |
| [58] | Lu, C. R.; Fang, H. X.; Lu, P. X.; Ji, L. C. Electron. J. Emerging Infect. Dis. 2021, 6, 368. (in Chinese) |
| [58] | (卢春容, 房宏霞, 陆普选, 季乐财, 新发传染病电子杂志, 2021, 6, 368.) |
| [59] | Li, C Y. M.S. Thesis, Southwest University, Chongqing, 2018. (in Chinese) |
| [59] | (李春燕, 硕士论文, 西南大学, 重庆, 2018.) |
| [60] | Beatty, K. E.; Williams, M.; Carlson, B. L.; Swarts, B. M.; Warren, R. M.; van Helden, P. D.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 12911. |
| [61] | Tallman, K. R.; Beatty, K. E. ChemBioChem 2015, 16, 70. |
| [62] | Tallman, K. R.; Levine, S. R.; Beatty, K. E. ACS Chem. Biol. 2016, 11, 1810. |
| [63] | Levine, S. R.; Beatty, K. E. Chem. Commun. 2016, 52, 1835. |
| [64] | Li, B.; Fu, Y. Y.; Cheng, J. G. Prog. Chem. 2021, 33, 1461. (in Chinese) |
| [64] | (李斌, 付艳艳, 程建功, 化学进展, 2021, 33, 1461.) |
| [65] | Lu, Y. X. Inside Outside Classroom (Sci. Fans) 2018, 12, 20. (in Chinese) |
| [65] | (陆远熙, 课堂内外(科学Fans), 2018, 12, 20.) |
| [66] | Amitai, G.; Adani, R.; Yacov, G.; Yishay, S.; Teitlboim, S.; Tveria, L.; Limanovich, O.; Kushnir, M.; Meshulam, H. Toxicology 2007, 233, 187. |
| [67] | Murakami, M.; Taketomi, Y.; Miki, Y.; Sato, H.; Hirabayashi, T.; Yamamoto, K. Prog. Lipid Res. 2011, 50, 152. |
| [68] | Mawn, T. M.; Popov, A. V.; Beardsley, N. J.; Stefflova, K.; Milkevitch, M.; Zheng, G.; Delikatny, E. J. Bioconjugate Chem. 2011, 22, 2434. |
| [69] | Chiorazzo, M. G.; Tunset, H. M.; Popov, A. V.; Johansen, B.; Moestue, S.; Delikatny, E. J. Sci. Rep. 2019, 9, 6122. |
| [70] | Satoh, T.; Hosokawa, M. Chem.-Biol. Interact. 2006, 162, 195. |
| [71] | Ma, H. Y.; Yang, J. D.; Hou, J.; Zou, L. W.; Jin, Q.; Hao, D. C.; Ning, J.; Ge, G. B.; Yang, L. Toxicol. in Vitro 2017, 44, 280. |
| [72] | Hong, W.; Zhao, X. X.; Wu, C. X.; Rao, F. Q.; Cheng, Y. M.; Zhang, T.; Qi, X. L.; Yu, W. F.; Guan, Z. Z. J. Guizhou Med. Univ. 2019, 44, 1370. (in Chinese) |
| [72] | (洪伟, 赵行行, 吴昌学, 饶凤琴, 程玉梅, 张婷, 齐晓岚, 禹文峰, 官志忠, 贵州医科大学学报, 2019, 44, 1370.) |
| [73] | Minta, A.; Kao, J. P. Y.; Tsien, R. Y. J. Biol. Chem. 1989, 264, 8171. |
| [74] | Tung, C. H.; Qing, Z.; Khalid, S.; Kim, D. E.; Dawid, S.; Ralph, W. Cancer Res. 2004, 64, 1579. |
| [75] | Zhang, G. J.; Chen, T. B.; Connolly, B.; Lin, S. A.; Hargreaves, R.; Vanko, A.; Bednar, B.; Macneil, D. J.; Sur, C.; Williams, D. L. Assay Drug Dev. Technol. 2009, 7, 391. |
| [76] | Kahkoska, A. R.; Pokaprakarn, T.; Alexander, G. R.; Crume, T. L.; Dabelea, D.; Divers, J.; Dolan, L. M.; Jensen, E. T.; Lawrence, J. M.; Marcovina, S.; Mottl, A. K.; Pihoker, C.; Saydah, S. H.; Kosorok, M. R.; Mayer-Davis, E. J. Diabetes Care 2022, 45, 108. |
| [77] | Zhi, L. C.; Zhang, L. Y.; Liang, X. Y.; Xia, Q.; Cheng, J.; Ren, D. D.; He, Y. H.; Wang, Q. K. J. Food Saf. Qual. 2021, 12, 2276. (in Chinese) |
| [77] | (郅丽超, 张琳依, 梁馨元, 夏青, 程晶, 任丹丹, 何云海, 汪秋宽, 食品安全质量检测学报, 2021, 12, 2276.) |
| [78] | Qian, M. M.S. Thesis, Tianjin Medical University, Tianjin, 2018. (in Chinese) |
| [78] | (钱盟, 硕士论文, 天津医科大学, 天津, 2018.) |
| [79] | Dong, Y. Q. Med. Diet Health 2020, 18, 106. (in Chinese) |
| [79] | (董玉芹, 医学食疗与健康, 2020, 18, 106.) |
| [80] | Otani, K.; Tanigawa, T.; Watanabe, T.; Shimada, S.; Nadatani, Y.; Nagami, Y.; Tanaka, F.; Kamata, N.; Yamagami, H.; Shiba, M.; Tominaga, K.; Fujiwara, Y.; Arakawa, T. Digestion 2017, 95, 22. |
| [81] | Feng, L.; Yang, Y. L.; Huo, X. K.; Tian, X. G.; Feng, Y. J.; Yuan, H. W.; Zhao, L. J.; Wang, C.; Chu, P.; Long, F. D.; Wang, W.; Ma, X. C. ACS Sens. 2018, 3, 1727. |
| [82] | Moin, S. F.; Bin Omar, M. N. Protein Pept. Lett. 2014, 21, 707. |
| [83] | Liu, J. Y.; Jiao, G. B.; You, X. J.; Liao, X. R.; Sun, L. P. Biotechnol. Bull. 2016, 32, 24. (in Chinese) |
| [83] | (刘家扬, 焦国宝, 有小娟, 廖祥儒, 孙利鹏, 生物技术通报, 2016, 32, 24.) |
| [84] | Tian, Z. H.; Yan, Q. S.; Feng, L.; Deng, S.; Wang, C.; Cui, J. N.; Wang, C. J.; Zhang, Z. J.; James, T. D.; Ma, X. C. Chem. Commun. 2019, 55, 3951. |
| [85] | Gultepe, I.; Basaranoglu, M.; Zorlu, M.; Senyigit, A.; Taskale, E. Z.; Zarali, S.; Atay, K.; Koroglu, E. Turk. J. Gastroenterol. 2016, 27, 197. |
| [86] | Li, K.; Shan, G. L.; Ma, X. B.; Zhang, X. Y.; Chen, Z. B.; Tang, Z. H.; Liu, Z. Colloids Surf., B 2019, 179, 153. |
| [87] | Rathinaswamy, P.; Gaikwad, S. M.; Suresh, C. G.; Prabhune, A. A.; Brannigan, J. A.; Dodson, G. G.; Pundle, A. V. Int. J. Biol. Macromol. 2012, 50, 25. |
| [88] | Castellano, I.; Di Salle, A.; Merlino, A.; Rossi, M.; La Cara, F. Extremophiles 2011, 15, 259. |
| [89] | Luo, Z. L.; Feng, L. D.; An, R. B.; Duan, G. F.; Yan, R. Q.; Shi, H.; He, J.; Zhou, Z. Y.; Ji, C. G.; Chen, H. Y.; Ye, D. J. Chem.-Eur. J. 2017, 23, 14778. |
| [90] | Wang, C.; Tian, Z. H.; Wang, Y. F.; Zhang, M.; Zhang, B. J.; Feng, L.; Tian, X. G.; Huang, H. L.; Cui, J. N.; Ma, X. C. Sens. Actuators, B 2021, 329, 129225. |
| [91] | Bartucci, R.; Salvati, A.; Olinga, P.; Boersma, Y. L. Int. J. Mol. Sci., 2019, 20, 3891. |
| [92] | Xia, W. K.; Hu, H. J. Chin. Physician 2020, 22, 1594. (in Chinese) |
| [92] | (夏文楷, 胡宏, 中国医师杂志, 2020, 22, 1594.) |
| [93] | Tanaka, M.; Yagyu, K.; Sackett, S.; Zhang, Y. M. Cells 2019, 8, 491. |
| [94] | Medeiros, P.; Oliveira-Silva, M.; Negrini-Ferrari, S. E.; Medeiros, A. C.; Elias-Filho, D. H.; Coimbra, N. C.; de Freitas, R. L. Brain Res. Bull. 2020, 165, 118. |
| [95] | Esoda, C. N.; Kuehn, M. J. mBio 2019, 10, |
| [96] | Zhang, M.; Tian, Z. H.; Wang, J. Y.; Tian, X. G.; Wang, C.; Cui, J. N.; Huo, X. K.; Feng, L.; Yu, Z. L.; Ma, X. C. ACS Sens. 2021, 6, 3604. |
| [97] | Ito, S.; Miyahara, R.; Takahashi, R.; Nagai, S.; Takenaka, K.; Wada, H.; Tanaka, F. J. Thorac. Cardiovasc. Surg. 2009, 57, 591. |
| [98] | Feng, L.; Tian, Z. H.; Zhang, M.; He, X.; Tian, X. G.; Yu, Z. L.; Ma, X. C.; Wang, C. Chin. Chem. Lett. 2021, 32, 3053. |
| [99] | Abe, K.; Watanabe, N.; Kosaka, T.; Yamada, M.; Tokui, T.; Ikeda, T. Biol. Pharm. Bull. 2003, 26, 1528. |
| [100] | Wang, C.; Tian, Z. H.; Zhang, M.; Deng, Y.; Tian, X. G.; Feng, L.; Cui, J. N.; James, T. D.; Ma, X. C. Anal. Chim. Acta 2022, 1191, 339280. |
| [101] | Ma, E.; Chen, P.; Wilkins, H. M.; Wang, T.; Swerdlow, R. H.; Chen, Q. Free Radical Biol. Med. 2017, 113, 36. |
| [102] | Hou, J. L.; Qian, M.; Zhao, H. H.; Li, Y. C.; Liao, Y. F.; Han, G. F.; Xu, Z. L.; Wang, F.; Song, Y. G.; Liu, Y. P. Anal. Chim. Acta 2018, 1024, 169. |
| [103] | Yang, B.; Chen, Y.; Shi, J. L. Chem. Rev. 2019, 119, 4881. |
| [104] | Chen, X. Q.; Tian, X. Z.; Shin, I.; Yoon, J. Y. Chem. Soc. Rev. 2011, 40, 4783. |
| [105] | Deng, Y. Z.; Feng, S. M.; Xia, Q. F.; Gong, S. Y.; Feng, G. Q. Talanta 2020, 215, 120901. |
| [106] | Zarrin, A. A.; Bao, K.; Lupardus, P.; Vucic, D. Nat. Rev. Drug Discovery 2021, 20, 39. |
| [107] | Tay, M. Z.; Poh, C. M.; Renia, L.; MacAry, P. A.; Ng, L. F. P. Nat. Rev. Immunol. 2020, 20, 363. |
| [108] | Wang, Z.; Wang, W. W.; Wang, P. Z.; Song, X. J.; Mao, Z. Q.; Liu, Z. H. Anal. Chem. 2021, 93, 3035. |
| [109] | Mironczuk-Chodakowska, I.; Witkowska, A. M.; Zujko, M. E. Adv. Med. Sci. 2018, 63, 68. |
| [110] | He, H.; Luo, Y.; Qiao, Y.; Zhang, Z. Y.; Yin, D.; Yao, J. G.; You, J. G.; He, M. Food Funct. 2018, 9, 4404. |
| [111] | Ji, K. Y.; Shan, J. P.; Wang, X.; Tan, X. L.; Hou, J. L.; Liu, Y. P.; Song, Y. G. Free Radical Biol. Med. 2021, 167, 36. |
| [112] | Jermendy, G.; Ruggenenti, P. Diabetes/Metab. Res. Rev. 2007, 23, 100. |
| [113] | Seedher, N.; Kanojia, M. Chem. Biol. Drug Des. 2008, 72, 290. |
| [114] | Jin, Q.; Feng, L.; Zhang, S. J.; Wang, D. D.; Wang, F. J.; Zhang, Y.; Cui, J. N.; Guo, W. Z.; Ge, G. B.; Yang, L. Anal. Chem. 2017, 89, 9884. |
| [115] | Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250. |
| [116] | Zereini, F.; Wiseman, C. L.; Puttmann, W. Environ. Sci. Technol. 2012, 46, 10326. |
| [117] | Xia, Q. F.; Feng, S. M.; Liu, D. D.; Feng, G. Q. Sens. Actuators, B 2018, 258, 98. |
| [118] | Feng, S. M. M.S. Thesis, Central China Normal University, Wuhan, 2018. (in Chinese) |
| [118] | (冯书敏, 硕士论文, 华中师范大学, 武汉, 2018.) |
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