Chinese Journal of Organic Chemistry >
Recent Advances of Fe(II) Fluorescence Probes Based on N-Oxide Structure
Received date: 2024-07-27
Revised date: 2024-10-09
Online published: 2024-11-08
Supported by
Scientific Research Cultivating Fund of Capital Medical University(PYZ21023)
Iron is widely distributed in the human body, participating in numerous biochemical reactions. Iron exists in the forms of Fe2＋ and Fe3＋ in cells, playing crucial roles in maintaining normal cellular functions. In the reducing environment of living cells, the labile iron primarily exists in the form of Fe2＋ ions. The labile Fe2＋ can serve as a catalyst for the Fenton reaction, generating reactive oxygen species (ROS) within the cell, which can cause severe damage to the cell and lead to a range of related diseases. Therefore, visual monitoring Fe2＋ in the physiological environment is necessary to contribute to a deeper understanding of the pathogenesis and progression of the disease. In recent years, several researchers have focused on designing and synthesizing fluorescent probes with excellent optical properties that can be used to monitor Fe2＋ in vivo and in vitro. Among them, the N-oxide-based fluorescence probes have been concerned by researchers because of its advantages of strong selectivity, high sensitivity, and in-situ real-time imaging. The structures, design considerations, optical properties, and applications of N-oxide-based Fe2＋ fluorescence probes are discussed.
Key words： Fe2＋; N-oxide chemistry; fluorescence probe; bioimaging
Hanyue Xiang , Shaoyin Wei , Yuji Wang , Nao Xiao . Recent Advances of Fe(II) Fluorescence Probes Based on N-Oxide Structure[J]. Chinese Journal of Organic Chemistry, 2025 , 45(4) : 1137 -1152 . DOI: 10.6023/cjoc202407041
| [1] | Siri-Angkul, N.; Xie, L. H.; Chattipakorn, S. C.; Chattipakorn, N. Front. Physiol. 2018, 9, 1615. |
| [2] | Andreini, C.; Putignano, V.; Rosato, A.; Banci, L. Metallomics 2018, 10, 1223. |
| [3] | Kamal, A.; Kumar, N.; Bhalla, V.; Kumar, M.; Mahajan, R. K. Sens. Actuators, B 2014, 190, 127. |
| [4] | Jiang, T.; Huang, J.; Ran, G.; Song, Q.; Wang, C. Anal. Sci. 2023, 39, 325. |
| [5] | Wu, Y.; Zhang, S.; Gong, X.; Tam, S.; Xiao, D.; Liu, S.; Tao, Y. Mol. Cancer 2020, 19, 39. |
| [6] | Anita, P. K.; Alireza, B.; Zohreh, S. G.; Jahan, B. G. J. Mol. Struct. 2022, 1252, 131978. |
| [7] | Liu, H.; Mo, T.; Zhou, Y.; Gong, H.; Zhao, D. Microchem. J. 2022, 183, 108106. |
| [8] | Siahcheshm, P.; Heiden, P. J. Photochem. Photobiol., A 2023, 435, 114284. |
| [9] | Goetze, O.; Schmitt, J.; Spliethoff, K.; Theurl, I.; Weiss, G.; Swinkels, D. W.; Tjalsma, H.; Magginorini, M.; Krayenbuhl, P.; Rau, M.; Fruehauf, H.; Wojtal, K. A.; Mullhaupt, B.; Fried, M.; Gass- mann, M.; Lutz, T.; Geier, A. Hepatology 2013, 58, 2153. |
| [10] | Hirayama, T. Acta Histochem. Cytochem. 2018, 51, 137. |
| [11] | Zhang, S.; Xin, W.; Anderson, G. J.; Li, R.; Gao, L.; Chen, S.; Zhao, J.; Liu, S. Cell Death Dis. 2022, 13, 40. |
| [12] | Dong, X.; Cheng, X.; Mills, E.; Delling, M.; Wang, F.; Kurz, T.; Xu, H. Biophys. J. 2009, 96, 266a. |
| [13] | Ji, R.; Jia, F.; Chen, X.; Wang, Z.; Jin, W.; Yang, J. Arch. Biochem. Biophys. 2022, 715, 109094. |
| [14] | Li, J.; He, R.; Duan, S.; Li, J.; Han, X.; Ye, Y. Chin. J. Org. Chem. 2022, 42, 2428 (in Chinese). |
| [14] | (李嘉欣, 贺如艳, 段森林, 黎锦华, 韩校净, 叶勇, 有机化学, 2022, 42, 2428.) |
| [15] | Zi, Y.; Wang, X.; Zi, Y.; Yu, H.; Lan, Y.; Fan, Y.; Ren, C; Liao, K.; Chen, H. Free Radical Biol. Med. 2023, 200, 73. |
| [16] | Li, D.; Zhang, G.; Wang, Z.; Guo, J.; Liu, Y.; Lu, Y.; Qin, Z.; Xu, Y.; Cao, C.; Wang, B.; Guo, Q.; Wang, Y.; Liu, G.; Cui, X.; Zhang, J.; Tang, J. Eur. J. Pharmacol. 2023, 943, 175569. |
| [17] | Wang, Y.; Wang, M.; Liu, Y.; Tao, H.; Banerjee, S.; Srinivasan, S.; Nemeth, E.; Czaja, M. J.; He, P. Redox Biol. 2022, 55, 102407. |
| [18] | Dixon, S. J.; Lemberg, K. M.; Lamprecht, M. R.; Skouta, R.; Zaitsev, E. M.; Gleason, C. E.; Patel, D. N.; Bauer, A. J.; Cantley, A. M.; Yang, W. S.; Morrison, B.; Stockwell, B. R. Cell 2012, 149, 1060. |
| [19] | Li, J.; Xiao, W.; Wei, W.; Wu, M.; Xiong, K.; Lyu, J.; Li, Y. Mol. Immunol. 2023, 158, 79. |
| [20] | Lee, J.; Roh, J. L. Cancer Lett. 2023, 559, 216119. |
| [21] | Yan, J.; Lee, S.; Zhang, A.; Yoon, J. Chem. Soc. Rev. 2018, 47, 6900. |
| [22] | Singh, H.; Tiwari, K.; Tiwari, R.; Pramanik, S. K.; Das, A. Chem. Rev. 2019, 119, 11718. |
| [23] | Zhu, J.; Miao, C.; Wang, X. J. Photochem. Photobiol.,A 2023, 440, 114659. |
| [24] | Zhu, J.; Miao, C.; Wang, X. Spectrochim. Acta, Part A 2023, 294, 122546. |
| [25] | Wei, X.; Zhu, T.; Ma, Y.; Sun, J.; Zheng, G.; Ma, T.; Yang, X.; Song, X.; Lv, Y.; Zhang, J.; Yan, M. Sens. Actuators, B 2023, 380, 133392. |
| [26] | Xiang, H.; Wang, T.; Tang, S.; Wang, Y.; Xiao, N. Spectrochim. Acta, Part A 2022, 267, 1386. |
| [27] | Li, H.; An, Y.; Gao, J.; Yang, M.; Luo, J.; Li, X.; Lv, J.; Li, X.; Yuan, Z.; Ma, H. Chemosensors 2022, 10, 233. |
| [28] | Guo, L.; Chen, X.; Xie, R.; Han, L. J. Mol. Struct. 2023, 1275, 134615. |
| [29] | Tanaka, H.; Kurokawa, Y.; Takechi, M.; Ohbuchi, A. Talanta Open 2021, 3, 100031. |
| [30] | Patel, M.; Bisht, N.; Prabhakar, P.; Sen, R. K.; Kumar, P.; Dwivedi, N.; Ashiq, M.; Mondal, D. P.; Strivastava, A. K.; Dhand, C. Environ. Res. 2023, 221, 115317. |
| [31] | Siyal, P.; Nafady, A.; Sirajuddin.; Memon, R.; Sherazi, S. T. H.; Nisar, J.; Siyal, A. A.; Shah, M. R.; Mahesar, S. A.; Bhagat, S. Spectrochim. Acta, Part A 2021, 254, 119645. |
| [32] | El-Bindary, M. A.; Shahat, A.; El-Deen, I. M.; Khalil, M. A.; Hassan, N. J. Mol. Liq. 2023, 382, 121946. |
| [33] | Toit, J. P.; Krieg, H. M.; Mans, N. J. Power Sources 2023, 533, 232178. |
| [34] | Wu, D.; Sedgwick, A. C.; Gunnlaugsson, T.; Akkaya, E. U.; Yoon, J.; James, T. D. Chem. Soc. Rev. 2017, 46, 7105. |
| [35] | Yin, J.; Zhan, J.; Hu, Q.; Huang, S.; Lin, W. Chem. Soc. Rev. 2023, 52, 2011. |
| [36] | La, D. D.; Bhosale, S. V.; Jones, L. A.; Bhosale, S. V. ACS Appl. Mater. Interfaces 2018, 10, 12189. |
| [37] | Guo, L.; Li, L.; Wang, X.; Zhang, Y.; Cui, F. ACS Omega 2023, 8, 37098. |
| [38] | Lu, Y.; Ruan, G.; Du, W.; Li, J.; Yang, N.; Wu, Q.; Lu, L.; Zhang, C.; Li, L. Dyes Pigm. 2021, 190, 109337. |
| [39] | Kumar, N.; Bhalla, V.; Kumar, M. Analyst 2014, 139, 543. |
| [40] | Wang, X.; Zhang, S.; Zhao, B. Spectrochim. Acta, Part A 2020, 227, 117699. |
| [41] | Yan, H.; Xu, X.; Li, J.; Xie, P.; Cao, W.; Yang, X.; Ye, Y. J. Photochem. Photobiol., A 2023, 440, 114638. |
| [42] | Duangkamol, C.; Muangsopa, P.; Rattanopas, S.; Wongsuwan, P.; Khrrotkaew, T.; Chueakwon, P.; Niamnont, N.; Chansaenpak, K.; Kamkaew, A. Dyes Pigm. 2023, 216, 111365. |
| [43] | Meng, X.; Zhao, J.; Ma, W. Chin. J. Org. Chem. 2020, 40, 276 (in Chinese). |
| [43] | (孟宪娇, 赵晋忠, 马文兵, 有机化学, 2020, 40, 276.) |
| [44] | Guo, L.; Chen, X.; Xie, R.; Han, L.; Zhu, N. J. Mol. Struct. 2023, 1275, 134615. |
| [45] | Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Chem. Rev. 2003, 103, 3899. |
| [46] | Sedgwick, A. C.; Wu, L.; Han, H. H.; Bull, S. D.; He, X. P.; James, T. D.; Sessler, J. L.; Tang, B. Z.; Tian, H.; Yoon, J. Chem. Soc. Rev. 2018, 47, 8842. |
| [47] | Wu, L.; Huang, C.; Emery, B. P.; Sedgwick, A. C.; Bull, S. D.; He, X. P.; Tian, H.; Yoon, J.; Sessler, J. L.; James, T. D. Chem. Soc. Rev. 2020, 49, 5110. |
| [48] | Xing, W.; Xu, H.; Ma, H.; Abedi, S. A. A.; Wang, S.; Zhang, X.; Liu, X.; Xu, H.; Wang, W.; Lou, K. Chem. Commun. 2022, 58, 2979. |
| [49] | Li, Z.; Xiao, M.; Zheng, Y.; Zhao, B. Spectrochim. Acta, Part A 2022, 279, 121397. |
| [50] | Li, K.; Xu, S.; Xiong, M.; Huan, S. Y.; Yuan, L.; Zhang, X. B. Chem. Soc. Rev. 2021, 50, 11766. |
| [51] | Huang, W.; Yang, Y.; Ye, D. Chin. J. Chem. 2023, 41, 2382. |
| [52] | Yin, J.; Huang, L.; Wu, L.; Li, J.; James, T. D.; Lin, W. Chem. Soc. Rev. 2021, 50, 12098. |
| [53] | Wang, X.; Ding, Q.; Groleau, R. R.; Wu, L.; Mao, Y.; Che, F.; Kotova, O.; Scanlan, E. M.; Lewis, S. E.; Li, P.; Tang, B.; James, T. D.; Gunnlaugsson, T. Chem. Rev. 2024, 124, 7106. |
| [54] | Owens, E. A.; Henary, M.; Fakhri, G. E.; Choi, H. S. Acc. Chem. Res. 2016, 49, 1731. |
| [55] | Li, H.; Kim, Y.; Jung, H.; Hyun, J. Y.; Shin, I. Chem. Soc. Rev. 2022, 51, 8957. |
| [56] | Zhang, Y.; Zhang, G.; Zeng, Z.; Pu, K. Chem. Soc. Rev. 2022, 51, 566. |
| [57] | Fujita, K.; Urano, Y. Chem. Rev. 2024, 124, 4021. |
| [58] | Liu, Y.; Li, Y.; Koo, S.; Sun, Y.; Liu, Y.; Liu, X.; Pan, Y.; Zhang, Z.; Du, M.; Lu, S.; Qiao, X.; Gao, J.; Wang, X.; Deng, Z.; Meng, X.; Xiao, Y.; Kim, J.S.; Hong, X. Chem. Rev. 2022, 122, 209. |
| [59] | Xu, G.; Li, N.; Sun, Y.; Gao, C.; Ma, L.; Song, P.; Xia, L. Chem. Eng. J. 2021, 414, 128741. |
| [60] | Kouser, R.; Zehra, S.; Khan, R. A.; Alsalme, A.; Arjmand, F.; Tabassum, S. Spectrochim. Acta, Part A 2021, 247, 119156. |
| [61] | Guan, J.; Tu, Q.; Chen, L.; Yuan, M.; Wang, J. Spectrochim. Acta, Part A 2019, 220, 117114. |
| [62] | Zhang, J.; Yang, Y.; Zhang, J.; She, W. Chin. J. Org. Chem. 2024, 44, 1337 (in Chinese). |
| [62] | (张继东, 杨垚, 张杰, 厍伟, 有机化学, 2024, 44, 1337.) |
| [63] | Pinheiro, G. E. G.; Ihmels, H. J. Fluoresc. 2021, 31, 269. |
| [64] | Sarkar, D.; Chowdhury, M.; Das, P. K. J. Mater. Chem. B 2021, 9, 494. |
| [65] | Hou, X.; Song, Y.; Lv, Y.; Wang, P.; Chen, K.; Li, G.; Guo, L. Spectrochim. Acta, Part A 2023, 290, 122254. |
| [66] | Khomami, A. P.; Badiei, A.; Ghavami, Z. S.; Ghasemi, B. J. J. Mol. Struct. 2022, 1252, 131978. |
| [67] | Khunkhong, N.; Kitchawengkul, N.; Wongnongwa, Y.; Jungsuttiwong, S.; Keawin, T.; Promarak, V.; Nalaoh, P.; Suttisintong, K.; Chansaenpak, K.; Jarujamrus, P. Dyes Pigm. 2022, 208, 110869. |
| [68] | Yun, L.; Cheng, X. Cellulose 2023, 30, 933. |
| [69] | Zhang, S.; Cheng, X. Mater. Today Commun. 2023, 36, 106696. |
| [70] | Chao, M.; Zhang, H.; Hu, Q.; Ma, S.; Cui, X.; Zhu, X.; Wang, H.; Yu, X.; Han, B. Anal. Bioanal. Chem. 2024, 416, 6473. |
| [71] | Nan, X.; Huyan, Y.; Li, H.; Sun, S.; Xu, Y. Coord. Chem. Rev. 2021, 426, 213580. |
| [72] | Xu, G.; Li, N.; Sun, Y.; Gao, C.; Ma, L.; Song, P.; Xia, L. J. Lumin. 2022, 250, 119069. |
| [73] | Grimm, J. B.; Tkachuk, A. N.; Patel, R.; Hennigan, T. S.; Gutu, A.; Dong, P.; Gandin, V.; Osowski, A. M.; Holland, K. L.; Liu, Z. J.; Brown, T. A.; Lavis, L. D. J. Am. Chem. Soc. 2023, 145, 23000. |
| [74] | Liu, D.; He, Z.; Zhao Y.; Yang, Y.; Shi, W.; Li, X.; Ma, H. J. Am. Chem. Soc. 2021, 143, 17136. |
| [75] | Hirayama, T.; Okuda, K.; Nagasawa, H. Chem. Sci. 2013, 4, 1250. |
| [76] | Niwa, M.; Hirayama, T.; Okuda, K.; Nagasawa, H. Org. Biomol. Chem. 2014, 12, 6590. |
| [77] | Hirayama, T.; Tsuboi, H.; Niwa, M.; Miki, A.; Kadota, S.; Ikeshita, Y.; Okuda, K.; Nagasawa, H. Chem. Sci. 2017, 8, 4858. |
| [78] | Dong, B.; Song W.; Lu, Y.; Tian, M.; Kong, X.; Mehmood, A. H.; Lin, W. Sens. Actuators, B 2020, 305, 127470. |
| [79] | Hirayama, T.; Inden, M.; Tsuboi, H.; Niwa, M.; Uchida, Y.; Naka, Y.; Hozumib, I.; Nagasawa, H. Chem. Sci. 2019, 10, 1514. |
| [80] | Kawai, K.; Hirayama, T.; Imai, H. Murakami, T.; Inden, M.; Hozumi, I.; Nagasawa, H. J. Am. Chem. Soc. 2022, 144, 3793. |
| [81] | Huang, X. C.; Tang, H.; Wei, X.; He, Y.; Hu, S.; Wu, J.; Xu, D.; Qiao, F.; Xue, J.; Zhao, Y. Nat. Commun. 2024, 15, 6864. |
| [82] | Yan, L.; Li, X.; Li, J. ChemistrySelect 2018, 3, 10157. |
| [83] | Chen, S.; Wang, H.; Wu, B.; Li, Q.; Gong, J.; Zhao, Y.; Zhao, Y.; Xiao, X.; Lam, J. W. Y.; Zhao, Z.; Luo, X.; Tang, B. Z. ACS Cent. Sci. 2023, 9, 883. |
| [84] | Ahmmed, E.; Mondal, A.; Sarkar, A.; Chakraborty, S.; Lohar, S.; Saha, N. C.; Dhara, K.; Chattopadhyay, P. ACS Appl. Bio Mater. 2020, 3, 4074. |
| [85] | Khatun, S.; Biswas, S.; Binoy, A.; Podder, A.; Mishra, N.; Bhuniya, S. J. Photochem. Photobiol., B 2020, 209, 111943. |
| [86] | Yang, X.; Wang, Y.; Liu, R.; Zhang, Y.; Tang, J.; Yang, E.; Zhang, D.; Zhao, Y.; Ye, Y. Sens. Actuators, B 2019, 288, 217. |
| [87] | Yang, L.; Chen, Q.; Gan, S.; Guo, Q.; Zhang, J.; Zhang, H.; Xie, Y.; Xiao, H.; Wang, W.; Sun, H. Dyes Pigm. 2021, 190, 109271. |
| [88] | Zheng, J.; Feng, S.; Gong, S.; Xia, Q.; Feng, G. Sens. Actuators, B 2020, 309, 127796. |
| [89] | Zhu, M.; Zhao, Z.; Liu, X.; Chen, P.; Fan, F.; Wu, X.; Hua, R.; Wang, Y. J. Hazard. Mater. 2021, 406, 124767. |
| [90] | Zeng, X.; Chen, J.; Yu, S.; Liu, Z.; Ma, M. J. Lumin. 2022, 250, 119069. |
| [91] | Xiang, H.; Song, Y.; Wang, Y.; Xiao, N. Mater. Adv. 2024, 5, 5624. |
| [92] | Xu, C.; Zou, H.; Zhao, Z.; Zhang, P.; Kwok, R. T. K.; Lam, J. W. Y.; Sung, H. H. Y.; Williams, I. D.; Tang, B. Z. Adv. Funct. Mater. 2019, 29, 1903278. |
| [93] | Ga, G.; Wang, X.; Wang, Z.; Jin, X.; Ou, L.; Zhou, J.; Xie, P. Talanta 2020, 215, 120908. |
| [94] | Zhang, Y.; Gong, S.; Song, J.; Li, M.; Qin, A.; Gao, Y.; Wang, Z.; Wang, S. Dyes Pigm. 2021, 194, 109590. |
| [95] | Liang, Y.; Zhang, Y.; Li, M.; Meng, Z.; Gao, Y.; Yin, J.; Yang, Y.; Wang, Z.; Wang, S. Anal. Bioanal. Chem. 2021, 413, 6267. |
| [96] | Xu, W.; Wu, P.; Li, X.; Liu, S.; Feng, L.; Xiong, H. Talanta 2021, 233, 122601. |
| [97] | Shen, Z.; Yang, Y.; Gong, S.; Meng, Z.; Liang, Y.; Zhang, Y.; Wang, Z.; Wang, S. Microchem. J. 2023, 195, 109519. |
| [98] | Hirayama, T.; Miki, A.; Nagasawa, H. Metallomics, 2019, 11, 111. |
| [99] | Hirayama, T.; Niwa, M.; Hirosawa, S.; Nagasawa, H. ACS Sens. 2020, 5, 2950. |
| [100] | Niwa, M.; Hirayama, T.; Oomoto, I.; Wang, D.O.; Nagasawa, H. ACS Chem. Biol. 2018, 13, 1853. |
| [101] | Feng, S.; Zheng, J.; Zhang, J.; Gui, Z.; Feng, G. Sens. Actuators, B 2022, 371, 132512. |
| [102] | Lee, Y. H.; Verwilst, P.; Kim, H. S.; Ju, J.; Kim, J. S.; Kim, K. Chem. Commun. 2019, 55, 12136. |
| [103] | Shao, C.; Liu, Y.; Chen, Z.; Qin, Y.; Wang, X.; Wang, X.; Yan, C.; Zhu, H.; Zhao, J.; Qian, Y. Cell Chem. Biol. 2022, 29, 43. |
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