基于N-氧化物结构Fe2＋荧光探针的研究进展

doi:10.6023/cjoc202407041

摘要/Abstract

铁离子在人体内分布广泛, 参与一系列生化反应. 细胞中的铁离子主要以Fe^2＋与Fe^3＋的形式存在, 对维持细胞正常功能发挥着重要作用. 在活细胞还原环境中, 细胞内游离铁主要以Fe^2＋离子形式存在. 游离Fe^2＋可作为芬顿反应催化剂, 使细胞内产生活性氧物种(ROS), 对细胞造成严重损伤, 引起一系列与之相关的疾病. 因此, 在生理环境中对Fe^2＋的可视化监测具有必要性, 有助于进一步了解疾病的发病机制和进展. 近年来, 已有一些研究人员致力于设计并合成具有优异光学性能并可用于体内外监测Fe^2＋的荧光探针. 其中, N-氧化物结构的荧光探针凭借其选择性强、灵敏度高及可进行原位实时成像等优势受到了研究人员的广泛关注. 针对N-氧化物类Fe^2＋荧光探针的结构、设计思路、光学性质与应用等方面进行了介绍.

关键词: Fe^2＋, N-氧化物结构, 荧光探针, 生物成像

Iron is widely distributed in the human body, participating in numerous biochemical reactions. Iron exists in the forms of Fe^2＋ and Fe^3＋ 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 Fe^2＋ ions. The labile Fe^2＋ 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 Fe^2＋ 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 Fe^2＋ 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 Fe^2＋ fluorescence probes are discussed.

Key words: Fe^2＋, N-oxide chemistry, fluorescence probe, bioimaging

引用此文

相韩悦, 魏少荫, 王玉记, 肖猱. 基于N-氧化物结构Fe^2＋荧光探针的研究进展[J]. 有机化学, 2025, 45(4): 1137-1152.

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.

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参考文献 103

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Probe	E_x/E_m/nm	Time/min	Solvent	Response mode	Co-localization
1	540/575	60	HEPES buffer	Turn-On	—
2	550/575	20	HEPES buffer (0.2% DMF)	Turn-On	Lysosome
3	550/578	60	HEPES buffer (0.2% DMF)	Turn-On	Lysosome
4	515/535	60	HEPES buffer (0.2% DMF)	Turn-On	—
5	515/535	60	HEPES buffer (0.2% DMF)	Turn-On	—
6	575/660	30	HEPES buffer	Turn-On	Endoplasmic reticulum
7	580/630	10	HEPES buffer (5% MeOH)	Turn-On	—
8	630/665	30	HEPES buffer (30% dioxane)	Turn-On	Golgi
9	490/535	30	HEPES buffer (0.2% DMSO)	Turn-On	—
10	400/515	—	HEPES buffer (5% DMSO)	Turn-On	—
11	390/460	60	HEPES buffer (0.2% DMSO)	Turn-On	—
12	540/690	15	PBS buffer (50% DMSO)	Turn-On Two-photon	—
13	480/630	5	Sodium borate buffer (pH=7.4)	Turn-On	—
14	540/700	5	HEPES buffer (40% DMSO)	Turn-On	Lipid droplet
15	400/675	5	PBS buffer (40% DMSO)	Turn-On	—
16	467/625	20	PBS buffer (30% EtOH)	Turn-On	—
17	540/720	5	PBS buffer (2.5% EtOH, 1 mmol/L CTAB)	Turn-On	Lysosome
18	362/519	10	PBS buffer	Turn-On	—
19	365/520	10	PBS buffer	Turn-On	—
20	360/515	10	PBS buffer	Turn-On	—
21	350/489	20	Tris-HCl buffer (20% DMSO)	Turn-On	—
22	295/495	30	HEPES buffer	Turn-On	Endoplasmic reticulum
23	425/603	0.67	PBS buffer (20% EtOH)	Turn-On	—
24	380/495	1	PBS buffer (20% EtOH)	Turn-On	—
25	640/671	2	DMSO (1% TFA)	Turn-Off	Lysosome
26	370/486	0.42	PBS solution (90% ACN, 10 mmol/L, v/v)	Turn-On	—
27	400/518	0.58	PBS solution (90% ACN, 10 mmol/L, v/v)	Turn-On	—
28	510/535	30	HEPES buffer	Turn-On	—
29	540/575	60	HEPES buffer (0.2% DMSO)	Turn-On	—
30	540/575	60	HEPES buffer (0.2% DMSO)	Turn-On	Cell membrane
31	430/675	30	Tris-HCl buffer (30% DMSO)	Ratiometric	—
32	395/540	30	Aqueous solution (0.5% CH₃CN)	Turn-On	—
33	450/530	50	HEPES buffer	Turn-On	—
34	456/640	10	PBS buffer (1% DMSO, 1 mmol/L CTAB)	Turn-On Two-photon	Lysosome

Probe	E_x/E_m/nm	Time/min	Solvent	Response mode	Co-localization
1	540/575	60	HEPES buffer	Turn-On	—
2	550/575	20	HEPES buffer (0.2% DMF)	Turn-On	Lysosome
3	550/578	60	HEPES buffer (0.2% DMF)	Turn-On	Lysosome
4	515/535	60	HEPES buffer (0.2% DMF)	Turn-On	—
5	515/535	60	HEPES buffer (0.2% DMF)	Turn-On	—
6	575/660	30	HEPES buffer	Turn-On	Endoplasmic reticulum
7	580/630	10	HEPES buffer (5% MeOH)	Turn-On	—
8	630/665	30	HEPES buffer (30% dioxane)	Turn-On	Golgi
9	490/535	30	HEPES buffer (0.2% DMSO)	Turn-On	—
10	400/515	—	HEPES buffer (5% DMSO)	Turn-On	—
11	390/460	60	HEPES buffer (0.2% DMSO)	Turn-On	—
12	540/690	15	PBS buffer (50% DMSO)	Turn-On Two-photon	—
13	480/630	5	Sodium borate buffer (pH=7.4)	Turn-On	—
14	540/700	5	HEPES buffer (40% DMSO)	Turn-On	Lipid droplet
15	400/675	5	PBS buffer (40% DMSO)	Turn-On	—
16	467/625	20	PBS buffer (30% EtOH)	Turn-On	—
17	540/720	5	PBS buffer (2.5% EtOH, 1 mmol/L CTAB)	Turn-On	Lysosome
18	362/519	10	PBS buffer	Turn-On	—
19	365/520	10	PBS buffer	Turn-On	—
20	360/515	10	PBS buffer	Turn-On	—
21	350/489	20	Tris-HCl buffer (20% DMSO)	Turn-On	—
22	295/495	30	HEPES buffer	Turn-On	Endoplasmic reticulum
23	425/603	0.67	PBS buffer (20% EtOH)	Turn-On	—
24	380/495	1	PBS buffer (20% EtOH)	Turn-On	—
25	640/671	2	DMSO (1% TFA)	Turn-Off	Lysosome
26	370/486	0.42	PBS solution (90% ACN, 10 mmol/L, v/v)	Turn-On	—
27	400/518	0.58	PBS solution (90% ACN, 10 mmol/L, v/v)	Turn-On	—
28	510/535	30	HEPES buffer	Turn-On	—
29	540/575	60	HEPES buffer (0.2% DMSO)	Turn-On	—
30	540/575	60	HEPES buffer (0.2% DMSO)	Turn-On	Cell membrane
31	430/675	30	Tris-HCl buffer (30% DMSO)	Ratiometric	—
32	395/540	30	Aqueous solution (0.5% CH₃CN)	Turn-On	—
33	450/530	50	HEPES buffer	Turn-On	—
34	456/640	10	PBS buffer (1% DMSO, 1 mmol/L CTAB)	Turn-On Two-photon	Lysosome