席夫碱型荧光探针对氨基酸化学选择性识别研究进展

doi:10.6023/cjoc202503015

有机化学 ›› 2025, Vol. 45 ›› Issue (9): 3301-3313.DOI: 10.6023/cjoc202503015 上一篇下一篇

综述与进展

席夫碱型荧光探针对氨基酸化学选择性识别研究进展

彭澳霈^a, 李扬^a, 朱园园^b^,^*(), 吴广文^a^,^*(), 古双喜^a^,^*()

^a 武汉工程大学化工与制药学院绿色化工过程教育部重点实验室&新型反应器与绿色化学工艺湖北省重点实验室武汉 430205
^b 武汉工程大学化学与环境工程学院武汉 430205

收稿日期:2025-03-16 修回日期:2025-04-18 发布日期:2025-05-15
基金资助:
国家自然科学基金(22377097); 国家自然科学基金(22307036); 国家自然科学基金(22074114); 湖北省自然科学基金(2020CFB623); 湖北省自然科学基金(2021CFB556); 磷资源开发利用教育部工程研究中心(LCX202305)

Advances in Chemoselective Recognition of Amino Acids by Schiff Base Fluorescent Probes

Aopei Peng^a, Yang Li^a, Yuanyuan Zhu^b^,^*(), Guangwen Wu^a^,^*(), Shuangxi Gu^a^,^*()

^a Key Laboratory for Green Chemical Process of Ministry of Education & Hubei Key Laboratory of Novel Reactor and Green Chemical Technology, School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430205
^b School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205

Received:2025-03-16 Revised:2025-04-18 Published:2025-05-15
Contact: *E-mail: yyzhu531@163.com; wuguangwen_028@163.com; shuangxigu@163.com
Supported by:
National Natural Science Foundation of China(22377097); National Natural Science Foundation of China(22307036); National Natural Science Foundation of China(22074114); Natural Science Foundation of Hubei Province(2020CFB623); Natural Science Foundation of Hubei Province(2021CFB556); Engineering Research Center of Phosphorus Resources Development and Utilization of Ministry of Education(LCX202305)

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摘要/Abstract

氨基酸作为组成蛋白质的基本单元, 是构成生命的基本砌块. 不同结构的氨基酸在生命体内发挥着各自重要的功能. 另外, 氨基酸也是食品药品工业、功能材料及有机合成的重要原料. 对20种常见氨基酸的精准化学选择性识别是一项意义重大的研究工作. 含C=N双键的席夫碱结构具有特有的碱性、共轭性、与金属的强配位性以及强的氢键形成能力, 在荧光探针分子的构建中具有独特的优势. 综述了近十年席夫碱结构的荧光探针对氨基酸化学选择性识别的研究进展, 包括探针分子结构特征、识别机制、应用潜能等, 并总结分析了目前氨基酸精准识别研究的难点, 以及要突破的科学问题.

关键词: 席夫碱, 氨基酸, 荧光探针, 化学选择性识别

Amino acids, as the fundamental building blocks of proteins, are essential components of life. Different amino acids, with their unique structures, play vital roles in biological systems. Additionally, amino acids serve as important raw materials in the food and pharmaceutical industries, functional materials, and organic synthesis. The precise chemoselective recognition of the 20 common amino acids represents a highly significant research endeavor. Schiff base structures, characterized by the C=N double bond, possess unique properties such as alkalinity, conjugation, strong metal coordination capability, and hydrogen bond formation capacity, rendering them particularly advantageous for constructing fluorescent probes. The research progress over the past decade on Schiff base-based fluorescent probes for the chemoselective recognition of amino acids is summarized, including the structural features of the probes, recognition mechanisms, and potential applications. Furthermore, the current challenges in the precise recognition of amino acids are analyzed and the key scientific issues that require further exploration are highlighted.

Key words: Schiff base, amino acid, fluorescent probe, chemoselective recognition

引用此文

彭澳霈, 李扬, 朱园园, 吴广文, 古双喜. 席夫碱型荧光探针对氨基酸化学选择性识别研究进展[J]. 有机化学, 2025, 45(9): 3301-3313.

Aopei Peng, Yang Li, Yuanyuan Zhu, Guangwen Wu, Shuangxi Gu. Advances in Chemoselective Recognition of Amino Acids by Schiff Base Fluorescent Probes[J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3301-3313.

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图/表 15

图1. 荧光探针1~5的分子结构及对氨基酸的荧光响应[31-33]

Figure 1. Molecular structures of probes 1~5, and the fluorescence response toward amino acids[31-33] Among (a), (b), (c), and (e), F-F0 represents the increment in the fluorescence response intensity of the probe to the amino acids, where F0 and F are the fluorescence intensity of probe before and after interaction with the amino acids. (d) shows the fluorescence spectra of probe 4 for 0~2 mmol/L Arg.

图2. (a)探针6的分子结构; (b)探针6与各种氨基酸作用后在自然光下的照片; (c)探针6对半胱氨酸(0~100 μmol/L)的荧光光谱; (d)探针6的荧光响应强度对低浓度半胱氨酸的(0到10 μmol/L)线性相关性[35]

Figure 2. (a) Molecular structure of probe 6; (b) Photographs of probe 6 treated by several amino acids and irradiated under natural light; (c) Fluorescence spectra of probe 6 after its interaction with Cys (0~100 μmol/L); (d) The linear relationship between the fluorescence intensity of probe 6 and low concentrations of Cys (0~10 μmol/L)[35]

图3. (a)探针7-Cu2＋与Cys的作用机理; (b)探针7-Cu2＋对氨基酸的荧光响应; (c)探针7-Cu2＋对MCF-7细胞成像[孵育7-Cu2＋ 30 min(上); 经过硫醇封闭试剂NEM孵育后再孵育7-Cu2＋ 30 min(下)[36]

Figure 3. (a) Interaction mechanism of probe 7-Cu2＋with Cys; (b) Fluorescence response of probe 7-Cu2＋to amino acids; (c) Imaging of MCF-7 cells with probe 7-Cu2＋ (incubation with 7-Cu2＋for 30 minutes (top); incubation with thiol-blocking reagent NEM followed by incubation with 7-Cu2＋for 30 min (bottom)[36]

图4. (a)探针8的分子结构及与Cys的作用机理; (b) 8＋Cu2＋对不同量Cys的UV-Vis吸收光谱; (c) 8＋Cu2＋对不同量Cys的荧光光谱; (d) HeLa细胞中8＋Cu2＋对Cys的荧光成像[(A1)~(A3) 0.5 mmol/L NEM预孵育30 min的HeLa细胞共聚焦荧光图像; (D1)~(D3) HeLa细胞用0.5 mmol/L NEM预孵育, 然后用8-Cu2＋(20 μmol/L)处理30 min; (E1)~(E3) HeLa细胞用0.5 mmol/L NEM预孵育30 min, 然后用8-Cu2＋(20 μmol/L)和Cys(0.1 mmol/L)处理15 min[37]]

Figure 4. (a) Molecular structure of probe 8 and its interaction mechanism with Cys; (b) UV-Vis absorption spectra of 8＋Cu2＋with different equivalents of Cys; (c) Fluorescence spectra of 8＋Cu2＋with different equivalents of Cys; (d) Fluorescence imaging of Cys in HeLa cells using 8＋Cu2＋ ((A1)~(A3) Confocal fluorescence images of HeLa cells pre-incubated with 0.5 mmol/L NEM for 30 min; (D1)~(D3) HeLa cells pre-incubated with 0.5 mmol/L NEM and then treated with 8-Cu2＋(20 μmol/L) for 30 min; (E1)~(E3) HeLa cells pre-incubated with 0.5 mmol/L NEM for 30 min and then treated with 8-Cu2＋(20 µmol/L) and Cys (0.1 mmol/L) for 15 min[37])

图5. (a)探针9的分子结构及在Cu2＋参与条件下对Cys的识别机制; (b)~(c)探针9-Cu2＋分别与Cys及其它8种氨基酸和9种不同阴离子作用后的UV-Vis吸收光谱和荧光光谱[38]

Figure 5. (a) Molecular structure of probe 9 and its recognition mechanism for Cys in the presence of Cu2＋; (b)~(c) UV-Vis absorption spectra and fluorescence spectra of probe 9-Cu2＋upon interaction with Cys, eight other amino acids, and nine different anions[38]

图6. (a)探针10的分子结构及与Zn2＋离子的作用模式; (b)探针10对不同金属离子的荧光响应; (c) 10＋Zn2＋对不同氨基酸的荧光响应[39]

Figure 6. (a) Molecular structure of probe 10 and its interaction mode with Zn2＋ions; (b) Fluorescence response of probe 10 to different metal ions; (c) Fluorescence response of 10＋Zn2＋to different amino acids[39]

图7. (a)探针11的分子结构; (b)在Zn2＋存在条件下探针11对20种氨基酸(包括Lys)的荧光响应; (c)探针11＋Zn2＋与20种氨基酸作用后分别在自然光下和紫外灯照射下的照片[41]

Figure 7. (a) Molecular structure of probe 11; (b) Fluorescence response of probe 11 to 20 amino acids (including Lys) in the presence of Zn2＋; (c) Photographs of probe 11＋Zn2＋respectively treated by 20 amino acids then irradiated under natural light and UV light[41]

Figure 8. (a)探针12与Phe的作用模式; (b)探针12对Al3＋离子的选择性荧光增强; (c)探针12对Phe的选择性荧光淬灭[43] (a) Interaction mode of probe 12 with Phe; (b) Selective fluorescence 增强 of probe 12 toward Al3＋ions; (c) Selective fluorescence quenching of probe 12 toward Phe[43]

图9. (a)探针13的分子结构; (b)探针13与金属离子作用后溶液颜色的变化; (c) 13-Cu2＋复合物对8种不同结构氨基酸的荧光响应; (d) 13-Cu2＋复合物与8种不同结构氨基酸作用后的溶液照片[45]

Figure 9. (a) Molecular structure of probe 13; (b) Color changes of probe 13 after interaction with metal ions; (c) Fluorescence response of the 13-Cu2＋complex to 8 amino acids; (d) Photographs of the 13-Cu2＋complex solution after interaction with 8 amino acids[45]

图10. 探针14的分子结构及与Trp的作用模式; (b)~(c)探针14对不同氨基酸的UV-Vis吸收光谱和荧光光谱[46]

Figure 10. (a) Molecular structure of probe 14 and its interaction mode with Trp; (b)~(c) UV-Vis absorption spectra and fluorescence spectra of probe 14 with different amino acids[46]

图11. 探针15的分子结构及与Ser之间的电荷转移, 探针15对Ser的荧光响应[48]

Figure 11. Molecular structure of probe 15 and its charge transfer with Ser, and the fluorescence response of probe 15 to Ser[48]

图12. 化合物16和17的合成路线[51]

Figure 12. Synthetic routes of compounds 16 and 17[51]

图13. (a)探针17-Al3＋对13种氨基酸(包括Glu)的荧光响应; (b)探针17、17-Al3＋和17-Al3＋-Glu在MDA-MB-231乳腺癌细胞中的共聚焦荧光成像(从左至右依次是10 µmol/L的DCFH-DA、DAPI及DAPI＋DCFH-DA染色定位)[51]

Figure 13. (a) Fluorescence response of probe 17-Al3＋to 13 amino acids (including Glu); (b) Confocal fluorescence imaging of probe 17, 17-Al3＋, and 17-Al3＋-Glu in MDA-MB-231 breast cancer cells, showing staining localization with 10 µmol/L DCFH-DA, DAPI, and DAPI＋DCFH-DA from left to right[51]

图14. 化合物17与Al3＋、复合物17-Al3＋与L-Glu的作用机制; 17-Al3＋与L-Glu复合物的分子模型及HOMO和LUMO轨道电荷分布及能级值(Hartree理论水平)[51]

Figure 14. Interaction mechanism of compound 17 with Al3＋ and the complex 17-Al3＋ with L-Glu; molecular model of the 17-Al3＋- L-Glu complex along with the charge distribution of HOMO and LUMO orbitals and their energy level values (Hartree level of theory)[51]

氨基酸		探针	荧光响应	检测限	溶剂	pH	金属离子	识别机理
酸性	Glu	17^[51]	增强	185.0 nmol/L	EtOH/H₂O (V/V=1/4)	7.0	Al^3＋	C=N、氨基酸的氨基和羰基与Al^3＋的共配位作用
碱性	Arg	1^[31]	增强		DMSO/H₂O (V/V=1/1)	7.0	No	与Arg的作用改变了C=N与OH之间氢键上电子转移
		2^[32]	增强		DMSO/H₂O (V/V=1/1)	7.0	No	与Arg作用后C=N与NO₂之间氢键变化
		3^[33]	增强		DMSO/H₂O (V/V=1/1)	7.0	No	与Arg的作用改变了C=N与OH之间氢键上电子转移
		4^[33]	无响应		DMSO/H₂O (V/V=1/1)	7.0	No
		5^[33]	增强		DMSO/H₂O (V/V=1/1)	7.0	No	与Arg的作用改变了C=N与OH之间氢键上电子转移
		11^[41]	增强	13.07 nmol/L	THF/H₂O	7.0	Zn^2＋	C=N、Arg的氨基和羧基与Zn^2＋的共配位作用, C=N与Arg胍基质子氢键作用
		16^[51]	增强	148.0 nmol/L	EtOH/H₂O (V/V=1/4)	7.0	Cu^2＋	C=N、Arg的氨基和羧基与Cu^2＋的共配位作用
	Lys	11^[41]	增强	12.53 nmol/L	H₂O/1.25% THF	7.0	Zn^2＋	C=N、Lys的氨基、羧基与Zn^2＋的共配位作用, C=N与Lys氨基质子氢键作用
非极性	Phe	12^[43]	淬灭	18.45 μmol/L	MeOH/H₂O (V/V=6/4)	7.0	No	C=N、三唑环、OCH₂与Phe的氨基、羧基之间的氢键作用
	Trp	13^[45]	增强		DMSO/H₂O (V/V=9/1)	7~11	Cu^2＋	竞争配位与共配位形成三元复合物
	Trp	14^[46]	增强	130.7 μmol/L	MeOH	2~12	No	C=O、C=C与Trp的氨基、羧基之间通过氢键作用, 形成包含C=N的大环
极性	Cys	6^[35]	增强	3.6 nmol/L	CH₃CN-PBS (V/V=1/2)	7.2	No	探针醛基与Cys巯基发生环化反应后通过分子内氢键形成五元环, 抑制C=N异构化诱导的荧光淬灭
		7^[36]	增强	9 μmol/L	HEPES buffer/1% MeCN	7.4	Cu^2＋	Cys对Cu^2＋的竞争配位, C=N水解释放荧光素
		8^[37]	增强	0.64 nmol/L	PBS buffer	7.4	Cu^2＋	探针的C=N, C=O, OH与Cu²的配位作用淬灭荧光, Cys对Cu^2＋的竞争配位, 释放探针分子, 荧光恢复
		9^[38]	淬灭	1.2 μmol/L	MeOH/H₂O (V/V=3/7)	7.0	Cu^2＋	Cys对Cu^2＋的竞争配位, 释放罗丹明分子且使其内酰胺环重新形成, 荧光淬灭
		10^[39]	淬灭	1.23 μmol/L	MeCN/H₂O (V/V=8/2)	7.0	Zn^2＋	Cys对Zn^2＋的竞争配位, 释放探针分子
	Ser	15^[48]	增强	1.74 nmol/L	DMF	7.0	No	Ser与探针分子之间的电荷转移

氨基酸		探针	荧光响应	检测限	溶剂	pH	金属离子	识别机理
酸性	Glu	17^[51]	增强	185.0 nmol/L	EtOH/H₂O (V/V=1/4)	7.0	Al^3＋	C=N、氨基酸的氨基和羰基与Al^3＋的共配位作用
碱性	Arg	1^[31]	增强		DMSO/H₂O (V/V=1/1)	7.0	No	与Arg的作用改变了C=N与OH之间氢键上电子转移
		2^[32]	增强		DMSO/H₂O (V/V=1/1)	7.0	No	与Arg作用后C=N与NO₂之间氢键变化
		3^[33]	增强		DMSO/H₂O (V/V=1/1)	7.0	No	与Arg的作用改变了C=N与OH之间氢键上电子转移
		4^[33]	无响应		DMSO/H₂O (V/V=1/1)	7.0	No
		5^[33]	增强		DMSO/H₂O (V/V=1/1)	7.0	No	与Arg的作用改变了C=N与OH之间氢键上电子转移
		11^[41]	增强	13.07 nmol/L	THF/H₂O	7.0	Zn^2＋	C=N、Arg的氨基和羧基与Zn^2＋的共配位作用, C=N与Arg胍基质子氢键作用
		16^[51]	增强	148.0 nmol/L	EtOH/H₂O (V/V=1/4)	7.0	Cu^2＋	C=N、Arg的氨基和羧基与Cu^2＋的共配位作用
	Lys	11^[41]	增强	12.53 nmol/L	H₂O/1.25% THF	7.0	Zn^2＋	C=N、Lys的氨基、羧基与Zn^2＋的共配位作用, C=N与Lys氨基质子氢键作用
非极性	Phe	12^[43]	淬灭	18.45 μmol/L	MeOH/H₂O (V/V=6/4)	7.0	No	C=N、三唑环、OCH₂与Phe的氨基、羧基之间的氢键作用
	Trp	13^[45]	增强		DMSO/H₂O (V/V=9/1)	7~11	Cu^2＋	竞争配位与共配位形成三元复合物
	Trp	14^[46]	增强	130.7 μmol/L	MeOH	2~12	No	C=O、C=C与Trp的氨基、羧基之间通过氢键作用, 形成包含C=N的大环
极性	Cys	6^[35]	增强	3.6 nmol/L	CH₃CN-PBS (V/V=1/2)	7.2	No	探针醛基与Cys巯基发生环化反应后通过分子内氢键形成五元环, 抑制C=N异构化诱导的荧光淬灭
		7^[36]	增强	9 μmol/L	HEPES buffer/1% MeCN	7.4	Cu^2＋	Cys对Cu^2＋的竞争配位, C=N水解释放荧光素
		8^[37]	增强	0.64 nmol/L	PBS buffer	7.4	Cu^2＋	探针的C=N, C=O, OH与Cu²的配位作用淬灭荧光, Cys对Cu^2＋的竞争配位, 释放探针分子, 荧光恢复
		9^[38]	淬灭	1.2 μmol/L	MeOH/H₂O (V/V=3/7)	7.0	Cu^2＋	Cys对Cu^2＋的竞争配位, 释放罗丹明分子且使其内酰胺环重新形成, 荧光淬灭
		10^[39]	淬灭	1.23 μmol/L	MeCN/H₂O (V/V=8/2)	7.0	Zn^2＋	Cys对Zn^2＋的竞争配位, 释放探针分子
	Ser	15^[48]	增强	1.74 nmol/L	DMF	7.0	No	Ser与探针分子之间的电荷转移

表1. 化学选择性识别氨基酸的席夫碱型荧光探针汇总

Table 1. Summary of Schiff-base fluorescence probes for chemoselective recogniton on amino acids

表1. 化学选择性识别氨基酸的席夫碱型荧光探针汇总

Table 1. Summary of Schiff-base fluorescence probes for chemoselective recogniton on amino acids

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席夫碱型荧光探针对氨基酸化学选择性识别研究进展

Advances in Chemoselective Recognition of Amino Acids by Schiff Base Fluorescent Probes

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