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

doi:10.6023/cjoc202503015

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (9): 3301-3313.DOI: 10.6023/cjoc202503015 Previous Articles Next Articles

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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

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)

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

Cite this article

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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Fig. & Tab. 15

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.

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]

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]

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])

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]

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]

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 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]

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]

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

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

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

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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