监测微环境理化性质和活性硫物质的萘酰亚胺衍生物光学探针研究进展

doi:10.6023/cjoc202205009

摘要/Abstract

萘酰亚胺衍生物具有出色的光物理特性, 已被设计为光学探针并应用于各种生物学场景. 作为生物学中重要的微环境和活性硫物质在生物系统中发挥着重要作用, 有必要对其进行高效的检测. 综述了萘酰亚胺衍生物探针对微环境和活性硫物质的检测. 从pH值、粘度、极性和温度四个方面对微环境的检测进行阐述, 讨论了探针的设计方案和各类荧光性能的比较. 从检测策略角度把机制分为亲核取代策略、亲核加成策略、取代基的还原策略、重金属置换策略和其他策略, 对活性硫物质进行论述, 并对这些探针的各类荧光性能进行汇总与比较. 最后, 描述了这类探针的设计和实际应用中的一些不足, 并对这一领域未来前景进行了展望.

关键词: 萘酰亚胺衍生物, 微环境, 活性硫物质, 光学探针, 光物理

Naphthalimide derivatives have been designed as optical probes and applied in various biological scenarios due to their excellent photophysical properties. As an important microenvironment and active sulfur substance in biology plays an important role in biological system, it is necessary to detect it efficiently. The detection of naphthalimide derivatives for microenvironment and active sulfur substances is reviewed. The detection of microenvironment is described from four aspects of pH value, viscosity, polarity and temperature, and the design scheme of the probe and the comparison of all kinds of fluorescence properties are discussed. From the point of view of detection strategy, the mechanism is divided into nucleophilic substitution strategy, nucleophilic addition strategy, substituent reduction strategy, heavy metal replacement strategy and other strategies, and the fluorescence properties of these probes are summarized and compared. Finally, some shortcomings in the design and practical application of this kind of probe are described, and the future prospect of this field is prospected.

Key words: naphthalimide derivatives, microenvironment, active sulfur substances, optical probes, photophysics

引用此文

夏鹏鹏, 陈江太, 施高凡, 张蒙蒙, 尧婉辰, 林祥德, 曾冬冬. 监测微环境理化性质和活性硫物质的萘酰亚胺衍生物光学探针研究进展[J]. 有机化学, 2022, 42(11): 3620-3639.

Pengpeng Xia, Jiangtai Chen, Gaofan Shi, Mengmeng Zhang, Wanchen Yao, Xiangde Lin, Dongdong Zeng. Research Progress of Naphthalimide Derivatives Optical Probes for Monitoring Physical and Chemical Properties of Microenvironment and Active Sulfur Substances[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3620-3639.

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Probe	λ_ex/nm	λ_em/nm	pK_a	pH response	Mechanism	Target	Ref.
NA01(1) NA01(2) NA01(3)	405	517	5.98 5.90 6.83	4.5~7.5	PeT	Lysosomes	[20]
NA02	409	525	6.18±0.049	5.0~7.5	PeT	Mitochondria	[21]
NA03	430	535	—	5.0~7.0	—	Endoplasmic reticulum	[22]
NA04	405	467, 525	6.01	4.0~10.0	PeT, FRET	Intracell	[23]
NA05	462	550, 580	5.23	—	PeT, FRET	Lysosomes	[24]

Probe	λ_ex/nm	λ_em/nm	pK_a	pH response	Mechanism	Target	Ref.
NA01(1) NA01(2) NA01(3)	405	517	5.98 5.90 6.83	4.5~7.5	PeT	Lysosomes	[20]
NA02	409	525	6.18±0.049	5.0~7.5	PeT	Mitochondria	[21]
NA03	430	535	—	5.0~7.0	—	Endoplasmic reticulum	[22]
NA04	405	467, 525	6.01	4.0~10.0	PeT, FRET	Intracell	[23]
NA05	462	550, 580	5.23	—	PeT, FRET	Lysosomes	[24]

Probe	λ_ex/nm	λ_em/nm	Target	Mechanism	Ref.
NA13	460	535	Lysosomes	TICT	[36]
NA14	440	560	Cell membranes	ICT	[37]
NA15	405	470	Intracell	TICT	[38]
NA16(1) NA16(2) NA16(3)	510 547 533	580 614 630	Mitochondrial	TICT	[39]
NA17	—	452, 473	—	AIE, TICT	[40]
NA18	360	526	—	TICT, FRET	[41]
NA19	580	635	Mitochondrial	TICT	[42]

Probe	λ_ex/nm	λ_em/nm	Target	Mechanism	Ref.
NA13	460	535	Lysosomes	TICT	[36]
NA14	440	560	Cell membranes	ICT	[37]
NA15	405	470	Intracell	TICT	[38]
NA16(1) NA16(2) NA16(3)	510 547 533	580 614 630	Mitochondrial	TICT	[39]
NA17	—	452, 473	—	AIE, TICT	[40]
NA18	360	526	—	TICT, FRET	[41]
NA19	580	635	Mitochondrial	TICT	[42]

Detection target	λ_ex/nm	λ_em/nm	Response time	Detection limit	Mechanism	Ref.
H₂S	450	557	—	17.4 nmol/L	ICT	[54]
H₂S	426	550	—	0.78 μmol/L	—	[55]
H₂S	405	450 550	45 min	40 nmol/L	ICT	[12]
H₂S	440	532	150 s	0.02 μmol/L	ICT	[14]
H₂S	388	452	10 s	1.5 μmol/L	PeT, ICT	[13]
H₂S	450	550	60 min	0.523 nmol/L	FRET	[56]
H₂S_n	450	548	6 min	0.15 μmol/L	ICT	[57]
H₂S_n	405	478 546	10 min	0.01 μmol/L	ICT	[58]
H₂S	—	550	—	—	PeT	[59]
H₂S	365	450	200 min	—	—	[11]
H₂S	310	550	5 min	0.23 μmol/L	PeT, ICT	[60]