无需催化剂的光介导生物正交荧光探针实例

doi:10.6023/A25040102

化学学报 ›› 2025, Vol. 83 ›› Issue (8): 816-826.DOI: 10.6023/A25040102 上一篇下一篇

研究论文

无需催化剂的光介导生物正交荧光探针实例

赵玉强^a, 那迪^a, 和晓波^a, 朱立平^b, 周莹^b^,^*(), 曾广智^a^,^*(), 樊保敏^a^,^*()

^a 云南民族大学化学与环境学院、云南省手性功能物质研究与利用重点实验室昆明 650504
^b 云南大学化学科学与工程学院昆明 650091

投稿日期:2025-04-01 发布日期:2025-05-08
通讯作者: 周莹, 曾广智, 樊保敏
基金资助:
云南省手性功能物质研究与利用重点实验室(202402AN360010); 云南省科技厅-基础研究专项-重大项目(202401BC070018); 云南省科技厅-云南大学联合特殊项目(202201BF070001-001); 国家自然科学基金(22067019); 国家自然科学基金(22367023)

A Catalyst-Free Example of Photomediated Biological Orthogonal Fluorescence Probes

Yu-Qiang Zhao^a, Di Na^a, Xiaobo He^a, Liping Zhu^b, Ying Zhou^b^,^*(), Guang-Zhi Zeng^a^,^*(), Baomin Fan^a^,^*()

^a Yunnan Key Laboratory of Chiral Functional Substance Research and Application, School of Chemistry & Environment, Yunnan Minzu University, Kunming 650504, Yunnan, China
^b College of Chemical Science and Technology, Yunnan University, Kunming 650091, Yunnan, China

Received:2025-04-01 Published:2025-05-08
Contact: Ying Zhou, Guang-Zhi Zeng, Baomin Fan
Supported by:
Yunnan Key Laboratory of Chiral Functional Substance Research and Application(202402AN360010); Yunnan Provincial Department of Science and Technology-Basic Research-Major project(202401BC070018); Yunnan Provincial Science and Technology Department-Yunnan University Joint Special Project(202201BF070001-001); National Natural Science Foundation of China(22067019); National Natural Science Foundation of China(22367023)

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摘要/Abstract

将具有生物正交反应活性的1,2,4,5-四氮嗪基团引入到1,8-萘酰亚胺荧光团上设计合成了光介导生物正交荧光探针NATz. 光谱测试显示, NATz与trans-cyclooctene (TCO)在磷酸盐缓冲液中反应后荧光被激活, 理论计算清晰解释了NATz的猝灭机制和荧光激活机制. 最重要的是, 在不加光催化剂的条件下, 365 nm紫外光显著提高了NATz与TCO的反应速率. 高分辨质谱和反应路径计算表明, 光对生物正交反应的促进效应是通过克服NATz与TCO之间的环加成反应能垒实现的. 细胞毒性测试证明了NATz具有良好的生物相容性, 在此基础上实现了细胞和多细胞生物(秀丽隐杆线虫)水平上的光介导生物正交成像. 最后, 基于NATz的结构, 引入吗啉基因设计并合成了具有溶酶体靶向能力的生物正交荧光探针Lyso-NATz. 一系列实验证明了Lyso-NATz在保持光介导生物正交荧光成像特性的同时, 实现了对溶酶体的靶向作用.

关键词: 光介导, 生物正交化学, 荧光探针, 四氮嗪, 溶酶体靶向

A bioorthogonal fluorescent probe, NATz, was meticulously crafted by incorporating 1,8-naphthalimide onto a 1,2,4,5-tetrazine group endowed with bioorthogonal reaction activity. The spectral examination revealed the activation of fluorescence following the interaction between NATz and trans-cyclooctene (TCO) in a phosphate buffer saline (PBS) solution. Systematic time-dependent density functional theory (TDDFT) calculations elucidate that the fluorescence quenching and activation of NATz are predominantly mediated by a photoinduced electron transfer (PET) mechanism, involving excited-state charge redistribution between the tetrazine moiety and naphthalimide fluorophore. Significantly, the UV light at 365 nm substantially accelerated the reaction rate between NATz and TCO. High-resolution mass spectrometry (HRMS) confirmed that 365 nm UV irradiation exclusively promotes inverse electron-demand Diels-Alder (IEDDA) adduct formation, with no detectable photodegradation byproducts under the experimental conditions. Integrated with reaction pathway calculations, these data conclusively establish that light enhances the bioorthogonal IEDDA reaction between 1,2,4,5-tetrazine (NATz) and TCO by photon energy transfer surpassing the reaction energy barrier. The MTS cytotoxicity assay revealed that NATz, even at elevated concentrations (40 μmol/L), maintained cell proliferation inhibition rates below 30% across five cell lines (LO2, BEAS-2B, HeLa, HepG2, and A549), thereby confirming its favorable biocompatibility. Laser scanning confocal microscopy (LSCM) confirms NAtz's suitability for light-activated bioimaging applications, achieving cellular-resolution visualization in single cells and intact multicellular organisms (e.g., Caenorhabditis elegans). In order to further verify the applicability of light-mediated bioorthogonal fluorescent probes, a lysosome-targeted morpholine group was introduced on the basis of NATz, and the lysosome-targeted bioorthogonal fluorescent probe Lyso-NATz was prepared. The spectral test results indicated that after the introduction of the morpholine group, this series of probes still maintained the characteristics of photomediated bioorthogonal imaging. Meanwhile, the cytotoxicity experiment proved that the introduction of the morpholine group did not affect its biocompatibility. Finally, Lyso-NATz was used to achieve photomediated bioorthogonal fluorescence imaging targeting lysosomes at the cellular level.

Key words: photomediated, bioorthogonal chemistry, fluorescence probe, tetrazine, targeting to lysosomes

引用此文

赵玉强, 那迪, 和晓波, 朱立平, 周莹, 曾广智, 樊保敏. 无需催化剂的光介导生物正交荧光探针实例[J]. 化学学报, 2025, 83(8): 816-826.

Yu-Qiang Zhao, Di Na, Xiaobo He, Liping Zhu, Ying Zhou, Guang-Zhi Zeng, Baomin Fan. A Catalyst-Free Example of Photomediated Biological Orthogonal Fluorescence Probes[J]. Acta Chimica Sinica, 2025, 83(8): 816-826.

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图/表 8

图式1. NATz的合成路线示意图

Scheme 1. Schematic representation of the synthesis route of NATz

图1. (a)、(c)实测(实线)和模拟的(虚线)紫外光谱; NATz (b)和NATz-TCO (d)激发态的空穴电荷分布和前沿轨道贡献, 其中蓝色等值面代表空穴, 绿色等值面代表电荷. (e)与TCO反应后的NATz荧光光谱(实线)和激发光谱(虚线). (f)不同溶剂中与TCO反应后的NATz荧光强度(H->L表示HOMO能级至LUMO能级的跃迁)

Figure 1. (a), (c) The measured (solid line) and calculated (dashed line) UV spectra; The hole charge distribution and frontier orbital contributions for the fourth excited state of NATz (b) and NATz-TCO (d) with blue isosurfaces representing holes and green isosurfaces representing charges. (e) The fluorescence spectrum (solid line) and excitation spectrum (dashed line) of NATz after the reaction with TCO. (f) The fluorescence intensity of NATz after reacting with TCO in different solvents (H->L represents the transition from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO))

图2. (a)通过前沿轨道能级差预测PET过程的概念图解; (b) NATz轨道能级差和电子分布示意图; (c) NATz激发态信息和前线轨道电子的相应分布; (d) NATz-TCO的激发态信息以及相应的前线轨道电子分布

Figure 2. (a) Conceptual illustration predicting the PET process through the energy level difference of frontier orbitals; (b) Schematic diagram depicting the orbital energy level difference and electron distribution of NATz; (c) Depiction of NATz's excited state information and corresponding distributions of frontier orbital electrons; (d) Excited state information of NATz-TCO along with corresponding distributions of frontier orbital electrons

图3. (a)~(c)不同条件下NATz荧光光谱; (d) 不同条件下450 nm处NATz的荧光强度. 1: NATz; 2: NATz＋TCO (1 h); 3: NATz＋TCO (24 h); 4: NATz＋TCO (48 h); 5: NATz＋TCO (72 h); 6: NATz＋TCO (1 h)＋UV (10 min); 7: NATz＋UV (10 min)

Figure 3. (a)~(c) Fluorescence spectra of NATz under diverse conditions; (d) Fluorescence intensity at 450 nm under diverse conditions. 1: NATz, 2: NATz＋TCO (1 h), 3: NATz＋TCO (24 h), 4: NATz＋TCO (48 h), 5: NATz＋TCO (72 h), 6: NATz＋TCO (1 h)＋UV (10 min), 7: NATz＋UV (10 min)

图4. (a) TCO和四氮嗪衍生物之间光介导反应的概念图; (b) NATz的高分辨率质谱; (c)与TCO反应1 h后NATz的高分辨率质谱; (d) NATz与TCO反应1 h加紫外线照射10 min后的高分辨率质谱

Figure 4. (a) Conceptual diagram depicting the photocatalytic reaction between TCO and tetrazine; (b) High-resolution mass spectrum of NATz; (c) High-resolution mass spectrum of NATz after one hour of reaction with TCO; (d) High-resolution mass spectrum of NATz after one hour of reaction with TCO followed by 10 min of UV light exposure

图5. (a)四嗪和TCO之间的IEDDA反应路径示意图; (b)四氮嗪衍生物与TCO环加成反应的过渡态和反应途径; (c)四氮嗪衍生物和TCO环加成过程中不同中间体的能量分布

Figure 5. (a) Illustration of the IEDDA reaction pathway between tetrazine and TCO; (b) Transition states and reaction pathway for the cycloaddition reaction between tetrazine and TCO; (c) Energy profiles of different intermediates in the cycloaddition process of tetrazine and TCO

图6. (a) NATz在HepG2细胞内的光介导正交成像; (b)秀丽隐杆线虫体内NATz的光介导正交成像; (c) NATz (40 μmol/L)的细胞毒性评价; (d)图(a)中细胞内平均荧光强度; (e)图(d)中线虫体内的平均荧光强度. 比例尺: 10 μm或200 μm. **: P<0.01, ***: P<0.001

Figure 6. (a) Photocatalytic orthogonal imaging of NATz within HepG2 cells; (b) Photocatalytic orthogonal imaging of NATz inside the body of elegant hidden worms (C. elegans); (c) Cellular toxicity assessment of NATz (40 μmol/L); (d) Average fluorescence intensity within cells as depicted in (a); (e) Average fluorescence intensity within worms as shown in (d). scale bar: 10 μm/200 μm. **: P<0.01, ***: P<0.001

图7. (a) Lyso-NATz的合成路线; (b) Lyso-NATz光介导催化激活荧光光谱; (c) Lyso-NATz细胞毒性评价; (d) Lyso-NATz与溶酶体标记物的共定位成像(LysoTracker Red). 比例尺: 10 μm

Figure 7. (a) Synthesis pathway of Lyso-NATz; (b) Photocatalytic orthogonal fluorescence spectra of Lyso-NATz; (c) Evaluation of cellular toxicity for Lyso-NATz; (d) Co-localization imaging of Lyso-NATz with lysosomal markers (LysoTracker Red). scale bar: 10 μm

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无需催化剂的光介导生物正交荧光探针实例

A Catalyst-Free Example of Photomediated Biological Orthogonal Fluorescence Probes

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