Recent Progress of Photocage Molecules and Materials

doi:10.6023/A20080361

Acta Chimica Sinica ›› 2021, Vol. 79 ›› Issue (1): 58-70.DOI: 10.6023/A20080361 Previous Articles Next Articles

Special Issue: 分子探针、纳米生物学与生命分析化学

Review

光笼分子与材料研究进展

魏廷文^a, 江龙^a, 陈亚辉^a, 陈小强^a^,^*()

a 南京工业大学化工学院材料化学工程国家重点实验室南京 211816

投稿日期:2020-08-13 发布日期:2020-09-27
通讯作者: 陈小强

作者简介:

魏廷文, 博士, 1990年出生于江苏, 2019年12月于南京工业大学获得工学博士学位, 随后进入南京工业大学材料化学工程国家重点实验室从事博士后研究工作. 主要从事荧光染料、光控活性物质释放和荧光成像的研究.

江龙, 男, 1989年出生于湖北, 2016年毕业于湖北民族大学, 2018年加入南京工业大学陈小强课题组攻读博士学位, 研究方向为化学发光探针的设计及应用.

陈亚辉, 男, 1990年出生于河南, 2015年本科毕业于重庆理工大学, 随后加入南京工业大学陈小强课题组攻读硕士和博士学位, 研究方向为聚集诱导荧光发射(Aggregation-Induced emission, AIE)材料的设计、制备与应用.

陈小强, 博士, 现为南京工业大学教授, 博导. 2008年1月于大连理工大学获得工学博士学位; 2008年1月至2010年2月于韩国梨花女子大学从事博士后工作; 2010年3月进入南京工业大学材料化学工程国家重点实验室工作至今. 主要研究方向: 荧光染料、化学与生物传感器、酶活性荧光探针. 国家自然科学基金优秀青年基金获得者、江苏省杰出青年基金获得者、江苏省“六大人才高峰高层次人才(B类)、江苏省“青蓝工程中青年学术带头人、江苏省“333工程培养对象. 承担国家自然科学基金、江苏省杰出青年基金、省教育厅重点基金等多个项目. 以一作或通讯作者在Chem. Rev.,Chem. Soc. Rev.,Acc. Chem. Res.,Nature Protocols,J. Am. Chem. Soc.,Angew. Chem. Int. Ed.,Biomaterials,Biosensors and Bioelectronics,ACS Appl. Mater. Interfaces,Chem. Commun.,Org. Lett.,Ind. Eng. Chem. Res.等国际学术期刊发表SCI文章100余篇, 获授权专利9项. 论文被他人引用10000余次, 11篇论文入选ESI高被引论文.

* E-mail: chenxq@njtech.edu.cn; Fax: 025-83587856

基金资助:
国家自然科学基金(21722605); 国家自然科学基金(21978131); 中国博士后科学基金(2020M671462); 江苏省六人才高峰项目(XCL034)

Recent Progress of Photocage Molecules and Materials

Tingwen Wei^a, Long Jiang^a, Yahui Chen^a, Xiaoqiang Chen^a^,^*()

a State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 211816, China

Received:2020-08-13 Published:2020-09-27
Contact: Xiaoqiang Chen
Supported by:
the National Natural Science Foundation of China(21722605); the National Natural Science Foundation of China(21978131); China Postdoctoral Science Foundation(2020M671462); the Six Talent Peaks Project in Jiangsu Province(XCL034)

The photocage is a light sensitive substance for photo-controlled release, which is formed by combining the target substance with photosensitive group and other functional groups through physical and chemical methods. Under the irradiation of the specified band, the photocage releases the target substance. It is widely concerned because it can realize space-time control, which means that the time and place of release are controllable. The advantages of simple operation, easy control, strong modification ability and small body damage make it widely used in chemistry, biology, materials science and medicine. In this paper, we introduced and discussed the research progress of photocages in photo-controlled release of metal ions, gases, fluorescent substances, amino acids, peptides, enzymes, proteins, drugs and other target substances in recent 10 years.

Key words: molecular photocage, metal ion, fluorescence imaging, drug release, photo-release, biological application

Cite this article

Tingwen Wei, Long Jiang, Yahui Chen, Xiaoqiang Chen. Recent Progress of Photocage Molecules and Materials[J]. Acta Chimica Sinica, 2021, 79(1): 58-70.

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Fig. & Tab. 38

Figure 1. Structure of the photocage 1 and its photoreaction mechanism

Figure 2. (a) The photoreaction mechanism of photocages 2~8 and (b) structure of the photocage 2~8

Figure 3. (a) The photoreaction mechanism of photocages9~17 and (b) Structures of the photocages9~17

Figure 4. Structures of photocages 18, 19 and 20

Figure 5. Mechanism of photo-activated detection of zinc ions by photocage 21

Figure 6. Mechanism of photo-activated detection of H2Sn (n>1) by photocage 22

Figure 7. Mechanism of photo-activated detection of tyrosine enzyme by photocage23

Figure 8. Structure of the photocage 24 and its mechanism of regulating Fe3+

Figure 9. Structure of the photocage 25 and its mechanism of regulating Zn2+

Figure 10. The binding mode of photocage26 with Zn2+ and its mechanism of photo-controlled release Zn2+

Figure 11. The binding mode of photocage27 with Zn2+ and its mechanism of photo-controlled release Zn2+

Figure 12. The binding mode of photocages28and29 with Zn2+ and its mechanism of photo-controlled release Zn2+

Figure 13. The mechanism of photo-controlled release Zn2+ by photocages 30 and 31, and illustration of the regulation of NMDA receptors by photocages 30 and 31

Figure 14. The binding mode of photocage 32 with Ca2+ and its mechanism of photo-controlled release Ca2+

Figure 15. The binding mode of photocage 33 with Ca2+ and its mechanism of photo-controlled release Ca2+

Figure 16. The binding mode of photocages34~37 with Ca2+ and its mechanism of photo-controlled release Ca2+

Figure 17. Structure of photocage 38 and its mechanism of photo-controlled release NO

Figure 18. The schematic diagram of photocages 39 and 40 and the mechanism of their photo-controlled release NO

Figure 19. The schematic diagram of photocage41 and the mechanism of its photo-controlled release NO

Figure 20. The schematic diagram of photocage42and the mechanism of its photo-controlled release H2S

Figure 21. The schematic diagram of photocage 43 and the mechanism of its photo-controlled release H2S

Figure 22. The schematic diagram of photocage 44 and the mechanism of its photo-controlled release H2S

Figure 23. The structure of photocage 45 and schematic illustration of fluorescent probe 45P detection of photo-release CO from 45

Figure 24. (a) The structure of photocage46; (b) schematic illustration of photo-controlled release CO

Figure 25. The structure of photocage 47 and schematic illustration of photo-controlled release tryptophan

Figure 26. The structure of photocage 48 and schematic illustration of photo-controlled release N-terminal peptide

Figure 27. The synthetic route of photocage 49 and schematic illustration of photo-controlled release of C-Terminal peptide

Figure 28. The structure of photocage50 and schematic illustration of photo-controlled release G-quadruplex

Figure 29. (a) Schematic diagram of adenylate kinase with ATP and AMP; (b) the structure of HCK; (c) schematic diagram of light regulation ATP by photocage51

Figure 30. The structure of photocage 52 and schematic illustration of photo-controlled release Pt(IV) prodrug and fluorescence

Figure 31. Structure of photocage 53 and schematic illustration of photo-controlled release Vemurafenib

Figure 32. The structures of photocages 54 and 55, and schematic illustration of targeted release ciprofloxacin

Figure 33. The synthetic route of photocage 56 and schematic illustration of photo-controlled release of the doxorubicin

Figure 34. The structure of photocage 57 and schematic illustration of photo-controlled release comptothecin

Figure 35. The structure of photocage 58 and schematic illustration of photo-controlled release chlorambucil

Figure 36. The structure of photocage 59 and schematic illustration of its photo-controlled release of free radical compounds

Figure 37. The structure of photocage 60 and the mechanism of its photo-controlled release of sunscreen substance

Figure 38. (a) Structures of photocages 61, 62 and 63; (b) the mechanism of photo-controlled formaldehyde release from photocage

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光笼分子与材料研究进展

Recent Progress of Photocage Molecules and Materials

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[1]	Feida Che, Xiaoming Zhao, Xin Zhang, Qi Ding, Xin Wang, Ping Li, Bo Tang. Fluorescence Imaging of Active Molecules Associated with Depression^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1255-1264.
[2]	Hongyue Wu, Rui Guo, Hanwen Chi, Yonghe Tang, Sirui Song, Enxiang Ge, Weiying Lin. Viscosity Fluorescent Probes Based on Quinoline Group and Its Applications [J]. Acta Chimica Sinica, 2023, 81(8): 905-911.
[3]	Yongxue Li, Yu Liu. Supramolecular Secondary Assembly Based on Amphiphilic Calix[4]arenes and Its Biological Applications^★ [J]. Acta Chimica Sinica, 2023, 81(8): 928-936.
[4]	Xin Lv, Yi Wu, Boran Zhang, Wei Guo. Design, Synthesis and Photodynamic Therapy of a H₂O₂-Activatable Near Infrared Borondipyrromethene （BODIPY） Photosensitizer [J]. Acta Chimica Sinica, 2023, 81(4): 359-370.
[5]	Yanqin Huang, Lijun Li, Shupei Yang, Rui Zhang, Xingfen Liu, Quli Fan, Wei Huang. HA-AuNPs/FDF for Highly Sensitive Detection of Hyaluronidase, Tumor-targeting Fluorescence Cell Imaging and Phototherapy [J]. Acta Chimica Sinica, 2023, 81(12): 1687-1694.
[6]	Li Sun, Yajing Wang, Tao Li, Yingshu Guo, Shusheng Zhang. Au Nanocages Probes for Mitochondrial Imaging and Photothermal Damage Cells^★ [J]. Acta Chimica Sinica, 2023, 81(10): 1301-1310.
[7]	Sirui Song, Yonghe Tang, Liangguang Sun, Rui Guo, Guanfan Jiang, Weiying Lin. Development of a Novel Fluorescent Probe Based on Coumarin Fluorophore for Polarity Detection and Its Imaging Applications [J]. Acta Chimica Sinica, 2022, 80(9): 1217-1222.
[8]	Qi Wang, Hui Xia, Yanwei Xiong, Xinmin Zhang, Jie Cai, Chong Chen, Yicong Gao, Feng Lu, Quli Fan. Simple Preparation of Near-infrared-II Organic Small Molecule-based Phototheranostics by Manipulation of the Electron-donating Unit [J]. Acta Chimica Sinica, 2022, 80(11): 1485-1493.
[9]	Lixiang Pan, Yanqin Huang, Kuang Sheng, Rui Zhang, Quli Fan, Wei Huang. Applications of Hyaluronic Acid Nanomaterials in Fluorescence/Photoacoustic Imaging and Phototherapy [J]. Acta Chimica Sinica, 2021, 79(9): 1097-1106.
[10]	Tengfei Yan, Shengda Liu, Yichen Luo, Yingping Zou, Junqiu Liu. Research Progress on the Macrocycle-Derived Artificial Transmembrane Ion Channels [J]. Acta Chimica Sinica, 2021, 79(8): 999-1007.
[11]	Suhang Wang, Lingna Sun, Han Cao, Yiming Zhong, Zhengzhong Shao. Development of a Dual-drug-loaded Silk Fibroin Hydrogel and Study on Its Drugs Release Behaviors [J]. Acta Chimica Sinica, 2021, 79(8): 1023-1029.
[12]	Sang Ruoyu, Xu Xingpeng, Wang Qi, Fan Quli, Huang Wei. Near-Infrared-II Fluorescence Probes Based on Organic Small Molecules [J]. Acta Chimica Sinica, 2020, 78(9): 901-915.
[13]	Liu Yanhong, Zhang Dongxu, Mao Baodong, Huang Hui, Liu Yang, Tan Huaqiao, Kang Zhenhui. Progress in Carbon Dots from the Perspective of Quantum Dots [J]. Acta Chimica Sinica, 2020, 78(12): 1349-1365.
[14]	Guan, Xiaolin, Wang, Lin, Li, Zhifei, Liu, Meina, Wang, Kailong, Lin, Bin, Yang, Xueqing, Lai, Shoujun, Lei, Ziqiang. Preparation of Multi-stimulus Responsive Polymer Nanospheres Based on AIE Effect and Its Cell Tracing Application [J]. Acta Chimica Sinica, 2019, 77(10): 1036-1044.
[15]	Zhang Yanyan, Wu Minghao, Wu Mingjie, Guo Linpei, Cao Lin, Wu Hongyi, Zhang Xuening. Study of Fluorescence and CT Bimodal Imaging of Ultrasmall Gold Nanoclusters [J]. Acta Chim. Sinica, 2018, 76(9): 709-714.