有机光敏剂结构与性能调控及其光诊疗应用★

doi:10.6023/A23050243

化学学报 ›› 2023, Vol. 81 ›› Issue (11): 1642-1662.DOI: 10.6023/A23050243 上一篇下一篇

所属专题：庆祝《化学学报》创刊90周年合辑

综述

有机光敏剂结构与性能调控及其光诊疗应用^★

闫英红^a, 梁平兆^a, 邹杨^b, 袁林^a^,^*(), 彭孝军^b, 樊江莉^b^,^*(), 张晓兵^a^,^*()

a 湖南大学化学化工学院化学生物传感与计量学国家重点实验室长沙 410082
b 大连理工大学化工学院精细化工国家重点实验室智能材料化工前沿科学中心辽宁大连 116024

投稿日期:2023-05-20 发布日期:2023-07-17

作者简介:

闫英红, 湖南大学化学化工学院在读硕士研究生, 导师是张晓兵教授与尹霞教授, 研究方向是近红外小分子荧光探针对肿瘤的成像与治疗.

梁平兆, 湖南大学化学化工学院在读博士研究生, 导师是张晓兵教授. 研究方向是用于肿瘤治疗的可激活光学探针的设计与应用.

邹杨, 大连理工大学化工学院在读博士研究生, 导师是樊江莉教授. 研究方向是有机光敏染料设计及其在肿瘤光疗中的应用.

袁林, 博士, 现任湖南大学化学与化工学院教授、博士生导师. 主要从事荧光染料性能调控、小分子荧光探针设计及应用方向的研究.

彭孝军, 博士, 大连理工大学化工学院教授, 中国科学院院士. 国家杰出青年基金获得者, 教育部“长江学者”特聘教授、国务院学科评议组成员. 主要从事精细化工研究, 包括高性能染料、荧光探针、光学材料, 在数码彩色打印等领域获得产业化应用.

樊江莉, 博士, 现任大连理工大学化工学院教授, 博士生导师. 国家杰出青年基金获得者, 国家“万人计划”科技创新领军人才. 主要从事精细化工研究, 包括高性能染料、光学材料等, 在血液细胞分析系统等领域获得产业化应用.

张晓兵, 博士, 湖南大学教授, 现任化学化工学院院长、化学生物传感与计量学国家重点实验室副主任. 长江学者特聘教授、国家杰出青年科学基金获得者、国家“万人计划”科技创新领军人才. 研究方向主要集中在高性能荧光探针开发及其生物医学应用.

^★庆祝《化学学报》创刊90周年.

基金资助:
国家自然科学基金重点项目(22234003)

Structure and Properties Regulation of Organic Photosensitizers and Application in Photodiagnosis and Treatment^★

Yinghong Yan^a, Pingzhao Liang^a, Yang Zou^b, Lin Yuan^a(), Xiaojun Peng^b, Jiangli Fan^b(), Xiaobing Zhang^a()

a State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
b State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, College of Chemical Engineering, Dalian University of Technology, Dalian 116024

Received:2023-05-20 Published:2023-07-17
Contact: *E-mail: lyuan@hnu.edu.cn; fanjl@dlut.edu.cn; xbzhang@hnu.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
Key Program of National Natural Science Foundation of China(22234003)

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摘要/Abstract

光动力治疗(Photodynamic Therapy, PDT)作为一种新兴的高效治疗方式, 具有毒性低、非侵入性和可控等优点, 已被广泛用于增生性皮肤疾病和肿瘤等疾病治疗. 然而, 已开发的PDT光敏剂在实际生物应用中仍面临诸多挑战, 如: 肿瘤乏氧环境降低治疗效果, 光敏剂靶向性差易造成对正常组织的损伤. 为了解决上述问题, 研究者们开发了许多有效改善有机光敏剂治疗效果的方法. 在此, 主要综述了有机光敏剂的结构与性能调控策略. 此外, 对有机光敏剂在抗肿瘤、抗菌治疗以及余辉成像中的应用进行了介绍. 最后, 对有机小分子光敏剂的设计策略进行了总结与展望, 以期促进该领域的发展.

关键词: 光敏剂, 有机染料, 光动力治疗, 诊疗, 成像

Photodynamic therapy (PDT), as an efficient treatment method, has the advantages of low toxicity, non-invasiveness and controllability, which has been widely used in the treatment of proliferative skin diseases and tumors. However, the reported PDT photosensitizers still face many challenges in practical biological applications, such as the efficacy of PDT is significantly reduced by the tumor hypoxic environment; the poor targeting of photosensitizers can easily cause damage to normal tissues. In order to solve the above problems, researchers have proposed many effective strategies to improve the therapeutic efficacy of organic photosensitizers. Herein, the structure and property regulation strategies of organic photosensitizers are reviewed. In addition, the practical applications of photosensitizers in antitumor, antibacterial therapy, and afterglow imaging are introduced. In the end, the design strategies of organic small molecule photosensitizers are summarized and prospected in order to promote the development of this field.

Key words: photosensitizers, organic dyes, photodynamic therapy, theranostics, imaging

引用此文

闫英红, 梁平兆, 邹杨, 袁林, 彭孝军, 樊江莉, 张晓兵. 有机光敏剂结构与性能调控及其光诊疗应用^★[J]. 化学学报, 2023, 81(11): 1642-1662.

Yinghong Yan, Pingzhao Liang, Yang Zou, Lin Yuan, Xiaojun Peng, Jiangli Fan, Xiaobing Zhang. Structure and Properties Regulation of Organic Photosensitizers and Application in Photodiagnosis and Treatment^★[J]. Acta Chimica Sinica, 2023, 81(11): 1642-1662.

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图/表 21

图1. I型、II型和III型PDT机制的示意图

Figure 1. Schematic illustration of type I, type II, and type III PDT mechanisms

图2. 有机光敏剂结构与性能调控及其光诊疗应用概括图

Figure 2. Summary of structure and property regulation of organic photosensitizers and their application in light diagnosis and treatment

图3. 基于重原子引入策略的光敏剂1~19

Figure 3. Photosensitizers 1~19 based on heavy atom introduction strategy

图4. (a) SOCT-ISC的机制示意图. (b)基于SOCT-ISC机制的光敏剂20~30

Figure 4. (a) Schematic illustration of SOCT-ISC mechanism. (b) Photosensitizers 20~30 based on the SOCT-ISC mechanism

图5. 基于REISC机制的光敏剂31~35

Figure 5. Photosensitizers 31~35 based on REISC mechanism

图6. (a) D-A型光敏剂36~40. (b)引入不同供-受体的AIE光敏剂41~44. (c)基于BODIPY骨架的光敏剂45~49

Figure 6. (a) D-A type photosensitizers 36~40. (b) AIE photosensitizers 41~44 containing different donor-receptors. (c) Photosensitizers 45~49 based on BODIPY skeleton

图7. (a)聚合增强光敏效应的机制图. (b)聚合物光敏剂50~55

Figure 7. (a) Mechanism diagram of polymerization enhancing photosensitivity effect. (b) Polymer photosensitizers 50~55

图8. 引入不同供受体的光敏剂56~60

Figure 8. Photosensitizers 56~60 containing different donor-receptors

图9. (a) J聚集红移波长的光敏剂61~62. (b)双光子激发的光敏剂63~65. (c)双光子激发示意图

Figure 9. (a) Photosensitizers 61~62 whose wavelength is redshifted due to J aggregation. (b) Photosensitizers 63~65 using two photon excitation. (c) Schematic diagram of two-photon excitation

图10. (a) I型光敏剂66~69. (b)光敏剂70产生碳自由基的机制

Figure 10. (a) Type I photosensitizers 66~69. (b) The production mechanism of carbon free radicals of photosensitizer 70

图11. 非氧依赖型光敏剂通过光氧化水产生羟基自由基的原理图

Figure 11. Schematic diagram of hydroxyl radical produced by oxygen independent photosensitizer through photooxidation of water

图12. (a)引入靶向基团FA的光敏剂71. (b)基于双受体介导的生物正交激活方法增强光敏剂的选择性

Figure 12. (a) Photosensitizer 71 introducing targeting group FA. (b) Enhancing the selectivity of photosensitizers using a dual receptor mediated biological orthogonal activation method

图13. 可激活光敏剂72~76

Figure 13. Activatable photosensitizers 72~76

图14. “双锁”光敏剂PMB的激活过程

Figure 14. Activation process of “double lock” photosensitizer PMB

图15. (a) BH 1024NPs的制备和应用示意图. (b) 4T1小鼠经不同治疗后相对肿瘤体积变化. (c)不同实验组小鼠的存活率. (d)不同治疗方式肿瘤的H&E染色

Figure 15. (a) Preparation and application diagram of BH 1024NPs. (b) Relative tumor volume of 4T1 mice after different treatments. (c) Survival rate of mice in different experimental groups. (d) H&E staining of tumors with different treatment modalities

图16. (a) NBS-1MT的PDT与免疫调节示意图. (b)免疫荧光染色检测4T1肿瘤中CD8+T细胞和Treg细胞浸润. (c)小鼠经不同治疗后原位肿瘤相对体积变化. (d)小鼠经不同治疗后近端肿瘤相对体积变化

Figure 16. (a) Schematic diagram of PDT and immunomodulation of NBS 1MT. (b) Immunofluorescence staining detection of CD8+T cells and Treg cells infiltration in 4T1 tumors. (c) Relative volume of primary tumor in mice after different treatments. (d) Relative volume of in mice after different treatments

图17. (a) PNPS的药物释放及光敏激活示意图. (b) PNPS在HCT116荷瘤小鼠肿瘤局部的响应.

Figure 17. (a) Schematic diagram of drug release and photosensitive activation of PNPS. (b) Local tumor response of PNPS in HCT116 tumor -bearing mice

图18. (a) CS-P的结构及光照下的治疗示意图; (b)不同处理小鼠肿瘤相对体积变化; (c)不同处理小鼠肿瘤重量

Figure 18. (a) Structure of CS-P and schematic diagram of treatment under light. (b) Relative tumor volume changes of mice with different treatments. (c) Tumor weight of the mice with different treatment

图19. (a)光敏剂TriPE-NT的结构. (b) TriPE-NT加白光照射创面第3 d、第7 d的照片. (c)光敏剂DTTPB通过PDT对病毒的灭活示意图. (d) HCoV-229E病毒的RNA表达

Figure 19. (a) Structure of photosensitizer TriPE-NT. (b) Photographs of wounds treated by TriPE-NT plus white-light irradiation on day 3, day 7. (c) Schematic diagram of photosensitizer DTTPB inactivation of virus via PDT. (d) RNA expression of HCoV-229E virus

图20. (a)局部注射SPN后肿瘤和皮肤的荧光和余辉发光图像. (b)局部注射SPN后肿瘤和皮肤的荧光和余辉强度

Figure 20. (a) Fluorescence and afterglow luminescence images of tumor and skin after local injection of SPN. (b) Fluorescence and afterglow intensities of tumor and skin after local injection of SPN

图21. (a) MAP分子设计及余辉机理. (b)活体小鼠在不同时间点静脉注射MAP-$\mathop{{O}}_{2}^{{\mathop{}^{-·}}}$后的荧光和余辉成像. (c)注射MAP-$\mathop{{O}}_{2}^{{\mathop{}^{-·}}}$后肝脏区域的荧光和余辉强度. (d)注射MAP-$\mathop{{O}}_{2}^{{\mathop{}^{-·}}}$后肝脏区域的荧光和余辉信背比

Figure 21. (a) Molecular design and afterglow mechanism of MAP. (b) Fluorescence and afterglow images of living mice after injection of MAP-$\mathop{{O}}_{2}^{{\mathop{}^{-·}}}$ at different time points. (c) Fluorescence and afterglow intensities of liver areas after injection of MAP-$\mathop{{O}}_{2}^{{\mathop{}^{-·}}}$. (d) SBR for fluorescence and afterglow of liver areas after injection of MAP-$\mathop{{O}}_{2}^{{\mathop{}^{-·}}}$

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有机光敏剂结构与性能调控及其光诊疗应用^★

Structure and Properties Regulation of Organic Photosensitizers and Application in Photodiagnosis and Treatment^★

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有机光敏剂结构与性能调控及其光诊疗应用★

Structure and Properties Regulation of Organic Photosensitizers and Application in Photodiagnosis and Treatment★

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有机光敏剂结构与性能调控及其光诊疗应用^★

Structure and Properties Regulation of Organic Photosensitizers and Application in Photodiagnosis and Treatment^★