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用于超低光功率密度照射的光动力疗法及双光子成像的红色发射氮杂苯并蒽酮衍生物

Red-emissive azabenzanthrone derivatives for photodynamic therapy irradiated with ultralow light power density and two-photon imaging.

作者信息

Zang Qiguang, Yu Jiayi, Yu Wenbin, Qian Jun, Hu Rongrong, Tang Ben Zhong

机构信息

State Key Laboratory of Luminescent Materials and Devices , Center for Aggregation-Induced Emission , South China University of Technology , Guangzhou 510640 , China . Email:

State Key Laboratory of Modern Optical Instrumentation , Centre for Optical and Electromagnetic Research , Zhejiang Provincial Key Laboratory for Sensing Technologies , Zhejiang University , Hangzhou , China.

出版信息

Chem Sci. 2018 Apr 24;9(23):5165-5171. doi: 10.1039/c8sc00633d. eCollection 2018 Jun 21.

DOI:10.1039/c8sc00633d
PMID:29997869
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6000979/
Abstract

Photodynamic therapy has proved to be an effective strategy for cancer therapy, and advanced photosensitizers for image-guided photodynamic therapy require biocompatibility, intense absorption, high ROS generation efficiency, phototoxicity, low irradiation power density and efficient emission. In this work, four red emissive azabenzanthrone derivatives have been designed and synthesized, which generally exhibit efficient aggregated state emission. Through structural optimization, 3-diphenylamino-11-azabenzanthrone was found to show satisfactory photo-induced ROS generation and high emission efficiency in the aggregated state. Under the irradiation of a white LED lamp with an ultralow power density of 1.67 mW cm, this compound demonstrates significant photo-induced cytotoxicity toward HeLa cells. Moreover, deep tissue penetration can be realized by two-photon imaging of mouse brain vessels with these azabenzanthrone derivatives at vertical depths of up to 280 μm, attributed to the large emission wavelength and efficient emission.

摘要

光动力疗法已被证明是一种有效的癌症治疗策略,用于图像引导光动力疗法的先进光敏剂需要具备生物相容性、强吸收性、高活性氧生成效率、光毒性、低辐照功率密度和高效发射等特性。在这项工作中,设计并合成了四种红色发射的氮杂苯并蒽酮衍生物,它们通常表现出高效的聚集态发射。通过结构优化,发现3-二苯胺基-11-氮杂苯并蒽酮在聚集态下表现出令人满意的光诱导活性氧生成和高发射效率。在超低功率密度为1.67 mW/cm的白色LED灯照射下,该化合物对HeLa细胞表现出显著的光诱导细胞毒性。此外,这些氮杂苯并蒽酮衍生物对小鼠脑血管进行双光子成像时,在垂直深度高达280μm处可实现深部组织穿透,这归因于其较大的发射波长和高效发射。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/668146c91ead/c8sc00633d-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/01b6ba2792c1/c8sc00633d-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/5c1f446a98ae/c8sc00633d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/1172a6d71831/c8sc00633d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/ab82a632caa2/c8sc00633d-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/212165a968a5/c8sc00633d-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/668146c91ead/c8sc00633d-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/01b6ba2792c1/c8sc00633d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/2ac7cdc52f8a/c8sc00633d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/5c1f446a98ae/c8sc00633d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/1172a6d71831/c8sc00633d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/ab82a632caa2/c8sc00633d-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/212165a968a5/c8sc00633d-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3e42/6000979/668146c91ead/c8sc00633d-f6.jpg

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