Rational Design of Organic Probes for Turn-On Two-Photon Excited Fluorescence Imaging and Photodynamic Therapy

被引:59
作者
Sun, Chun-Lin [1 ]
Li, Jun [1 ,7 ]
Wang, Xiao-Zhen [1 ]
Shen, Rong [5 ]
Liu, Sha [5 ]
Jiang, Jian-Qiao [1 ]
Li, Ting [6 ]
Song, Qi-Wei [1 ]
Liao, Qing [4 ]
Fu, Hong-Bing [4 ]
Yao, Jian-Nian [2 ,3 ]
Zhang, Hao-Li [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Key Lab Special Funct Mat & Struct Design, Lanzhou 730000, Gansu, Peoples R China
[2] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Molecules Sci, State Key Lab Struct Chem Unstable & Stable Speci, Beijing 100190, Peoples R China
[3] Chinese Acad Sci, Inst Chem, Key Lab Photochem, Beijing 100190, Peoples R China
[4] Capital Normal Univ, Dept Chem, Beijing Key Lab Opt Mat & Photon Devices, Beijing 100048, Peoples R China
[5] Lanzhou Univ, Sch Basic Med Sci, Lanzhou 730000, Gansu, Peoples R China
[6] Lanzhou Univ, Sch Life Sci, Lanzhou 73000, Gansu, Peoples R China
[7] Northwestern Polytech Univ, Sch Nat & Appl Sci, MOE Key Lab Space Appl Phys & Chem, Joint Lab Nanofluid & Interfaces, Xian 710072, Shaanxi, Peoples R China
来源
CHEM | 2019年 / 5卷 / 03期
基金
中国国家自然科学基金; 北京市自然科学基金;
关键词
ONE-PHOTON; PHOTOSENSITIZERS; DERIVATIVES; ABSORPTION; EXCITATION;
D O I
10.1016/j.chempr.2018.12.001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The rational design of two-photon absorption (2PA) organic dyes with 2PA cross-section (delta) values tunable by mild stimuli under physiological conditions remains a challenge. Using a simulation-assisted structure screening method, we have designed an acetal terminated distyrylbenzene derivative (Ace-DSB), which can be readily converted into aldehyde terminated molecules (Ald-DSB) to exhibit a significant increase in delta values at 760 nm. The conversion reaction, which dramatically turns on the 2PA absorption capability of the molecules, can occur in an intracellular environment. Furthermore, Ald-DSB exhibits 40 times higher efficiency of two-photon generation of singlet oxygen than Ace-DSB. These turn-on features allow enhanced two-photon laser confocal scanning microscopic imaging and two-photon excited photodynamic therapy (2PE-PDT) for MCF-7 cancer cells and melanoma tumors. This work opens a new avenue toward the design of turn-on-type two-photon absorption molecules for both in vitro and in vivo tumor imaging and 2PA-PDT.
引用
收藏
页码:600 / 616
页数:17
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