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Issue 25, 2020
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Regioisomer-manipulating thio-perylenediimide nanoagents for photothermal/photodynamic theranostics

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Abstract

Thionated perylenediimides (PDIs) can potentially generate thermal and reactive oxygen species and thus can be used as theranostic agents for photothermal/photodynamic therapy. Herein, thionated cis-/trans-isomer PDI-CS and PDI-TS were designed and prepared to investigate thionation engineering on therapeutic performance. The results revealed that the photodynamic performance is less associated with the positon of sulfur atoms. By contrast, trans-isomer PDI-TS showed a photothermal conversion efficiency of up to 58.4%, which was 40% higher than that of PDI-CS (∼41.6%). An in vitro half-maximal inhibitory concentration of ∼7.78 μg mL−1 was achieved for PDI-TS, which was 1.7-fold smaller than that of PDI-CS, strongly reasserting the regioisomer-modulated phototheranostic performance. Notably, the strong π–π and C⋯S interactions in PDI-TS nanoagents are essential factors attributed to their excellent photothermal performance, indicating that the optimization of non-bonding interactions is an ingenious way to improve phototheranostic performance. This work provides a facile means of creating thio-perylenediimides that possess excellent antitumor properties and a novel proof of concept to improve therapeutic performance through the optimization of non-bonding interactions.

Graphical abstract: Regioisomer-manipulating thio-perylenediimide nanoagents for photothermal/photodynamic theranostics

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Supplementary files

Article information


Submitted
02 Mar 2020
Accepted
20 May 2020
First published
22 May 2020

J. Mater. Chem. B, 2020,8, 5535-5544
Article type
Paper

Regioisomer-manipulating thio-perylenediimide nanoagents for photothermal/photodynamic theranostics

Z. Liu, Y. Gao, X. Jin, Q. Deng, Z. Yin, S. Tong, W. Qing and Y. Huang, J. Mater. Chem. B, 2020, 8, 5535
DOI: 10.1039/D0TB00566E

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