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

Abstract

Thionated perylenediimide (PDI) 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. Results revealed that photodynamic performance is less associated with the positon of sulfur atoms. By contrast, trans-isomer PDI-TS showed photothermal conversion efficiency of up to 58.4%, which is 40% higher than that of PDI-CS (~41.6%). In vitro half-maximal inhibitory concentration of ~7.78 µg mL−1 was achieved for PDI-TS, which is 1.7-fold smaller than that of PDI-CS, strongly reasserting regioisomer-modulated phototheranostic performance. Notably, the strong π–π and C···S interactions in PDI-TS nanoagents are the 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 property and a novel proof of concept to improve therapeutic performance through the optimization of non-bonding interactions.

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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, Accepted Manuscript
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, Accepted Manuscript , DOI: 10.1039/D0TB00566E

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