A Thienyl-Substituted Diketopyrrolopyrrole Derivative with Efficient Reactive Oxygen Species Generation for Photodynamic Therapy

Huaxia Shi, Wucheng Sun, Qiang Wang, Guiying Gu, Weili Si, Wei Huang, Qi Zhang, Xiaochen Dong

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25 引用 (Scopus)

摘要

Reducing the energy gap of photosensitizer between singlet and triplet states (ΔEST) can improve the efficiency of intersystem crossing, further enhancing the resulting generation of reactive oxygen species for photodynamic therapy. In this study, two photosensitizer chromophores—phenyl-substituted diketopyrrolopyrrole and thienyl-substituted diketopyrrolopyrrole (TDPP)—were synthesized. Theoretical calculations indicate that TDPP can greatly reduce the ΔEST (0.48 eV) relative to that of diketopyrrolopyrrole (0.66 eV). Experiments confirmed that TDPP generates reactive oxygen species more efficiently than diketopyrrolopyrrole. After conjugation of TDPP with methoxy poly(ethylene glycol)carboxyl (mPEG-COOH), the resulting TDPP-mPEG has excellent water solubility, biocompatibility and photostability. When it serves as photosensitizer for photodynamic therapy, in vitro and in vivo measurements indicate that TDPP-mPEG can effectively inhibit tumor growth and shows great potential for the treatment of cancer in the clinic.

源语言英语
页(从-至)515-520
页数6
期刊ChemPlusChem
81
6
DOI
出版状态已出版 - 1 6月 2016
已对外发布

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