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A Thienyl‐Substituted Diketopyrrolopyrrole Derivative with Efficient Reactive Oxygen Species Generation for Photodynamic Therapy
Author(s) -
Shi Huaxia,
Sun Wucheng,
Wang Qiang,
Gu Guiying,
Si Weili,
Huang Wei,
Zhang Qi,
Dong Xiaochen
Publication year - 2016
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201600101
Subject(s) - photosensitizer , singlet oxygen , photodynamic therapy , intersystem crossing , photochemistry , ethylene glycol , reactive oxygen species , chromophore , biocompatibility , materials science , oxygen , chemistry , singlet state , organic chemistry , excited state , biochemistry , physics , nuclear physics
Reducing the energy gap of photosensitizer between singlet and triplet states (Δ E ST ) 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 Δ E ST (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.