A fullerene-rhodamine B photosensitizer with pH-activated visible-light absorbance/fluorescence/photodynamic therapy

The development of smart photosensitizers with tumor microenvironment-activable fluorescence turn-on and singlet oxygen generation plays an important role in tumor bioimaging and photodynamic therapy. Herein, a pH-activable heavy-atom-free photosensitizer (C -RB) has been successfully synthesized th...

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Bibliographic Details
Published in:Journal of materials chemistry. B, Materials for biology and medicine Materials for biology and medicine, 2018-05, Vol.6 (18), p.2778-2784
Main Authors: Tang, Qianyun, Xiao, Wanyue, Li, Jiewei, Chen, Dapeng, Zhang, Yewei, Shao, Jinjun, Dong, Xiaochen
Format: Article
Language:English
Subjects:
Absorbance
Buckminsterfullerene
Cancer
Converters
Energy gap
Fluorescence
Fullerenes
Medical imaging
Nanoparticles
Oxygen
pH effects
Photodynamic therapy
Rhodamine
Singlet oxygen
Tumors
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Summary:The development of smart photosensitizers with tumor microenvironment-activable fluorescence turn-on and singlet oxygen generation plays an important role in tumor bioimaging and photodynamic therapy. Herein, a pH-activable heavy-atom-free photosensitizer (C -RB) has been successfully synthesized through introducing a fullerene unit onto rhodamine B hydrazide. Under acidic conditions, C -RB, having a spirolactam structure, can be activated to its ring-opened structure C -RB-H and thus, visible-light absorbance enhancement, fluorescence turn-on and triplet excited state generation can be accomplished. In the presence of hydrion, the fullerene unit in C -RB C -RB-H acting as an intramolecular spin converter can cause good intersystem crossing, and the energy gap between S and T (ΔE ) is lowered to 0.017 eV. Through encapsulation with amphiphilic DSPE-mPEG , water-soluble nanoparticles (NPs) of C -RB are obtained. In vitro experiments indicate that C -RB NPs are capable of universal cellular uptake and lysosomal activation (pH 4.5-5.0), and they also exhibit excellent photodynamic therapeutic effect. The fluorescence turn-on and efficient singlet oxygen generation enabled by pH-activated C -RB NPs testify their great potential applications for cancer diagnosis and treatment.
ISSN:2050-750X
2050-7518
DOI:10.1039/c8tb00372f