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Issue 18, 2018
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A fullerene-rhodamine B photosensitizer with pH-activated visible-light absorbance/fluorescence/photodynamic therapy

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Abstract

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 (C60-RB) has been successfully synthesized through introducing a fullerene unit onto rhodamine B hydrazide. Under acidic conditions, C60-RB, having a spirolactam structure, can be activated to its ring-opened structure C60-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 C60-RB C60-RB-H acting as an intramolecular spin converter can cause good intersystem crossing, and the energy gap between S1 and T1EST) is lowered to 0.017 eV. Through encapsulation with amphiphilic DSPE-mPEG2000, water-soluble nanoparticles (NPs) of C60-RB are obtained. In vitro experiments indicate that C60-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 C60-RB NPs testify their great potential applications for cancer diagnosis and treatment.

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

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Publication details

The article was received on 06 Feb 2018, accepted on 03 Apr 2018 and first published on 03 Apr 2018


Article type: Paper
DOI: 10.1039/C8TB00372F
Citation: J. Mater. Chem. B, 2018,6, 2778-2784
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    A fullerene-rhodamine B photosensitizer with pH-activated visible-light absorbance/fluorescence/photodynamic therapy

    Q. Tang, W. Xiao, J. Li, D. Chen, Y. Zhang, J. Shao and X. Dong, J. Mater. Chem. B, 2018, 6, 2778
    DOI: 10.1039/C8TB00372F

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