A simple hydrogen peroxide-activatable Bodipy for tumor imaging and type I/II photodynamic therapy

Fangqing Ge,  ‡a   Yujie Sun,‡b   Yu Wang,b   Dan Yu,b   Zhijia Wang【王智佳】,  *ab   Fabiao Yu【于法标】,  *c   Bingran Yu  *b  and  Hongbing Fu  a  

    Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Capital Normal University, Beijing 100048, P. R. China

Laboratory of Biomedical Materials and Key Lab of Biomedical Materials of Natural Macromolecules, Beijing University of Chemical Technology, Beijing 100029, P. R. ChinaKey Laboratory of Emergency and Trauma, Ministry of Education, Key Laboratory of Haikou Trauma, Key Laboratory of Hainan Trauma and Disaster Rescue, Engineering Research Centre for Hainan Bio-Smart Materials and Bio-Medical Devices, Key Laboratory of Hainan Functional Materials and Molecular Imaging, The First Affiliated Hospital of Hainan Medical University, Hainan Medical University, Haikou 571199, China

Abstract

Tumor microenvironment-activatable photosensitizers have gained significant attention for cancer theranostics. Considering the hypoxic environment of solid tumors, activatable phototheranostic agents with type I PDT are desired to obtain improved cancer treatment efficiency. Herein, we report a simple, effective and multifunctional Bodipy photosensitizer for tumor imaging and type I/II photodynamic therapy. The photosensitizer featuring a methylphenylboronic acid pinacol ester group at the meso-position of Bodipy specifically responds to tumor-abundant H2O2. Its photophysical properties were characterized using steady-state and time-resolved transient optical spectroscopies. The fluorescence (ΦF = 0.09%) and singlet oxygen efficacy (ΦΔ = 10.2%) of the Bodipy units were suppressed in the caged dyads but significantly enhanced (ΦF = 0.72%, ΦΔ = 20.3%) upon H2O2 activation. Fluorescence emission spectroscopy and continuous wave electron paramagnetic resonance (EPR) spectroscopy confirmed that the Bodipy photosensitizer generates reactive oxygen species (ROS) via both electron transfer-mediated type I and energy transfer-mediated type II mechanisms. In vitro experiments demonstrated rapid internalization into tumor cells, enhanced brightness stimulated by tumor microenvironments, and tumor cell death (phototoxicity, IC50 = 0.5 μM). In vivo fluorescence imaging indicated preferential accumulation of this Bodipy photosensitizer in tumor sites, followed by decaging by tumor-abundant H2O2, further elevating the signal-to-background ratio (SBR) of imaging. Besides outstanding performance in tumor imaging, a prominent inhibition of tumor growth was observed. Given its simple molecular skeleton, this Bodipy photosensitizer is a competitive candidate for cancer theranostics.

• This article is part of the themed collections: Materials Chemistry of Fluorescence Bioimaging and Journal of Materials Chemistry B HOT Papers

Article information

DOI   https://doi.org/10.1039/D4TB01650E

J. Mater. Chem. B, 2024,12, 11165-11171

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