Citation: Yiling Li, Zekun Gao, Xiuxiu Yue, Minhuan Lan, Xiuli Zheng, Benhua Wang, Shuang Zhao, Xiangzhi Song. FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy[J]. Chinese Chemical Letters, ;2024, 35(7): 109133. doi: 10.1016/j.cclet.2023.109133 shu

FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy

Yiling Li ^{a, 1} ,
Zekun Gao ^{b, 1} ,
Xiuxiu Yue ^a ,
Minhuan Lan ^{a, *,} ,
Xiuli Zheng ^{b, *,} ,
Benhua Wang ^a ,
Shuang Zhao ^c ,
Xiangzhi Song ^{a, *,}

a.
College of Chemistry & Chemical Engineering, Central South University, Changsha 410083, China
b.
Key Laboratory of Photochemical Conversion and Optoelectronic Materials and City U-CAS Joint Laboratory of Functional Materials and Devices, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China
c.
Department of Dermatology, Xiangya Hospital, Central South University, Changsha 410083, China

minhuanlan@csu.edu.cn

zhengxiuli@mail.ipc.ac.cn

xzsong@csu.edu.cn

Received Date: 23 June 2023
Revised Date: 12 September 2023
Accepted Date: 20 September 2023
Available Online: 9 October 2023

Figures(5)

To overcome the conflict between the long-wavelength excitation and high singlet oxygen quantum yield of photosensitizers, we conjugated a two-photon fluorophore, tetrahydroquinoxaline coumarin (TQ), and an efficient photodynamic therapeutic agent, benzo[a]phenothiazinium (NBS-NH₂), through a hexamethylene linker to build a two-photon photosensitizer, TQ-NBS. In TQ-NBS, TQ served as an energy donor and NBS-NH₂ acted as an energy acceptor; and TQ-NBS was a Förster resonance energy transfer (FRET) cassette with a 92.8% efficiency. The large two-photon absorption cross-section of TQ allowed photosensitizer TQ-NBS to work in a 900 nm two-photon excitation (TPE) mode, which greatly benefited the deep tissue penetration in PDT treatment. Meanwhile, the excellent phototoxicity and near-infrared fluorescence of NBS-NH₂ was kept in TQ-NBS under a TPE mode via a FRET process. Photosensitizer TQ-NBS exhibited a high phototoxic efficacy in living cells and tumor-bearing mice.
- Photodynamic therapy,
- Two-photon excitation,
- FRET-based photosensitizer,
- Singlet oxygen,
- Near-infrared fluorescence
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