A dibenzochrysene-based type i photosensitizer and a preparation method and application thereof

By designing a Type I photosensitizer based on dibenzo-rich ene, the problems of strong oxygen dependence and poor photodynamic effect of existing photosensitizers with xanthones were solved, and a high-yield, low-cytotoxic near-infrared photosensitizer was prepared, which is suitable for fluorescence imaging and photodynamic therapy.

CN117865860BActive Publication Date: 2026-06-02SICHUAN UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
SICHUAN UNIV
Filing Date
2024-01-04
Publication Date
2026-06-02

AI Technical Summary

Technical Problem

Existing type I photosensitizers are highly oxygen-dependent, resulting in incomplete efficacy of photodynamic therapy in hypoxic tumor environments. Furthermore, existing zeatin nucleus compounds have poor photodynamic effects.

Method used

A Type I photosensitizer based on dibenzo-fullen was designed and synthesized via a Buchwald-Hartwig coupling reaction. The photosensitizer with a dibenzo-fullen structure was controlled by the molar ratio of 3,6-dibromofluorenone, alkyl or aryl amine, ligand, palladium catalyst, and basic substance. The synthesis conditions were mild and the yield was high.

Benefits of technology

The prepared photosensitizer has a long fluorescence emission and a large Stokes shift, avoids background spectral crosstalk, possesses Type I photodynamic potential, near-infrared emission characteristics, low cytotoxicity, and is suitable for fluorescence imaging and photodynamic therapy.

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Abstract

The application discloses a dibenzofulvene-based Type I photosensitizer and a preparation method and application thereof, and the preparation method comprises the following steps: (1) Buchwald-Hartwig coupling is carried out on 3,6-dibromofluorenone, alkyl or aryl amine, a ligand, a palladium catalyst and an alkaline substance under heating reflux condition to obtain an intermediate 1; (2) the intermediate 1 is dissolved in an organic solvent, an organic halide is added, and stirring reaction is carried out to obtain an intermediate 2; and (3) the intermediate 2 is dissolved in an organic solvent, an electron-withdrawing group and an organic base are added, and stirring reaction is carried out to obtain the dibenzofulvene-based Type I photosensitizer. The preparation method is simple, the synthesis condition is mild, the synthesis efficiency is high, and the yield is high. The prepared Type I photosensitizer has long fluorescent emission and large Stokes shift, can effectively avoid background spectral crosstalk, has Type I photodynamic potential, has the characteristics of near-infrared emission, has low cytotoxicity, and has the ability to produce active oxygen.
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