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A kind of red fluorescent protein two-photon photosensitizing dye and its preparation method and application

A red fluorescent protein and photosensitizing dye technology, which is applied in the field of red fluorescent protein-based two-photon photosensitizing dye RFP-Ac and its preparation, can solve the problems of large Stokes shift and low toxicity, and achieve large Stokes shift , low cytotoxicity and good biocompatibility

Active Publication Date: 2022-07-08
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a fluorophore in living organisms, fluorescent proteins have excellent biocompatibility, low toxicity, large Stokes shift, little interference from the background of the organism itself, and are safe and reliable. However, in the prior art based on red fluorescent protein Structured near-infrared two-photon photosensitizing dyes are rarely reported

Method used

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  • A kind of red fluorescent protein two-photon photosensitizing dye and its preparation method and application
  • A kind of red fluorescent protein two-photon photosensitizing dye and its preparation method and application
  • A kind of red fluorescent protein two-photon photosensitizing dye and its preparation method and application

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Embodiment 1

[0023] (1) Preparation of red fluorescent protein two-photon photosensitizing dye RFP-Ac:

[0024] Under nitrogen protection and 110°C, 0.23g of phenothiazine fluorescent protein analog RFP-Me was weighed and dissolved in 30mL of dry toluene, 0.12g of p-hydroxybenzaldehyde was added, and then 5d of glacial acetic acid was added dropwise, and the reaction was stirred for 6h. After the reaction, it was separated and purified by column chromatography. 0.08 g of the resultant was weighed and dissolved in 20 mL of dry dichloromethane, 0.15 g of acryloyl chloride was added dropwise in an ice-water bath at 0°C, and then the reaction was raised to room temperature for 8 h. After the reaction, through extraction, washing, drying and column chromatography separation, the red fluorescent protein two-photon photosensitizing dye RFP-Ac was obtained, and the yield was 52%.

[0025] The synthetic route of the red fluorescent protein two-photon photosensitive dye RFP-Ac is as follows:

[00...

Embodiment 2

[0033] Example 2 Preparation of red fluorescent protein two-photon photosensitizing dye RFP-Ac

[0034] Under nitrogen protection and 110°C, 0.23g of phenothiazine fluorescent protein analog RFP-Me was weighed and dissolved in 30mL of dry toluene, 0.09g of p-hydroxybenzaldehyde was added, 5d of glacial acetic acid was added dropwise, and the reaction was stirred for 6h to complete the reaction. and isolate the resultant. 0.08 g of the resultant was weighed and dissolved in 20 mL of dry dichloromethane, 0.15 g of acryloyl chloride was added dropwise in an ice-water bath at 0°C, and then the reaction was raised to room temperature for 8 h. After the reaction, the red fluorescent protein two-photon photosensitizing dye RFP-Ac is obtained through extraction, washing, drying and column chromatography separation, and the yield is 50%.

Embodiment 3

[0035] Example 3 Preparation of red fluorescent protein two-photon photosensitizing dye RFP-Ac

[0036] Under nitrogen protection and 110 °C, 0.20 g of phenothiazine fluorescent protein analog RFP-Me was weighed and dissolved in 30 mL of dry toluene, 0.06 g of p-hydroxybenzaldehyde was added, and 5d of glacial acetic acid was added dropwise, and the reaction was stirred for 6 h to complete the reaction. and isolate the resultant. 0.08 g of the resultant was weighed and dissolved in 20 mL of dry dichloromethane, 0.15 g of acryloyl chloride was added dropwise in an ice-water bath at 0°C, and then the reaction was raised to room temperature for 8 h. After the reaction, through extraction, washing, drying and column chromatography separation, the red fluorescent protein two-photon photosensitizing dye RFP-Ac was obtained, and the yield was 47%.

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Abstract

The invention discloses a red fluorescent protein-based two-photon photosensitizing dye RFP-Ac and a preparation method and application thereof. The red fluorescent protein-based two-photon photosensitizing dye RFP-Ac comprises phenothiazine, vinylbenzene and fluorescent protein methylene The conjugated structure of the base imidazolidinone, and the aryl acrylate was introduced at the end group of the fluorescent chromophore as an active thiol recognition site and a photosensitizer targeting group. The red fluorescent protein-based photosensitizing dye molecule RFP-Ac of the present invention has two-photon absorption characteristics, a Stokes shift of more than 200 nm, strong anti-interference ability, high sensitivity, low cytotoxicity, good biocompatibility, and singlet oxygen production. It can be used as two-photon photosensitizing dyes and fluorescent probes with high performance in near-infrared wavelengths for fluorescence sensing, endogenous or exogenous bioactive thiol detection, two-photon fluorescence imaging, fluorescent labeling, two-photon light Dynamic therapy has a wide range of applications.

Description

technical field [0001] The invention relates to a fluorescent protein-based photosensitizing dye, in particular to a red fluorescent protein-based two-photon photosensitizing dye RFP-Ac and a preparation method and application thereof. Background technique [0002] Under light excitation, the photosensitizing dye generates singlet oxygen at the tumor site through photo-controlled energy transfer. Singlet oxygen is highly toxic to tumor cells, and can react with DNA, RNA, lipid and protein molecules in tumor cells, leading to apoptosis and realizing photodynamic therapy of tumor cells. Cysteine ​​and glutathione are the most representative active thiols in cells, and their concentrations are higher in tumor cells than in normal cells. Overexpression of cysteine ​​and glutathione will deplete intracellular reactive oxygen species and reduce the effect of photodynamic therapy. [0003] At present, most of the photosensitizing dyes used for photodynamic therapy are located in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/14C07D417/06C09K11/06A61K41/00A61K49/00A61P35/00
CPCC09B23/145C07D417/06C09K11/06A61K41/008A61P35/00A61K49/003C09K2211/1037C09K2211/1044C09K2211/1007
Inventor 钱鹰项雯晖刘巴蒂
Owner SOUTHEAST UNIV
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