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Near-infrared two-photon photosensitive dye SBOPI as well as preparation method and application thereof

A photosensitizing dye and two-photon technology, applied in the field of photosensitizing dyes, can solve the problems of difficult to meet the photodynamic therapy of biological systems, low singlet oxygen yield, limited application scope, etc., so as to inhibit the migration of cancer cells and promote the apoptosis of tumor cells. , the effect of wide application

Active Publication Date: 2021-03-26
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the photosensitive dyes used in photodynamic therapy in the prior art are located in the visible light region, with poor biocompatibility and low singlet oxygen yield, which is difficult to meet the requirements of photodynamic therapy in biological systems, which greatly limits its application range.

Method used

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  • Near-infrared two-photon photosensitive dye SBOPI as well as preparation method and application thereof
  • Near-infrared two-photon photosensitive dye SBOPI as well as preparation method and application thereof
  • Near-infrared two-photon photosensitive dye SBOPI as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (1) Preparation of near-infrared two-photon photosensitizing dye SBOPI:

[0022] Under nitrogen protection and 110°C, weigh 0.20 g of iodothiophene-fluoroboropipyrrole SBOP and dissolve it in 15 mL of dry toluene, add 0.09 g of 1-(2-morpholine ethyl)-1H-indole-3-carbaldehyde, Add 0.5 mL of glacial acetic acid dropwise, and stir for 6 h. After the reaction was completed, the photosensitizing dye SBOPI was obtained by vacuum distillation and column chromatography purification with a yield of 38%.

[0023] The synthetic route of photosensitizing dye SBOPI is as follows:

[0024]

[0025] Among them, iodothiophene-fluorobodipyrrole SBOP was prepared according to the literature method (Antoine Mirloup, Pascal Retailleau, Raymond Ziessel, Luminescent molecular solar concentrators made of multi-Bodipy dyes. Tetrahedron Letters, 2013, 54, 4456-4462).

[0026] (2) Structural characterization of near-infrared two-photon photosensitizing dye SBOPI:

[0027] H NMR spectrum 1...

Embodiment 2

[0032] The preparation of the near-infrared two-photon photosensitizing dye SBOPI is the same as in Example 1. Under nitrogen protection and 110°C, weigh 0.20 g of thiophene-fluoroboropipyrrole SBOP and dissolve it in 15 mL of dry toluene, add 0.11 g of 1-(2-morpholine ethyl Base)-1H-indole-3-carbaldehyde, then drop into 0.5mL glacial acetic acid, and stir for 6h. After the reaction, the near-infrared two-photon photosensitizing dye SBOPI was obtained by vacuum distillation and column chromatography purification, with a yield of 30.4%.

Embodiment 3

[0034] The preparation of the near-infrared two-photon photosensitizing dye molecule SBOPI is the same as in Example 1. Under nitrogen protection and 110°C, weigh 0.20g of thiophene-fluoroborate dipyrrole SBOP and dissolve it in 15mL of dry toluene, add 0.15g of 1-(2-morpholine Ethyl)-1H-indole-3-carbaldehyde, then dropwise into 0.5mL glacial acetic acid, and stirred for 6h. After the reaction, the near-infrared two-photon photosensitizing dye SBOPI was obtained by vacuum distillation and column chromatography purification, with a yield of 26.6%.

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Abstract

The invention discloses a near-infrared two-photon photosensitive dye SBOPI as well as a preparation method and application thereof. The near-infrared two-photon photosensitive dye SBOPI comprises a push-pull electronic conjugated structure of thiophene-boron dipyrromethene and indole and a lysosome targeting site. The preparation method of the near-infrared two-photon photosensitive dye SBOPI comprises the step that the near-infrared two-photon photosensitive dye SBOPI is prepared by reacting iodo thiophene-boron dipyrromethene SBOP with 1-(2-morpholinoethyl)-1H-indole-3-formaldehyde. According to the application of the near-infrared two-photon photosensitive dye SBOPI, under irradiation of near-infrared light, the near-infrared two-photon photosensitive dye SBOPI can efficiently releasesinglet oxygen, inhibit tumor cell migration and promote tumor cell apoptosis. As a near-infrared band two-photon photosensitizer and fluorescent dye with excellent performance, the near-infrared bandtwo-photon photosensitizer has wide application in the aspects of near-infrared band fluorescence imaging, fluorescence sensing, fluorescence labeling and two-photon photodynamic therapy.

Description

technical field [0001] The invention relates to a photosensitive dye, in particular to a near-infrared two-photon photosensitive dye SBOPI and its preparation method and application. Background technique [0002] Upon light excitation, the sensitizing dye generates singlet oxygen at the tumor site through photocontrolled energy transfer. Singlet oxygen has high toxicity to tumor cells, can promote the apoptosis of tumor tissue cells, and realize the photodynamic therapy of tumor cells. Photodynamic therapy has many advantages, such as less tissue trauma, shorter treatment time, and a wide range of applications. However, most of the photosensitive dyes used in photodynamic therapy in the prior art are located in the visible light region, with poor biocompatibility and low singlet oxygen yield, which is difficult to meet the requirements of photodynamic therapy in biological systems, which greatly limits its application range. . Near-infrared two-photon photosensitizing dye...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B23/10A61K41/00A61K49/00A61P35/00
CPCC07F5/022C09K11/06A61K41/008A61P35/00A61K49/0028C09B23/105C09K2211/1029C09K2211/1033C09K2211/1055C09K2211/1092
Inventor 钱鹰刘苗白金刘巴蒂
Owner SOUTHEAST UNIV
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