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Preparation and application of a mitochondria-targeted stimulus-responsive photosensitizer

A stimuli-responsive, mitochondrial technology, applied in medical preparations containing active ingredients, photodynamic therapy, wave energy or particle radiation treatment materials, etc., can solve the problem of not having switch controllability and reducing the quantum yield of singlet oxygen and other issues to achieve the effect of improving the photodynamic ability

Active Publication Date: 2022-03-29
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the mitochondria-targeted photosensitizers do not have on-off controllability, and their application in biological media is limited by their low water solubility, which leads to the formation of massive aggregates and reduces the singlet oxygen quantum yield.

Method used

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  • Preparation and application of a mitochondria-targeted stimulus-responsive photosensitizer
  • Preparation and application of a mitochondria-targeted stimulus-responsive photosensitizer
  • Preparation and application of a mitochondria-targeted stimulus-responsive photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Synthesis of Compound 7, the synthetic route is attached figure 1

[0025] Methyl gallate (3.0g, 16.3mmol) was dissolved in dry DMF (15mL), potassium carbonate (4.5g, 32.6mmol) and potassium iodide (0.27g, 1.63mmol) were added, stirred at 80°C for 10min, dropwise A dry DMF (5 mL) solution containing compound 1 (5.68 g, 16.3 mmol) was added dropwise and stirred overnight at this temperature. After the reaction, the solvent was removed by rotary evaporation, the mixture was dissolved in ethyl acetate, washed 3 times with saturated brine, dried over anhydrous sodium sulfate, the solvent was removed by rotary evaporation, and column chromatography was performed with petroleum ether and ethyl acetate as eluents. Compound 2 (1.82 g, 31.0%) was obtained as a colorless oily substance. 1 H NMR (400MHz, CDCl 3 )δ (ppm) 7.63 (s, 2H), 7.15 (s, 2H), 4.20-4.14 (t, J=3.2Hz, 2H), 3.85 (s, 3H), 3.74 (m, 8H), 3.69 (s , 4H), 3.62(t, J=4.4Hz, 2H), 3.48-3.38(s, 1H). 13 C NMR...

Embodiment 2

[0031] Embodiment two: synthesis mito-PN PS, the synthetic route is attached figure 1

[0032] Compound 7 (129mg, 0.14mmol), azide P.S. Se-I (100mg, 0.14mmol), sodium ascorbate (2.8mg, 0.014mmol) and anhydrous copper sulfate (2.2mg, 0.0014mmol) were dissolved in a mixed solution of tetrahydrofuran / water (4mL / 1mL), and reacted at room temperature for 24h. After the reaction, extract with dichloromethane, dry over anhydrous sodium sulfate, remove the solvent by rotary evaporation, and use dichloromethane and methanol as eluents for column chromatography to obtain a black-green solid compound mito PS (0.15 g, 65.6%). 1 H NMR (400MHz, CDCl 3 )δ (ppm) 8.99 (s, 1H), 8.17 (s, 1H), 8.08 (s, 1H), 7.81-7.56 (m, 18H), 7.53-7.41 (m, 2H), 7.34 (s, 2H) , 7.13(d, J=8.8Hz, 1H), 6.75(d, J=15.6Hz, 1H), 6.64(d, J=16.0Hz, 1H), 4.86-4.66(m, 4H), 4.45(s, 2H), 4.15(m, 6H), 3.92-3.71(m, 10H), 3.66(m, 4H), 3.64-3.53(m, 10H), 3.50(m, 4H), 3.38-3.30(m, 8H) , 3.26(m, 2H), 3.21(m, 2H). 13 C NMR (...

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Abstract

The invention discloses a preparation method and application of a mitochondria-targeted stimulus-responsive photosensitizer. A water-soluble mitochondrial targeting reagent was creatively synthesized, and the mitochondrial targeting reagent and the photosensitizer with reserved azide functional group ( azide P.S. Se‑1 ) to connect, and then etherify the stimuli-responsive group. The photosensitizer has good biocompatibility, stimulus responsiveness and mitochondrial targeting.

Description

technical field [0001] The invention relates to the preparation and application of a mitochondria-targeted photosensitizer, belonging to the technical field of photodynamic therapy. Background technique [0002] As an essential organelle for cellular respiration, mitochondria provide energy for cell metabolism and play a key role in programmed cell death such as apoptosis. Mitochondria are therefore promising therapeutic targets for clinical applications. As we all know, photodynamic therapy is an emerging treatment method, which produces cytotoxic singlet oxygen by irradiating photosensitizers with effective light sources, thereby causing irreversible damage to patient cells. Combining the above two, mitochondria-targeted photosensitizers emerge as the times require, which can lead to the death of patient cells by creating mitochondrial dysfunction, thereby achieving the purpose of treatment. However, most mitochondria-targeted photosensitizers do not possess on-off contr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6596A61K41/00
CPCA61K41/0057C07F9/6596
Inventor 李昌华翟文豪刘明
Owner NANKAI UNIV
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