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Water-soluble mitochondria-targeted silicon phthalocyanine axially substituted by ethyoxyl bromopropyl imidazole and preparation method and application thereof

A technology of bromopropyl and silicon phthalocyanine, applied in the field of complexes, to achieve the effect of improving the interaction between positively charged phthalocyanine and negatively charged mitochondrial membranes

Pending Publication Date: 2021-10-01
福州量衍科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no reports on water-soluble mitochondria-targeted bis-(1-(2-ethoxy)-3-(3-bromopropyl)imidazole) axially substituted silicon phthalocyanine complexes

Method used

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  • Water-soluble mitochondria-targeted silicon phthalocyanine axially substituted by ethyoxyl bromopropyl imidazole and preparation method and application thereof
  • Water-soluble mitochondria-targeted silicon phthalocyanine axially substituted by ethyoxyl bromopropyl imidazole and preparation method and application thereof
  • Water-soluble mitochondria-targeted silicon phthalocyanine axially substituted by ethyoxyl bromopropyl imidazole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment 1

[0019] 1) Dichlorosilicon phthalocyanine (SiPcCl 2 )Synthesis

[0020] Add 1,3-diiminoisoindoline (7.28 g, 50.15 mmol), silicon tetrachloride (8.30 mL) and quinoline (83 mL) into a 250 mL three-necked flask, and stir at 220 °C Reflux for 1 h, when the reaction solution drops to 70°C, pour it into 500 mL of methanol solution, stir and let stand, then filter, wash the precipitate with acetone, methanol, dichloromethane and other solvents, and vacuum dry to obtain 3.68 g of purple-red solid , and the yield was 48.62%.

[0021] ) Synthesis of 1-(2-hydroxyethyl)-3-(3-bromopropyl) imidazole (abbreviated as Br-ID in the present invention)

[0022] Add 1-(2-hydroxyethyl)imidazole (0.09 g, 0.80 mmol) and 1,3-dibromopropane (0.16 g, 0.80 mmol) into a 100 mL three-necked flask, then add 30 mL of acetonitrile to dissolve them, N 2 Stir and reflux at 80°C for 24 h under protection. After the reaction was completed, it was left to cool for 8 h, and a white solid was precipitated. The so...

Embodiment 1

[0026] In Example 1, in process 2), 1-(2-hydroxyethyl)imidazole was changed to 0.18 g, 1,3-dibromopropane was changed to 0.32 g, other reaction conditions were the same, and the yield was 41.50%.

[0027] In process 3), 1-(2-hydroxyethyl)-3-(3-bromopropyl) imidazole was changed to 0.60 g, dichlorosilicon (IV) phthalocyanine was changed to 0.40 g, other reaction conditions were the same, and the yield is 35.00%.

specific Embodiment 3

[0029] In Example 1, in process 2), 1-(2-hydroxyethyl)imidazole was changed to 0.18 g, 1,3-dibromopropane was changed to 0.48 g, and the yield was 48.92%.

[0030] In process 3), 1-(2-hydroxyethyl)-3-(3-bromopropyl)imidazole was changed to 0.60 g, dichlorosilicon(IV) phthalocyanine was changed to 0.40 g, and the reaction temperature was changed to 150°C. Other reaction conditions are the same, and the yield is 33.85%.

[0031] Mitochondrial-targeted bis-(1-(2-ethoxy)-3-(3-bromopropyl)imidazole) axially substituted silicon phthalocyanine (Br-ID-SiPc) in ovarian cancer cell fluorescence imaging and mitochondria position

[0032] HO-8910 ovarian cancer cells in logarithmic growth phase were digested and centrifuged, resuspended in Dulbecco's Modified Eagle Medium (DMEM) cell culture medium and re-counted, in 1×10 4 The number of cells per well (volume 200 μL) was inoculated in a 20 mm confocal dish, and incubated in a 37 °C constant temperature incubator for 4 h. After the cell...

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Abstract

The invention discloses a water-soluble mitochondria-targeted silicon phthalocyanine axially substituted by ethyoxyl bromopropyl imidazole as well as a preparation method and an application of the water-soluble mitochondria-targeted silicon phthalocyanine, and particularly relates to water-soluble mitochondria-targeted di-(1-(2-ethyoxyl)-3-(3-bromopropyl) imidazole) axially substituted silicon phthalocyanine as well as a preparation method and an application thereof. According to the invention, 1-(2-ethoxyl)-3-(3-bromopropyl) imidazole and dichlorosilicon (IV) phthalocyanine are used for preparing di-(1-(2-ethoxyl)-3-(3-bromopropyl) imidazole) axially-substituted silicon phthalocyanine, and the invention discloses an application of the di-(1-(2-ethoxyl)-3-(3-bromopropyl) imidazole) axially-substituted silicon phthalocyanine as a novel photosensitizer for mitochondrial targeting labeling and fluorescence imaging guided photodynamic therapy in photodynamic therapy.

Description

technical field [0001] The invention belongs to the field of complexes, in particular to water-soluble mitochondria-targeted bis-(1-(2-ethoxy)-3-(3-bromopropyl)imidazole) axially substituted silicon phthalocyanine and its preparation method and application , the complex acts as an anticancer photosensitizer. The complex is used as a photosensitizer for mitochondrial targeting labeling and fluorescence imaging-guided photodynamic therapy. Background technique [0002] Photodynamic therapy (PDT) is a new approach to treat cancer, HIV, and wet macular degeneration-like diseases. The key to photodynamic therapy is the photosensitizer. Phthalocyanine complexes are considered to be a class of very high quantum yields due to their high singlet oxygen quantum yield, stable structure and easy modification, maximum absorption wavelength at around 670 nm, easy penetration through the red light region of human tissue, and easy preparation of pure products. Photosensitizer with potent...

Claims

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Application Information

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IPC IPC(8): C07F7/10G01N21/64A61K41/00A61P35/00
CPCC07F7/10A61K41/0057A61P35/00G01N21/6428G01N21/6456
Inventor 陈奎治彭亦如
Owner 福州量衍科技有限公司
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