Positively charged water-soluble arm-type dendritic ligand silicon phthalocyanine complex and its preparation method and application

A positively charged, water-soluble technology, used in organic silicon compounds, pharmaceutical formulations, chemical instruments and methods, etc., can solve the problem of shortening the quantum yield and lifetime of singlet and triplet states, easy aggregation, and reducing the fluorescence quantum of phthalocyanine molecules. Yield and other issues, to achieve the effect of improving bioavailability and water solubility

Active Publication Date: 2019-07-30
FUJIAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the strong π-π interaction between phthalocyanine molecules, it is easy to aggregate, thereby reducing the fluorescence quantum yield of phthalocyanine molecules, shortening the quantum yield and lifetime of singlet and triplet states, thereby reducing the photosensitization efficiency

Method used

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  • Positively charged water-soluble arm-type dendritic ligand silicon phthalocyanine complex and its preparation method and application
  • Positively charged water-soluble arm-type dendritic ligand silicon phthalocyanine complex and its preparation method and application
  • Positively charged water-soluble arm-type dendritic ligand silicon phthalocyanine complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment 1

[0035] 1) Dichlorosilicon phthalocyanine (SiPcCl 2 )Synthesis

[0036] Add 1,3-diiminoisoindoline (7.28 g, 50.15 mmol), silicon tetrachloride (8.3 mL) and quinoline (83 mL) respectively into a three-necked flask, stir and reflux for 30 min at 220 °C , cooled to room temperature, poured it into 500mL methanol solution, stirred and stood for about 1h, filtered, and washed the filter residue with 35 mL each of acetone, methanol, dichloromethane, methanol and other solvents, and dried to obtain 3.6759 g of a purple solid. The yield was 48.62%.

[0037] ) Synthesis of 3,5-bis(bromopropoxy)benzyl alcohol (abbreviated as M1 in the present invention)

[0038] Add 3,5-dihydroxybenzyl alcohol (1.4018 g, 10 mmol) into a 250 mL three-necked flask, add 52 mL of acetone solvent to dissolve it, add 1,3-dibromopropane (12.3683 g, 60 mmol), anhydrous K 2 CO 3 (8.2887 g, 60 mmol), 18-crown-6 (0.5244 g, 2 mmol). in N 2 Under protection, the reaction was stirred at reflux for more than 4h. ...

Embodiment 1

[0059] In Example 1, in process 2), 3,5-dihydroxybenzyl alcohol was changed to 2.10 g, 1,3-dibromopropane was 18.2683 g, other reaction conditions were the same, and the yield was 42.60%.

[0060] In process 3), 3,5-dihydroxybenzyl alcohol was changed to 2.10 g, 1,4-dibromobutane was changed to 19.1 g, the other reaction conditions were the same, and the yield was 40.62%.

[0061] In process 4), 3,5-bis(bromopropoxy)benzyl alcohol was changed to 1.60 g, 3-methylpyridine was changed to 2.94 g, and the other reaction conditions were the same, and the yield was 67.24%.

[0062] In process 5), 3,5-bis(bromobutoxy)benzyl alcohol was changed to 1.90 g, isoquinoline was changed to 6.78 g, the reaction temperature was changed to 70°C, and other reaction conditions were the same, yield: 57.1%.

[0063] In process 6), 3,5-bis(bromopropoxy)benzyl alcohol was changed to 0.78 g, and dichlorosilicon phthalocyanine was changed to 0.30 g. Other reaction conditions were the same, and the yield...

specific Embodiment 3

[0068] In embodiment one,

[0069] In process 2), 3,5-dihydroxybenzyl alcohol was changed to 4.20 g, 1,3-dibromopropane was 21.60 g, and the yield was 45.30%.

[0070] In process 3), 3,5-dihydroxybenzyl alcohol was changed to 4.50 g, 1,4-dibromobutane was changed to 26.2 g, and the yield was 39.42%.

[0071] In process 4), 3,5-bis(bromopropoxy)benzyl alcohol was changed to 3.20 g, 3-picoline was changed to 2.94 g, and the yield was 59.78%.

[0072] In process 5), 3,5-bis(bromobutoxy)benzyl alcohol was changed to 1.90 g, isoquinoline was changed to 5.23, the reaction temperature was changed to 70°C, and the yield was 57.1%.

[0073] In process 6), 3,5-bis(bromopropoxy)benzyl alcohol was changed to 0.78 g, dichlorosilicon phthalocyanine was changed to 0.30 g, the reaction temperature was changed to 80°C, and the yield was 19.2%.

[0074] In process 7), 3,5-bis(bromobutoxy)benzyl alcohol was changed to 0.10 g, dichlorosilicon phthalocyanine was changed to 0.42 g, the reaction t...

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Abstract

The invention discloses positively charged water-soluble arm type dendritic ligand silicon phthalocyanine complexes as well as preparation methods and an application thereof. The complexes comprise di-(3,5-di(1',3'-methylpyridine propoxy)butanyloxy) axially substituted silicon phthalocyanine and di-(3,5-di(1',4'-isoquinoline butanyloxy)butanyloxy) axially substituted silicon phthalocyanine, wherein di-(3,5-di(1',3'-methylpyridine propoxy)butanyloxy) axially substituted silicon phthalocyanine is prepared from 3,5-di(1',3'-methylpyridine propoxy) phenyl methanol and silicon(IV) phthalocyanine dichloride or from 3,5-di-bromopropoxy) phenyl methanol and excessive methylpyridine and silicon(IV) phthalocyanine dichloride; di-(3,5-di(1',4'-isoquinoline butanyloxy)butanyloxy) axially substituted silicon phthalocyanine is prepared from 3,5-di(1',4'-quinoline butoxy) phenyl methanol and silicon(IV) phthalocyanine dichloride, or from 3,5-di(bromobutoxy) phenyl methanol and excessive isoquinoline and silicon(IV) phthalocyanine dichloride. The application of the complexes as a photosensitizer in photodynamic therapy is disclosed, especially the application to photoinactivation of MDRAB (multidrug-resistant acinetobacter baumannii).

Description

technical field [0001] The invention belongs to the field of complexes, in particular to a water-soluble arm-type dendritic ligand silicon phthalocyanine complex and its preparation method and application. The complex is used as an anti-photosensitizer. The complex is used as a photosensitizer for photoinactivation of multidrug-resistant Acinetobacter baumannii, cancer treatment and cell imaging. Background technique [0002] With the widespread use of broad-spectrum antibiotics, multidrug-resistant Acinetobacter baumannii (MDRAB) is increasing day by day. In 2007, the drug resistance monitoring of China CHINET Acinetobacter baumannii found that MDRAB had reached 47.7%, and 2.8% of the strains were found to be pan-drug-resistant strains (Pandrug-resistant Acinettobacter baumanii, PDRAB). Multidrug-resistant Acinetobacter baumannii can cause serious infections in high-risk groups, and its risk factors include the use of broad-spectrum antibiotics, mechanical ventilation, inv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/02A61K41/00A61P35/00A61P31/04
CPCA61K41/0076C07F7/025
Inventor 彭亦如吕华飞于荣国
Owner FUJIAN NORMAL UNIV
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