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Trianilino fluoroaryl benzyl ether dendrimer substituted silicon phthalocyanine and its preparation method and application

A technology of triphenylamine-based aryl benzyl ether and fluoroaryl benzyl ether, which is applied in the field of complexes to achieve the effects of strong resistance to temperature and oxidation, inhibition of self-aggregation behavior, and strong solubility

Active Publication Date: 2020-08-25
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Finally, there is no report about the substitution of silicon phthalocyanine with triphenylamino-fluorinated aryl benzyl ether dendrimers at home and abroad.

Method used

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  • Trianilino fluoroaryl benzyl ether dendrimer substituted silicon phthalocyanine and its preparation method and application
  • Trianilino fluoroaryl benzyl ether dendrimer substituted silicon phthalocyanine and its preparation method and application
  • Trianilino fluoroaryl benzyl ether dendrimer substituted silicon phthalocyanine and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 1) Dichlorosilicon phthalocyanine (SiPcCl 2 )Synthesis

[0027] 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 into 500mL methanol solution, stirred and stood for about 1h, filtered, and the filter residue was washed with 35 mL each of acetone, methanol, dichloromethane, methanol and other solvents, and after drying, 3.6759 g of purple solid was obtained. The yield was 48.62%.

[0028] ) Synthesis of 4'-(diphenylamino)-[1,1'-biphenyl]-4-carboxylic acid (abbreviated as TPA-COOH in the present invention)

[0029] In a three-neck round bottom flask (250mL), add 4-bromotriphenylamine (1.260 g, 3.89 mmol), 4-carboxyphenylboronic acid (0.64 g, 3.86 mmol), tetrakis(triphenylphosphine) palladium Pd(PPh 3 ) 4 (0.140 g, 0.120 mmol), after anhydrous and anaerobic operation, inject ethylene glycol dimethyl ethe...

Embodiment 2

[0039] The specific steps are the same as in Example 1: in process 2), 4-bromotriphenylamine was changed to (2.52 g, 7.78 mmol), 4-carboxyphenylboronic acid was changed to (1.28 g, 7.72 mmol), and the reaction temperature was changed to 90°C; The time was changed to 36 h. Other reaction conditions were the same, and 1.574 g of tan powder was obtained with a yield of 55.8%.

[0040] The specific steps are the same as in Example 1: Process 3) TPA-COOH is changed to (0.36 g, 1.00 mmol), fluorobisphenol A is changed to (0.504 g, 1.50 mmol), DMAP is changed to (36 mg, 0.3 mmol), EDC HCl was changed to (0.25 g, 1.30 mmol), the reaction time was changed to two nights, and other reaction conditions were the same, and 0.40 g of yellow powder was obtained with a yield of 58.8%.

[0041] The specific steps are the same as in Example 1: Process 4) TPA-COOH was changed to (0.36 g, 1.00 mmol), bisphenol A was changed to (0.342 g, 1.50 mmol), DMAP was changed to (36 mg, 0.3 mmol), EDC HCl w...

Embodiment 3

[0045] Evaluation of Photodynamic Activity of TPA-FBPA-SiPc on MCF-7 Breast Cancer Cells

[0046] Inoculate a 96-well plate, 100 uL per well containing 5×10 3 After culturing for 24 hours, TPA-FBPA-SiPc was added to the culture medium. Without laser irradiation, the drug is protected from light for 24 hours. Cells cultured without adding nanoparticles, only adding blank solvent (normal saline) and without laser radiation were used as the negative control group. CCK-8 measures cell viability. See figure 1 , figure 1 Cell viability under different conditions: TPA-FBPA-SiPc(5μM), Laser (100 J / cm2)) (*p<0.05, ***p<0.001, statistical analysis compared with PBS.

[0047] From figure 1 It can be seen that DSPE-PEG 2000 @TPA-FBPA-SiPc nanoparticles have obvious inhibitory effect on breast cancer.

[0048] Photodynamic Activity Evaluation of MCF-7 Breast Cancer Cells

[0049] Inoculate a 96-well plate, 100 uL per well containing 5×10 3 After culturing for 24 hours, TPA-BPA-Si...

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Abstract

The invention discloses silicon phthalocyanine substituted by a trianilino fluoro aryl benzyl ether dendritic ligand and a preparing method and application thereof. Firstly, 4'-(diphenylamino)-[1,1'-biphenyl]-4-carboxylic acid is synthesized from 4-bromotriphenylamine and phenylboronic acid, and is then subjected to condensation with hexafluorobisphenol A or bisphenol A respectively to prepare 4-(diphenylamino)-1-biphenylcarboxylic acid-1-carbobenzoxy-1,1,1,3,3,3-hexafluoropropyl phenol and 4-(diphenylamino)-1-biphenylcarboxylic acid-1-carbobenzoxy propyl phenol; and finally, the 4-(diphenylamino)-1-biphenylcarboxylic acid-1-carbobenzoxy-1,1,1,3,3,3-hexafluoropropyl phenol and the 4-(diphenylamino)-1-biphenylcarboxylic acid-1-carbobenzoxy propyl phenol react separately with silicon phthalocyanine dichloride to synthesize bis-(4-(diphenylamino)-1-biphenylcarboxylic acid-1-carbobenzoxy-4-(1,1,1,3,3,3-hexafluoropropyl-4-phenoxy) axially substituted silicon phthalocyanine and bis-(4-(diphenylamino)-1-biphenylcarboxylic acid-1-carbobenzoxypropylphenoxy) axially substituted silicon phthalocyanine. The products can be used as fluorescence imaging agents and photodynamic therapy photosensitizers.

Description

technical field [0001] The invention belongs to the field of complexes, in particular to a trianilinyl fluorinated aryl benzyl ether branch ligand substituted silicon phthalocyanine and a preparation method and application thereof. The complex is used as an anticancer photosensitizer and a fluorescent imaging agent. Background technique [0002] Photodynamic therapy (PDT) is a method used to treat neoplastic and non-neoplastic diseases. The three elements of PDT are: photosensitizer, light and molecular oxygen. It uses light to excite enriched photosensitizer molecules (Photosensitizer, PS) in tumor tissue to generate highly cytotoxic singlet oxygen ( 1 o 2 ), killing cancer cells from inside the cell. without harming normal tissues. Phthalocyanine complexes are very promising second-generation photosensitizers, which have the advantages of good photothermal stability, tissue compatibility and low cytotoxicity, but due to the existence of conjugated systems of phthalocya...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10C09K11/06A61K41/00A61P35/00
CPCA61K41/0052A61K41/0071A61P35/00C07F7/10C09K11/06
Inventor 彭亦如郭秋梅林昌铨
Owner FUJIAN NORMAL UNIV
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