Preparation and application of fluorescent star-shaped block copolymer

A technology of block copolymers and copolymers, which can be used in preparations for in vivo tests, medical preparations with non-active ingredients, and pharmaceutical formulas, etc., which can solve the problem of peryleneimide's easy aggregation, weak fluorescence properties, and limited applications, etc. problem, to achieve the effect of good optical performance, good fluorescence characteristics, excellent biocompatibility

Active Publication Date: 2016-04-20
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the inherent π-π stacking effect, perylene imides are easy to aggregate in aqueous solution, showing poor solubility and weak fluorescence properties, which limit their applications in the biomedical field.

Method used

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  • Preparation and application of fluorescent star-shaped block copolymer
  • Preparation and application of fluorescent star-shaped block copolymer
  • Preparation and application of fluorescent star-shaped block copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Synthesis of eight-arm initiator compound 2: as attached figure 1 As shown, compound 5 (100mg, 0.08mmol), 4-dimethylaminopyridine (42mg, 0.32mmol) and triethylamine (0.23mL, 1.6mmol) were added to 16mL of tetrahydrofuran, under nitrogen protection and 0°C conditions, A 10 mL tetrahydrofuran solution in which compound 6 (1.06 g, 3.2 mmol) was dissolved was added dropwise. After the dropwise addition, it was stirred at room temperature (25°C) for 24 hours. After the reaction, the tetrahydrofuran was removed by a rotary evaporator, the resulting mixture was dissolved in 20 mL of dichloromethane, and then saturated NaHSO 4 Wash with aqueous solution (3×50 mL), saturated NaCl aqueous solution (3×50 mL) and deionized water (3×50 mL). The organic phase was purified with a silica gel column to obtain 135 mg of intermediate product, which was designated as PDI-ester, and the yield was 90%. The intermediate product PDI-ester (100mg, 0.053mmol) was dissolved in 20mL methanol, ...

Embodiment 2

[0051] (1) PDI-star-PLA prepared in step 2) of Example 1 8 (100mg, 0.0053mmol) and monomer 4 (R1 is ) (400 mg, 1.50 mmol) was added to 0.4 mL of dichloromethane to dissolve it, and 3 freeze-pump cycles were performed. Under the protection of nitrogen, the catalyst 1,8-diazabicyclo[5.4.0]undec-7-ene (0.05 mL) was added, and after freezing and pumping again, the reaction was carried out at 35°C for 10 hours. After the reaction, it was precipitated in ether (3×50 mL), and the solid obtained was dried to constant weight under vacuum to obtain a copolymer, which was recorded as PDI-star-(PLA 13 -b-PPEEABoc 18 ) 8 , The yield is 56.7%. PDI-star-(PLA 13 -b-PEEABoc 18 ) 8 (200mg) dissolved in 0.6mL of dichloromethane, under nitrogen protection and room temperature, add 0.6mL of trifluoroacetic acid dropwise, continue to stir for 3 hours; after the completion of the reaction, remove the trifluoroacetic acid with a rotary evaporator, and precipitate in ether (3×50mL), the obtained solid...

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Abstract

The invention discloses a preparation method for a fluorescent star-shaped block copolymer and application of the fluorescent star-shaped block copolymer serving as a medicine carrier. According to the preparation method, the fluorescent star-shaped block copolymer is prepared according to ring opening polymerization by taking amphipathic polylactic acid-polyphosphoester as an arm and taking a perylene bisimide derivative as a core. The fluorescent star-shaped block copolymer is self-assembled in an aqueous solution to form fluorescent supramolecular micelles, have good fluorescence characteristics, and can serve as a fluorescent probe and be used for cell and in-vivo imaging. The fluorescent supramolecular micelles prepared by the preparation method can effectively carry hydrophobic medicines and realize pH stimulation release. The analysis of a laser scanning confocal microscope and a flow cytometer show that the fluorescent supramolecular micelles are easily swallowed by cancer cells and can realize cellular internalization. In in-vitro and in-vivo tumor growth inhibition experiments, compared with a free medicine, the inhibition effect of the fluorescent supramolecular micelles to tumor growth is more obvious, so that the fluorescent supramolecular micelles have potential application value in the fields of biological imaging and cancer treatment.

Description

Technical field [0001] The invention belongs to the technical field of pharmaceutical carrier preparation, and specifically relates to the preparation of a fluorescent star block copolymer and its application as a pharmaceutical carrier in cancer treatment. Background technique [0002] Cancer seriously threatens human life and is the main cause of high morbidity and mortality. Chemotherapy, as a traditional treatment method, together with surgery and radiotherapy, is called the three major treatment methods for cancer. However, traditional anticancer drugs have poor water solubility, low bioavailability, and low treatment efficiency. Therefore, the research on drug carriers is the focus of recent domestic and foreign research. In order to increase the solubility and bioavailability of drugs, and reduce the side effects of anti-cancer drugs, in recent years, researchers have prepared a series of nano drug carriers, such as dendrimers, nano micelles, polymer coupled drugs, and li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G79/04C08G63/08C08G63/87A61K49/00A61K47/34
CPCA61K47/34A61K49/0019A61K49/0065C08G63/08C08G63/823C08G79/04
Inventor 尹梅贞孙盟盟尹文艳
Owner BEIJING UNIV OF CHEM TECH
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