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ATRA-PBAE prodrug copolymer as well as preparation method and application thereof

A technology of copolymers and prodrugs, applied in drug combinations, pharmaceutical formulations, anti-tumor drugs, etc., can solve the problems of short biological half-life, low bioavailability of ATRA, poor water solubility, etc.

Pending Publication Date: 2022-08-02
HEILONGJIANG UNIV OF CHINESE MEDICINE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is to provide a kind of ATRA-PBAE prodrug copolymer in order to overcome the shortcomings of ATRA low bioavailability, poor water solubility and short biological half-life in vivo

Method used

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  • ATRA-PBAE prodrug copolymer as well as preparation method and application thereof
  • ATRA-PBAE prodrug copolymer as well as preparation method and application thereof
  • ATRA-PBAE prodrug copolymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The present embodiment provides the synthesis and characterization of ATRA-PBAE, and the specific operations are as follows:

[0048] 1. Instruments and Reagents

[0049] The experimental instruments, reagents and materials used in this example are all commercially available products.

[0050] 2. Experimental method

[0051] 2.1 Synthesis of poly(β-aminoester)

[0052] PBAE synthesis is by Michael addition reaction. Under the molar ratio of 1.2:1, 400 mg of 5-amino-1-pentanol and 640 mg of 1,4-butanediol diacrylate were precisely weighed, dissolved in dichloromethane, and stirred magnetically at 55 °C for 48 h. After the reaction, the reaction product was purified according to the following process: the product was placed in a 10 mL EP tube, 5 mL of ether was added, vortexed for 5 min, centrifuged (5600 rpm, 5 min), discarded the upper layer solution, and repeated 3 times. The organic solvent was removed by vacuum drying, and the product was obtained and stored at 4...

Embodiment 2

[0074] In this example, on the basis of the successful synthesis of the ATRA-PBAE prodrug polymer in Example 1, the formulation evaluation of the ATRA-PBAE prodrug nanoparticles was carried out.

[0075] 1. Instruments and materials

[0076] The experimental instruments, reagents and materials used in this example are all commercially available products.

[0077] 2. Experimental part

[0078] 2.1 Selection of HPLC conditions

[0079] Chromatographic column: DiamonsilC18 (4.6×250mm, 5μm); Mobile phase: methanol-water-glacial acetic acid (90:9.5:0.5);

[0080] Column temperature: 25°C; flow rate: 0.8 mL / min; detection wavelength: 340 nm; injection volume: 10 μL.

[0081] 2.2 Preparation of ATRA-PBAE prodrug nanoparticles

[0082] ATRA-PBAE prodrug nanoparticles were prepared by precipitation method. Accurately weigh 10 mg of ATRA-PBAE polymer and dissolve it with 1 mL of acetone; and under the action of magnetic stirring, slowly drop the prodrug acetone solution into an aqu...

Embodiment 3

[0115] This example is the study of the effect of ATRA-PBAE prodrug nanoparticles on tumor heterogeneous cells

[0116] CSCs are a class of tumor heterogeneous cells with high self-renewal ability and differentiation potential. They are closely related to tumorigenesis, recurrence and metastasis, and drug resistance, and are the main reason for breast tumor recurrence. Pin1 is involved in multiple mechanistic pathways of breast cancer tumors, and Pin1 is not only overexpressed in breast cancer cells, but also a key regulator of BCSCs. Therefore, regulating the activity of Pin1 can effectively control the growth or inhibition of breast tumor cells.

[0117] In this example, based on the successful preparation of ATRA-PBAE nanoparticles, the proliferation inhibitory effect and cellular uptake of ATRA prodrug nanoparticles on MCF-7 cells and MS cells were further studied, and the two cellular uptake mechanisms and drug effects in cells were investigated. transfer within.

[011...

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Abstract

The invention discloses an ATRA-PBAE prodrug copolymer as well as a preparation method and application thereof, and belongs to the technical field of medicines. According to the present invention, the ATRA-PBAE prodrug copolymer is provided, and the pH sensitive PBAE copolymer is synthesized through the Michael addition reaction; and then synthesizing the pH response type ATRA prodrug copolymer through esterification reaction. The prodrug compound disclosed by the invention has a remarkable effect on prevention and treatment of tumors, the invention also discloses a drug-loaded nano particle which is SchB / ATRA-PBAE and is obtained by entrapping SchB with an ATRA-PBAE prodrug copolymer, and the prodrug compound has a very obvious effect on prevention and / or treatment of tumors, especially breast tumors.

Description

technical field [0001] The invention relates to an ATRA-PBAE prodrug copolymer and a drug nanoparticle containing SchB, belonging to the technical field of drugs. Background technique [0002] At present, malignant tumor has become a common and frequently-occurring disease in all countries in the world, and its morbidity and mortality are increasing year by year. Among them, breast cancer (BC) has surpassed lung cancer to become the most common cancer in the world, and is the number one killer threatening women's health. Although survival rates for patients in most high-income countries have exceeded 80%, survival rates in low-income countries remain low. At present, breast cancer treatment still faces many problems, such as: low drug accumulation in tumor tissue, drug resistance, easy recurrence and metastasis. Many clinical anti-tumor small molecule chemotherapeutics are less bioselective due to their systemic distribution after administration, the drug concentration in ...

Claims

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Application Information

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IPC IPC(8): A61K47/59A61K31/07A61K9/51A61K47/34A61K31/36C08G73/02A61P35/00
CPCA61K31/07A61K47/59A61P35/00A61K31/36A61K9/5146C08G73/02A61K2300/00
Inventor 李伟男孙佳琳王艳宏
Owner HEILONGJIANG UNIV OF CHINESE MEDICINE
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