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A carbonylated polycaprolactone-based photodynamic therapy prodrug and its preparation method and application

A technology of polycaprolactone and carbonylation, which is applied in the field of carbonylated polycaprolactone-based photodynamic therapy prodrugs and preparations, can solve problems such as instability and poor fat solubility of ALA, and achieve high conversion rate and good photodynamic therapy Curative effect, good targeted effect

Active Publication Date: 2022-05-06
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to overcome the defects of poor fat solubility and instability of ALA, the object of the present invention is to provide a carbonylated polycaprolactone-based photodynamic therapy prodrug, which can increase the amount of ALA converted into PpIX, and can improve the lethality to tumor cells , thus improving the effect of photodynamic therapy

Method used

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  • A carbonylated polycaprolactone-based photodynamic therapy prodrug and its preparation method and application
  • A carbonylated polycaprolactone-based photodynamic therapy prodrug and its preparation method and application
  • A carbonylated polycaprolactone-based photodynamic therapy prodrug and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of CABALA:

[0042]

[0043]Add 1.68g of 5-aminolevulinic acid hydrochloride, 0.84g of sodium bicarbonate and 20ml of deionized water in sequence in a 50mL two-necked flask. After the above raw materials are completely dissolved, add 1.7g of benzyl chloroformate dropwise in an ice-water bath , reacted at room temperature overnight, concentrated and filtered to remove unreacted benzyl chloroformate and solvent, the resulting white solid was washed with methanol and dried to constant weight to obtain the compound CABALA. figure 1 is the compound CABALA 1 H NMR spectrum.

Embodiment 2

[0045] Synthesis of Polycaprolactone-Based Amphiphilic Copolymer mPEG-b-P(CL-co-OPD)

[0046]

[0047] x=20, y=30.

[0048] The 25mL reaction eggplant bottle was evacuated three times, and under the protection of argon, 1g of polyethylene glycol monomethyl ether 2000 (mPEG 2000), 1.28g of 4-carbonyl-ε-caprolactone (OPD) and 1.71g of ε- Caprolactone (ε-CL), vacuumize for 2h, add 10ml of dry toluene and catalyst Sn(Oct) 2 0.101g, reacted at 90°C for 24h. The reaction product was settled in glacial ether, and the sediment was suction-filtered with a sand core funnel, and vacuum-dried to constant weight to obtain polycaprolactone-based amphiphilic copolymer mPEG-b-P (CL-co-OPD). figure 2 It is a polycaprolactone-based amphiphilic copolymer mPEG-b-P (CL-co-OPD) 1 H NMR spectrum.

[0049] The preparation method of carbonylated polycaprolactone-based photodynamic therapy prodrug mPEG-b-P (CL-co-ALAOPD) comprises the following steps:

[0050]

[0051] x=20, y=30.

[0052...

Embodiment 3

[0057] Synthesis of Polycaprolactone-Based Amphiphilic Copolymer mPEG-b-P(CL-co-OPD)

[0058]

[0059] x=30, y=20.

[0060] The 25mL reaction eggplant bottle was evacuated three times, and under the protection of argon, 1g of polyethylene glycol monomethyl ether 2000 (mPEG 2000), 1.92g of 4-carbonyl-ε-caprolactone (OPD) and 1.14g of ε- Caprolactone (ε-CL), vacuumize for 2h, add 10ml of dry toluene and catalyst Sn(Oct) 2 0.101g, reacted at 90°C for 24h. The reaction product was settled in glacial ether, and the sediment was suction-filtered with a sand core funnel, and vacuum-dried to constant weight to obtain polycaprolactone-based amphiphilic copolymer mPEG-b-P (CL-co-OPD).

[0061] The preparation method of carbonylated polycaprolactone-based photodynamic therapy prodrug mPEG-b-P (CL-co-ALAOPD) comprises the following steps:

[0062]

[0063] x=30, y=20.

[0064] Access to hydrazine: Weigh 1g of polycaprolactone-based amphiphilic copolymer mPEG-b-P (CL-co-OPD) and...

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Abstract

The invention discloses a carbonylated polycaprolactone-based photodynamic therapy prodrug, the structure of which is as follows: in the formula, x=10-40, y=10-40. The carbonylated polycaprolactone-based photodynamic therapy prodrug of the present invention is an amphiphilic polymer, and can be prepared into micelles. Cell experiments have proved that, compared with pure 5-aminolevulinic acid, the prodrug micelles are converted into The amount of protoporphyrin is higher, and the lethality to tumor cells is better. The present invention adopts the method of chemical grafting to insert 5-aminolevulinic acid into functionalized polycaprolactone, and realizes 5-aminolevulinic acid The esterification of 5-aminolevulinic acid improves the fat solubility and stability of 5-aminolevulinic acid, and has better targeting, higher conversion rate and better photodynamic efficacy.

Description

technical field [0001] The invention belongs to carbonylated polycaprolactone-based photodynamic therapy prodrug, in particular to a carbonylated polycaprolactone-based photodynamic therapy prodrug, its preparation method and application. Background technique [0002] Photodynamic therapy (PDT) is a new technology that utilizes photodynamic effect for disease diagnosis and treatment. 5-Aminolevulinic acid (ALA) is a second-generation porphyrin photosensitizer developed in recent years. ALA is absorbed in cells and converted into protoporphyrin IX (PpIX) with strong photosensitivity. PpIX undergoes a photodynamic reaction after being activated by light of a specific wavelength to generate singlet oxygen with a killing effect on cells, thereby killing tumors cell. As the first photosensitizer prodrug approved by the US Food and Drug Administration (FDA) for topical PDT, ALA has been widely used clinically. However, ALA is a hydrophilic zwitterion with poor fat solubility an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K41/00A61K47/59A61P35/00C08G63/91C08G63/664
CPCC08G63/912C08G63/664A61K41/0057A61P35/00A61K47/593
Inventor 郎美东王申春王秀丽申抒展
Owner EAST CHINA UNIV OF SCI & TECH
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