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PDT (photodynamics therapy) prodrug based on carbonylated polycaprolactone as well as preparation method and application of PDT prodrug

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

Active Publication Date: 2020-06-05
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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  • PDT (photodynamics therapy) prodrug based on carbonylated polycaprolactone as well as preparation method and application of PDT prodrug
  • PDT (photodynamics therapy) prodrug based on carbonylated polycaprolactone as well as preparation method and application of PDT prodrug
  • PDT (photodynamics therapy) prodrug based on carbonylated polycaprolactone as well as preparation method and application of PDT prodrug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of CABALA:

[0042]

[0043] Add 1.68g 5-aminolevulinic acid hydrochloride, 0.84g sodium bicarbonate and 20ml deionized water in a 50mL two-necked flask. After the above raw materials are completely dissolved, add 1.7g benzyl chloroformate dropwise under ice-water bath conditions. , React overnight at room temperature, concentrate and filter to remove unreacted benzyl chloroformate and solvent, the white solid obtained is washed with methanol and dried to constant weight to obtain 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] Vacuum the 25mL reaction eggplant bottle three times and add 1g polyethylene glycol monomethyl ether 2000 (mPEG 2000), 1.28g 4-carbonyl-ε-caprolactone (OPD) and 1.71gε- under argon protection. Caprolactone (ε-CL), vacuum for 2h, add 10ml dry toluene and catalyst stannous isooctanoate Sn(Oct) 2 0.101g, reacted at 90°C for 24h. The reaction product was settled in glacial ether, and the sediment was filtered with a sand core funnel and dried in vacuum to a constant weight to obtain a 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) includes the following steps:

[0050]

[0051] x=20, y=30.

[0052] The access of ethoxylated ...

Embodiment 3

[0057] Synthesis of polycaprolactone-based amphiphilic copolymer mPEG-b-P(CL-co-OPD)

[0058]

[0059] x=30, y=20.

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

[0062]

[0063] x=30, y=20.

[0064] Access of ethoxylate: Weigh 1g polycaprolactone-based amphiphilic copolymer mPEG-bP (CL-co-OPD) and 0.438g ethoxylate in...

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Abstract

The invention discloses a PDT (photodynamics therapy) prodrug based on carbonylated polycaprolactone. The structure of the PDT prodrug is represented in the description, wherein x is equal to 10-40, and y is equal to 10-40. The PDT prodrug based on carbonylated polycaprolactone is an amphiphilic polymer and can be prepared into micelles. A cell experiment proves that compared with pure 5-aminolevulinic acid, the content of the prodrug micelles converted into protoporphyrin is higher, and the prodrug has better destruction property on tumor cells. 5-aminolevulinic acid is introduced into functionalized polycaprolactone with a chemical grafting method, esterification of the 5-aminolevulinic acid is realized, lipid solubility and stability of 5-aminolevulinic acid are improved, and the prodrug has better targeting performance, higher conversion rate and better photodynamic effect.

Description

Technical field [0001] The invention belongs to a carbonylation polycaprolactone-based photodynamic therapy prodrug, and particularly relates to a carbonylation polycaprolactone-based photodynamic therapy prodrug and a preparation method and application. Background technique [0002] Photodynamic therapy (PDT) is a new technology that uses photodynamic effects for disease diagnosis and treatment. 5-Aminolevulinic acid (ALA) is a second-generation porphyrin photosensitizer developed in recent years. ALA is absorbed in the cell 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 that can kill cells, thereby killing tumors cell. As the first photosensitizer prodrug approved by the U.S. Food and Drug Administration (FDA) for topical PDT, ALA has been widely used clinically. However, ALA is a hydrophilic zwitterion with poor fat solubility ...

Claims

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Application Information

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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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