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Poly (epsilon-caprolactone) supported anti-tumor prodrug and preparation method thereof

An anti-tumor drug, anti-tumor technology, applied in the direction of anti-tumor drugs, pharmaceutical formulations, medical preparations with inactive ingredients, etc. High rate, wide application, low cost effect

Inactive Publication Date: 2013-08-28
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The present invention aims at the defects that anti-tumor prodrugs in the prior art mainly use PEG-ε-caprolactone block copolymer as a carrier, which has low drug loading, PEG has no biodegradability, and cannot further modify molecules. One of the purposes The purpose is to provide a polyε-caprolactone-loaded antitumor prodrug with good water solubility, complete biodegradability, high drug loading, high purity, and a modifiable group

Method used

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  • Poly (epsilon-caprolactone) supported anti-tumor prodrug and preparation method thereof
  • Poly (epsilon-caprolactone) supported anti-tumor prodrug and preparation method thereof
  • Poly (epsilon-caprolactone) supported anti-tumor prodrug and preparation method thereof

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Embodiment 1

[0066] 1. Preparation of α-position bromocyclohexanone

[0067] Add 20.00g (0.20mol) cyclohexanone, 38.14g (0.21mol) N-bromosuccinimide, 1.54g (0.02mol) ammonium acetate and 300mL anhydrous ether into a 500mL bottom flask equipped with a magnet, Clamp it on the iron frame platform, then install a condenser tube, connect a nitrogen bag to the condenser tube, and react at 25°C for 0.5h; after the reaction is completed, filter and wash the filtrate three times with distilled water; dry the organic phase with anhydrous magnesium sulfate , filtered, and after concentrating the solvent, separated on a silica gel column (petroleum ether / ethyl acetate=10:1) to obtain 30.09 g (85.0%) of a light yellow oily liquid.

[0068] 2. Preparation of α-brominated ε-caprolactone

[0069] Add 17.70g (0.10mol) α-position bromocyclohexanone and 20.64g (0.12mol) m-chloroperoxybenzoic acid to a 500mL single-necked round bottom flask equipped with a magnet, then add 300mL dichloromethane, at 25°C Und...

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Abstract

The invention discloses a poly (epsilon-caprolactone) supported anti-tumor prodrug and a preparation method thereof. The preparation method comprises the following steps of: performing ring opening polymerization on alpha-site bromo-epsilon-caprolactone to generate poly (alpha-site bromo-epsilon-caprolactone); performing a click chemical reaction of mercapto-alpha-site bromo-ester of thiomalic acid on the alpha-site of the poly (alpha-site bromo-epsilon-caprolactone) to obtain poly (epsilon-caprolactone) containing a pendant carboxyl group; and performing a substitution reaction on the poly (epsilon-caprolactone) containing the pendant carboxyl group and anti-tumor medicinal molecules, neutralizing with a strong alkali and weak acid salt solution of an alkali metal, extracting to remove impurities, and dialyzing the purified solution to obtain the anti-tumor prodrug. The anti-tumor prodrug is high in water solubility, can be completely biodegraded, is high in drug carrying quantity and high in purity, and contains groups capable of being further modified; and the preparation method is economic, efficient and nontoxic, and can realize industrialized production.

Description

technical field [0001] The invention relates to an antitumor prodrug loaded with polyε-caprolactone and a preparation method thereof, belonging to the field of antitumor drug modification. Background technique [0002] Paclitaxel is an antineoplastic drug, and it has been proven to have good clinical effects in breast cancer, ovarian cancer, non-small cell lung cancer and prostate cancer. The toxicity of paclitaxel is caused by the interaction with microtubules in cells, which disrupts the mitosis of cancer cells and leads to the death of cancer cells. Although paclitaxel is a good anticancer agent, their super lipophilicity leads to poor solubility in water. [0003] In order to overcome the problem of the solubility of paclitaxel in water, the paclitaxel preparation currently used clinically is to dissolve paclitaxel in a mixed solution of polyoxyethylene castor oil and absolute ethanol (50:50, v / v) at a concentration of 7mmol / L. The trademark of this preparation is ...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K31/337A61P35/00
Inventor 张雪飞麻戈军
Owner XIANGTAN UNIV