Gemcitabine prodrug compound, biomimetic nano drug carrier and preparation method thereof

A biomimetic nano and gemcitabine technology, applied in the polymer field, can solve the problems of not greatly improving the chemotherapy effect of pancreatic cancer, not effectively achieving effective drug delivery and intelligent controlled release, etc., to achieve intelligent release, improve uptake, and overcome early leakage. Effect

Active Publication Date: 2021-10-08
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, the applicant found in the study of pancreatic cancer chemotherapy that the existing drug-loaded micelles are not completely ideal, and the effective delivery and intelligent controlled release of drugs from the tissue level to the cell level have not been effectively realized, so this method has not Dramatically improve the efficacy of chemotherapy for pancreatic cancer

Method used

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  • Gemcitabine prodrug compound, biomimetic nano drug carrier and preparation method thereof
  • Gemcitabine prodrug compound, biomimetic nano drug carrier and preparation method thereof
  • Gemcitabine prodrug compound, biomimetic nano drug carrier and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0047] The preparation method of the biomimetic drug carrier, comprising:

[0048] S1. Dissolve 10 g of 2-mercaptoethanol and 0.5 g of potassium iodide in a three-necked flask filled with 30 mL of ethyl acetate, and slowly add 1 mL of hydrogen peroxide while stirring. Stirring was continued at room temperature for 2 hours. After the stirring was completed, a saturated saline solution was added, and the aqueous phase was extracted with ethyl acetate, and finally the solvent was removed by rotary evaporation to obtain 2,2'-dithiodiethanol having the structural formula (I),

[0049]

[0050] The reaction equation for S1 is,

[0051]

[0052] S2. Dissolve 5g of 2,2'-dithiodiethanol (I) and 3.9g of triethylamine prepared in S1 in dichloromethane, place in an ice-water bath, and slowly add 3.5g of propylene dropwise under stirring acid chloride. After the dropwise addition was complete, stirring was continued at room temperature for 24 hours. After the reaction is finished...

Embodiment 2

[0083] S1. Dissolve 10 g of 2-mercaptoethanol and 0.5 g of potassium iodide in a three-necked flask filled with 30 mL of ethyl acetate, and slowly add 1 mL of hydrogen peroxide while stirring. Stirring was continued at room temperature for 2 hours. After the stirring was completed, a saturated saline solution was added, and the aqueous phase was extracted with ethyl acetate, and finally the solvent was removed by rotary evaporation to obtain 2,2'-dithiodiethanol having the structural formula (I),

[0084]

[0085] The reaction equation for S1 is,

[0086]

[0087] S2. Dissolve 5g of 2,2'-dithiodiethanol (I) and 3.9g of triethylamine prepared in S1 in dichloromethane, place in an ice-water bath, and slowly add 3.5g of propylene dropwise under stirring acid chloride. After the dropwise addition was complete, stirring was continued at room temperature for 24 hours. After the reaction is finished, add a saturated aqueous common salt solution, extract therein with dichloro...

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Abstract

The invention discloses a gemcitabine prodrug compound, a biomimetic nano-drug carrier and a preparation method thereof. PEI is first reacted with a reductively responsive prodrug segment to obtain a PEI with a positive charge on the surface and partially reacted amino groups, and then the Then react with the phosphorylcholine segment with aldehyde group, put it into a dialysis bag with MW=3500, and dialyze for 2 days to remove organic solvents and unreacted small molecules, and finally get a pH / GSH multi-level response biomimetic nano-drug carriers. The preparation method of the nano-microcarrier in the present invention is simple and novel, and the multi-level response is compared with the previously reported drug carrier. The charged PEI promotes the endocytosis of the prodrug molecule by the cell. After the prodrug molecule enters the cancer cell, a large amount of GSH in the cancer cell further decomposes the disulfide bond in the prodrug, precisely controls the release of the drug, and realizes the release of the drug. effective release and treatment of tumor cells.

Description

technical field [0001] The invention relates to the field of macromolecules, in particular to a gemcitabine prodrug compound, a bionic nano drug carrier and a preparation method thereof. Background technique [0002] In recent years, nano drug carriers covalently loaded chemotherapy drugs and are sensitive to biological signals (such as low pH value, high glutathione concentration) of tumor tissues have become an important idea for the development of new smart nano-microcarriers. Nevertheless, the applicant found in the study of pancreatic cancer chemotherapy that the existing drug-loaded micelles are not completely ideal, and the effective delivery and intelligent controlled release of drugs from the tissue level to the cell level have not been effectively realized, so this method has not Greatly improve the chemotherapy effect of pancreatic cancer. Contents of the invention [0003] The purpose of the present invention is to overcome the deficiencies of the prior art, e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/073C07H1/00C08G73/02C07H19/10A61P35/00A61K31/7068A61K9/107A61K47/34
CPCA61K9/1075A61K31/7068A61K47/34A61P35/00C07H1/00C07H19/073C07H19/10C08G73/0206
Inventor 熊俊杰刘续宝
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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