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Drug delivery material with pH and dual redox responsiveness and preparation method and application thereof

A responsive, drug-based technology, applied in drug delivery, medical formulations with inactive ingredients, and medical formulations containing active ingredients, etc., can solve the problem of unsatisfactory drug carrier stability, poor tumor treatment effect, and delayed drug release. and other problems, to achieve the effect of improving multi-drug resistance, wide application range and high drug content

Inactive Publication Date: 2018-11-16
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, drug delivery materials that respond to a single stimulus still have disadvantages, such as slow response, delayed drug release, and easy damage to normal tissues
In addition, most anticancer drugs are physically coated in the carrier, the stability of the drug carrier obtained in this way is not satisfactory, the drug loading is low, and the limited drug is not enough to enrich the tumor site
The various causes of cancer, the multi-drug resistance of the human body and the single drug are the important reasons for the little effect of tumor treatment

Method used

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  • Drug delivery material with pH and dual redox responsiveness and preparation method and application thereof
  • Drug delivery material with pH and dual redox responsiveness and preparation method and application thereof
  • Drug delivery material with pH and dual redox responsiveness and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 1. Preparation of N,N'-bis(tert-butoxycarbonyl)-L-cystine-(polyethylene glycol ester) 2

[0046] 0.30g (0.68mmol) of N,N'-bis(tert-butoxycarbonyl)-L-cystine shown in formula I (according to the literature "Hyun-Chul Kim, Eunjoo Kim, Tae-Lin Ha, Sang Won Jeong , Se Guen Lee, Sung Jun Lee, Boram Lee. Thiol-responsive Gemini poly(ethylene glycol)-poly(lactide) with a cystinedisulfide spacer as an intracellular drug delivery nanocarrier. Colloids and Surfaces B: Biointerfaces, 2015, 127, 206–212" published method prepared) and 3.26g (1.63mmol) of polyethylene glycol 2000 were dissolved in 50mL of anhydrous dichloromethane and nitrogen gas was bubbled in, and after adding 0.42g (2.05mmol) of N,N'-dicyclohexylcarbodiimide, room temperature The reaction was carried out for 48 hours. After the end, remove the insoluble matter by filtration, the filtrate is rotary evaporated to remove the solvent and precipitate in excess ether, the precipitate is dried in vacuum at room tempe...

Embodiment 2

[0063] 1. Preparation of N,N'-bis(tert-butoxycarbonyl)-L-cystine-(polyethylene glycol ester) 2

[0064] This step is the same as Step 1 of Example 1.

[0065] 2. Preparation of macromolecular initiator

[0066] This step is the same as Step 2 of Example 1.

[0067] 3. Preparation of N,N'-bis(tert-butoxycarbonyl)-L-cystine-(polyethylene glycol ester) 2 -b-(Polyferroceneformyloxyethyl methacrylate) 2 block polymer

[0068] 0.30g (6.38×10 -2 mmol) The macroinitiator shown in formula III-1 and 2.64g (7.66mmol) ferrocene formyloxyethyl methacrylate are dissolved in 8mL anhydrous N, N-dimethylformamide, add under nitrogen protection 79.50 μL (0.383 mmol) of pentamethyldiethylenetriamine and 31.60 mg (0.319 mmol) of cuprous chloride were then subjected to “freezing-vacuumizing-thawing” three times, and polymerized at 90° C. for 48 hours. After the reaction, the reaction solution was passed through a neutral alumina column, and the obtained liquid was rotary evaporated and precip...

Embodiment 3

[0077] 1. Preparation of N,N'-bis(tert-butoxycarbonyl)-L-cystine-(polyethylene glycol ester) 2

[0078] Dissolve 0.30 g (0.68 mmol) of N,N'-bis(tert-butoxycarbonyl)-L-cystine represented by formula I and 6.52 g (1.63 mmol) of polyethylene glycol 4000 in 75 mL of anhydrous dichloromethane Nitrogen gas was blown in, and 0.42 g (2.05 mmol) of N,N'-dicyclohexylcarbodiimide was added and reacted at room temperature for 48 hours. After the end, remove the insoluble matter by filtration, the filtrate is rotary evaporated to remove the solvent and precipitate in excess ether, the precipitate is dried in vacuum at room temperature to constant weight, the crude product is re-dissolved in water and transferred to a dialysis bag with a molecular weight cut off of 3500, and dialyzed with deionized water , freeze-dried to obtain N,N'-bis(tert-butoxycarbonyl)-L-cystine-(polyethylene glycol ester) shown in formula II-3 2 , the yield was 28%.

[0079]

[0080] 2. Preparation of macromole...

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Abstract

The invention discloses a drug delivery material with pH and dual redox responsiveness and a preparation method and application thereof. According to the preparation method, an esterification productof N,N'-bis(tertbutyloxycarbonyl)-L-cystine and polyethylene glycol reacts with 2-Bromoisobutyryl bromide to obtain a macroinitiator; and then through atom transfer radical polymerization, deprotection and coupling with doxorubicin, (doxorubicin)2-cystine-(macrogol ester)2-b-(polymethylacrylic ferrocene methanoylethyl ester)2, namely the drug delivery material is obtained. The material is convenient to prepare, can be used as a drug carrier for physical coating of paclitaxel or a dimer thereof. The drug loaded micelle has high drug content, strong stability and good biocompatibility and has pH, dual or triple redox responsiveness. As the product contains at least one anti-cancer drug, the material can improve multi-drug resistance of human body, and effective treatment of tumors is achieved through different therapeutic mechanisms.

Description

technical field [0001] The invention belongs to the technical field of biomedical materials, and specifically relates to a drug delivery material with strong stability, good biocompatibility and high drug content, which has pH and double redox responsiveness, and a preparation method and application of the material. Background technique [0002] For decades, how to make anticancer drugs "make the best use of them" and target the tumor site has been an important research topic. Therefore, stimuli-responsive drug delivery materials have been extensively studied. However, single-stimuli-responsive drug delivery materials still have disadvantages, such as slow response, delayed drug release, and easy damage to normal tissues. In addition, most anticancer drugs are physically coated in the carrier, the stability of the drug carrier obtained in this way is not satisfactory, the drug loading is low, and the limited drug is not enough to enrich the tumor site. The various causes o...

Claims

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Application Information

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IPC IPC(8): A61K47/69A61K47/60A61K9/107A61K47/34A61K31/704A61K31/337A61P35/00
CPCA61K9/1075A61K31/337A61K31/704A61K47/34A61K47/60A61K47/6907A61P35/00A61K2300/00
Inventor 徐峰徐静文罗延龄
Owner SHAANXI NORMAL UNIV
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