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A drug delivery material with pH and double redox responsiveness and its preparation method and application

A responsive, drug technology, applied in the direction of drug delivery, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., can solve the problem of low drug loading, unsatisfactory drug carrier stability, single drug, etc. question

Inactive Publication Date: 2021-04-09
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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  • A drug delivery material with pH and double redox responsiveness and its preparation method and application
  • A drug delivery material with pH and double redox responsiveness and its preparation method and application
  • A drug delivery material with pH and double redox responsiveness and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0046]0.30 g (0.68 mmol) of N, N'-bis (tert-butoxycarbonyl) -L-cystine (according to the literature "Hyun-chul Kim, Eunjoo Kim, Tae-Lin Ha, Sang Won Jeong , Se Guen Lee, Sung Jun Lee, BoramLee.Thiol-responsive Gemini poly (ethylene glycol) -poly (lactide) with a cystinedisulfide spacer as an intracellular drug delivery nanocarrier.Colloids andSurfaces B: Biointerfaces, 2015,127,206-212 "disclosed in Methods were prepared by 3.26 g (1.63 mmol) polyethylene glycol 2000 dissolved in 50 ml of anhydrous dichloromethane and drumped into nitrogen, add 0.42 g (2.05 mmol) N, N'-bicyclic hexyl carbon diimide back room temperature. The reaction was reacted for 48 hours. After the end, the insoluble matter was removed, and the filtration was evaporated to remove the solvent, precipitated in excess diethyl ether, and the precipitate vacuum was dried to constant weight, and the crude product was reinurated in ...

Embodiment 2

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

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

[0065]2. Preparation of macromolecular initiators

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

[0067]3, prepare N, N'-bis (tert-butoxycarbonyl) -L-cystine-(polyethylene glycol ester)2-B- (polymethyl methacrylate ferrousoxyeta)2Block polymer

[0068]0.30g (6.38 × 10)-2Mmol) Macromolecular initiator and 2.64 g (7.66 mmol) of methacrylate in 5 ml of anhydrous o, N-dimethylformamide, added under nitrogen protection 79.50 μL (0.383 mmol) 5 methylxide triamine and 31.60 mm (0.319 mmol) chloride were subsequently "frozen - evacuated - thaw" operation three times, and the polymerization was carried out at 90 ° C for 48 hours. After the reaction is completed, the reaction liquid passes through a neutral alumina column, and the resulting liquid is spurred and then precipitated three times in excess diethyl ether, and the vacuum is dried to constant we...

Embodiment 3

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

[0078]0.30 g (0.68 mmol) of N, N'-bis (tert-butoxycarbonyl) -L-cystine and 6.52 g (1.63 mmol) polyethylene glycol 4000 were dissolved in 75 ml anhydrous dichloromethane. The nitrogen was drumped, 0.42 g (2.05 mmol) N, N'-bicyclic hexyl carbon diamine reaction was added at 48 hours. After the end, the insoluble matter was removed, and the filtration was evaporated to remove the solvent, precipitated in excess diethyl ether, and the precipitate vacuum was dried to constant weight, and the crude product was reinurated in water into the dialysis bag of the trapped molecular weight of 3500. Dialysis , Freeze dry to obtain N, N'-bis (tert-butoxycarbonyl) -L-cystine-(polyethylene glycol ester) as shown in Formula II-32The yield is 28%.

[0079]

[0080]2. Preparation of macromolecular initiators

[0081]1.00 g (0.119 mmol) of N, N'-bis (tert-butoxycarbonyl) -L-cystine-(polyethylene glycol ester) of formula II-32...

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Abstract

The invention discloses a drug delivery material with pH and double redox responsiveness and its preparation method and application. The material adopts N,N'-bis(tert-butoxycarbonyl)-L-cystine and polyethylene The esterification product of alcohol reacts with 2-bromoisobutyryl bromide to obtain a macromolecular initiator, which is obtained by atom transfer radical polymerization, deprotection, and coupling with doxorubicin (doxorubicin) 2 ‑Cystine‑(polyethylene glycol ester) 2 ‑b‑(Polyferroceneformyloxyethyl methacrylate) 2 , the drug delivery material. The material is easy to prepare and can be used as a drug carrier to physically coat paclitaxel or its dimer. The obtained drug-loaded micelles have high drug content, strong stability, good biocompatibility, and pH, double or triple redox responsiveness. Because it contains at least one anticancer drug, the material can improve the multi-drug resistance of the human body, and realize effective treatment of tumors through different treatment mechanisms.

Description

Technical field[0001]The present invention belongs to the technical field of biopharmaceutical material, and more particularly to a pharmaceutical delivery material having a strong stability, good biocompatibility, high drug content having a pH and dual redox reducing responsiveness, and the preparation method and application of the material.Background technique[0002]For decades, how to make anti-cancer drugs "drugs" and targeted acting on tumor sites is an important topic of research. Therefore, drug delivery materials with stimulating responsiveness have been widely studied. However, a single stimulating drug delivery material still has a drawback, such as slow response, drug release lag, is easy to damage normal tissue. In addition, most anticancer drugs are covered in the vector in the carrier in a physical form, which is not satisfactory with the drug carrier, and the drug amount is low, and the drug is not sufficient to enrich in the tumor site. The cause of cancer, the multi-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/69A61K47/60A61K9/107A61K47/32A61K31/704A61K31/337A61P35/00
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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