Preparation and application of polymer gel fluorescent probe based on azo reduction response

A polymer and azobenzene technology, which is applied in the preparation and application of polymer gel fluorescent probes, can solve the problems of less research on hydrogel drug-loading systems, and achieve high sensitivity

Active Publication Date: 2019-10-25
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

AIE-based DDSs are widely used to detect drug distribution, drug activation and in situ therapy [Ref: Yuan, Y.Y.; Liu, B., Visualization of drug delivery processes using AIEgens. Chem. Sci. 2017, 8, 2537-2546.] , most of the public reports in the prior art are based on micellar drug loading, and there are relatively few studies on visualized hydrogel drug loading systems, especially in the field of colonic drug delivery systems.

Method used

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  • Preparation and application of polymer gel fluorescent probe based on azo reduction response
  • Preparation and application of polymer gel fluorescent probe based on azo reduction response
  • Preparation and application of polymer gel fluorescent probe based on azo reduction response

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] The preparation method of the cross-linking agent based on azobenzene reduction responsiveness comprises the following steps:

[0083] 1. Synthesis of TPE-2OH:

[0084] Add zinc powder (45.63g, 0.70mol) and 4-hydroxybenzophenone (34.75g, 0.175mol) to a 500mL dry three-necked flask, add about 300mL dry THF to dissolve, place in an ice bath and stir with argon . Titanium tetrachloride (46.20 mL, 0.42 mol) was slowly added dropwise to the mixture, and after the dropwise addition, the reaction was continued in an ice bath for 0.5 h, and then returned to room temperature for another 0.5 h. Then transfer to an oil bath and gradually heat up to reflux. After 24 hours, the reaction was stopped, returned to room temperature, suction filtered, concentrated by rotary evaporation, poured into 10wt% potassium carbonate solution and stirred, a large amount of solid was produced, and a yellow filtrate was obtained by suction filtration. The filtrate was dried and concentrated, and ...

Embodiment 2

[0098] A method for preparing a hydrogel fluorescent probe with azobenzene reduction responsiveness, comprising the following steps:

[0099] A certain proportion of PEGMA (500 g / mol) and AAc, the cross-linking agent TPE-2TEGAzoMA prepared in Example 1, the initiator AIBN and the solvent DMF were added to a 10 mL ampoule. Wherein, the molar ratio of PEGMA and AAc is 1-8:1, the cross-linking agent based on azobenzene accounts for 0.005-0.03 of the total moles of PEGMA and AAc, and the AIBN accounts for 0.002 of the total moles of PEGMA and AAc. After mixing evenly, seal the tube with nitrogen to remove oxygen, place it in an oil bath at 70°C for about 5 hours, take it out, invert the reaction bottle and no liquid flows down, and then obtain the polymer P(PEGMA-co -AAc), its synthetic route is as follows:

[0100]

[0101] Using THF as solvent, the polymer P(PEGMA-co-AAc) was purified by fat Soxhlet extraction for 24 hours to remove the residual reactant and solvent DMF. Th...

Embodiment 3

[0116] Embodiment three packs the preparation of carrying bovine serum albumin (BSA) hydrogel

[0117] Soak 19.2 mg of the polymer P (PEGMA-co-AAc) xerogel prepared in Example 2 in a bovine serum albumin (BSA) solution containing 5 mg / mL, and when it reaches swelling equilibrium, take out the gel and use Wash the surface of the gel with a small amount of high-purity water, and then place it in an oven at 40°C for drying until the weight does not change, and then the drug-loaded xerogel can be obtained.

[0118] The fluorescence characteristic peaks and the UV-Vis spectrophotometer are used to detect the drug loading rate of the xerogel conveniently and effectively, respectively, and the drug release can also be effectively monitored through the change of the UV absorption peak of BSA. The method is as follows:

[0119] (1) Determination of BSA standard curve:

[0120] Prepare a BSA buffer solution with a concentration of 1 mg / mL, pipette 3 mL into a cuvette for UV testing, an...

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Abstract

The invention relates to preparation of a tetraphenyl ethylene polymer with azobenzene reduction response and application of tetraphenyl ethylene polymer in a hydrogel fluorescent probe. The tetraphenyl ethylene polymer is obtained under the action of a double-head acrylic ester cross-linking agent (TPE-2AzoMA) containing tetraphenyl ethylene and an azobenzene group, and a polyethylene glycol monomer and a crylic acid monomer are subjected to free radical polymerization under the action of an initiator. An obtained cross-linked random copolymer is subjected to swelling processing in water to obtain the hydrogel for wrapping medicine. After Na2S2O4 or azo reductase is added, with degradation of the gel, a solution generates fluorescence and the fluorescence is gradually enhanced with time,and the wrapped medicine is further released gradually. A fluorescence spectrophotometer tests the fluorescence strength change in the solution in the process to monitor the drug release process. Theazo reductase mainly exists in colon of a human body, and therefore, the polymer hydrogel is a potential colon locating drug controlled release carrier.

Description

technical field [0001] The invention relates to the fields of polymer preparation technology and biomaterials, in particular to the preparation and application of a polymer gel fluorescent probe based on azo reduction response. Background technique [0002] In order to make materials more versatile and dynamically changing, smart responsive materials have emerged and have shown a growing trend in the past few decades. Responsive materials are a class of materials whose physical or chemical properties will undergo corresponding reversible or irreversible changes under the action of small stimuli in the external environment. Common stimuli include light, temperature, pH, ionic strength, redox, enzymes, electric and magnetic fields, etc. Smart materials designed based on these diverse responsiveness have been widely used in various fields, especially some bioresponsive materials have been It is widely used in the fields of controlled release of drugs, imaging contrast agents, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F283/06C08F222/22C07C245/08C09K11/06A61K9/06A61K38/38A61K47/32A61K49/00
CPCA61K9/06A61K38/385A61K47/32A61K49/0019A61K49/0073C07C245/08C08F283/065C09K11/06C09K2211/1425C08F220/06
Inventor 周年琛刘蕾李立山刘敏胡安张正彪张伟
Owner SUZHOU UNIV
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