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A photoreduction degradation composition and its preparation method and application

A technology of a composition and a reducing agent, applied in the field of photoreduction and degradation composition and its preparation, can solve the problems of low drug release efficiency, inability to adjust, synergistic response, etc. Compatibility effect

Active Publication Date: 2021-11-23
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing photosensitive materials mainly change the hydrophilicity and hydrophobicity of the polymer and the intermolecular interaction through the shedding or isomerization of the photoresponsive group, which causes the structural change of the self-assembly, resulting in a low drug release efficiency.
However, the main chain photodegradable polymer needs to introduce a large number of photosensitive groups in the polymer main chain to achieve the complete degradation of the main chain, which has a great impact on the physical and chemical properties and biocompatibility of the matrix, and also limits the Types of photosensitive polymers
On the other hand, the existing light-sensitive polymer materials mainly rely on exogenous stimuli, and cannot adjust and respond synergistically according to the stimuli level in the organism, so the intelligence and response efficiency need to be improved.

Method used

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  • A photoreduction degradation composition and its preparation method and application
  • A photoreduction degradation composition and its preparation method and application
  • A photoreduction degradation composition and its preparation method and application

Examples

Experimental program
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Embodiment 1

[0052] Taking Example 1 as an example, the present invention provides a photoreduction degradation composition, which includes a photosensitive o-nitrobenzene (ONB) group-modified dithiothreitol (DTT) reducing agent, and simultaneously includes two The reduction sensitive polyurethane of sulfur bond; This photoreduction degradation composition can respond to the GSH (10mM) of level in tumor cell to realize the scission of main chain in normal reductive physiological environment; And in the absence of reducing agent, this polymer can The ONB is removed under light conditions, and the reducing agent molecule DTT is generated in situ to attack the reduction-sensitive polyurethane containing disulfide bonds, thereby achieving the reductive degradation of the reduction-sensitive polyurethane.

[0053] The photoreductive degradation composition provided in Example 1 can produce the reducing agent DTT under exogenous light stimulation; since DTT is generated in situ near the disulfide...

Embodiment 2

[0061] In this example, photoreduction degradation composition 2 was prepared.

[0062] Get dithioerythritol (3.08g) dissolved in NaOH ethanol solution (40mL), ice bath cooling; dropwise add 2-(1-bromobutyl)-1,3-dinitrobenzene (13.9g) in ethanol The solution (40 mL) was naturally returned to room temperature and reacted for 6 hours, and the formed precipitate was suction-filtered, freeze-dried, and stored in the dark to obtain the modified reducing agent 2.

[0063] Dissolve modified reducing agent 2 (5 mg) and polyurethane (10 mg) containing diselenide bonds in tetrahydrofuran (1 mL), slowly add it dropwise to rapidly stirred deionized water (9 ml) at a speed of 30 s / d, dropwise After finishing, continue to stir overnight, make tetrahydrofuran volatilize completely; Then liquid is transferred to the dialysis bag that molecular weight cut off is 3500, dialyzes in deionized water 3 days, changes water once every 3 hours; Then liquid centrifugation (3500r / min ), filtered (0.45 ...

Embodiment 3

[0065] In this example, photoreduction degradation composition 3 was prepared.

[0066] Get glutathione (6.14g) dissolved in NaOH ethanol solution (40mL), ice bath cooling; dropwise add N-dodecyl-2-iodo-2-(6-nitro-3,4-methylene Dioxyphenyl)-acetamide (9.1g) in ethanol solution (40mL), naturally returned to room temperature and reacted for 6 hours, the product was concentrated, precipitated with ether, purified by column chromatography, stored in the dark, and modified Reductant 3.

[0067] Dissolve the modified reducing agent 3 (10 mg) in acetone, add it to the vial, and blow it dry with nitrogen; then add polyester-polyethylene glycol copolymer micelles (10 mL) containing disulfide bonds, and ultrasonicate for 4 hours; then The liquid was transferred to a dialysis bag with a molecular weight cut-off of 3500, dialyzed in deionized water for 3 days, and the water was changed every 3 hours; then the liquid was centrifuged (3500r / min), filtered (0.45μm), and constant volume to o...

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Abstract

The invention relates to the technical field of intelligent materials, in particular to a photoreduction degradation composition and its preparation method and application. The invention provides a photoreduction degradation composition, which is characterized in that the photoreduction degradation composition includes a reduction-sensitive polymer and a modified reducing agent, and the modified reducing agent is a reducing agent and a substance containing a photosensitive group The substance obtained by the reaction; the photoreduction degradation composition generates a reducing agent in situ due to the removal of the photosensitive group under the action of external light stimulation, and the reducing agent further reacts with the reduction-sensitive polymer to make the reduction-sensitive high molecule Molecules undergo reductive degradation. The resulting photoreductive degradation composition can respond to the intracellular level of GSH to achieve the reductive degradation of the reduction-sensitive polymer in a normal reducing physiological environment; and in the absence of a reducing agent, the photoreductive degradation composition can be in situ under light conditions The generation of reducing agent molecules can also achieve the reductive degradation of reduction-sensitive polymers.

Description

technical field [0001] The invention relates to the technical field of smart materials, in particular to a photoreduction degradation composition and its preparation method and application. Background technique [0002] Stimuli-responsive polymer materials have attracted great attention in the past few decades. They can receive stimuli signals from the external environment and cause major changes in their physical state or chemical structure, thereby affecting their physical and chemical properties and functions. It has the functions of sensing, processing and execution. Nano self-assemblies (micelles, microspheres, vesicles, etc.) or hydrogel materials prepared by stimuli-responsive polymer materials have a wide range of applications in various fields such as biosensing, drug release, bioengineering, and chemical catalysis. prospect. [0003] Polymer nanosystems that respond to physiological endogenous stimuli such as pH, redox, and enzymes have high application value in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08L75/04C08L67/00C08L69/00C08L75/02C08L77/04C08L71/00C08K5/375A61K47/34A61K49/00
CPCA61K47/34A61K49/0021A61K49/0054C08K5/3725C08K5/375C08L75/04C08L67/00C08L69/00C08L75/02
Inventor 丁明明王昭丁段芳红陈浩东李子芬谭鸿傅强
Owner SICHUAN UNIV