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Triple stimuli-responsive block polymer micelle and its preparation method and application

A block polymer, stimuli-responsive technology, used in drug combination, drug delivery, pharmaceutical formulation, etc., can solve problems such as poor therapeutic effect and inability to fully release loaded drugs

Inactive Publication Date: 2021-09-14
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Finally, in cancer therapy, the environment in the human body is complex, and nanocarriers with a single sensitivity may not be able to fully release the loaded drug, resulting in poor therapeutic effect

Method used

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  • Triple stimuli-responsive block polymer micelle and its preparation method and application
  • Triple stimuli-responsive block polymer micelle and its preparation method and application
  • Triple stimuli-responsive block polymer micelle and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052]

[0053] 1 Oxalyl chloride (20.00mL, 233.07mmol) and anhydrous dichloromethane (DCM, 60.00mL) was added to a 100mL one-neck round flask, 2-propyn-1-ol was added dropwise under ice-cooling (5.00 g, 89.28mmol), was added dropwise at room temperature the reaction after 3h. After reaction, the reaction solution was distilled off under reduced pressure at 98 ℃, to give a colorless transparent oily propynyloxy oxalyl chloride (8.65g, 65% yield).

[0054] Bis (2-hydroxyethyl) disulfide (1.84g, 11.93mmol), TEA (2.40g, 24.00mmol) and purified THF (10.00mL) was added to a 100mL one-neck round flask dropwise under ice propynyloxy oxalyl chloride was added (3.00g, 20.47mmol), The reaction was added dropwise at room temperature after 12h, to give a colorless transparent liquid, i.e., a compound of formula I (6.17g, 80% yield).

[0055] 2, under nitrogen, 5- (2-hydroxyethoxy) -2-nitrobenzyl alcohol (2.50g, 11.68mmol), TEA (3.05g, 29.90mmol) and THF (80.00mL) was added to 250mL three-ne...

Embodiment 2

[0064]

[0065] 1 Oxalyl chloride (22.00mL, 256.38mmol) and anhydrous dichloromethane (DCM, 60.00mL) was added to a 100mL one-neck round flask, 2-propyn-1-ol was added dropwise under ice-cooling (5.00 g, 89.28mmol), was added dropwise at room temperature after the reaction 2h. After reaction, the reaction solution was distilled off under reduced pressure at 98 ℃, to give a colorless transparent oily propynyloxy oxalyl chloride (8.72g, 66% yield).

[0066] Bis (2-hydroxyethyl) disulfide (1.62g, 10.50mmol), TEA (2.40g, 24.00mmol) and purified THF (10.00mL) was added to a 100mL one-neck round flask dropwise under ice propynyloxy oxalyl chloride was added (3.00g, 20.47mmol), was added dropwise at room temperature after the reaction 10H, to give a colorless transparent liquid, i.e., a compound of formula I (6.22g, 81% yield).

[0067] 2, under nitrogen, 5- (2-hydroxyethoxy) -2-nitrobenzyl alcohol (2.50g, 11.68mmol), TEA (6.30g, 62.26mmol) and THF (80.00mL) was added to 250mL three-ne...

Embodiment 3

[0074]

[0075] 1 Oxalyl chloride (25.00mL, 291.34mmol) and anhydrous dichloromethane (DCM, 60.00mL) was added to a 100mL one-neck round flask, 2-propyn-1-ol was added dropwise under ice-cooling (10.00 g, 178.57mmol), was added dropwise at room temperature the reaction after 3h. After reaction, the reaction solution was distilled off under reduced pressure at 98 ℃, to give a colorless transparent oily propynyloxy oxalyl chloride (17.32g, yield 65%).

[0076] Bis (2-hydroxyethyl) disulfide (1.84g, 11.93mmol), TEA (2.40g, 24.00mmol) and purified THF (10.00mL) was added to a 100mL one-neck round flask dropwise under ice propynyloxy oxalyl chloride was added (5.00g, 34.12mmol), was added dropwise at room temperature after the reaction 13H, to give a colorless transparent liquid, i.e., a compound of formula I (6.17g, 80% yield).

[0077] 2, under nitrogen, 5- (2-hydroxyethoxy) -2-nitrobenzyl alcohol (2.50g, 11.68mmol), TEA (4.00g, 39.53mmol) and THF (80.00mL) was added to 250mL three...

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Abstract

The invention discloses a triple-stimuli-responsive block polymer micelle and its preparation method and application. Or two stimuli-responsive groups monomer click chemical reaction synthesis, the polymer dialyzed in N,N-dimethylformamide can form micelles. The polymer micelles of the present invention have triple stimuli responsiveness to light, oxidation and reduction, and have good in vitro stability. The polymer structure contains a large number of azole rings. When used as a drug delivery carrier, it can be combined with certain drugs (such as DOX, etc.) Hydrogen bonding occurs to improve drug loading efficiency; in drug controlled release, drugs can be released under the trigger of different single stimuli, and can also be released under the common trigger of multiple stimuli. Direction and rapid release, it has broad application prospects in the fields of anticancer drug delivery and controlled release.

Description

Technical field [0001] The present invention belongs to the technical field stimuli-responsive polymer material, particularly relates to an optical, oxidation, reduction, triple stimuli-responsive block polymer micelles, as well as the preparation and application of polymeric micelles. Background technique [0002] Smart polymers, also known as the stimuli-responsive polymer, is capable of making a feedback-based polymer material according to small changes in the external environment. In the presence of external stimuli, physical structure or chemical properties of this type of polymer will change, this change in structure or properties may be reversible, may be irreversible, light, voltage, temperature, sugar, and enzymes, acid, oxidizing / reducing substance is a common stimulus. Thus, this polymer is widely used in intelligent catalyst, sensors, drug delivery, solar energy and other fields. Block polymers ease of preparation and storage, can be used to increase the solubility ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G81/00C08G65/333A61K47/69A61K47/34A61K9/107A61P35/00
CPCA61K9/1075A61K47/34A61K47/6907A61P35/00C08G65/333C08G81/00
Inventor 雷忠利郭琼杨红
Owner SHAANXI NORMAL UNIV
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