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Polymer, light response micelle, light response drug-loading micelle and preparation methods thereof

A technology of drug-loaded micelles and polymers, applied in the field of nanomedicine, can solve the problem of low controllability

Active Publication Date: 2014-07-30
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, the widely used intelligent responsive nano drug-loaded micelles are pH-sensitive and redox-sensitive. Sensitive drug delivery systems (DDS) require a specific chemical environment, and this chemical environment is divided into two types, one is the environment that the organism itself can provide, which is less controllable in this case, while the other is It needs to be achieved through external regulation, and this external invasion is bound to involve issues such as biocompatibility, biodegradability and biotoxicity

Method used

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  • Polymer, light response micelle, light response drug-loading micelle and preparation methods thereof
  • Polymer, light response micelle, light response drug-loading micelle and preparation methods thereof
  • Polymer, light response micelle, light response drug-loading micelle and preparation methods thereof

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preparation example Construction

[0077] The present invention also provides a method for preparing a polymer having a structure of formula (I), comprising the following steps:

[0078] (1) Use adipic hydrazide (ADH) to chemically modify hyaluronic acid (HA) in an acidic aqueous solution to obtain a hyaluronic acid grafted adipic hydrazide polymer (HA-ADH) with a structure of formula (II) :

[0079]

[0080] Wherein, n is the degree of polymerization, and n is an integer between 25 and 500; x and y+z are relative mole numbers, and 0.5≤x / (x+y+z)<1.

[0081] The reaction formula is:

[0082]

[0083] Wherein, n is the degree of polymerization, and n is an integer between 25 and 500; x, y+z are relative moles, 0.5≤x / (x+y+z)<1;

[0084] (2) Take o-nitrobenzyl alcohol and succinic anhydride to react at room temperature to obtain an o-nitrobenzyl alcohol derivative (NBS) with a structure of formula (Ⅲ), and then perform an activation reaction on the o-nitrobenzyl alcohol derivative to obtain O-nitrobenzyl a...

Embodiment 1

[0132] A photoresponsive micelle, the photoresponsive micelle includes an amphiphilic polymer and deionized water, the amphiphilic polymer uses hyaluronic acid as the hydrophilic main chain, and is grafted with o-nitrobenzyl alcohol derivatives The segment is the hydrophobic end. The synthesis of the photoresponsive micelles comprises the following steps:

[0133] (1) Dissolve 20g (0.05mol) of hyaluronic acid (HA, MW10K) in 5L of deionized water, add 44g (0.25mol) of adipic dihydrazide (ADH) to its aqueous solution, and use 0.1M hydrochloric acid solution under rapid stirring Adjust the pH to 4.5-4.8. Add 4.8g (0.025mol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) in the above-mentioned reaction solution, then adjust the pH value at After 4.5-4.8, react at room temperature for 1 hour to obtain a white solid hyaluronic acid grafted adipic hydrazide polymer (HA-ADH). Take 10g HA-ADH and dissolve it in 2.4L formamide for later use;

[0134] (2) Dissolve ...

Embodiment 2

[0141] A photoresponsive drug-loaded micelle includes a photoresponsive micelle formed by an amphiphilic polymer and a hydrophobic anticancer drug. Among them, the mass ratio of the amphiphilic polymer to the hydrophobic anticancer drug is 1:0.1. The preparation method of the photoresponsive drug-loaded micelles is as follows:

[0142] Dissolve 10 mg of amphiphilic polymer with P1 structure in 10 ml of formamide, then dissolve 1 mg of chlorin e6 (Ce6) in 1 ml of formamide, and then add the formamide solution containing Ce6 dropwise to The amphiphilic polymer solution with the P1 structure was stirred and reacted for 30 minutes, and finally the above reaction solution was added to a dialysis bag with a molecular weight of 3500MW. After dialysis for 12 hours, the amphiphilic polymer-encapsulated chlorin e6 could be obtained. (Ce6) photoresponsive drug-loaded micelles.

[0143] The schematic diagram of the photoresponsive drug-loaded micelles is shown in Figure 6 As shown, th...

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Abstract

The invention provides a polymer with a structure shown in a formula (I) which can be seen in the specification, wherein n is polymerization degree and is an integer between 25 and 500, x, y and z are relative mole numbers; x / (x+y+z) is less than 1 and greater than or equal to 0.5; z / (y+z) is less than or equal to 1 and greater than or equal to 0.1. The polymer comprises a hyaluronic acid hydrophilic main chain and a hydrophobic nitrobenzyl alcohol derivative-grafted chain segment, wherein the polymer can form the micelle (containing a hydrophobic chain segment at the inside and a hydrophilic chain segment at the outside) in a water solution, and the drug can be wrapped inside the hydrophobic chain segment to achieve slow release of the drug when the polymer is used as a drug carrier. In the polymer, the hyaluronic acid has an active targeting effect and the nitrobenzyl alcohol derivative chain segment has photosensitivity; therefore, the polymer can make response to external photic stimulation to realize slow release of the drug when being used as a drug carrier. The invention also provides preparation methods of the polymer, the light response micelle and the light response drug-loading micelle thereof. The methods have broad application prospects in clinic.

Description

technical field [0001] The invention belongs to the field of nanomedicine, and in particular relates to a polymer, a light-responsive micelle, a light-responsive drug-loaded micelle and a preparation method thereof. Background technique [0002] With the development of nanobiotechnology, more and more people pay more and more attention to smart responsive nano drug-loaded micelles, as a new drug carrier, smart responsive nano drug loaded micelles have been widely used in the field of targeted drug loading And has good development prospects. After the smart responsive nano drug-loaded micelles selectively deliver the drug to a specific target, they can release the loaded drug responsively after being excited by chemical signals, temperature, pH, light stimulation and other "triggers". Nanocarriers can be divided into active targeted delivery systems and passive targeted delivery systems; among them, the active targeted delivery system has attracted more and more attention fr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K41/00A61K9/107A61K47/36A61K45/00A61P35/00A61K31/704
Inventor 蔡林涛潘正银李文军
Owner SHENZHEN INST OF ADVANCED TECH
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