Hexaminoacid ester phenoxyl cyclotriphosphazene, its fluorescent nano-microsphere and preparation method thereof

A technology of ester phenoxy cyclotriphosphazene and carboxyphenoxy cyclotriphosphazene is applied in the field of cyclotriphosphazene and its fluorescent nano-microspheres and preparation, and achieves the effects of simple process, high yield and stable structure

Inactive Publication Date: 2012-04-11
NORTHEAST FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are six active chlorine atoms in the structure that can be replaced to produce a variety of cyclotriphosphazene derivatives. There have been some reports on the synthesis and application of cyclotriphosphazene derivatives, but cyclotriphosphazene derivatives are used in biomedicine There are few studies on it, only Sohn et al. have synthesized amphiphilic cyclic triphosphazene derivatives, which are used to include anticancer drugs, improve the targeting of drug delivery, and reduce the physiological toxicity of anticancer drugs

Method used

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  • Hexaminoacid ester phenoxyl cyclotriphosphazene, its fluorescent nano-microsphere and preparation method thereof
  • Hexaminoacid ester phenoxyl cyclotriphosphazene, its fluorescent nano-microsphere and preparation method thereof
  • Hexaminoacid ester phenoxyl cyclotriphosphazene, its fluorescent nano-microsphere and preparation method thereof

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specific Embodiment approach 1

[0024] Specific embodiment one: the present embodiment is six amino acid ester phenoxycyclotriphosphazene, and its general structural formula is as follows:

[0025]

[0026] Wherein, M is an amino acid ester, and the amino acid in the amino acid ester is glycine, tryptophan, phenylalanine, alanine, valine, leucine, isoleucine or methionine; Certain esters are methyl, ethyl or benzyl.

[0027] The hexaamino acid ester phenoxycyclotriphosphazene of this embodiment is a light yellow powder with a stable structure, good biocompatibility, easy degradation, and the advantages of non-toxic degradation products and no inflammatory reaction. The ester bond in the hexaamino acid ester phenoxycyclotriphosphazene of the present invention is easily hydrolyzed in the acidic environment of the human body, and the amino acid obtained further promotes the degradation of the whole molecule in the body, and the degradation products are phosphoric acid, ammonia and alcohol, which are non-toxi...

specific Embodiment approach 2

[0028] Embodiment 2: This embodiment is different from Embodiment 1 in that M is glycine methyl ester or tryptophan ethyl ester. Other parameters are the same as in the first embodiment.

specific Embodiment approach 3

[0029]Specific embodiment three: This embodiment is the preparation method of hexaamino acid ester phenoxycyclotriphosphazene as described in specific embodiment one, which is achieved through the following steps: 1. The dried six-p-carboxyphenoxy Cyclotriphosphazene is put into the four-necked flask, and then the reaction device is obtained after installation of nitrogen drying, spherical condenser, thermometer, stirring, gas recovery and heating device, and then nitrogen is blown into the reaction device; 2. In the four-necked flask Add thionyl chloride, then reflux and stir at 60-90°C for 2-20 hours, and then separate the remaining thionyl chloride from the reaction device to obtain hexa-p-formyl chloridephenoxycyclotriphosphazene; Add tetrahydrofuran into the bottle, stir to dissolve, then add amino acid ester hydrochloride and acid-binding agent, and then reflux at 60-90°C for 20-36 hours to obtain the post-reaction system, then concentrate the post-reaction system, and th...

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Abstract

Relating to cyclotriphosphazene and its fluorescent nano-microsphere as well as a preparation method, the invention provides hexaminoacid ester phenoxyl cyclotriphosphazene, its fluorescent nano-microsphere and a preparation method thereof. Hexaminoacid ester phenoxyl cyclotriphosphazene has a general structural formula as shown in the picture, wherein, M is amino acid x ester. And hexaminoacid ester phenoxyl cyclotriphosphazene is prepared by first reacting 6 pairs of carboxyphenoxyl cyclotriphosphazene with thionyl chloride, and then adding amino-acid ester hydrochloride and an acid binding agent for reaction. Composed of hexaminoacid ester phenoxyl cyclotriphosphazene, the fluorescent nano-microsphere is prepared by the steps of: dissolving hexaminoacid ester phenoxyl cyclotriphosphazene in an organic solvent, then adding distilled water dropwisely, and pouring water, then conducting dialysis and freeze-drying, thus obtaining the fluorescent nano-microsphere. Hexaminoacid ester phenoxyl cyclotriphosphazene has stable structure, good biocompatibility, easy degradation, degradation product free of toxicity and inflammatory response, and its preparation method has a yield up to over 80%, mild reaction conditions, and a simple process, thus boasting very good industrial application prospects. Under ultraviolet excitation, the fluorescent nano-microsphere can generate a fluorescence phenomenon, and can serve as a carrier of targeting drug delivery.

Description

technical field [0001] The invention relates to a cyclotriphosphazene, fluorescent nanometer microspheres and a preparation method thereof. Background technique [0002] Phosphazene polymers are a new class of macromolecular compounds with phosphorus and nitrogen atoms alternately arranged as the main chain structure, and different functional substituent groups are connected to the phosphorus atoms to obtain special properties. Its special structure leads to this These compounds combine stability and activity. Its stability is mainly reflected in the fact that the inorganic main chain of phosphazenes has excellent properties such as water resistance, solvent resistance, oil and chemical resistance, radiation resistance, high and low temperature resistance, flame retardancy, good optical transparency, and high light and heat stability. ; On the other hand, active chlorine atoms are easily substituted to introduce different functional groups, thereby preparing different funct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6596C09K11/06B82Y40/00A61K47/24
Inventor 李晓丽李斌许苗军张诗尧邴柏春
Owner NORTHEAST FORESTRY UNIVERSITY
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