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Vesicle with two-photon excitation controlled-release function, and preparation method and application thereof

A two-photon excitation and controlled release technology, which is applied in organic chemistry, liposome delivery, etc., can solve the problems of high preparation cost, low response efficiency, and small two-photon absorption cross section, and achieve good two-photon responsiveness and biophase Capacitive, repeatable, low-cost effect

Active Publication Date: 2013-09-18
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current two-photon-responsive drug carriers generally have problems such as small two-photon absorption cross-section, low response efficiency, or high preparation cost. significance

Method used

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  • Vesicle with two-photon excitation controlled-release function, and preparation method and application thereof
  • Vesicle with two-photon excitation controlled-release function, and preparation method and application thereof
  • Vesicle with two-photon excitation controlled-release function, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The two-photon-sensitive amphiphile is prepared, and its structure is shown in formula (A).

[0039]

[0040] Formula (A)

[0041] Its reaction scheme is as follows:

[0042]

[0043] Add 1 equivalent of 4-hydroxymethyl-7-aminocoumarin, 6 equivalents of n-dodecane bromide and 8 equivalents of potassium carbonate to dry DMF to dissolve completely; reflux reaction under nitrogen protection 36 hours; after the reaction was completed, cooled, suction filtered, the filtrate was washed with water, dried, separated and purified by silica gel column chromatography to obtain a yellow solid. 1 H NMR (400MHz, CDCl 3 )δ(ppm), 7.35(d, 1H), 6.68(dd, 1H), 6.58(s, 1H), 6.30(s, 1H), 4.88(s, 2H), 3.32(t, 4H), 1.59( m, 4H), 1.31 ~ 1.28 (m, 36H), 0.89 (t, 6H). MALDI-TOF MS (m / z): [M+H] + 528.4;

[0044]Add 1 equivalent of the previously obtained compound and 1 equivalent of bromoacetic acid and a catalytic amount of 4-dimethylaminopyridine (DMAP) into dry dichloromethane to dis...

Embodiment 2

[0046] The two-photon-sensitive amphiphile is prepared, and its structure is shown in formula (B).

[0047]

[0048] Formula (B)

[0049] Its reaction scheme is as follows:

[0050]

[0051] Add 1 equivalent of 3-methyl-4-hydroxymethyl-6-chloro-7-aminocoumarin and 6 equivalents of n-dodecane bromide and 8 equivalents of potassium carbonate to dry DMF to make completely Dissolved; reflux reaction under the protection of nitrogen for 36 hours; after the reaction was completed, cooled, filtered with suction, washed the filtrate with water, dried, separated and purified by silica gel column chromatography to obtain a yellow solid product. 1 H NMR (400MHz, CDCl 3 )δ(ppm), 7.03(s, 1H), 6.71(s, 1H), 4.88(s, 2H), 3.32(t, 4H), 2.01(s, 3H), 1.59(m, 4H), 1.31~ 1.28 (m, 36H), 0.89 (t, 6H). MALDI-TOF MS (m / z): [M+H] + 576.4;

[0052] Add 1 equivalent of the previously obtained compound and 1 equivalent of bromoacetic acid and a catalytic amount of 4-dimethylaminopyridine (DMAP)...

Embodiment 3

[0054] The two-photon-sensitive amphiphile is prepared, and its structure is shown in formula (C).

[0055]

[0056] Formula (C)

[0057] Its reaction scheme is as follows:

[0058]

[0059] Add 1 equivalent of 4-hydroxymethyl-6-methoxy-7-aminocoumarin, 6 equivalents of n-dodecane bromide and 8 equivalents of potassium carbonate into dry DMF to dissolve completely; Under the protection of nitrogen, the reaction was carried out under reflux for 36 hours; after the reaction was completed, it was cooled, filtered with suction, the filtrate was washed with water, dried, separated and purified by silica gel column chromatography to obtain a yellow solid. 1 H NMR (400MHz, CDCl 3 )δ(ppm), 6.55(s, 1H), 6.49(s, 1H), 6.21(s, 1H), 4.88(s, 2H), 3.79(s, 3H), 3.32(t, 4H), 1.59( m, 4H), 1.31 ~ 1.28 (m, 36H), 0.89 (t, 6H). MALDI-TOF MS (m / z): [M+H] + 558.2;

[0060] Add 1 equivalent of the previously obtained compound and 1 equivalent of bromoacetic acid and a catalytic amount of ...

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Abstract

The invention discloses a vesicle with a two-photon excitation controlled-release function, and a preparation method and application thereof. The preparation method for the vesicle comprises the following steps of: synthesizing two-photon sensitive amphiphilic molecules shown as a general formula (I); and performing ultrasonic dispersion on the amphiphilic molecules in water, and standing. The vesicle can coat hydrophobic or water-soluble substrate molecules. The two-photon sensitive amphiphilic molecules are subjected to cleavage reaction under two-photon excitation, the vesicle is disassociated, and the release process of the substrate molecules is controlled. Infrared or near-infrared pulse laser adopted in two-photon excitation has the advantages of small biological damage, high penetrability, high stereoselectivity and the like, so the vesicle is expected to be applied to the controlled release of medicines in organisms.

Description

technical field [0001] The present invention relates to a photosensitive controllable release vesicle, a preparation method and its use; in particular, it relates to a vesicle with two-photon excitation controlled release function, a preparation method and its use. Background technique [0002] For a long time, environment-responsive drug carriers have been one of the research hotspots of the majority of medical researchers. Compared with traditional drug carriers, environment-responsive drug carriers can not only increase the stability of drugs in the body and prolong the circulation time of drugs in the human body, but more importantly, it is an active drug delivery method that can The difference in pH and temperature of the site, or the introduction of external stimuli such as light, electric field, or magnetic tape can cause changes in the carrier structure, and the loaded drug molecules can be released, thereby reducing the toxic and side effects of the drug and improvi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C07D311/18C07D405/12C08G65/00A61K9/127
Inventor 曾毅董建明李嫕陈金平李迎迎
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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