Temperature sensitive type water-soluble polymers based on D-pi-A structure as well as preparation method and application of water-soluble polymers

A water-soluble polymer, temperature-sensitive technology, applied in the direction of organic chemistry, can solve the problems of short life of active oxygen species, unfavorable synthesis and preparation, limited migration distance, etc., to achieve high singlet oxygen yield, high efficiency singlet oxygen Yield, effects of good biocompatibility

Active Publication Date: 2018-07-27
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, some problems about photodynamic therapy are that the apoptosis, necrosis and autophagy of cells are mostly concentrated in the site where the photosensitizer is located, which is caused by the short lifespan and limited migration distance of reactive oxygen species. The first generation, second generation The new generation of photosensitizers have complex structures, which are not conducive to synthesis and preparation. In addition, the difficulty of photosensitizers entering cells is also a problem that needs to be considered.

Method used

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  • Temperature sensitive type water-soluble polymers based on D-pi-A structure as well as preparation method and application of water-soluble polymers
  • Temperature sensitive type water-soluble polymers based on D-pi-A structure as well as preparation method and application of water-soluble polymers
  • Temperature sensitive type water-soluble polymers based on D-pi-A structure as well as preparation method and application of water-soluble polymers

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: Preparation of polymerized monomer containing D-π-A structure

[0039]

[0040] Preparation of compound 2: Under the catalysis of copper powder (7mmol), 1 (30mmol) and p-bromobenzaldehyde (10mmol)), anhydrous potassium carbonate (40mmol) were stirred and reacted for 24 hours under a nitrogen atmosphere at 180°C , distilled under reduced pressure to remove nitrobenzene, filtered to remove potassium carbonate and copper powder, then extracted three times with water and dichloromethane to collect the organic phase, dried and removed water, and then rotary evaporated to remove the organic solvent, and the obtained oily mixture was purified through a column. 2 was obtained as a yellow solid. Yield: 43%.

[0041] 1 H NMR (400MHz, CDCl 3 )δ=10.12(s,1H),8.19–8.09(m,4H),7.85–7.76(m,2H),7.54–7.48(m,2H),7.44(ddd,J=8.3,7.1,1.2Hz, 2H), 7.34 (ddd, J=8.3, 8.0, 1.2Hz, 2H).

[0042] Preparation of compound 3: N-bromosuccinimide (20mmol) was dissolved in dichloromet...

Embodiment 2

[0056] Embodiment 2: the preparation of polymer PM-1, PM-2

[0057] The preparation of polymer PM-1: compound 11 (0.08mmol), [3-(acrylamido) propyl] trimethylammonium chloride (0.1 mmol) and n-propylacrylamide (3.8mmol), azobis Add isobutyronitrile (0.004mmol) into the polymerization tube and seal it, add redistilled tetrahydrofuran solvent, stir and react at 80°C under nitrogen atmosphere for 24 hours, cool down to room temperature, then slowly add the reaction solution dropwise into diethyl ether, settle and filter, and then use The yellow floc product PM-1 was obtained by extraction with toluene.

[0058]

[0059] Among them, x=2, y=2.5, z=95.5.

[0060] Preparation of Polymer PM-2: The experimental procedure is the same as the preparation of Polymer PM-1 above.

[0061]

[0062] Wherein, x=2, y=8, z=90.

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Abstract

The invention discloses temperature sensitive type water-soluble polymers based on a D-pi-A structure as well as a preparation method and an application of the water-soluble polymers. The structural formula of the polymers is shown in the description. The temperature sensitive type polymers are prepared through polymerization of molecules of the simple D-pi-A structure with water-soluble molecules. Phase-transition temperature of the polymers is 25-45 DEG C in which human physiological temperature of 37 DEG C is included, the polymers have better nano-size, good water solubility and higher singlet oxygen yield and can be applied to bioimaging and time-resolved optics, and photodynamic therapy can be realized.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to a kind of temperature-sensitive water-soluble polymer based on D-π-A structure, its preparation method and its application in the fields of cell imaging and photodynamic therapy. Background technique [0002] Cancer has always been a problem that plagues human beings. The traditional methods of treating tumors include: surgical resection, chemotherapy, radiotherapy, etc. The existing problems are limited invasiveness, weak pertinence, and potential side effects. A new method of cancer treatment can generate reactive oxygen species in tumor cells, and these reactive oxygen species can destroy protein, fat, nucleic acid and other biomacromolecular structures, and further damage tumor cells. [0003] Molecules with D-π-A structure, the electron donating and electron donating groups are linked by π bonds in the molecule, and the electron donating an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/54C08F220/36C08F220/60C08F220/56C07D405/10
CPCC07D405/10C08F220/54C08F220/36C08F220/60C08F220/56
Inventor 赵强刘淑娟李义鹏余琦杨会然李飞阳
Owner NANJING UNIV OF POSTS & TELECOMM
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