Method for preparing water-soluble copolymer by using pyrenemethyl acrylate

A technology of pyrene methyl acrylate and water-soluble copolymers, applied in the field of functional polymers, can solve complex synthesis and operation, reduce the detection accuracy of fluorescent probes, and reduce the thermal stability of hybrid double chains of fluorescent probes and targeting molecules and other issues to achieve good biocompatibility

Inactive Publication Date: 2012-07-11
UNIV OF SCI & TECH BEIJING
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Problems solved by technology

The research results show that the disadvantage of labeled fluorescent probes for detecting nucleic acid molecules is that the introduction of fluorescent groups will reduce the thermal stability of the hybrid double strands of fluorescent probes and target molecules, thereby reducing the detection accuracy of fluorescent probes; A labeled fluorescent probe needs to link the fluorescent group to the oligonucleotide molecular chain through a covalent bond to achieve specific recognition of the nucleic acid molecule, and the synthesis and operation are complicated.

Method used

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  • Method for preparing water-soluble copolymer by using pyrenemethyl acrylate
  • Method for preparing water-soluble copolymer by using pyrenemethyl acrylate
  • Method for preparing water-soluble copolymer by using pyrenemethyl acrylate

Examples

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example 1

[0018] A 50ml clean three-neck bottle was placed in ice cubes, and N 2 , first add 35ml of dry THF, then add 0.3g of pyrenemethanol, then dropwise add 0.23ml of dry triethylamine, and finally add 0.2ml of acryloyl chloride dissolved in THF slowly with a dropping funnel, so that the reaction gradually Reach room temperature, react 28h. After the reaction, the insoluble precipitate was filtered off, the filtrate was rotary evaporated, and saturated bicarbonate and dichloromethane were added to the filtrate for extraction, saturated sodium bicarbonate was used to neutralize the by-product acrylic acid, and the solution was layered until the organic solution in the lower layer was neutral. Stop extraction. The organic phase was separated, rotary evaporated, and then recrystallized in 95% ethanol to obtain relatively pure pyrene methyl acrylate powder.

example 2

[0020] Add 40ml of dry-treated 1,4-dioxane to a 50ml clean shlenk bottle, and blow N into it 2 , and then add 0.05mmol pyrenemethyl acrylate, 20mmol dimethylaminoethyl methacrylate and 0.1mmol azobisisobutylcyanide (AIBN) (recrystallized) respectively, and react in an oil bath at 60°C for 5h, After reaction finishes, in the sherwood oil that reaction product is added dropwise in 500ml, precipitates three times, because initiator and monomer dissolve in solvent, and polymer is precipitation in solvent, polymer can be separated by this method, Dry overnight in a vacuum oven at 70°C to obtain the final dried product. Elemental analysis and NMR analysis were done on the obtained product. In the elemental analysis, the nitrogen element content is 7.97%, the carbon element content is 57.17%, and the hydrogen element content is 9.16%. The copolymerization ratio x:y=1:54 is calculated. GPC results show: Mn=1941, Mw=7309, Mz=15296, Mz / Mw=2.092786.

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Abstract

The invention discloses a method for preparing a water-soluble copolymer by using pyrenemethyl acrylate, and belongs to the technical field of functional polymers. The fluorescent copolymer is prepared by the following steps of: performing esterification reaction on pyrenemethanol and acryloyl chloride to obtain the pyrenemethyl acrylate; and performing copolymerization reaction on the pyrenemethyl acrylate and dimethylaminoethyl methacrylate to obtain the water-soluble fluorescent copolymer, and performing a series of characterizations on the copolymer. The invention has the advantages that: the synthetic process for the water-soluble fluorescent copolymer is simple and feasible; a side chain of the synthesized polymer is provided with a pyrene fluorescence group with relatively high yield of fluorescent quanta and a hydrophilic amino group; and the polymer has temperature and pH responsiveness, and the like, is easy to operate in the aspect of the application of biological monitoring, and has a great scientific significance and important application value for disclosing diseases and gene mutation and the like.

Description

technical field [0001] The invention discloses a method for preparing a water-soluble copolymer by using pyrene methyl acrylate, which belongs to the technical field of functional polymers. Background technique [0002] The application of functional polymers in the field of biomedicine, especially the study of fluorescent polymers in the analysis and detection of biological macromolecules, has attracted the close attention of scientists at home and abroad. This research direction is a research hotspot in frontier science in the world. Some small molecular fluorescent dyes such as acridine, phenanthridine dyes, cyanine dyes, fluorescein and rhodamine dyes, thiazine and oxazine dyes are currently widely used nucleic acid fluorescent probes. These simple fluorescent dyes It cannot specifically recognize the sequence of nucleic acid molecules and belongs to non-specific small molecule probes. In order to overcome the above shortcomings, scientists have linked fluorescent groups...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/34C08F220/18C07C69/54C07C67/14C09K11/06
Inventor 王国杰杨领叶赵敏董杰王亚妮
Owner UNIV OF SCI & TECH BEIJING
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