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Photosensitive coupling molecule and synthesis method and application thereof

A molecular and coupling technology, applied in the field of chemistry and materials, can solve the problems of the limitation of the total amount of modification, the restriction of the effect of material modification, and the low coupling efficiency of macromolecular end groups, so as to achieve the effect of improving efficiency

Inactive Publication Date: 2011-08-03
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For most common polymer molecules (such as polyethylene, polypropylene, polyethylene glycol, polylactic acid, etc.), there are not many functional groups on the molecular chain that can react with protein polypeptides. When the molecular weight of the modified polymer When the size is large, the method of end group modification limits the total amount of modification, and due to the influence of steric hindrance and reactivity, the coupling efficiency of the end group of macromolecules is not very high. These reasons restrict the modification of materials to a certain extent. Effect

Method used

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  • Photosensitive coupling molecule and synthesis method and application thereof
  • Photosensitive coupling molecule and synthesis method and application thereof
  • Photosensitive coupling molecule and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the preparation of compound (1), structural formula is as follows,

[0026]

[0027] Add 3.5 mL of 2 mol / L sodium nitrite solution into a 100 mL flask, then add 10 mL of 2 mol / L hydrochloric acid, take 430 mg (~ 2.8 mmol) p-aminophenylacetic acid, add it to the solution, and place in a low-temperature ice bath, Protect from light for 30 min; then slowly add 3.2 mL of 1 mol / L sodium azide aqueous solution, and complete the addition in about 1.5 h. The mixture was transferred to a sand core funnel for filtration, the solid phase was transferred and dissolved in ethyl acetate, 10 g of anhydrous magnesium sulfate powder was added, stirred and dried for 24 h, and then filtered with a dry sand core funnel, and the filtrate was rotary evaporated to remove the solvent.

[0028] Take 260 mg of the above product (~ 1.5 mmol) into a 100 mL flask filled with dry argon, add 6 mL of dehydrated dichloromethane, and add 350 mg (~ 3.0 mmol) of For NHS, take 7.5 mg of D...

Embodiment 2

[0029] Embodiment 2: the preparation of compound (2), structural formula is as follows,

[0030]

[0031] Add 3.5 mL of 2 mol / L sodium nitrite solution to a 100 mL flask, then add 10 mL of 2 mol / L hydrochloric acid, take 460 mg (~ 2.8 mmol) of m-aminophenylpropionic acid, add it to the solution, and place in a low-temperature ice bath , and reacted in the dark for 30 min; then slowly added 3.2 mL of 1 mol / L sodium azide aqueous solution, and the addition was completed in about 1.5 h. The mixture was transferred to a sand core funnel for filtration, the solid phase was transferred and dissolved in ethyl acetate, 10 g of anhydrous magnesium sulfate powder was added, stirred and dried for 24 h, and then filtered with a dry sand core funnel, and the filtrate was rotary evaporated to remove the solvent.

[0032] Take 285 mg of the above product (~ 1.5 mmol) into a 100 mL flask filled with dry argon, add 6 mL of dehydrated dichloromethane, and add 350 mg (~ 3.0 mmol) of For NHS,...

Embodiment 3

[0033] Embodiment 3: the preparation of compound (3), structural formula is as follows,

[0034]

[0035] Add 3.5 mL of 2 mol / L sodium nitrite solution into a 100 mL flask, then add 10 mL of 2 mol / L hydrochloric acid, take 495 mg (~ 2.8 mmol) p-aminobenzenebutyric acid, add it to the solution, and place in a low-temperature ice bath, Protect from light for 30 min; then slowly add 3.2 mL of 1 mol / L sodium azide aqueous solution, and complete the addition in about 1.5 h. The mixture was transferred to a sand core funnel for filtration, the solid phase was transferred and dissolved in ethyl acetate, 10 g of anhydrous magnesium sulfate powder was added, stirred and dried for 24 h, and then filtered with a dry sand core funnel, and the filtrate was rotary evaporated to remove the solvent.

[0036]Take 300 mg of the above product (~ 1.5 mmol) into a 100 mL flask filled with dry argon, add 6 mL of dehydrated dichloromethane, and add 350 mg (~ 3.0 mmol) of For NHS, take 7.5 mg of ...

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Abstract

The invention belongs to the field of chemistry and materials, and in particular relates to a photosensitive coupling molecule containing azide groups and application thereof. The compound molecule contains azide functional groups, which can chemically react with polymer materials to be fixed on polymer molecular chains while being irradiated by ultraviolet lights; and the other end of the coupling molecule contains functional groups capable of reacting with amino or sulfydryl. Therefore, bioactive molecules like proteins and polypeptides can be grafted to the polymer molecule through this coupling molecule. The coupling molecule can be applied to the aspects of surface modifications of biomaterials, fixations and modifications of proteins and the like.

Description

technical field [0001] The invention belongs to the technical field of chemistry and materials, and in particular relates to a photosensitive compound coupling molecule containing an azide group, a synthesis method and application thereof. Background technique [0002] With the rapid development of materials, chemistry and biotechnology, polymers have not only been used as structural materials, but more and more polymer materials have been functionally modified in biosensing, tissue repair, drug targeting and controlled release. and other fields play an important role. In order to endow polymers with specific biological functions, most polymer molecules need to be chemically combined with active biomolecules (such as proteins and biopeptide molecules). For most common polymer molecules (such as polyethylene, polypropylene, polyethylene glycol, polylactic acid, etc.), there are not many functional groups on the molecular chain that can react with protein polypeptides. When t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K1/10C07D207/46C07D207/448C07C247/16
Inventor 丁建东张正
Owner FUDAN UNIV
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