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Squaric acid derivative, maleic anhydride derivative and maleimide biological coupling material as well as preparation methods and applications thereof

A technology of squaraine derivatives and maleimide, applied in the field of biomaterial synthesis, can solve the problems of low reactivity, complex pre-modification, difficult synthesis of raw materials, etc., and achieve the effect of overcoming no fluorescence

Active Publication Date: 2022-01-11
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these traditional coupling methods have problems such as low reactivity, easy hydrolysis and unstable products, complex pre-modification, toxic metal catalysis, or difficult synthesis of raw materials, which limit their vigorous development to a certain extent. Therefore, the invention of a highly efficient Spontaneous and mild bioconjugation reactions are necessary

Method used

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  • Squaric acid derivative, maleic anhydride derivative and maleimide biological coupling material as well as preparation methods and applications thereof
  • Squaric acid derivative, maleic anhydride derivative and maleimide biological coupling material as well as preparation methods and applications thereof
  • Squaric acid derivative, maleic anhydride derivative and maleimide biological coupling material as well as preparation methods and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] A squaraine derivative (SQ-PhOCH 3 ) Preparation of materials

[0062]

[0063] The synthetic route is as follows:

[0064]

[0065] a) 3,4-dichlorocyclo-3-ene-1,2-dione (2): Add squaraine (1g, 8.78mmol) in a 100ml two-necked flask, then add thionyl chloride (10mL, 137mmol ), heated to 60°C, then added 1mL of N,N-dimethylformamide, and reacted for 6 hours. After the reaction was completed, the excess thionyl chloride was removed by a rotary evaporator, the product was collected, and the next reaction was carried out directly.

[0066] b) Synthesis of 3,4-bis(4-methoxyphenyl)cyclo-3-ene-1,2-dione (3) (SQ-PhOCH 3 ): Add aluminum trichloride (2.58g, 19.32mmol) in a 100ml two-necked bottle, nitrogen-pump-nitrogen cycle 3 times (10 minutes each time), and then dissolve the compound (2) obtained in step (a) In 20ml of dichloromethane, inject into the reaction vial. Then anisole (2.09 g, 13.93 mmol) was added, heated to 55°C, and reacted for 5 hours. After the react...

Embodiment 2

[0068] Preparation of a squaraine derivative (SQ-TPA) material

[0069]

[0070] The synthetic route is as follows:

[0071]

[0072] Synthesis of 3,4-bis(4-(diphenylamino)phenyl)cyclo-3-ene-1,2-dione (SQ-TPA): Add aluminum trichloride (2.58g, 19.32 mmol) and triphenylamine (4.73g, 19.32mmol), nitrogen-pumping-nitrogen circulation 3 times (10 minutes each time), then the compound (2) obtained in step (a) in Example 1 was dissolved in 20mL Chloromethane, injected into the reaction flask, then added 40mL, heated to 55°C, and reacted for 5 hours. After the reaction was completed, it was extracted with dichloromethane / water (the volume ratio of the dichloromethane to water was 1 / 1), dried over anhydrous magnesium sulfate for 2 hours, separated and purified by column chromatography to obtain red pink (3,49g) , the yield was 70%. 1 H NMR (500MHz, CDCl 3 )δ7.98(d, J=8.9Hz, 2H), 7.34(t, J=7.9Hz, 4H), 7.23–7.08(m, 6H), 7.03(d, J=8.9Hz, 2H).

Embodiment 3

[0074] Preparation of a squaraine derivative (SQ-CZ) material

[0075]

[0076] The synthetic route is as follows:

[0077]

[0078] Synthesis of 3,4-bis(9-phenyl-9H-carbazol-3-yl)cyclobutene-1,2-dione (SQ-CZ): Add aluminum trichloride (2.58g , 19.32mmol) and triphenylamine (4.69g, 19.32mmol), nitrogen-pumping-nitrogen circulation 3 times (each 10 minutes), then the compound (2) obtained in step (a) in embodiment 1 was dissolved in Inject 20mL of dichloromethane into the reaction flask, then add 40mL, heat to 55°C, and react for 5 hours. After the reaction was completed, it was extracted with dichloromethane / water (the volume ratio of the dichloromethane to water was 1 / 1), dried over anhydrous magnesium sulfate for 2 hours, separated and purified by column chromatography to obtain yellow pink (3,52g) , the yield was 71%. 1 H NMR (400MHz, CDCl 3 )δ9.10,9.10,8.25,8.25,8.23,8.23,8.20, 8.18,7.68,7.66,7.64,7.60,7.60,7.58,7.56,7.54,7.52,7.50,7.48,7.46,7.44,7.42,7.37,7.37 ...

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Abstract

The invention discloses a squaric acid derivative, a maleic anhydride derivative, a maleimide biological coupling material as well as preparation methods and applications thereof. Thionyl chloride and squaric acid are subjected to acylating chlorination, and then Friedel-Crafts acylation reaction is performed on the product with an aromatic compound to obtain the squaric acid derivative; then maleic anhydride derivative is generated under the induction of ultraviolet light, and the compound can be subjected to specific biological coupling with aliphatic primary amine compounds to generate maleimide biological coupling products with aggregation-induced emission properties. The method disclosed by the invention is a novel efficient biological coupling method capable of generating the aggregation-induced emission material. Through the method, natural biomolecules, drug molecules and natural proteins can be modified to endow the natural biomolecules, drug molecules and natural proteins with aggregation-induced emission properties, the defect of quenching caused by no fluorescence or aggregation of raw materials is overcome, and the method has a wide prospect in biological application.

Description

technical field [0001] The invention belongs to the field of biological material synthesis, and in particular relates to a class of squaraine derivatives, maleic anhydride derivatives, maleimide biocoupling materials and their preparation methods and applications. Background technique [0002] Bioconjugation refers to the connection of functional groups or molecules (such as fluorescent groups, targeting groups, drug molecules, etc.) The rapid development of material science and biomedicine. There are many potential biological researches in nature that require bioconjugation, such as natural polysaccharides, proteins, lipids, nucleic acids, synthetic biofunctional polymers, biocompatible polyethylene glycol (PEG), colloidal particles, and even living organisms etc. These biomolecules usually have one or more functional groups including amino, carboxyl, sulfhydryl and hydroxyl groups for conjugation, efficient bioconjugation. [0003] At present, scientific researchers have...

Claims

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Application Information

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IPC IPC(8): C07C49/753C07C225/22C07D209/86C07D307/60C07D405/14C07D207/448C07D207/452C09K11/06C08G65/331G01N21/64
CPCC07C49/753C07C225/22C07D209/86C07D307/60C07D405/14C07D207/448C07D207/452C09K11/06C08G65/331G01N21/643C08G2650/04C09K2211/1029C09K2211/1007C09K2211/1466C09K2211/1425
Inventor 唐本忠王志明李银
Owner SOUTH CHINA UNIV OF TECH
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