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Preparation method and application of atypical fluorescent material succinimide derivative

A technology of succinimide and dithiosuccinimide, which is applied in the field of polymer chemistry, can solve the problems of increasing the cost of reaction raw materials, increasing the difficulty of fluorescent groups, etc., and achieves the effects of saving the cost of raw materials and simple preparation method.

Active Publication Date: 2015-08-26
JIANGSU INST OF NUCLEAR MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, if you want to introduce functional groups at the 2 and 3 positions, you can only use functionalized maleic anhydride, which will inevitably increase the cost of the reaction raw materials
On the other hand, succinimide is prone to charge transfer between protein and protein, so it is a commonly used protein fluorescence quencher, similar to maleimide, usually by introducing a conjugated fluorescent group at the nitrogen atom position group to synthesize corresponding fluorescent compounds for the preparation of organic photoelectric materials, but the large steric hindrance of the 2 and 3 positions increases the difficulty of introducing fluorescent groups
There is no report on the fluorescent properties of 2,3 aliphatic substituted succinimide, and the labeling of proteins and polymers

Method used

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  • Preparation method and application of atypical fluorescent material succinimide derivative
  • Preparation method and application of atypical fluorescent material succinimide derivative
  • Preparation method and application of atypical fluorescent material succinimide derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Atypical fluorescent succinimide derivatives and preparation method thereof

[0034] Preparation of 2-thiomaleimide

[0035]

[0036] Bromomaleimide (401.2mg, 2.28mmol) was dissolved in 15mL of ether, and deoxygenated by argon for 10min. n-Butanethiol was added to the above reaction solution and stirred for 5 min, then the reaction solution was cooled to 0° C. in an ice bath. Triethylamine (242.4mg, 2.40mmol) was slowly added dropwise into the solution, and a white precipitate was precipitated immediately. After the dropwise addition of triethylamine was completed, the reaction solution was stirred overnight at room temperature. After the reaction, the reaction solution was diluted with 60 mL of ether, washed with water and brine (30 mL), and dried over anhydrous sodium sulfate. The organic phases were combined, filtered, concentrated, and purified by column chromatography (stationary phase silica gel, eluent: n-hexane / ethyl acetate=3:1) to obtain a yellow oily sol...

Embodiment 2

[0050] Detection of Atypical Fluorescent Properties of Succinimide Derivatives

[0051] The sequence regular copolymer containing maleimide and succinimide units will be prepared, and the dynamic fluorescence results show that the four-sequence monomer (end group is thiomaleimide) and the five-sequence copolymer (end group The reaction solution of sulfur / nitrogen succinimide) has strong fluorescence ( figure 1 ). The fluorescence of the four-sequence monomer may be derived from thiomaleimide, because the three-sequence monomer (terminated by a sulfhydryl group) is non-fluorescent. However, it is difficult to explain why the five-sequence copolymer is also fluorescent, because the amine group and maleimide undergo Michael addition reaction and then convert to succinimide. In order to rule out the possibility of fluorescence sources and impurities, the polymer was precipitated to remove unreacted small molecules, dried, and the polymer solution redissolved in DMF still had str...

Embodiment 3

[0057] Analysis of Succinimide Derivatives and Detection of Heavy Metal Ions

[0058] Fluorescent materials are widely used in real-time and spatial analysis and detection of heavy metal ions. We choose polystyrene succinimide to study its binding ability to metal ions. Li was added to the DMF solution of poly(styrene-alt-2-nitromaleimide) + , Na + , K + , Ag + , Ca 2+ ,Mg 2+ ,Zn 2+ ,Cu 2+ ,Hg 2+ ,Cd 2+ ,Pb 2+ ,Co 2+ and Cr 3+ Plasma (five equivalents), and follow the change in fluorescence. After the addition of mercury ions, the fluorescence of the solution was quenched immediately, while the addition of other metal particles basically did not change the fluorescence intensity of the solution. The ultraviolet absorption spectrum is used to quantitatively characterize the fluorescence quenching process of mercury ions. When the amount of mercury ions is added to two equivalents, the ultraviolet absorption red shifts from 353nm to 398nm, and the formation of imine...

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Abstract

The invention provides an atypical fluorescent succinimide derivative, as well as a preparation method and an application of the derivative. The derivative is sulfur / nitrogen succinimide; further, sulfur / nitrogen succinimide is particularly 2-sulfur maleimide, 2,3-dithio-succinimide and 2-nitrogen succinimide; the succinimide derivative can be widely used for the field of protein labeling, bacterium detection, heavy metal ion screening and the like.

Description

technical field [0001] The invention belongs to the field of polymer chemistry, and relates to a succinimide derivative, a preparation method and application thereof. technical background [0002] Due to their excellent optical properties, fluorescent materials are widely used in scientific fields such as protein labeling, bacterial detection, and heavy metal ion screening. Due to their excellent optical properties, fluorescent materials are widely used in scientific fields such as protein labeling, bacterial detection, and heavy metal ion screening, and provide new insights into fluorescent photophysical processes. Generally, fluorescent materials are prepared by functionalizing fluorophores with conjugated structures. Recently, atypical fluorescent materials have shown promising applications in biochemical sensing and imaging. Pucci et al. found that polyisobutylene succinic anhydride / imide had atypical fluorescence and attributed it to the aggregation-induced fluorescen...

Claims

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Application Information

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IPC IPC(8): C07D207/416C09K11/06G01N21/64
CPCC07D207/416C09K11/06C09K2211/1029G01N21/6428G01N2021/6432
Inventor 严骏杰杨敏潘栋辉徐宇平杨润琳王立振赵富宽张波
Owner JIANGSU INST OF NUCLEAR MEDICINE
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