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Visible light biocompatible reactive composition and application thereof

A biocompatible, visible light technology, applied in luminescent materials, organic chemistry, instruments, etc., can solve the problems of low phototoxicity and achieve the effect of time and space resolution imaging

Active Publication Date: 2021-09-28
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with ultraviolet light, visible light has lower phototoxicity to biological systems, but biocompatible reactions triggered by visible light are rarely reported

Method used

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  • Visible light biocompatible reactive composition and application thereof
  • Visible light biocompatible reactive composition and application thereof
  • Visible light biocompatible reactive composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1, the synthesis of phenanthrenequinone and rhodamine modified phenanthrenequinone

[0035]

[0036] 1. Compound 2a

[0037] 18-crown-6 (1.4g, 14mmol) and chromium trioxide (15g, 57mmol) were dissolved in a mixture of 200mL acetic acid and 20mL water, compound 1a (8.5g, 38.3mmol) was dissolved in 30mL acetic acid, and reacted at 60°C After 10 hours, TLC detected that the raw materials were consumed, and the reaction was completed. Add 100mL of water, a large amount of yellow precipitate was formed, filtered, and the solid was washed twice with acetic acid / water (volume ratio 1:1), dichloromethane, and dried to obtain The light yellow solid is compound 2a (8 g, 80%).

[0038] 2. Compound 4a

[0039] Compound 2a (200mg, 0.79mmol), DCC (246mg, 0.95mmol), NHS (109mg, 0.95mmol) were dissolved in THF 100mL, stirred at room temperature for 12 hours, a large amount of white solid precipitated out. TLC detects that the raw materials are consumed, and the reactio...

Embodiment 2

[0042] Embodiment 2, the synthesis of ethylene glycol vinyl ether activated ester

[0043]

[0044] Add ethylene glycol vinyl ether (888mg, 10mmol) successively in 20mL of dichloromethane, pyridine (4.89g, 6mmol), slowly add p-nitrophenylchloroformic acid (4.43g, 22mmol) under ice-bath condition, reaction process A large amount of white precipitate was formed. After adding the raw materials, gradually return to room temperature, the white precipitate gradually dissolves, continue to stir and react for 12 hours, TLC detects that the original disappears after the reaction is completed, add 50mL of water, extract the liquid with dichloromethane, and extract the aqueous phase twice with dichloromethane , the organic layers were combined, dried over anhydrous sodium sulfate, and spin-dried to obtain a crude product, which was purified by column chromatography to obtain a colorless liquid (2 g, 80%).

Embodiment 3

[0045] The light click reaction of embodiment 3, phenanthrenequinone and ethylene glycol vinyl ether

[0046]

[0047] 2a (50 mg, 0.2 mmol) and ethylene glycol vinyl ether (176 mg, 20 mmol) were dissolved in 100 mL of acetonitrile / PBS=1:1 mixed solvent. Under the irradiation of a portable visible light lamp, the mixture was stirred for 20 minutes, and the reaction was complete after the disappearance of the original detected by TLC. The product was separated and purified by preparative HPLC to obtain a pale yellow solid (34 mg, 50%).

[0048] Such as figure 1 As shown, the product of this reaction has fluorescence properties, and the fluorescence intensity gradually increases after different time of illumination.

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Abstract

Visible light biocompatible reaction composition and its application belong to the technical field of biomolecular labeling. The composition is composed of phenanthrenequinone and enyl ether. Visible light irradiation on the composition can realize the labeling of biomacromolecules in buffer and living cells Imaging can also realize time- and space-resolved imaging of biological macromolecules.

Description

technical field [0001] The invention belongs to the technical field of biomolecular labeling, and in particular relates to a visible light biocompatible reaction composition and its application. Background technique [0002] Currently available biocompatible reactions for biomolecular labeling include copper-catalyzed or ring-strain-induced click chemistry reactions, Staudinger reactions, tetrazine reactions, etc. Although these biocompatible reactions have been widely used in the labeling of different biomacromolecules, none of them can be realized in biomolecular labeling at different temporal and spatial resolution scales. Light is an ideal time and space regulation tool. The use of UV light to generate reactive dipoles or strained alkynes using UV light-induced photoclick chemistry provides a time- and spatial-scale labeling method. However, these UV-induced reactive intermediates have high reactivity to nucleophilic sulfhydryl groups or water. Therefore, it is partic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/07C07D311/82G01N33/533
CPCG01N33/533
Inventor 张艳李金波孔好黄磊
Owner NANJING UNIV
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