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Synthesis and application of a fast-response long-wavelength fluorescent probe for hydrogen peroxide

A hydrogen peroxide, fast-response technology, used in compounds containing Group 3/13 elements of the periodic table, fluorescence/phosphorescence, material analysis by optical means, etc. , poor biocompatibility, long response time, etc., to achieve good cell membrane penetration, high selectivity, and rapid response.

Active Publication Date: 2021-10-26
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the literature of the currently reported hydrogen peroxide fluorescent probes, there are generally emission wavelengths lower than 600 nm (CN201510853987.6; Yang W, ZhiyingL, Youming S, ACS Omega 2019, 4, 16242-16246; Yuchao Du, Bowei Wang , Di Jin, Analytica Chimica Acta 1103(2020) 174e182), poor biocompatibility (CN 201910896625.3; Peng Wang, Ke Wang, ueqing Gu, Sensors and Actuators B 228(2016) 174–179), long response time (Jun L, Jingjing L, Chuanliu W, Analytical Chemistry, 2019; Xueyuan Bi, Yingying Wang, Dandan Wang, RSC Adv, 2020, 10, 26874; Fangyuan Xu, Wei Tang, SaisaiKang, Dyes and Pigments 153(2018)61–66) and other characteristics, which lead to the detection of the probe at the cellular level is susceptible to background fluorescence interference, low signal-to-noise ratio (John V Frangioni, Current Opinion in Chemical Biology 2003, 7:626–634), poor water solubility, and difficult to enter the cell membrane Internal, difficult to achieve rapid detection and high-throughput detection and other defects

Method used

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  • Synthesis and application of a fast-response long-wavelength fluorescent probe for hydrogen peroxide
  • Synthesis and application of a fast-response long-wavelength fluorescent probe for hydrogen peroxide
  • Synthesis and application of a fast-response long-wavelength fluorescent probe for hydrogen peroxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The synthesis of embodiment 1 probe

[0053] Synthesis of Compound 1:

[0054]

[0055] Add 1,1,2-trimethyl-1H-benzindole (5.0 g, 24.0 mmol) into a 100 mL round bottom flask, dissolve in 20 ml of toluene, add CH 3 I (4.0g, 28.2mmol), refluxed for 6 hours, the reaction was completed, and cooled to room temperature. A large amount of off-white precipitate was produced, and the off-white solid was obtained by filtration, washed five times with toluene, and dried to obtain off-white solid powder.

[0056] Synthesis of Compound 2:

[0057]

[0058] At 0°C, phosphorus tribromide (0.9mL, 9.5mmol) was slowly added to a mixed solution of DMF (1.2mL, 15.5mmol) and chloroform (10ml), and after stirring for 1 hour, cyclohexanone (0.4mL , 3.9mmol) was dissolved in chloroform (10ml), slowly added dropwise to the mixed system, stirred at room temperature for 18 hours, and the reaction was completed. The mixture was poured into ice, and the pH was adjusted to neutral with sod...

Embodiment 2

[0071] Embodiment 2 Probe TC-BOR reacts with hydrogen peroxide before and after the change of absorption spectrum

[0072] Dissolve the probe 1 prepared in Implementation 1 in DMSO to make a 1.0mmol / L probe mother solution (the concentration of probe 1 is 1.0mmol / L); hydrogen peroxide is made into a mother solution with a concentration of 1mol / L, and diluted to the desired concentration. Take two centrifuge tubes, take 30μL from the probe mother solution and add it to a 4mL centrifuge tube, add 270μL DMSO solution, add 300μL PBS buffer solution (concentration 100mmol / L, pH=7.4) and 2100μL deionized water, then add 300μL of hydrogen peroxide solution with a concentration of 20mmol / L, the concentration of the prepared probe is 0.010mmol / L, the concentration of hydrogen peroxide is 2.0mmol / L, the test solution containing 10% DMSO, and the other without adding 300μL with a concentration of 20mmol / L Hydrogen peroxide solution was replaced with an equal amount of water. First test...

Embodiment 3

[0073] Embodiment 3 Probe TC-BOR reacts with hydrogen peroxide before and after fluorescence change spectrogram

[0074] Take 30 μL of the probe mother solution in Example 2 and add it to a 4 mL centrifuge tube, prepare the mother solution with a concentration of 1 mol / L of hydrogen peroxide, and dilute to the desired concentration. Take one of the two centrifuge tubes and take 30 μL from the probe mother solution and add it to a 4 mL centrifuge tube, add 270 μL of DMSO solution, add 300 μL of PBS buffer solution (concentration 100 mmol / L, pH=7.4) and 2.1 mL of deionized water, and then Add 300 μL of hydrogen peroxide solution with a concentration of 20 mmol / L to prepare a test solution with a probe concentration of 0.010 mmol / L, hydrogen peroxide of 2.0 mmol / L, and 10% DMSO, and the other without adding 300 μL with a concentration of 20 mmol / L L of hydrogen peroxide solution, replaced with an equal amount of water. Depend on Figure 5 The experimental results show that when...

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Abstract

The invention relates to the synthesis and application of a novel fluorescent probe for rapid detection of hydrogen peroxide, which belongs to the technical field of rapid analysis and detection of hydrogen peroxide. Based on the principle that boric acid esters can be selectively oxidized and hydrolyzed by hydrogen peroxide, 4-bromomethylphenylboronic acid pinacol ester was condensed with the hemicyanine parent skeleton to synthesize the hydrogen peroxide molecular fluorescent probe TC-BOR, which has a large The conjugated and strong push-pull electron system accelerates the response to hydrogen peroxide and emits long-wavelength near-infrared fluorescence (723 nm). The response time to hydrogen peroxide is as low as 7 minutes, the fluorescence intensity is increased by 55 times, the detection limit is 2.27 μM, and it can resist the interference of various ions. The probe has good cell membrane penetration and low background fluorescence, and the applicable pH range is 7.4‑10. The probe has the characteristics of rapidity, high sensitivity, and strong selectivity. It is used in the rapid detection of hydrogen peroxide content in food, with excellent indicators, fully meeting the requirements of rapid detection.

Description

technical field [0001] The invention relates to the synthesis and application of a fast-response hydrogen peroxide long-wavelength fluorescent probe, which belongs to the technical field of rapid analysis and detection of hydrogen peroxide. Background technique [0002] Oxygen is inseparable from the human life process. At the cellular level, reactive oxygen species (ROS) are mainly produced by the mitochondrial electron transport chain, which includes a series of active oxygen-containing substances. Under normal circumstances, ROS is the main medium for phagocytosis and killing by phagocytes; however, under pathological conditions, the abnormal level of ROS in the human body will cause damage to the human body. Hydrogen peroxide (H 2 o 2 ) as an important reactive oxygen species, using it as an entry point to qualitatively and quantitatively study the level of human ROS has become the focus of medical workers. [0003] Hydrogen peroxide has a bleaching effect on food and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/02C09K11/06C09K2211/1029C09K2211/1088C09K2211/1096G01N21/6428
Inventor 崔京南田艺浓刘涛何深贵赵鑫陈立森朱新月
Owner DALIAN UNIV OF TECH
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