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Synthesis of bifunctional fluorescent probe and application of bifunctional fluorescent probe in simultaneous distinguishing of H2O2 and HClO
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A technology of H2O2, fluorescent probe, applied in the field of analytical chemistry, can solve the problem of small discrimination
Pending Publication Date: 2022-03-18
HUNAN NORMAL UNIVERSITY
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Problems solved by technology
At present, fluorescent probes for the detection of both have been reported, but only one of them can be detected or the discrimination is small
Method used
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Embodiment 1
[0022] Example 1. Synthesis of 9-(trifluoromethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-F]pyrido[3,2,1- ij] quinoline-11-thione
[0023] . Under nitrogen protection, 2.00 g (6.47 mmol) of 9-(trifluoromethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-F]pyridine Add 3.92 g (9.72 mmol) of base [3,2,1-ij] quinolin-11-one and Lawson's reagent 1:1.5 into 20 mL of dry redistilled toluene, stir at 110°C for 12 hours, and obtain a red solution;
[0024] . Spin the red reaction solution in step a to dryness, and recrystallize from ethyl acetate to obtain a red solid, namely 9-(trifluoromethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano The yield of [2,3-F]pyrido[3,2,1-ij]quinoline-11-thione 1.4 g was 66.54%.
Embodiment 2
[0025] Embodiment 2. synthesis ( E )-2-(pyrimidin-4-yl)-2-(9-(trifluoromethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-F ]pyridin[3,2,1-ij]quinoline-11-ethylene)acetonitrile
[0026] . Under argon protection and light shielding conditions, 0.47 g (4.0 mmol) of 2-(pyrimidin-4-yl) acetonitrile and an equivalent of NaH (0.16 g, 4.00 mmol) were stirred in anhydrousacetonitrile at room temperature for 30 minutes. Then add 9-(trifluoromethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-F]pyrido[3,2,1-ij]quinoneAcetonitrile solution of 1.00 g (3.07 mmol) of phen-11-thione was stirred at room temperature for 2 hours, and finally 0.68 g (4.0 mmol) of silver nitrate was added to react for 90 minutes to terminate the reaction;
[0027] . The reaction solution was purified by column chromatography to obtain a purple solid ( E )-2-(pyrimidin-4-yl)-2-(9-(trifluoromethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-F ]pyridin[3,2,1-ij]quinoline-11-ethylene)acetonitrile; 1.00 g, yield 79.28%....
Embodiment 3
[0028] Example 3. Synthesis of bifunctional fluorescent probes ( E )-1-(4-boraaminobenzyl)-4-(cyano(9-(trifluoromethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2 ,3-F]pyrido[3,2,1-ij]quinolin-11-ylidene)methyl)pyrimidin-1-ammoniumbromide
[0029] 1.00 g (2.44 mmol) ( E )-2-(pyrimidin-4-yl)-2-(9-(trifluoromethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-F ]pyridin[3,2,1-ij]quinoline-11-ethylene)acetonitrile and 0.72 g (2.44 mmol) 4-bromomethylphenylboronic acid pinacol ester 1:1 equivalent in acetonitrile solvent at 80°C Refluxed for 12 hours, a solid precipitated, filtered, washed and dried to obtain a dark blue solid (E)-1-(4-boronaminobenzyl)-4-(cyano(9-(trifluoromethyl)-2,3 ,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-F]pyrido[3,2,1-ij]quinolin-11-ylidene)methyl)pyrimidine-1- Ammoniumbromide was 0.70 g, and the yield was 45.9%.
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Abstract
The invention discloses a bifunctional fluorescent molecular probe for simultaneously distinguishing hydrogenperoxide (H2O2) and hypochlorous acid (HClO) through red and green fluorescence emission signals. The chemical structural formula of the fluorescent probe is shown in the specification. The fluorescent probe can generate different fluorescent substances by utilizing different chemical reactions between the probe and H2O2 and HClO under the same detection condition, so that red and green fluorescence can be emitted under a specific excitation wavelength, and the purpose of simultaneously distinguishing and detecting H2O2 and HClO is achieved. After the probe reacts with H2O2, red light with the wavelength of 648 nm is emitted under the excitation wavelength of 560 nm, and after the probe reacts with HClO, green light with the wavelength of 548 nm is emitted under the excitation wavelength of 427 nm. The probe has the advantages of being high in sensitivity, good in selectivity, large in discrimination degree and the like when used for detecting H2O2 and HClO, and has a huge application prospect in the technical fields of analytical chemistry, life science, environmental science and the like.
Description
technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a dual-channel simultaneously distinguishing hydrogenperoxide (H 2 o 2 ) and hypochlorous acid (HClO) fluorescent probe synthesis, and the probe simultaneously quantitatively detects H in the environment 2 o 2 and HClO, dual-channel fluorescence imaging of cellular endogenous H 2 o 2 and application of HClO. Background technique [0002] Reactive oxygen species (ROS, including H 2 o 2 , O 2 − with 1 o 2 ) maintains a certain concentration range under normal physiological conditions and plays an important role in maintaining cell morphology and basic functions ( Anal. Chem. , 2014, 86, 9970–9976). Reactive oxygen species as endogenous metabolites are considered indicators of oxidative stress. Of which hydrogenperoxide (H 2 o 2 ) is one of the most important ROS. When H 2 o 2 When produced in a controlled manner at low concentrations (&l...
Claims
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