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Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in simultaneously distinguishing Hcy, Cys, SO2 and GSH

A fluorescent probe and fluorescent molecular probe technology, applied in the field of analytical chemistry, can solve the problem that multi-signal fluorescent probes cannot be distinguished and detected

Active Publication Date: 2022-03-29
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the structure and reactivity of the small molecular biothiols Hcy, Cys and GSH are similar, some fluorescent probes have been developed for the detection of Hcy, Cys, GSH and SO 2 2 or 3 of the ( Angew. Chem. Int. Ed., 2018, 57, 4991–4994, etc.), but the reported multi-signal fluorescent probes have not been able to use four different fluorescent channels to simultaneously detect Hcy, Cys, SO 2 and GSH

Method used

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  • Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in simultaneously distinguishing Hcy, Cys, SO2 and GSH
  • Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in simultaneously distinguishing Hcy, Cys, SO2 and GSH
  • Synthesis of multi-signal fluorescent probe and application of multi-signal fluorescent probe in simultaneously distinguishing Hcy, Cys, SO2 and GSH

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1. Synthesis of 9-(butylthio)-11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3- f ]pyrido[3,2,1- ij ]quinoline-10-carbaldehyde

[0023]a. Add 2.0 g (6.58 mmol) of 9-chloro-11-oxo-2,3,6,7-tetrahydro-1H,5H,11Hpyrano[2,3- f ]pyrido[3,2,1- ij ] quinoline-10-carbaldehyde and 0.715 mg (7.90 mmol) n-butanethiol were added to 20 mL of anhydrous dichloromethane, 0.2 mL of triethylamine was added dropwise, and the reaction was stirred at room temperature;

[0024] b. The reaction solution in step a is spin-dried under reduced pressure, recrystallized with an appropriate amount of absolute ethanol, filtered, and dried to obtain 9-(butylthio)-11-oxo-2,3,6,7-tetrahydro -1H, 5H, 11H-pyrano[2,3- f ]pyrido[3,2,1- ij ] Quinoline-10-carbaldehyde 1.8 g, the productive rate is 76.5%.

Embodiment 2

[0025] Example 2. Synthesis of multi-signal fluorescent probe tert-butyl ( E )-3-(9-(butylthio)-11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3- f ]pyrido[3,2,1- ij ]quinolin-10-yl)-2-cyanoacrylate (R 1 = n-butyl, R 2 = tert-butyl)

[0026] . 1.0 g (2.8 mmol) of 9-(butylthio)-11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3- f ]pyrido[3,2,1- ij ] quinoline-10-carbaldehyde and 0.435 g (3.08 mmol) tert-butyl cyanoacetate were added in 20 mL of anhydrous dichloromethane, then 0.3 mL of triethylamine was added dropwise, and the reaction was stirred at room temperature;

[0027] . After the reaction is complete, the step The middle reaction liquid is added dropwise in 30 mL absolute ethanol, filters, and the gained solid is dried, obtains the multi-signal fluorescent molecular probe tert-butyl group described in claim 1 ( E )-3-(9-(butylthio)-11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3- f ]pyrido[3,2,1- ij ] Quinoline-10-yl)-2-cyanoacrylate 740mg, productive rate...

Embodiment 3

[0028] Example 3. Multi-signal fluorescent molecular probes (here in R 1 = ethyl, R 2 = tert-butyl probe as an example, no special instructions, other probes have similar operation steps) Differentiate detection of Hcy, Cys, NaHSO in vitro 3 and GSH applications

[0029] The multi-signal fluorescent molecular probe spectral property experiment described in the present invention: the probe is dissolved in dimethyl sulfoxide (DMSO) to configure a probe solution with a concentration of 1 mM, and Cys and Hcy with a concentration of 1 mM are respectively configured NaHSO 3 (SO 2 Under physiological conditions, it mainly exists in the form of sulfite) and GSH aqueous solution. The specific test method is: take 20 μL of 1 mM probe solution, 780 μL of analytically pure DMSO, the required amount of PBS buffered aqueous solution and the required amount of 1 mM Cys / Hcy / NaHSO 3 / GSH aqueous solution in a 2 mL sample tube, and all tests kept the volume ratio of the organic phase to ...

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Abstract

The invention discloses a multi-signal fluorescent molecular probe for simultaneously distinguishing and detecting homocysteine (Hcy), cysteine (Cys), sulfur dioxide (SO2) and glutathione (GSH) through four different fluorescent channels, the chemical structural general formula of the multi-signal fluorescent molecular probe is shown in the specification, in the formula, R1 is alkyl, and R2 is alkyl / aryl. The multi-signal fluorescent probe can be subjected to different chemical reactions with Hcy, Cys, NaHSO3 and GSH to generate different fluorescent substances, so that the purpose of simultaneously distinguishing and detecting Hcy, Cys, SO2 and GSH is achieved. The probe emits blue fluorescence of about 466 nm after reacting with Hcy, emits cyan fluorescence of about 496 nm after reacting with Cys, emits green fluorescence of about 535 nm after reacting with NaHSO3, and emits yellow fluorescence of about 568 nm after reacting with GSH. The multi-signal fluorescent molecular probe can be used for simultaneously quantifying in an in-vitro environment and simultaneously distinguishing fluorescence imaging Hcy, Cys, SO2 and GSH in biological systems such as cells, tissues and the like.

Description

[0001] Application field [0002] The invention belongs to the technical field of analytical chemistry, and in particular relates to the synthesis of a class of multi-signal fluorescent probes, and the simultaneous quantitative detection of Hcy, Cys, and SO in the environment by the probes. 2 Simultaneously differentiate and image Hcy, Cys, SO in biological systems such as cells, tissues, and living organisms 2 and GSH applications. Background technique [0003] Small molecule biothiols such as cysteine ​​(Cys), homocysteine ​​(Hcy), glutathione (GSH) and sulfur dioxide (SO 2 , which mainly exist in the form of sulfite under physiological conditions) play an extremely important role in biological systems, and can be transformed into each other through the transsulfurization pathway in vivo. Hcy in the cell can be converted into Cys through the methionine cycle, and Cys is the precursor substance for the synthesis of GSH, SO 2 It is a metabolite of Cys and GSH, and the relat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/16C09K11/06G01N21/64
CPCC07D491/16C09K11/06G01N21/6428C09K2211/1033
Inventor 尹鹏连春华尹国兴
Owner HUNAN NORMAL UNIVERSITY