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A two-photon fluorescent probe for the detection of hypochlorous acid in the endoplasmic reticulum

A two-photon fluorescence, endoplasmic reticulum technology, applied in fluorescence/phosphorescence, luminescent materials, measurement devices, etc., can solve the problems of poor water solubility, narrow detection interval, and poor linear relationship.

Inactive Publication Date: 2020-07-07
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there have been some reports on the application of fluorescent probes in endoplasmic reticulum targeting, but their application is limited due to their shortcomings such as poor water solubility, poor selectivity, narrow detection range, and poor linear relationship.

Method used

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  • A two-photon fluorescent probe for the detection of hypochlorous acid in the endoplasmic reticulum
  • A two-photon fluorescent probe for the detection of hypochlorous acid in the endoplasmic reticulum
  • A two-photon fluorescent probe for the detection of hypochlorous acid in the endoplasmic reticulum

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Synthesis of Fluorescent Probes

[0039] (1) Dissolve 120mg of 4-methylthio-1,8-naphthalic anhydride in about 150mL of ethanol and heat under reflux to 90°C for 20min. Dissolve BOC-hexamethylenediamine in 2mL of ethanol and add dropwise to the reaction solution. Continue to reflux and stir for 4 hours, filter after cooling, spin the filtrate to dryness, and use ethyl acetate:petroleum ether=3:1 (v / v) to go through silica gel column chromatography to obtain a yellow product (compound 1);

[0040] (2) The product obtained in step (1) was dissolved in about 20 mL of dichloromethane at room temperature, and 2.5 mL of trifluoroacetic acid dissolved in about 1.2 mL of dichloromethane was added dropwise to the reaction solution, and stirred at room temperature for 3 hours. Then the product was spin-dried, and passed through a silica gel chromatography column with methanol:dichloromethane:triethylamine=15:1:0.05 (v / v) as the eluent to obtain a yellow product (compound...

Embodiment 2

[0043] Example 2 Responses of fluorescent probes to different concentrations of hypochlorous acid

[0044] The probe obtained in Example 1 was dissolved in ethanol, and then prepared into a 10 μM probe buffer solution (containing 10% ethanol) with PBS buffer at pH 7.4. Take 26 parts of the above probe solution, add the same volume of water or sodium hypochlorite solution respectively, so that the concentration of hypochlorite is 0, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 120, 140 , 160, 180, 200, 220, 240, 260, 280, 300, 320, 340, 360, 380, 400 μM. Then perform a fluorescence scan (λ Ex =405 nm); calculate the relative fluorescence intensity in each system. The response of probe NHS-ER to different concentrations of hypochlorous acid is as follows: figure 2 Shown: Its maximum fluorescence intensity peak is 502nm. The corresponding light intensity at 502 nm (I 502nm ) is the ordinate, and the hypochlorite concentration is the abscissa, we get image 3 , we know that I ...

Embodiment 3

[0045] Example 3 Selectivity of Fluorescent Probes

[0046]The probe obtained in Example 1 was dissolved in ethanol, and then prepared into a 10 μM probe buffer solution (containing 10% ethanol) with PBS buffer at pH 7.4. Take 20 parts of the above probe solution and add 400 μL of Hcys and Na at a concentration of 40 mM respectively. 2 S, Na 2 SO 3 、H 2 o 2 , Cys, NaNO 2 , and metal ions in PBS solution, and then perform fluorescence scanning (λ Ex = 405 nm); calculate the relative fluorescence intensity in each system; the response of probe NHS-ER to different concentrations of hypochlorous acid is as follows Figure 4 As shown in (a); the corresponding light intensity at 502 nm (I 502nm ) is the ordinate, and the histogram of the response of the probe to different substances is obtained, such as Figure 4 As shown in (b): Among them, 1-20 represent 1, blank; 2, KI; 3, CaCl 2 ; 4, FeSO 4 ; 5, Cys; 6, CoCl 2 ; 7, MgCl 2 ;8, NaBr; 9, NaF; 10, CuSO 4 ; 11, GSH; 12, ...

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Abstract

The invention provides a two-photon fluorescent probe for detecting hypochlorous acid in a cellular endoplasmic reticulum. The two-photon fluorescent probe can be obtained through a three-step reaction by using 4-methylthio-1,8-naphthalic anhydride, trifluoroacetic acid and p-toluenesulfonyl chloride as raw materials. The two-photon fluorescent probe can be applied to detection of the hypochlorousacid in a solution or the cellular endoplasmic reticulum. The fluorescent probe can be obtained through chemical synthesis, a synthesis technology is simple and easy to implement, the raw materials are cheap and easy to obtain, the preparation cost is low, and the fluorescent probe is easy to popularize, has high specificity, is not interfered by other components, can be applied to real-time determination of the hypochlorous acid in the endoplasmic reticulum of a living cell and has a broad application prospect.

Description

technical field [0001] The invention relates to a two-photon fluorescent probe for detecting hypochlorous acid in the endoplasmic reticulum of cells and an application thereof, belonging to the field of small molecule fluorescent materials. Background technique [0002] As an important organelle in cells, endoplasmic reticulum (ER) plays a very important role in the whole cell. It is involved in intracellular protein synthesis, folding, Ca 2+ reserve and Ca 2+ It is an important place involved in intracellular signal transduction, and it is also a place for the synthesis of steroids, cholesterol and other lipids. The main physiological functions of the endoplasmic reticulum include regulation of protein synthesis, folding and localization, and maintenance of intracellular Ca 2+ balance. However, changes in the internal environment of the endoplasmic reticulum are highly sensitive, so when cells are stimulated by chemical toxic substances, the normal physiological functio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/6428G01N2021/6432
Inventor 林伟英宋文辉董宝利孔秀琪张楠卢雅茹李敏赵畅
Owner UNIV OF JINAN
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