An organosilicon small molecule fluorescent probe for detecting hypochlorous acid

A technology for detecting hypochlorous acid and fluorescent probes, applied in the field of analytical chemistry, can solve the problems of poor anti-interference, single recognition site, and difficult to obtain raw materials, and achieve the effects of rapid response, simple synthesis and strong specificity

Inactive Publication Date: 2021-04-20
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Aiming at the current problems of fluorescent probes for detecting hypochlorous acid, such as unavailable raw materials, complex synthesis steps and operations, poor anti-interference performance, and single recognition site, the present invention provides an organic probe with two-photon properties for detecting hypochlorous acid. Silicon small molecule fluorescent probe, novel recognition site, fluorescence recovery, fast response, strong anti-interference ability

Method used

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  • An organosilicon small molecule fluorescent probe for detecting hypochlorous acid
  • An organosilicon small molecule fluorescent probe for detecting hypochlorous acid
  • An organosilicon small molecule fluorescent probe for detecting hypochlorous acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthesis of embodiment 1 fluorescent probe BSi-1

[0032]

[0033] In a 250 mL round bottom flask, add 0.25 g of 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane dissolved in 100 mL of ethanol, then add 0.49 g5 -Methylthio-1,8-naphthalene dicarboxylic anhydride, heated and stirred at reflux at 78 °C for 24 h, rotary evaporated, dried, using dichloromethane:methanol (V / V)=20:1 as the eluent, and obtained by column chromatography Compound BSi-1. That 1 H NMR spectrum such as figure 1 shown.

Embodiment 2

[0034] Embodiment 2 Different concentrations of hypochlorous acid are detected by fluorescence titration of probe BSi-1

[0035] Prepare 10 mL of an aqueous solution with a concentration of 100 mM hypochlorous acid and a mother solution of the fluorescent probe BSi-1 obtained in Example 1 with a concentration of 1 mM as spares.

[0036] Prepare the probe at a concentration of 10 μM, interact with different concentrations of hypochlorous acid (0, 1, 2, 3, 4, 5, 6, 8, 10, 12, 14, 16, 18, 20 μM), and Perform fluorescence detection (λ ex =405 nm, λ em =485 nm), calculate the fluorescence intensity in each system, and establish a standard curve of fluorescence intensity and hypochlorous acid concentration, such as figure 2 . Depend on figure 2 It can be seen that as the concentration of hypochlorous acid increases, the fluorescence intensity of the reaction system decreases rapidly, and when the concentration of hypochlorous acid reaches 20 μM, the fluorescence of the reactio...

Embodiment 3

[0037] Example 3 Kinetic test of interaction between probe BSi-1 and hypochlorous acid

[0038] Prepare 10 mL of an aqueous solution with a concentration of 100 mM hypochlorous acid and a mother solution of the fluorescent probe BSi-1 obtained in Example 1 with a concentration of 1 mM as spares.

[0039] The solutions of probe BSi-1 and hypochlorous acid were prepared, the concentration of which was 10 μM of the probe; the concentration of hypochlorous acid was 20 μM. Perform fluorescence detection (λ ex =405 nm, λ em =485 nm), in the first 30s, test every 5s; after that, test every 10s, about 3 minutes. Calculate the fluorescence intensity changing with time in each system, and establish a standard curve of fluorescence intensity and action time, such as image 3 shown. Depend on image 3 It can be seen that the fluorescence of the reaction system is basically quenched after 30 s of reaction.

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Abstract

The invention provides an organic silicon small molecule fluorescent probe for detecting hypochlorous acid, and the chemical structural formula is: The probe itself is in a fluorescent state and emits fluorescence of naphthalimide. After the addition of hypochlorous acid, the naphthalimide in the probe interacts with hypochlorous acid to affect the intramolecular charge transfer (ICT) process, resulting in partial fluorescence quenching of the probe naphthalimide. When glutathione was added, the quenched fluorescence was recovered. The probe has novel recognition site, fluorescence recovery, fast response speed and strong anti-interference ability. It is synthesized by heating 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane and 5-methylthio-1,8-naphthalenedicarboxylic anhydride in ethanol to synthesize The raw materials are readily available and the process is simple. The probe has potential application value in the field of laser-excited fluorescent biomarkers and the study of the physiological function of hypochlorous acid in biological samples.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a fluorescent probe for detecting hypochlorous acid and an application thereof. Background technique [0002] Active oxygen is a general term for some oxygen-containing free radicals, hydrogen free radicals, superoxide anion free radicals and non-free radical hypochlorous acid and hypochlorous acid that play a very important role in many physiological and pathological processes in organisms. Under physiological and pathological conditions such as oxidative stress and inflammation, various reactive oxygen species are produced through enzymatic and non-enzymatic reactions in living organisms. Modern biomedical studies have shown that the production of glycosides in the body is closely related to the occurrence and development of some diseases and the aging of the body. [0003] Hypochlorous acid is a kind of active oxygen, as an efficient bactericide, it p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/64C07F7/08C09K11/06
Inventor 林伟英张宇左育静杨婷新王小妮
Owner UNIV OF JINAN
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