A kind of preparation method of fluorescent probe

A technology of ratiometric fluorescent probes and compounds, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of poor water solubility, complex synthesis, poor selectivity, etc., and achieve sensitive response, simple synthesis, and good stability Effect

Active Publication Date: 2020-09-15
杭州佰迈贝生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are still some defects in the reported fluorescent probe analysis methods, such as low sensitivity, poor selectivity, poor water solubility, complex synthesis, etc.

Method used

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  • A kind of preparation method of fluorescent probe
  • A kind of preparation method of fluorescent probe
  • A kind of preparation method of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] (Scheme 1) Dissolve 200mg (0.38mmol) of benzothiazole-rhodamine compounds in 15mL of absolute ethanol, then add 57mg (1.14mmol) of hydrazine hydrate and reflux for 6h, and spin dry the solvent under reduced pressure. The crude product was separated by column chromatography with a mixed system of dichloromethane and methanol (v / v, 100:1) to obtain a pure product, 110 mg of a light yellow pure product with a yield of 54%.

[0033] (Scheme 2) Dissolve 200mg (0.38mmol) of benzothiazole-rhodamine compounds in 15mL of absolute ethanol, then add 95mg (1.9mmol) of hydrazine hydrate and reflux for 6h, and spin dry the solvent under reduced pressure. The crude product was separated by column chromatography with a mixed system of dichloromethane and methanol (v / v, 100:1) to obtain a pure product, 130 mg of a light yellow pure product with a yield of 64%.

[0034] (Scheme 3) 200 mg (0.38 mmol) of benzothiazole-rhodamine compounds were dissolved in 15 mL of absolute etha...

Embodiment 2

[0039] Figure 1ais the fluorescence spectrum of the probe (5 μM) before and after adding peroxynitrite (0-60 μM). Figure 1b It is a linear relationship graph of different concentrations of peroxynitrite (0-20 μM) to probe (5 μM).

[0040] Configure multiple parallel samples with a probe concentration of 5 μM in a 10mL colorimetric tube, then add different concentrations of peroxynitrite into the test system, shake it evenly and let it stand. The above-mentioned determination is carried out in DMSO: water=3: 7 (20mMPBS, pH 7.4) system, the probe used is the probe prepared in Example 1, and all spectral tests are all at 25 Measured at °C.

[0041] Fluorescence intensity changes were measured with a fluorescence spectrometer, from Figure 1a It can be clearly seen that as the concentration of peroxynitrite increases, the fluorescence intensity at 454 nm decreases, and the fluorescence intensity at 581 nm increases gradually. and, by Figure 1b It can be seen that after the f...

Embodiment 3

[0043] figure 2 is the response time of the probe (5 μM) after addition of peroxynitrite (50 μM). Take 50 μL from the probe mother solution and place it in a 10 mL test system, then add 50 μM peroxynitrite into the test system, shake it evenly, and measure the change of its fluorescence intensity with a fluorescence spectrometer immediately. The above-mentioned determination is carried out in DMSO: water=3: 7 (20mM PBS, pH7.4) system, the probe used is the probe prepared in Example 1, and all spectral tests are Measured at 25°C.

[0044] It can be clearly seen from the figure that after the addition of peroxynitrite, the fluorescence intensity reaches the maximum value and remains unchanged after detection for about 6 minutes, which indicates that the probe reacts rapidly with peroxynitrite and can be used for peroxynitrite. The determination of nitrate provides a rapid analytical method.

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Abstract

The invention relates to a fluorescent probe preparation method. Specifically, the probe disclosed by the invention is benzothiazole-rhodamine compound and can serve as a nitrite peroxide ratio fluorescent probe to be applied to nitrite peroxide detection. The preparation method disclosed by the invention utilizes a one-step synthesizing method, so that the preparation method has the advantages ofsimpleness in preparation and high yield.

Description

technical field [0001] The invention relates to a benzothiazole-rhodamine compound as a peroxynitrite ratio fluorescent probe, capable of highly selective and ultrasensitive analysis of peroxynitrite, or it can measure the concentration of peroxynitrite in a sample. Background technique [0002] Reactive oxygen and reactive nitrogen species are involved in a variety of physiological processes in living systems, including signal transduction, inflammation, and resistance to oxidative damage. As a strong oxidizing substance in active oxygen and active nitrogen, peroxynitrite is produced by the reaction of nitric oxide and superoxide radicals, and has high reactivity and instability. It is used in living systems It plays an important role in signal transduction and antibacterial effect. However, due to its nitration damage to proteins, nucleic acids, lipids, etc., peroxynitrite is also considered harmful, and abnormal accumulation of peroxynitrite in cells will lead to many di...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1037C09K2211/1088G01N21/643
Inventor 傅罗琴刘豫王瑞康
Owner 杭州佰迈贝生物科技有限公司
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