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Near-infrared fluorescent probe for bimodal detection of sulfur dioxide, and preparation method and application thereof

A technology of fluorescent probes and sulfur dioxide, applied in chemical instruments and methods, fluorescence/phosphorescence, and material analysis by observing the influence of chemical indicators, etc., can solve the problem of single signal output mode, false positive signal output, and probe distribution Uneven problems, to achieve broad application prospects, reduce light damage, and enhance the effect of signal-to-noise ratio

Active Publication Date: 2020-04-21
HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Currently, most of the developed SO 2 The fluorescent probes mainly have the following problems: 1) low selectivity, poor sensitivity, and are easily affected by other interfering substances in complex detection systems; 2) the signal output mode is single, the single fluorescence intensity or the color change of the probe solution and the probe Unequal distribution in organisms can easily cause false positives in signal output; 3) Absorption and emission of short wavelengths cause greater light damage to cells

Method used

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  • Near-infrared fluorescent probe for bimodal detection of sulfur dioxide, and preparation method and application thereof
  • Near-infrared fluorescent probe for bimodal detection of sulfur dioxide, and preparation method and application thereof
  • Near-infrared fluorescent probe for bimodal detection of sulfur dioxide, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of intermediate 1

[0038]

[0039] Compound 2,3,3-trimethyl-3H-indole (9.87g, 0.062mol) and compound iodoethane (14.5g, 0.093mol) were added to a 150mL round bottom flask, and then 50mL of anhydrous acetonitrile was added , The reaction was stirred at 85°C for 24h. After cooling to room temperature, the crystals were precipitated, filtered with suction, and the filter cake was washed 3 times with 3×10 mL ice ethanol to obtain Intermediate 1.

Embodiment 2

[0040] Example 2: Synthesis of near-infrared fluorescent probes

[0041]

[0042] Intermediate 1 (1g, 3.17mmol) and 4-(dimethylamino) cinnamaldehyde (0.67g, 3.8mmol) were dissolved in 30mL of absolute ethanol, and then 100μL (2 drops) of piperidine was added as a catalyst, at 80 The reaction was stirred at ℃ for 8 h, cooled to room temperature, and the solvent was removed by a vacuum rotary evaporator. The obtained crude product was purified by silica gel column chromatography, and the eluent ratio was dichloromethane / ethyl acetate / methanol=40 / 60 / 1( v / v) to obtain the target product.

[0043] Note: The synthesis of each compound in the general formula of the probe can be carried out according to the synthesis steps of the above-mentioned probe.

Embodiment 3

[0044] Embodiment 3: fluorescent probe to SO in water system 2 Visual colorimetric detection of

[0045] Take the fluorescent probe prepared in Example 2 and dissolve it in ethanol to configure a concentration of 1×10 -3 mol / L stock solution. Measure 2 mL of the probe stock solution and add it to a 100 mL volumetric flask, and make the volume to 100 mL with HEPES buffer solution (10 mM, pH=7.4), so that the final concentration of the probe is 20 μM. Add different concentrations of NaHSO to the probe solution 3 (SO 2 donor) solution to a final concentration of 0-150 μM. Determination of adding different concentrations of SO 2 Finally, the probe absorbs the peak intensity and wavelength changes, and uses a digital camera to record the probe and SO 2 The color change of the solution before and after the reaction. Photos of UV-Vis absorption spectrum and color change of fluorescent solution are shown in figure 1 . As shown in the figure, the probe has a strong absorption ...

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Abstract

The invention discloses a near-infrared fluorescent probe for bimodal detection of sulfur dioxide, and a preparation method and application thereof. The near-infrared fluorescent probe for bimodal detection of sulfur dioxide is a hemicyanine dye derivative, and the structure of the near-infrared fluorescent probe is shown in the specification. The fluorescent probe can be used for bimodal detection of sulfur dioxide in a water body by a colorimetric method and a ratio method, and after the sulfur dioxide reacts with the probe, two signals of probe solution color (dark blue-light powder) and fluorescence (near infrared-yellow region) are remarkably changed, so that high-selectivity and high-sensitivity dual visual detection of the sulfur dioxide in the water body is realized. The fluorescent probe provided by the invention can realize dual-channel ratio imaging and quantification of sulfur dioxide in living cells, and long-wavelength absorption and near-infrared emission of the probe can effectively avoid interference of biological background fluorescence and reduce light damage to the cells.

Description

technical field [0001] The invention relates to the field of synthesis and technical application, in particular to a near-infrared fluorescent probe for dual-mode detection of sulfur dioxide, a preparation method and application thereof. Background technique [0002] Sulfur dioxide (SO 2 ) is one of the main pollutants in the atmosphere, which is easily inhaled by organisms and converted into its derivatives - sulfite and bisulfite in blood or other body fluids, which can cause respiratory diseases, nervous system diseases, and even lung cancer. Studies have taken place that living organisms also contain SO 2 , is produced by sulfur-containing amino acids or hydrogen sulfide through biosynthetic pathways, such as mitochondrial detoxification of hydrogen sulfide, non-enzymatic reactions of reactive oxygen species, etc. Normal levels of SO in living organisms 2 It has the effects of lowering blood pressure, relaxing blood vessels, and inducing negative cardiac muscle streng...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/14C09K11/06G01N21/78G01N21/31G01N21/64
CPCC09B23/145C09K11/06G01N21/78G01N21/783G01N21/31G01N21/64G01N21/6456G01N21/6428G01N21/643C09K2211/1007C09K2211/1029G01N2021/6421G01N2021/6439G01N2021/6495G01N2021/6497
Inventor 王振洋杨林林张忠平刘变化韩光梅赵君
Owner HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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