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Malondialdehyde fluorescence probe, and preparation method and application thereof

A technology of fluorescent probe and malondialdehyde, which is applied in the field of analytical chemistry, can solve the problems such as non-destructive detection of malondialdehyde, and achieve the effect of high yield, simple synthesis, and detection

Inactive Publication Date: 2017-07-11
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires destructive treatment of biological samples and cannot perform non-destructive detection of malondialdehyde in a physiological environment

Method used

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  • Malondialdehyde fluorescence probe, and preparation method and application thereof
  • Malondialdehyde fluorescence probe, and preparation method and application thereof
  • Malondialdehyde fluorescence probe, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of compound 3:

[0032]

[0033] Will take 50mg 4-chloro-7-chlorosulfonyl-2,1,3-benzoxadiazole (1) (0.2mmol) and 80mg 3-propylaminotriphenylphosphine bromide (2) (0.2mmol ) As in the round bottom flask, add dichloromethane to make it dissolve completely, then dropwise add a drop of triethylamine, stir under nitrogen protection and normal temperature for 1 hour, after the reaction is completed, the solvent (dichloromethane) is distilled under reduced pressure by a rotary evaporator Removal gave the crude product. Using ethyl acetate and petroleum ether at a volume ratio of 2:1 as the eluent, the silica gel (200-300 mesh) chromatography column was used for purification to obtain 79 mg of light yellow solid 3 (yield: 63%). 1 H NMR (400MHz, CD 3 OD),δ(ppm):1.81-1.87(m,2H),3.15-3.16(2H),3.39-3.47(2H),7.64-7.66(d,J=7.6Hz,1H),7.73-7.75(7H ),7.77-7.79(4H),7.87(s,1H),7.88-7.91(3H),8.01-8.03(d,J=7.6Hz,1H); 13 C NMR (100MHz, CD 3 OD): δ (ppm): 20.23, 24.64, 44.02...

Embodiment 2

[0038] Fluorescence Spectrum Changes of Probe FDP Reacted with Different Concentrations of Malondialdehyde

[0039] The probe FDP prepared in Example 1 was dissolved in ethanol to make a probe mother solution with a concentration of 1 mM, and 220 mg of 1,1,3,3-tetraethoxypropane was dissolved in 80 mL of aqueous hydrochloric acid with a concentration of 10 mM. Heated at 50°C for 1 hour, cooled to room temperature, and then diluted to 100 mL with aqueous hydrochloric acid to obtain a mother liquor of malondialdehyde with a concentration of 100 mM. Take out 30 μ L from the probe mother liquor and join in the centrifuge tube of 5mL, add the malondialdehyde mother liquor of different equivalents (0-120eq) (the described equivalence refers to the material amount of malondialdehyde in the malondialdehyde mother liquor relative to the probe The multiple of the amount of substance of the probe in the mother liquor), diluted to 3mL with different volumes of PBS aqueous solution (concen...

Embodiment 3

[0041] Fluorescence changes of probe FDP and malondialdehyde with time

[0042] Take 30 μL from the fluorescent probe mother solution in Example 2 and add it to a 5mL centrifuge tube, add 30 μL of malondialdehyde mother solution with a concentration of 100mmol / L, and then dilute to 3mL with 2.94mL PBS buffer solution (concentration 25mM, pH 7.4) , prepared as a test solution with a probe concentration of 10 μmol / L and containing 1% ethanol. With an excitation wavelength of 373nm, its fluorescence spectrum changing with time was tested. Depend on Figure 7 It can be seen that as time increases, the fluorescence intensity at 554 nm gradually increases, and reaches the maximum value at about 15 minutes.

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Abstract

The invention discloses a malondialdehyde fluorescence probe, and a preparation method and an application thereof. The structural formula of the probe is shown in the description. The synthesis method of the above probe molecule is simple, the probe realizes the detection of malondialdehyde in an aqueous solution, and the probe also can realize the detection of malondialdehyde in mammal cells or plant tissue environment through carrying out fluorescence imaging on human cervical cancer cells or onion tissues respectively co-incubated with a fluorescence probe FDP and malondialdehyde by a confocal microscope and observing the change of a green channel fluorescence signal.

Description

technical field [0001] The invention relates to a malondialdehyde fluorescent probe and its preparation method and application, belonging to the technical field of analytical chemistry. Background technique [0002] Malondialdehyde (MDA) is a lipid peroxide formed by oxygen free radicals in the body attacking polyunsaturated fatty acids in biological membranes, and its production can also aggravate membrane damage. Due to its high biological activity, malondialdehyde is considered to be a toxic substance that can induce mutations in organisms and cause atherosclerosis. In humans, abnormal levels of malondialdehyde have been linked to diseases such as leukemia, diabetes, cancer, cardiovascular disease, asthma, and atherosclerosis. In the study of plant aging physiology and resistance physiology, MDA content is a commonly used indicator. Testing MDA content can reflect the degree of lipid peroxidation in the body and the degree of cell damage. Therefore, MDA content is a ver...

Claims

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Application Information

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IPC IPC(8): C07F9/653C09K11/06G01N21/64
CPCC07F9/65318C09K11/06C09K2211/1048C09K2211/1096G01N21/6428G01N21/6447G01N21/6486G01N2021/6443
Inventor 林伟英何隆薇杨雪玲徐凯欣
Owner UNIV OF JINAN
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