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A "triangular electronic push-pull" mitochondria-targeted assay for so 2 Fluorescent probe and its preparation method and application

A technology of fluorescent probes and mitochondria, which is applied in the field of analytical chemistry, can solve the problems of electron-donating groups detaching from the conjugation plane, affecting fluorescence intensity and sensitivity, etc., and achieves the effect of being suitable for optical detection, novel and unique luminescent mechanism, and novel principle

Active Publication Date: 2020-09-29
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reason for these problems is that SO 2 The reaction with the probe is often a new nuclear addition reaction, which will cause the generated electron donor group to leave the conjugation plane, thus affecting the intensity and sensitivity of the fluorescence

Method used

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  • A "triangular electronic push-pull" mitochondria-targeted assay for so <sub>2</sub> Fluorescent probe and its preparation method and application
  • A "triangular electronic push-pull" mitochondria-targeted assay for so <sub>2</sub> Fluorescent probe and its preparation method and application
  • A "triangular electronic push-pull" mitochondria-targeted assay for so <sub>2</sub> Fluorescent probe and its preparation method and application

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Experimental program
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Embodiment 1

[0059] Embodiment 1: Preparation of FHMI molecular probe

[0060] A "triangular electronic push-pull" mitochondria-targeted detection of SO 2 A method for preparing a fluorescent probe, the steps comprising:

[0061] (1) Dissolve 300mg of phenol in a mixed solution of 20ml of toluene and 25ml of glacial acetic acid, then add 983mg of hexamethylenetetramine, mix well, heat and reflux for 18h, until the color of the solution turns orange-red. After cooling to room temperature, 6M hydrochloric acid was added, followed by extraction with ethyl acetate (70 ml, extracted three times). The extracted organic layer was washed with 150ml of saturated brine, then dried with anhydrous sodium sulfate, and after the solvent was removed by rotary evaporation, it was purified through a silica gel column (dissolved in petroleum ether, and the eluent was petroleum ether: ethyl acetate = 10:1), to obtain a yellow solid, namely 4-hydroxyisophthalaldehyde.

[0062] (2) Add 4ml of 4-picoline, 12...

Embodiment 2

[0068] Embodiment 2: Preparation of FHMI molecular probe

[0069] A "triangular electronic push-pull" mitochondria-targeted detection of SO 2 A method for preparing a fluorescent probe, the steps comprising:

[0070] (1) Dissolve 240mg of phenol in a mixed solution of 20ml of toluene and 20ml of glacial acetic acid, then add 720mg of hexamethylenetetramine, mix well, heat and reflux for 16h, until the color of the solution turns orange-red. After cooling to room temperature, 7M hydrochloric acid was added, followed by extraction with ethyl acetate (40 ml, extracted three times). The extracted organic layer was washed with 120ml of saturated brine, then dried with anhydrous sodium sulfate, and after the solvent was removed by rotary evaporation, it was purified through a silica gel column (dissolved in petroleum ether, and the eluent was petroleum ether: ethyl acetate = 10:1), to obtain a yellow solid, namely 4-hydroxyisophthalaldehyde.

[0071] (2) Add 4ml of 4-picoline, 16...

Embodiment 3

[0075] Embodiment 3: Preparation of FHMI molecular probe

[0076] A "triangular electronic push-pull" mitochondria-targeted detection of SO 2 A method for preparing a fluorescent probe, the steps comprising:

[0077] 1) Dissolve 350mg of phenol in a mixed solution of 20ml of toluene and 30ml of glacial acetic acid, then add 1.400g of hexamethylenetetramine, mix well, heat and reflux for 20h, until the color of the solution turns orange-red. After cooling to room temperature, 8M hydrochloric acid was added, followed by extraction with ethyl acetate (100ml, three extractions). The extracted organic layer was washed with 200ml of saturated brine, then dried with anhydrous sodium sulfate, and after the solvent was removed by rotary evaporation, it was purified through a silica gel column (dissolved in petroleum ether, and the eluent was petroleum ether: ethyl acetate = 10:1), to obtain a yellow solid, namely 4-hydroxyisophthalaldehyde.

[0078] (2) Add 4ml of 4-picoline, 14ml o...

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Abstract

The invention relates to a triangular electron push-pull chondriosome targeted SO2 detection fluorescence probe as well as a preparation method and application thereof. Phenol is dissolved into toluene and glacial acetic acid; under the catalysis effect of formamine, 4-hydroxyisophthalaldehyde is obtained; then, 4-methylpyridine, diethyl ether and iodomethane are used to prepare 1,4 dimethyl pyridine iodized salts under the condition of normal-temperature stirring; the 4-methylpyridine and the 1,4 dimethyl pyridine iodized salts use ethyl alcohol as a solvent and piperidine as a catalyst to react under the nitrogen protection so as to obtain the fluorescence probe FHMI. The probe solves the problem of disengagement of electron-donating groups from a conjugated system caused by detection ondetected materials through nucleophilic reaction. The FHMI is applicable to the qualitative and quantitative analysis of SO2 in a biological sample; the detection is sensitive, accurate and fast. Thefluorescence probe can be applied to relevant fields of analytical chemistry, life organic analysis chemistry and the like.

Description

technical field [0001] The invention belongs to the field of analytical chemistry, and relates to a "triangular electronic push-pull" mitochondria-targeted detection of SO 2 Fluorescent probes and their preparation methods and applications. Suitable for SO in biological samples 2 Qualitative and quantitative analysis, real-time monitoring of SO in cell mitochondria 2 change. Background technique [0002] In recent years, the research on functionalized fluorescent dyes in biology and medicine has become one of the hot fields. Among them, fluorescent probes have the advantages of controllable structure, low synthesis cost, and recognition based on irreversible chemical reactions, which can realize real-time cell imaging. However, for practical applications in biological environments, the efficacy of organic fluorescent probes is limited by issues such as sensitivity, specificity, and response time. [0003] Mammalian cells are always in an oxidative environment, and their...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/48C09K11/06G01N21/64
Inventor 陈光周伟赵晨阳李震姜翱刘玉霞尤进茂
Owner QUFU NORMAL UNIV
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