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Two-photon fluorescent probe for double detection of sulfur dioxide and viscosity and preparation of two-photon fluorescent probe

A two-photon fluorescence, sulfur dioxide technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of not developing two-photon fluorescent probes, etc., and achieve large Stokes shift and biocompatibility. Good performance and stability

Inactive Publication Date: 2022-03-08
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To the best of our knowledge, no two-photon fluorescent probe has been developed for the dual detection of sulfur dioxide and viscosity

Method used

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  • Two-photon fluorescent probe for double detection of sulfur dioxide and viscosity and preparation of two-photon fluorescent probe
  • Two-photon fluorescent probe for double detection of sulfur dioxide and viscosity and preparation of two-photon fluorescent probe
  • Two-photon fluorescent probe for double detection of sulfur dioxide and viscosity and preparation of two-photon fluorescent probe

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Embodiment 1

[0026] A method for preparing a two-photon fluorescent probe for dual detection of sulfur dioxide and viscosity, the steps comprising:

[0027] 1) Synthesis of Compound 1:

[0028] 2,3,3-Trimethyl-3H-indole (0.96 g, 6 mmol) and iodoethane (561 μL, 6.6 mmol) were dissolved in acetonitrile solution (20 mL), and the mixture was refluxed at 80 °C Stir for 22 hours, cool to room temperature after the reaction, add the reaction liquid dropwise into cold diethyl ether to precipitate compound 1, and obtain solid compound 1 after filtration with a yield of 85%.

[0029] 2) Synthesis of Compound 2:

[0030] A mixture of ethyl bromide (1.47 g, 13.5 mmol), KOH (0.76 g, 13.5 mmol) and KI (0.18 g, 1.08 mmol) was dissolved in acetonitrile solution (15 mL) and heated to 60 ° C. After 1.5 hours of reaction, slowly Carbazole (1.5 g, 9 mmol) was added, refluxed for 13 hours, cooled to room temperature, the mixture was extracted with dichloromethane (20 mL×3), column purified (petroleum ether / d...

Embodiment 2

[0036] Spectroscopic Determination of Probe PVS Responses to Sulfur Dioxide and Viscosity

[0037] Prepare a stock solution by adding dimethyl sulfoxide (DMSO) to the 10 mL centrifuge tube containing the probe. The stock solutions were diluted into 3 mL of different solvents to obtain different test solutions, and the final concentration of each test solution was 10 μM. Subsequently, the probe was used to detect SO in aqueous phase by UV-Vis spectrophotometer and fluorescence spectrometer. 2 capability (SO 3 2- as SO 2 donor). With SO 2 (0-100 μM), the UV absorption peak of the probe PVS at 475 nm gradually decreased, and it showed an obvious fluorescence emission peak at 530 nm. and along with SO 2 With the increase of the concentration, the fluorescence intensity of PVS at 530 nm was enhanced by 42 times, and the limit of detection was 0.55 μM (LOD = 3Sb / k), which indicated that the probe was sensitive to SO 2 Has high sensitivity. Subsequently, the viscosity respon...

Embodiment 3

[0039] Response of Probe PVS to Sulfur Dioxide in High Viscosity Environment

[0040] Different concentrations of SO in PBS buffer solution (containing 50% glycerol) 2 Fluorescent titration of probe PVS was performed. The results showed that with SO 2 As the concentration increases, the corresponding fluorescence intensity gradually increases at 530 nm. This indicates that the probe PVS can sensitively respond to SO in a viscous environment 2 .

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Abstract

The invention discloses a two-photon fluorescent probe for sulfur dioxide and viscosity dual detection and a preparation method of the two-photon fluorescent probe. The compound structure of the fluorescent probe is shown as a compound PVS. The fluorescent probe realizes two-photon excitation response to viscosity by utilizing a twisted intramolecular charge transfer (TICT) mechanism between indole salt and carbazole. Meanwhile, the carbon-carbon double bond connected with the indole salt can realize response to sulfur dioxide through nucleophilic addition reaction. The PVS has the advantages that the PVS can track the fluctuation of sulfur dioxide and viscosity at the same time, and has two emissions which are easy to distinguish. The PVS can also accurately visualize the form of the mitochondria, and the real-time accurate monitoring of the sulfur dioxide and the viscosity in the mitochondria under the excitation of the two photons is successfully realized.

Description

technical field [0001] The present invention relates to a small molecule fluorescent probe compound, more specifically a fluorescent probe for dual detection of sulfur dioxide and viscosity in mitochondria based on a two-photon compound that distorts the intramolecular charge transfer mechanism, and belongs to fluorescent sensor probe compounds field. Background technique [0002] Mitochondria, as the "power factory" in cells, is an important place for material exchange and energy conversion in organisms, and participates in many physiological processes, such as signal transmission, cell differentiation, growth and death. The function of mitochondria is based on many important biomolecules, including various metal ions, reactive oxygen / nitrogen / sulfur species (ROS / RNS / RSS), etc. In addition, increased mitochondrial viscosity can lead to mutations in the mitochondrial reticulum, manifested by deterioration of mitochondrial morphology, which severely hinders material transpor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCC07D209/86C09K11/06G01N21/6428C09K2211/1029
Inventor 颜梅卫先哲张晶杨小凤朱彤李成芳于京华
Owner UNIV OF JINAN
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