A fluorescent probe with both hydrogen peroxide detection and photodynamic killing of cancer cells and its preparation method and application

A fluorescent probe and photodynamic technology, applied in photodynamic therapy, chemical instruments and methods, fluorescence/phosphorescence, etc., can solve the problems of no photodynamic killing cancer cell activity, limited application range, etc., and achieve strong light stability Anti-photobleaching ability, low background interference, and easy-to-operate effect

Active Publication Date: 2021-12-24
INNER MONGOLIA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, a few AIE molecules used to detect hydrogen peroxide have been reported in the literature, but there are very few AIE molecules that can detect hydrogen peroxide in lipid droplets in real time, and the existing AIE molecules for detecting hydrogen peroxide do not have photodynamic killing of cancer cells. The scope of application restricted

Method used

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  • A fluorescent probe with both hydrogen peroxide detection and photodynamic killing of cancer cells and its preparation method and application
  • A fluorescent probe with both hydrogen peroxide detection and photodynamic killing of cancer cells and its preparation method and application
  • A fluorescent probe with both hydrogen peroxide detection and photodynamic killing of cancer cells and its preparation method and application

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preparation example Construction

[0048] The present invention also provides a method for preparing the fluorescent probe described in the above technical solution, comprising the following steps:

[0049] (1) Mixing a compound having a structure shown in formula II, 4-(bromomethyl)phenylboronic acid and a first organic solvent for a salt-forming reaction to obtain a compound having a structure shown in formula III;

[0050]

[0051] Wherein, in formula II and formula III, R is hydrogen, alkyl, alkoxy, N,N-dimethyl, N,N-diethyl or N,N-diphenyl;

[0052] (2) Mix the compound having the structure shown in formula III with malononitrile, an organic base and a second organic solvent, and perform Knoevenagel reaction under a protective atmosphere to obtain a fluorescent probe having the structure shown in formula I.

[0053] In the present invention, the compound having the structure shown in formula II, 4-(bromomethyl)phenylboronic acid and the first organic solvent are mixed for a salt-forming reaction to obta...

Embodiment 1

[0075] The following formula 1 is the chemical reaction formula for preparing a fluorescent probe with both hydrogen peroxide detection and photodynamic killing of cancer cells in this embodiment:

[0076]

[0077] (1) Compound 1 (497.6 mg, 1.00 mmol), 4-(bromomethyl) phenylboronic acid (257.8 mg, 1.20 mmol) and toluene were mixed, refluxed at 130 ° C under the protection of nitrogen, and the reaction progress was monitored with a TLC plate Until the complete disappearance of compound 1, the salt-forming reaction was completed; then cooled to room temperature, anhydrous ether was added to the resulting reaction solution, and allowed to stand for 30 minutes, wherein the volume ratio of the reaction solution to anhydrous ether was 1:3, and then suction filtered to obtain Solid 370.5mg, the calculated yield is 52%;

[0078] Gained solid is carried out NMR characterization, the result is as follows:

[0079] 1 H NMR (400MHz, DMSO-d 6 )δ9.34(d, J=6.3Hz, 2H), 8.32(d, J=6.2Hz, ...

Embodiment 2

[0117] Compound 1 is replaced by the compound shown in the following formula II-2, and other conditions are the same as in Example 1,

[0118]

[0119] The obtained product was characterized by NMR, and it can be known that the obtained probe is the compound shown in I-2.

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Abstract

The invention provides a fluorescent probe capable of detecting hydrogen peroxide and photodynamically killing cancer cells, its preparation method and application, and belongs to the technical field of biochemical materials. The fluorescent probe provided by the present invention, which has the activity of hydrogen peroxide detection and photodynamic killing of cancer cells, has aggregation-induced luminescence characteristics, can specifically respond to hydrogen peroxide, and produces a substance with stronger fluorescence, which can be applied to the detection of intracellular hydrogen peroxide, and can selectively Locate the subcellular organelle lipid droplets in cells; the product of the fluorescent probe interacting with hydrogen peroxide has a large Stokes shift, which can avoid self-absorption and reduce background interference; the fluorescent probe and its product interacting with hydrogen peroxide have Strong photostability and anti-photobleaching ability, suitable for long-term tracer of hydrogen peroxide in living cells or in vivo; at the same time, the product of the interaction between the fluorescent probe and hydrogen peroxide also has the ability to generate active oxygen, which can be used for photodynamic killing of cancer cells , to construct a diagnostic and therapeutic reagent with both diagnostic and therapeutic functions.

Description

technical field [0001] The invention relates to the technical field of biochemical materials, in particular to a fluorescent probe with both hydrogen peroxide detection and photodynamic killing of cancer cells, a preparation method and application thereof. Background technique [0002] Hydrogen peroxide (H 2 o 2 ) is one of the important members of the reactive oxygen species family (Reactive Oxygen Species, ROS), which plays a key role in the physiology, pathology and cell signal transduction of living organisms. More and more literature reports have confirmed that the abnormal content of hydrogen peroxide in the body is closely related to various diseases, such as stroke, diabetes, arthritis, cardiovascular diseases and tumors. In particular, tumor hypoxia will induce tumor cells to produce more hydrogen peroxide and lipid droplets. Therefore, the development of a rapid, sensitive, and real-time method for the detection of endogenous hydrogen peroxide in intracellular li...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64A61K41/00A61P35/00
CPCC07F5/025C09K11/06A61K41/0057A61P35/00G01N21/6428C09K2211/1007C09K2211/1029C09K2211/1014G01N2021/6439G01N2021/6443G01N2021/6417
Inventor 王建国姜国玉刘祥
Owner INNER MONGOLIA UNIVERSITY
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