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A fluorescent probe with aggregation-induced luminescent properties and its preparation method and use

A technology of aggregation-induced luminescence and fluorescent probes, applied in the field of detection of heparin, can solve problems such as limited sensitivity and complex synthesis steps

Active Publication Date: 2019-07-12
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these fluorescent probes have complicated synthetic steps and limited sensitivity

Method used

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  • A fluorescent probe with aggregation-induced luminescent properties and its preparation method and use
  • A fluorescent probe with aggregation-induced luminescent properties and its preparation method and use
  • A fluorescent probe with aggregation-induced luminescent properties and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] According to the following synthetic route, the following compounds are specifically synthesized:

[0053]

[0054] (1) Synthesis of tributyl (3-formyl-4-hydroxybenzyl) phosphine (compound 3):

[0055] Add 5-(chloromethyl)-2-hydroxysalicylaldehyde (compound 1) (340 mg, 2 mmol) and tributylphosphine (compound 2) (740 μL, 3 mmol) into THF under reflux and stir for 1 hour (The temperature of reflux is 70 ℃), then continue to react for 10 hours after cooling to room temperature, obtain white solid precipitate, filter precipitate and dry under vacuum (drying temperature is 40 ℃), obtain compound 3, productive rate is 72% (535mg);

[0056] (2) Fluorescent probe tributyl (4-hydroxy-3-(4-oxo-3,4-dihydroquinazolin-2-yl) benzyl) phosphine iodide (HPQ-TBP-I) synthesis:

[0057] Tributyl (3-formyl-4-hydroxybenzyl) phosphine (372 mg, 1 mmol), 2-aminobenzamide (compound 4) (136 mg, 1 mmol) and iodine (254 mg, 1 mmol) were refluxed in ethanol for 6 After the reaction is complet...

Embodiment 2

[0063] Embodiment 2: detection of heparin

[0064] Add 30 μL of the DMSO (10 mM) mother solution of the fluorescent probe HPQ-TBP-I prepared in Example 1 into 2.970 mL of pure water containing different contents of heparin (Heparin content is 0-14 μM), vortex for 10 seconds, and use Fluorescence was measured with a spectrofluorometer (excitation wavelength 330 nm). Test results such as figure 2 with 3 shown.

[0065] The fluorescent probe HPQ-TBP-I forms a complex with heparin through electrostatic interaction to limit the intramolecular movement and prevent the water in the system from destroying the intramolecular hydrogen bonds of the compound, so as to realize the lighting of heparin.

[0066] figure 2 Middle A is the fluorescence emission spectrum of fluorescent probe HPQ-TBP-I in the heparin of different content (0-14 μ M), figure 2 Middle B is the change curve of the ratio of the fluorescence intensity of the fluorescent probe HPQ-TBP-I at 501nm to the fluoresce...

Embodiment 3

[0068] Embodiment 3: the detection of different water-soluble anionic polymers and ions

[0069] Add 30 μL of the DMSO (10 mM) mother solution of HPQ-TBP-I prepared in Example 1 to 2.970 mL containing different water-soluble anionic polymers (such as heparin (Hep), chondroitin sulfate (ChS), etc.), biomacromolecules (such as pig Hemoglobin (PHB), fetal bovine serum (BSA), hyaluronic acid (HA, etc.) and ions (such as: Na + ,K + ,Mg 2+ , Ca 2+ , Cl - ,PO 4 3– , SO 4 2– ) in pure water, vortexed for 10 s, and measured fluorescence with a spectrofluorometer (excitation wavelength: 330 nm). Test results such as Figure 4 shown.

[0070] Figure 4 It is a histogram of the ratio of the fluorescence intensity of the fluorescent probe HPQ-TBP-I at 501 nm to the fluorescence intensity of HPQ-TBP-I in water in different water-soluble anionic polymers, biomacromolecules and ions. The results show that the probe has a good recognition effect on water-soluble anionic polymers co...

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Abstract

The invention belongs to the technical field of fluorescent probes and discloses a fluorescent probe with an aggregation-induced emission property, a preparation method and an application. The structural formula of the fluorescent probe is shown as formula I, wherein R1 and R2 are independent hydrogen, C1-18 alkyl, halogen, C1-18 alkyl oxygen, C1-18 alkyl sulfenyl, aryl or heteto-aryl; R6 is linear chain and C1-6 alkylene; R3, R4 and R5 are C1-30 alkyl, C1-18 alkyl oxygen, C1-18 alkyl sulfenyl, aryl or heteto-aryl; A- is iodide ion. The fluorescent probe has the aggregation-induced emission property, has high selectivity and high sensitivity to a water-soluble anionic polymer and can be used for detecting the water-soluble anionic polymer.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and relates to a fluorescent probe with aggregation-induced luminescent properties and ion substitution synergistic effect, its preparation method and its application in the detection of water-soluble anionic polymers, especially its use in the detection of heparin the use of. Background technique [0002] Heparin is a sulfated polysaccharide with a high density of negative charges, which can bind to a variety of biologically important proteins with different functions. For example, it can interact with antithrombin to achieve anticoagulant function, and it is often used as an anticoagulant in clinical practice. However, excessive heparin can induce serious complications such as bleeding and thrombocytopenia, therefore, it is very important to develop a method for sensitive and quantitative detection of heparin to understand its normal and pathological functions. Fluorescent probes f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07F9/6512G01N21/64
CPCC07F9/6512C09K11/06C09K2211/1007C09K2211/1044G01N21/643G01N2021/6432
Inventor 唐本忠李诗武高蒙秦安军
Owner SOUTH CHINA UNIV OF TECH
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