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Compound, aggregation-induced emission probe and preparation method and application thereof

A compound and reaction technology, applied in the field of fluorescent probes, can solve the problems of small Stokes shift, poor photostability, and limited application of fluorescent reagents, and achieve high luminescence efficiency in aggregated states, large Stokes shifts, and biocompatibility good sex effect

Active Publication Date: 2019-01-25
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, traditional fluorescent reagents for staining Aβ plaques or fibers also have defects such as small Stokes shift, poor photostability, and low signal-to-noise ratio, which severely limit their application.

Method used

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  • Compound, aggregation-induced emission probe and preparation method and application thereof
  • Compound, aggregation-induced emission probe and preparation method and application thereof
  • Compound, aggregation-induced emission probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Example 1: Synthesis of aggregation-induced luminescent probe compound III-1

[0101] The synthetic route is:

[0102]

[0103] (1) Synthesis of Compound II-1:

[0104] The compound of formula I-1 (1.1g, 3.0mmol) and ammonium formate (1.16g, 15mmol) were dissolved in a mixed solvent of ethanol (30 mL) and N,N-dimethylformamide (5mL), followed by nitrogen protection Heated to reflux for 12 h; after the reaction was completed, cooled to room temperature and rotary evaporated under reduced pressure, the residue was extracted with dichloromethane (50mL×3), the combined dichloromethane layer was dried over anhydrous magnesium sulfate, and then Rotary evaporation under reduced pressure, the residue was separated by silica gel column chromatography, and the eluent was dichloromethane to obtain the compound of formula II-1 (yield 53%, 587 mg); the relevant structural characterization data of the compound of formula II-1 are as follows: 1 H NMR (DMSO-d 6 ,500MHz): δ9.84(br...

Embodiment 2

[0108] Embodiment 2: the synthesis of compound IV-1

[0109] The synthetic route is:

[0110]

[0111] Boron trifluoride diethyl ether (227mg, 1.6mmol) was added to a THF (10mL) solution of the compound of formula I (184mg, 0.5mmol), heated to reflux for 12h under nitrogen protection; after the reaction was completed, cool to room temperature and Rotary evaporation was performed under reduced pressure, and 10 mL of n-hexane was added to the residue to precipitate a red solid precipitate, which was filtered and dried under vacuum to obtain the compound of aggregation-induced luminescent probe formula IV-1 (yield 79%, 164 mg). The relevant structural characterization data are as follows: 1 H NMR (DMSO-d 6 ,500MHz):δ10.12(br s,2H), 7.94(s,1H),7.91(s,1H),7.48(d,J=2.0Hz,2H),7.35(dd,J 1 =8.5Hz,J 2 =1.5Hz, 2H), 7.04(s, 1H), 7.01(s, 1H), 6.88(d, J=8.0Hz, 2H), 6.46(s, 1H), 3.86(s, 6H); 13 C NMR (DMSO-d 6 ,125MHz):178.7,151.3,148.2,147.0,126.0,125.3,117.9,116.0,112.4,101.1,55.8...

Embodiment 3

[0112] Embodiment 3: the photophysical property characterization of compound III-1 and IV-1 ( Figure 2 to Figure 7 )

[0113] The ultraviolet-visible absorption test result of compound III-1 and IV-1 is as follows Figure 2-4 shown. figure 2 The ultraviolet absorption and fluorescence emission spectrograms of the aggregation-induced luminescent probe compound III-1 prepared for Example 1; (A) the normalized ultraviolet absorption spectrogram of compound III-1 in tetrahydrofuran (10 -5 mol L -1 ); (B) Fluorescence emission spectrum of compound III-1 in the mixed solution of tetrahydrofuran and water with increasing water content; (C) change of maximum emission wavelength and maximum emission fluorescence of compound III-1 in the mixed solution of tetrahydrofuran and water Ratio change graph of intensity. image 3 The ultraviolet absorption and fluorescence emission spectrograms of the aggregation-induced luminescence probe compound IV-1 prepared for Example 2; (A) the nor...

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Abstract

The invention belongs to the technical field of bio-imaging, and discloses a compound, an aggregation-induced emission probe and a preparation method and application thereof. The compound is shown inthe formula III or IV, and the aggregation-induced emission probe contains at least one of the compounds shown in the formula III or IV. The invention further discloses preparation methods of the compounds shown in the formula III and IV. The compound can effectively overcome the defect of aggregation induction quenching of traditional fluorescent pigment, achieves specificity and high signal to noise ratio fluorescent imaging of A beta plaques, has the advantages including high emission efficiency and large stokes shift, can serve as the aggregation-induced emission probe, and has the neuralprotection effect. In addition, the invention further discloses application of the compound to A beta plaque specificity fluorescence imaging agent and neural cell protection and monitoring of formingof A beta fiber or depolymerization of A beta fiber. (The formulas are shown in the description.).

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to a compound, an aggregation-induced luminescence probe, a preparation method and application thereof. Background technique [0002] Alzheimer's disease is a chronic progressive central nervous system degenerative disease that occurs in old age. With the advent of my country's aging society, the number of patients with Alzheimer's disease has also increased significantly, becoming an important medical and social problem that needs to be solved urgently. One of the current "gold standards" for diagnosing Alzheimer's disease is the detection of Aβ plaque formation. Aβ plaques and Aβ fibers are mainly composed of Aβ 1-42 The β-fold structure of the peptide, by destroying the synaptic membrane, has a toxic effect on the surrounding synapses and neurons, causing nerve cell death. Therefore, the specific detection of Aβ plaque formation is of great significance for the diag...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B57/00G01N21/64G01N1/30
CPCC07F5/022C09B57/00C09K11/06C09K2211/1007C09K2211/104C09K2211/1096G01N1/30G01N21/6486G01N2001/302G01N2021/6432
Inventor 唐本忠高蒙李诗武
Owner SOUTH CHINA UNIV OF TECH
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