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Water-soluble aggregation-induced luminescent probe as well as preparation method and application thereof

An aggregation-induced luminescence and water-soluble technology, which is applied in the field of fluorescent probes, can solve the problems of slow staining speed, detection, and inability to realize fluorescent probes for Aβ plaques, and achieve fast staining and good water-solubility effects

Active Publication Date: 2019-02-22
HUAZHONG UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention solves the technical problems that the fluorescent probes of Aβ plaques in the prior art cannot be detected in a water-soluble environment, and the dyeing speed is slow and the washing procedures after dyeing are cumbersome.

Method used

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  • Water-soluble aggregation-induced luminescent probe as well as preparation method and application thereof
  • Water-soluble aggregation-induced luminescent probe as well as preparation method and application thereof
  • Water-soluble aggregation-induced luminescent probe as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] A fluorescent probe as shown in formula (1), its name is abbreviated as PD-BZ-OH, wherein R 1 for Ar 1 is a benzene ring, Ar 2 for Its synthesis route is as follows figure 1 shown, including the following steps:

[0037] (1) Synthesis of compound 1: 4-picoline (5g, 53.76mmol, 1eq.) and 2-bromoethanol (6.67g, 53.76mmol, 1eq.) were dissolved in CH 3 CN (100 mL) was stirred at 90° C. for 16 hours. Concentration in vacuo afforded compound 1 (11.82 g, crude product) as a yellow oil, which was used in the next reaction without further purification. 1 H NMR (600MHz, DMSO-d 6 )δ8.94(d, J=6.6Hz, 2H), 8.02(d, J=6.6Hz, 2H), 5.17(brs, 1H), 4.67(t, J=4.8Hz, 2H), 3.85(t, J=4.8Hz, 2H), 2.63(s, 3H).

[0038] (2) Synthesis of PD-BZ-OH: ethanol solution of aldehyde 2 (1 eq.), compound 1 (1 eq.) and piperidine (catalytic amount), stirred at 80° C. for 16 hours. After concentration, the crude product was recrystallized from ethanol and ethyl acetate to obtain the title compound...

Embodiment 2

[0040] A fluorescent probe as shown in formula (1), its name is abbreviated as PD-NA-OH, wherein R 1 for Ar 1 is a naphthalene ring, Ar 2 for Its synthesis route is as follows figure 1 shown, including the following steps:

[0041] Synthesis of PD-NA-OH: Aldehyde 3 (1 eq.), Compound 1 (1 eq.) and piperidine (catalytic amount) in ethanol were stirred at 80°C for 16 hours. After concentration, the crude product was recrystallized from ethanol and ethyl acetate to obtain the title compound as a reddish-brown solid. 1 H NMR (600MHz, DMSO-d 6 )δ8.86(d, J=6.6Hz, 2H), 8.24(d, J=6.6Hz, 2H), 8.13(d, J=16.2Hz, 1H), 8.03(s, 1H), 7.83–7.79( m,2H),7.77(d,J=9.0Hz,1H),7.54(d,J=16.2Hz,1H),7.42(dd,J=9.0,2.4Hz,2H),7.20(s,1H), 5.28(t, J=5.3Hz, 1H), 4.56(t, J=5.4Hz, 2H), 3.86(q, J=5.4Hz, 2H), 3.35–3.33(m, 4H), 1.69–1.64(m ,4H),1.63–1.59(m,2H). 13 C NMR (151MHz, DMSO-d 6 )δ153.13,150.31,144.37,141.41,135.68,129.77,129.33,129.21,127.10,126.54,123.79,122.89,121.23,119.28,108.42,61.79,58...

Embodiment 3

[0043] A fluorescent probe as shown in formula (two), its name is abbreviated as PD-BZTh-OH, wherein R 1 for Ar 1 is a benzene ring, Ar 2 for Ar 3 for Its synthesis route is as follows figure 1 shown, including the following steps:

[0044] (1) Synthesis of compound 6: 4-piperidinylbromobenzene (500mg, 2.08mmol, 1eq.) 5-formyl-2-thiophene boronic acid (488mg, 3.12mmol, 1.5eq.), K 2 CO 3 (574mg, 4.16mmol, 2eq.) and Pd(PPh 3 ) 4 (240mg, 0.208mmol, 0.1eq.) and a mixture of toluene / water (20mL / 6mL), at 90°C under N 2 Stir under protection for 16 hours. EtOAc (50 mL) was added thereto, the organic phase was washed with water and brine, washed with Na 2 SO 4 Dry and concentrate in vacuo. The crude product was separated and purified by silica gel chromatography (petroleum ether: DCM=20-70%) to obtain compound 6 as a pale yellow solid (189 mg). 1 H NMR (600MHz, Chloroform-d) δ9.84(s,1H),7.69(d,J=3.9Hz,1H),7.57(s,2H),6.94(d,J=15.2Hz,2H),3.28 (s,4H),1.86–1.58(m,6H). ...

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Abstract

The invention discloses a water-soluble aggregation-induced luminescent probe as well as a preparation method and an application thereof and belongs to the technical field of fluorescent probes. The fluorescent probe has the structural general formula as shown in the description, wherein in the general formula, R1 is tertiary amine, Ar1 is a benzene ring or a naphthalene ring, Ar2 is onium salt containing pyridine or quinoline and Ar3 is an aromatic ring or a heteroaromatic ring. The fluorescent probe provided by the invention can be used for directly observing Abeta deposited plaques and hasexcellent targeting ability and sensitivity, so that the Abeta deposited plaques can be rapidly and accurately detected; and the Abeta deposited plaques of AD rat brain tissues can be subjected to washing-free rapid detection and fibrin, especially egg-white lysozyme fibers, can be quantitatively detected according to the intensity of fluorescent light.

Description

technical field [0001] The present invention relates to the field of fluorescent probes, more specifically, to a fluorescent probe with water-soluble aggregation-induced luminescent properties, its preparation method and application. Background technique [0002] Under certain conditions, the conformation of proteins undergoes irregular changes, unfolding or misfolding, and finally soluble proteins form insoluble regular or irregular aggregates, and the formed fibers rich in folded structures are called amyloid fiber. Amyloid fibrils have been shown to be associated with at least one of several serious human diseases of protein deposition, including diabetes, lysozyme amyloidosis, and neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease. [0003] Due to the advantages of high sensitivity, high contrast, high resolution, intuitive imaging and fast imaging speed, fluorescence microscopy has been widely used in the field of biomedicine. Biological st...

Claims

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Application Information

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IPC IPC(8): C07D409/06C07D213/36C09K11/06G01N21/64
CPCC07D213/36C07D409/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1092G01N21/6428G01N21/643
Inventor 朱明强王亚龙李冲余琦
Owner HUAZHONG UNIV OF SCI & TECH
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