Aggregation induced luminescent probe, preparation and application thereof in calcium ion detection and imaging

A technology of aggregation-induced luminescence and probe, which is applied in the field of calcium ion detection, can solve the problems of cumbersome operation, fluorescence self-quenching, low signal-to-noise ratio, etc., and achieve the effect of good solubility and low cytotoxicity

Active Publication Date: 2018-03-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have the following disadvantages: the need to use large fixed instruments, cumbersome operation, high cost, and difficulty in directly measuring the concentration of free calcium ions, etc., which are not conducive to popularization and use in primary hospitals
However, fluorescent materials with aggregation-quenched luminescence (ACQ) properties are prone to self-quenching of fluorescence in the aggregated state, so their detection range for calcium ions is limited, and they have high background noise in the solution state. Low signal-to-noise ratio after ionization

Method used

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  • Aggregation induced luminescent probe, preparation and application thereof in calcium ion detection and imaging
  • Aggregation induced luminescent probe, preparation and application thereof in calcium ion detection and imaging
  • Aggregation induced luminescent probe, preparation and application thereof in calcium ion detection and imaging

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Experimental program
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Embodiment 1

[0076] (1) Synthesis of formula IV-1 compound, its synthetic equation is as follows::

[0077]

[0078] 5-benzylchlorosalicylaldehyde (340mg, 2mmol), diethyl iminodiacetate (378mg, 2mmol), N,N-diisopropylethylamine (i-Pr 2 EtN) (330 μL, 258 mg, 2.0 mmol) was refluxed in acetonitrile (10 mL) for 2 hours. After the reaction was completed, it was cooled to room temperature, the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to obtain the compound of formula IV-1 (288mg, 89%). 1 H NMR (CDCl 3 ,500MHz)δ10.79(s,1H),9.72(s,1H),7.48(d,J=2.0Hz,1H),7.43(dd,J 1 =8.5Hz,J 2 =2.0Hz,1H),6.77(d,J=8.5Hz,1H),4.01(q,J=7.5Hz,4H),3.74(s,2H),3.39(s,4H),1.11(t,J =7.5Hz,6H); 13 C NMR (CDCl 3 ,125MHz)δ196.5,170.9,160.9,137.8,133.9,129.9,120.3,117.5,60.4,56.5,54.0,14.1.

[0079] (2) Synthesis of formula III-1 compound, its synthetic equation is as follows:

[0080]

[0081] Dissolve th...

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Abstract

Belonging to the technical field of calcium ion detection, the invention discloses an aggregation induced luminescent probe, preparation and application thereof in calcium ion detection and imaging. The aggregation induced luminescent probe has a structure shown as formula I, wherein R is hydrogen, alkyl, perfluoroalkyl, alkoxy, alkylthiol, alkyl amino, halogen, cyano, nitro, or heteroaryl; X is axial bond or alkylidene; Y is axial bond, arylidene, or heteroarylidene; A<+> is a cation. The aggregation induced luminescent probe is used for calcium ion detection and imaging. The probe for calcium ion detection has the characteristics of wide response range, strong fluorescence, high lightening ratio up to 10 times or more, and high signal-to-noise ratio, effectively overcomes the defect of aggregation quenching luminescence in traditional fluorescent materials. At the same time, the probe has the advantages of simple preparation, low cost and convenient operation, is suitable for specific imaging and detection in high concentration aggregation areas of calcium ions, and has good detection effect.

Description

technical field [0001] The invention belongs to the field of calcium ion detection, and in particular relates to an aggregation-induced luminescent probe, a preparation method thereof, and an application in calcium ion detection and imaging, wherein the application detects calcium ion based on a change in fluorescence signal. Background technique [0002] Calcium is one of the important constituent elements of the body. At the same time, calcium ions, as an important messenger in cells, regulate various physiological functions and play an important role in life activities. Therefore, calcium ion determination is of great significance in biomedical research. For example, hypercalcemia refers to the abnormal increase of total calcium and free calcium ion concentration in serum (total calcium is greater than 2.5mmol / L, free calcium is greater than 1.4mmol / L), and the cause of hypercalcemia is parathyroid Hyperthyroidism, metabolic acidosis, hypervitamin D, and various malignan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/88C07C249/16C07C229/24C07C227/16C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07C227/16C07C249/16C07C251/88C09K11/06C09K2211/1007G01N21/6402
Inventor 唐本忠高蒙
Owner SOUTH CHINA UNIV OF TECH
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