Near-infrared fluorescent probe targeting tumor cells and activated by beta-galactosidase and preparation method thereof

A technology of galactosidase and fluorescent probe, which is applied in the field of targeted small molecule fluorescent probe compounds, can solve the problems of low specificity and achieve the effects of increased fluorescence intensity, wide application range and wide application range

Inactive Publication Date: 2020-02-28
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, they still have low specificity due to some cross-reactivity wit

Method used

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  • Near-infrared fluorescent probe targeting tumor cells and activated by beta-galactosidase and preparation method thereof
  • Near-infrared fluorescent probe targeting tumor cells and activated by beta-galactosidase and preparation method thereof
  • Near-infrared fluorescent probe targeting tumor cells and activated by beta-galactosidase and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A method for preparing a fluorescent probe compound for β-galactosidase detection, the steps comprising:

[0041] 1) Synthesis of Compound 1:

[0042] Dissolve 2-chloro-1-formyl-3-(hydroxymethylene) compound (1.2 mmol, 1 eq) and indole derivative (3 mmol, 2.5 eq) in 30 mL butanol / benzene (5:2 ) solution, after reflux and stirring, remove the water with a water separator. The reaction solution was further stirred at 80°C for 8 hours. After removing the solvent by evaporation in vacuo, the residue was purified by silica gel column chromatography using CH 2 Cl 2 / CH 3 OH (20:1 to 1:1) was used as the eluent to obtain compound 1 as a green solid in 70% yield.

[0043] 2) Synthesis of Compound 2:

[0044] To the ethanol solution of compound one (0.5 mmol, 1 eq), di-tert-butyl carbonate (1.2 mmol, 2.4 eq) and TEA (1.2 mmol, 2.4 eq) were added, and the mixture was kept stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and the r...

Embodiment 2

[0056] Time-response changes of probe compound RN-gal to β-gal UV absorption and fluorescence emission

[0057] Take the RN-gal synthesized in Example 1 to prepare a 5 μM probe solution, add β-gal (5 U / mL) standard solution, and measure its ultraviolet absorption and fluorescence properties. The absorption peak at 608 nm decreased gradually, and a new absorption peak appeared at 692 nm, accompanied by a red shift of the UV-vis absorption. With 625 nm as the excitation light, the fluorescence emission at 710 nm also increased with time, and reached the maximum fluorescence intensity after 60 minutes. Through fluorescence synchronous scanning, the maximum fluorescence at 710 nm of the probe RN-gal activated by β-gal was about 240 times that before the reaction.

Embodiment 3

[0059] Measurement of the Fluorescence Linear Range of the Probe Compound RN-gal

[0060] Take the fluorescent probe solution (5 μM) in Example 2, add β-gal (0-10 U / mL) respectively, and perform fluorescence detection (λ ex =625 nm), indicating that the probe exhibits a linear relationship in the range of β-gal concentration 0-5 U / mL, and the linear correlation coefficient is R 2 =0.99863.

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Abstract

The invention discloses a preparation method of a near-infrared fluorescent compound which accurately targets tumor cells and is activated by beta-galactosidase, wherein the structure of the fluorescent compound is shown in a formula I. The probe compound combines a substrate alphaD-galactose (alphaD-gal) recognized by beta-galactosidase with cyanine near-infrared fluorophores to introduce an alphavbeta3-integrin receptor-targeted ligand c-RGD. The ability of the ligand c-RGD targeting tumor cells is utilized for near-infrared imaging of live mouse tumors overexpressing beta-galactosidase. Theprobe has the advantages that receptor-mediated cell uptake and molecular target activation are combined to realize real-time and non-invasive detection of beta-galactosidase in living tissues. The probe can be successfully applied to improve cancer imaging and promote effective cancer diagnosis.

Description

technical field [0001] The present invention relates to a targeted small molecule fluorescent probe compound, more specifically a near-infrared compound targeting specific receptors on the surface of tumor cells, which is an important marker of primary ovarian cancer β-galact The invention relates to the detection of glycosidase (β-gal), which belongs to the field of fluorescent sensor probe compounds. Background technique [0002] β-galactosidase (β-gal) is a typical glycosidase that can catalyze the hydrolysis of lactose into galactose and glucose, the key components for energy production, and plays a key role in organisms. Abnormally expressed β-gal is considered as a potential cancer biomarker, especially in ovarian cancer and colorectal cancer. Accurate detection of β-gal activity is of great significance for early diagnosis of cancer and prediction of treatment effect. But most activatable imaging probes for β-gal detection are designed by simply linking the β-gal-rec...

Claims

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Application Information

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IPC IPC(8): C07H17/04C09K11/06G01N21/64
CPCC07H17/04C09K11/06G01N21/6428C09K2211/1029C09K2211/1074C09K2211/1088G01N2021/6439G01N2021/6417
Inventor 颜梅卫先哲张晶杨小凤刘海云李增军于京华
Owner UNIV OF JINAN
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