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Dihalofluorescein derivative and application thereof

A fluorescein and derivative technology, applied in the field of fluorescent probes, can solve the problems of unreported non-labeled fluorescent probes, unfavorable selective detection, etc., achieve high selectivity and rapid response ability, prevent and detect cancer, high The effect of sensitivity

Inactive Publication Date: 2012-11-28
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the fluorescent probes used to detect carbonic anhydrase are mainly labeled, and the fluorescence intensity or wavelength of this type of labeled type does not change before and after binding to the target, which is not conducive to the elimination of interference to achieve selective detection
In addition, the design of unlabeled probes mainly focuses on the detection of CA I and CA II (Chemical Communications 2007, 2723-5), and there are basically no unlabeled fluorescent probes for the selective detection of CAIX

Method used

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  • Dihalofluorescein derivative and application thereof
  • Dihalofluorescein derivative and application thereof
  • Dihalofluorescein derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Add 22.0g (160mmol) of p-nitrotoluene to 53.0mL of chlorosulfonic acid, and react at 60°C for 48h. After the reaction was completed, it was cooled to room temperature, then slowly poured into crushed ice, and extracted with 1 L of ether. The organic phase was washed with saturated brine (500mL×3), and after combining the organic phases, 300mL of concentrated ammonia water was added, and heated to 50°C until all the ether was volatilized. The reaction solution was cooled to room temperature, filtered, and the crude product was recrystallized twice from water to obtain 12.1 g of light yellow needle-like crystals with a yield of 35%, m.p.182-183°C.

[0024]

[0025] 9.0 g (900 mmol) of chromium trioxide was dissolved in a mixed solvent of 84.0 mL of concentrated sulfuric acid and 67.0 mL of deionized water, stirred in an ice bath until cooled to room temperature. Then, 4.3 g (20 mmol) of compound 1 was added to the reaction solution in batches, and stirred ...

Embodiment 2

[0055] Spectral performance test of compound shown in formula I

[0056] 1) Determination of ultraviolet and fluorescence spectra:

[0057] After the compound shown in formula I (hereinafter abbreviated as Z1) was vacuum-dried, the sample was accurately weighed on the balance (accurate to 0.0001 gram), fixed to volume with dimethyl sulfoxide, and formulated as 10 -3 The solution of M is fixed in a 10mL volumetric flask, and this is used as mother liquor to prepare different concentrations of Z1 solutions for the absorption spectrum and excitation-emission spectrum tests. The results are shown in Table 1 (Z1 is in Tris-HCl (containing 0.01% DMSO , 0.1 mM ZnCl 2 ) spectral data of the buffer):

[0058] Table 1

[0059]

[0060] 2) The fluorescence responses of Z1 to carbonic anhydrase I, II and IX:

[0061] Will 1×10 -3The standard probe mother solution of mol / L is diluted to 0.1 μ M solution with Tris-HCl buffer solution (comprising 0.01% DMSO and 0.1 mM ZnCl 2 ), and ...

Embodiment 3

[0063] Determination of Z1 inhibition constants for carbonic anhydrase I, II and IX

[0064] We use the Stopped-flow method to determine the inhibition constant, the principle is to use carbonic anhydrase to catalyze CO 2 hydration, thereby changing the pH value of the test system, and then using the absorption of the detection phenol red indicator at 557nm at different pHs to calculate the inhibition constant of the probe and enzyme, specifically see Table 2 (Z1, AZA (control, purchased From Sigma Company) and EZA (control, purchased from Sigma Company) to carbonic anhydrase I, II and IX inhibition constants).

[0065] Table 2

[0066]

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Abstract

The invention relates to a dihalofluorescein derivative and application thereof. The dihalofluorescein derivative is a compound shown as a formula I or a pharmacologically acceptable salt thereof. The dihalofluorescein derivative is used for preparing label-free carbonic anhydrase IX fluorescent probes. In the formula I, R1 and R2 are respectively one of Cl and Br, and X is NH or O.

Description

technical field [0001] The present invention relates to a fluorescent probe for spatial photoinduced electron transfer (SPET) and its application, in particular to a dihalofluorescein derivative and its detection in carbonic anhydrase IX (Carbonic Anhydrase IX, CA IX) in the application. Background technique [0002] CA IX is a subtype of the carbonic anhydrase family. The main function of the carbonic anhydrase family in the human body is to catalyze a very simple reaction: the hydration of CO 2 This produces bicarbonate and hydrogen ions. Since the reaction involves CO 2 Absorption, regulation of hydrogen ion concentration, so many physiological and pathological processes in the body, such as CO 2 Carbonic anhydrase is required for the respiration and transportation of human body, the metabolism of bicarbonate in tissues and lungs, the secretion of electrolytes in various tissues and organs, the biosynthesis reactions of sugar, fat and urea, the absorption of bones, ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C09K11/06G01N21/64
CPCC09K11/06C09B11/08C09K2211/1007C09K2211/1037C09K2211/1088G01N33/582
Inventor 徐玉芳钱旭红张沈裔朱维平杨春梅黄瑾李洪林
Owner EAST CHINA UNIV OF SCI & TECH
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