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Coumarins compound containing aryl boric acid and application thereof in detection of sugar

An arylboronic acid and coumarin technology, applied in the field of sugar detection, can solve the problems of limited application and short emission wavelength, and achieve the effects of eliminating interference, good water solubility, and high detection sensitivity

Inactive Publication Date: 2013-01-23
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

Fluorescent probes that use boronic acid to covalently bond different chromophores to specifically recognize sugars have been reported, but most of the existing probes have short emission wavelengths, which limits their application in biological samples. The development of sugar probes with long emission wavelength and high sensitivity has high application value

Method used

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  • Coumarins compound containing aryl boric acid and application thereof in detection of sugar
  • Coumarins compound containing aryl boric acid and application thereof in detection of sugar
  • Coumarins compound containing aryl boric acid and application thereof in detection of sugar

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Embodiment 1

[0028]

[0029] Synthesis of compound CSP

[0030] (1) Synthesis of compound 1

[0031] Add 1.0g 4-bromoacetophenone (5.05mmol), 1.53g bis(pinacolate) diboron (6.03mmol), 1.48g potassium acetate (15.11mmol), 44.11mg [1, 1′-bis(diphenylphosphino)ferrocene]palladium dichloride (0.06mmol) and 15mL of dioxane were heated to reflux, followed by TLC spotting until the disappearance of the raw material. The solvent was removed, purified by silica gel column, and the developing solvent was petroleum ether: ethyl acetate = 50:1 (v / v) to obtain 1.15 g of light yellow viscous product 1 with a yield of 92.5%. 1 H NMR (400MHz, CDCl 3 )δ: 7.84(d, J=8.2Hz, 2H), 7.80(d, J=7.7Hz, 2H), 2.51(s, 3H), 1.26(s, 12H).

[0032] (2) Synthesis of 7-diethylaminocoumarin (compound 2)

[0033] Add 6.0g of 4-diethylamino salicylaldehyde (28.69mmol), 10.84g of diethyl malonate (67.75mmol), 90mL of absolute ethanol and 3mL of piperidine into a 250mL three-necked flask, the solution is dark red, and hea...

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Abstract

The invention relates to a coumarins compound containing aryl boric acid and an application of the coumarins compound containing aryl boric acid in detection of sugar, wherein a novel fluorescent molecular probe utilizes the property of combining aryl boric acid with polybasic alcohol; the spectrums of the compound before and after a reaction with sugar are evidently changed such that the compound has higher detection sensitivity to D-fructose and D-sorbitol; the emission wavelength reaches 620 nm and is located in a red light area; the compound provided by the invention is suitable for detecting the content of the sugar in an organism.

Description

【Technical field】 [0001] The invention relates to the technical field of sugar detection, in particular to an aryl borate-containing coumarin compound and its application in sugar detection. 【Background technique】 [0002] Sugars on the surface of mammalian cells mainly exist in the form of glycoproteins and glycolipids. These glycosylated biomolecules are closely related to many physiological and pathological processes, such as communication between cells, early embryonic development, apoptosis, inflammatory response, and some cancer metastasis. By labeling probe molecules that specifically respond to carbohydrate compounds on cells, it can help to study the above-mentioned physiological or pathological processes. Boronic acid is often used as a sugar recognition unit because it can specifically covalently bond with diols in monosaccharide molecules. Fluorescent probes that use boronic acid to covalently bond different chromophores to specifically recognize sugars have be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
Inventor 钱俊红张凌怡柏红艳张维冰田海玉孙倩
Owner EAST CHINA UNIV OF SCI & TECH
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