Xanthene fluorescence dye, preparation method and applications thereof

A fluorescent dye, xanthene technology, applied in the field of fluorescence sensing and detection, can solve the problems of reduced fluorescence quantum yield, poor specific selectivity, pH value sensitivity, etc., and achieves high selectivity, low cost, and wide pH value range. Effect

Inactive Publication Date: 2015-02-04
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
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  • Claims
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Problems solved by technology

The absorption and emission wavelengths of rhodamine derivatives are short, between 480 - 580 nm. Fluorescein derivatives have their own limitations, such as a small Stoke shift, which makes the interference of the sample background on the fluorescence relatively large; the fluorescence quantum The yield is sensitive to the pH value, and the fluorescence quantum yield decreases in the physiological environment of the organism; the specific selectivity is poor and the lipophilicity is poor, so it is not suitable for infiltration into cells, so the effect of cell research is poor

Method used

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  • Xanthene fluorescence dye, preparation method and applications thereof
  • Xanthene fluorescence dye, preparation method and applications thereof
  • Xanthene fluorescence dye, preparation method and applications thereof

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Embodiment 1

[0039] Embodiment 1, preparation of xanthene fluorescent dye molecular probe

[0040] The specific method is as follows:

[0041] The xanthene fluorescent dye molecular probe is 3',3''-bis(oxospiroisobenzofuran)-3-hydroxyl-7-(diethylamino)benzopyran-xanthene, the preparation steps as follows:

[0042] 1) Add 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid (313 mg, 1 mmol) and fluorescein (332 mg, 1 mmol) into concentrated sulfuric acid (8 mL) and stir. Protect from light and heat the oil bath at 95°C, and react for 5 hours;

[0043] 2) The above reaction solution was cooled to room temperature, poured into 80 mL of ice water and stirred, and the pH of the reaction solution was adjusted to neutral with 1.0 M sodium hydroxide aqueous solution. Then, the mixed solution was extracted several times with dichloromethane (50 mL). The collected organic phase was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude produ...

Embodiment 2

[0046] Embodiment 2, preparation of xanthene fluorescent dye molecular probe

[0047] The specific method is as follows:

[0048] The xanthene fluorescent dye molecular probe is 3',3''-bis(oxospiroisobenzofuran)-3-hydroxyl-7-(diethylamino)benzopyran-xanthene, and the steps are as follows :

[0049] 1) Add 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid (344 mg, 1.1 mmol) and fluorescein (398 mg, 1.2 mmol) into concentrated sulfuric acid (10 mL) and stir. Protect from light and heat the oil bath at 98°C, and react for 4 hours;

[0050] 2) The above reaction solution was cooled to room temperature, poured into 80 mL of ice water and stirred, and the pH of the reaction solution was adjusted to neutral with 1.0 M sodium hydroxide aqueous solution. Then, the mixed solution was extracted several times with dichloromethane (50 mL). The collected organic phase was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude pro...

Embodiment 3

[0053] Embodiment 3, preparation of xanthene fluorescent dye molecular probe

[0054] The specific method is as follows:

[0055] The xanthene fluorescent dye molecular probe is 3',3''-bis(oxospiroisobenzofuran)-3-hydroxyl-7-(diethylamino)benzopyran-xanthene, and the steps are as follows :

[0056] 1) Add 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid (312 mg, 1 mmol) and fluorescein (365 mg, 1.1 mmol) into concentrated sulfuric acid (12 mL) and stir. Protect from light and heat the oil bath at 100°C, and react for 3 hours;

[0057] 2) The above reaction solution was cooled to room temperature, poured into 80 mL of ice water and stirred, and the pH of the reaction solution was adjusted to neutral with 1.0 M sodium hydroxide aqueous solution. Then, the mixed solution was extracted several times with dichloromethane (50 mL). The collected organic phase was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude prod...

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Abstract

The invention relates to a xanthene fluorescence dye, a preparation method and applications thereof, wherein the fluorescence dye is 3',3''-bis(oxospiroisobenzofuran)-3-hydroxy-7-(diethylamino)benzopyran-xanthene. According to the present invention, the xanthene fluorescence dye is designed and synthesized, the dye has the double-spiro six-membered ring fused system, the optical signal release of the dye is controlled by the double-spiro structure, the opening / closing of the spiro structure regulates the fluorophore xanthene conjugation system (the quinone type system forms or disappears) in the whole molecular structure, and the absorption wavelength and the emission wavelength are expanded so as to make the optical signal intensity accordingly change; and the isothiocyanate derivative molecule fluorescence probe synthesized through further derivatization provides characteristics of rapid response, high selectivity, high detection sensitivity and low detection limitation on Hg<2+>. In summary, the present invention provides the xanthene fluorescence dye design synthesis method, and the dye is adopted to design the Hg<2+> detecting molecule fluorescence probe for the optical signal report gene.

Description

technical field [0001] The invention belongs to the technical field of fluorescent sensing and detection, and relates to a novel fluorescent molecular probe material synthesis and detection method, in particular to the design, synthesis and application of a novel xanthene fluorescent dye molecule and its probe material. Background technique [0002] As an important method in modern analytical chemistry, fluorescence analysis technology is an analysis and detection technology that uses fluorescent molecular probes as optical signal reagents to change the fluorescence optical signals such as fluorescence intensity or wavelength through the combination of probe materials and targets. . With the rapid development of computer science, optical imaging technology and new probe labeling technology, it has greatly promoted the development of fluorescence analysis technology in the fields of molecular biology, cell biology, medicine and new drug development, and the key to this techno...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06C07D493/22G01N21/64
Inventor 曾宪顺梁丽娟
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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