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Preparation method of fluorescein and rhodamine structures-fused optical signal controllable dark red xanthene dye

An optical signal and fluorescein technology, which is applied in the field of the preparation of molecular fluorescent dyes, can solve the problems of poor resistance to photobleaching, inability to reach deep red or near-infrared bands, and limited wide application.

Inactive Publication Date: 2016-03-16
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, among the above-mentioned dyes, except for a small number of dyes such as cyanine dyes, the maximum absorption and emission wavelengths of the remaining dyes are all in the ultraviolet-visible region, which cannot reach the deep red or near-infrared band, and cannot well meet the needs of biomolecular detection. Fluorescent dye absorption and fluorescence emission wavelength requirements
As far as cyanine dyes are concerned, although their absorption and emission wavelengths can be adjusted to deep red and near-infrared regions by changing the length of their methine chains, they generally have defects such as low quantum efficiency and poor photobleaching resistance, which limits their use. Wide application in biomolecular detection

Method used

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  • Preparation method of fluorescein and rhodamine structures-fused optical signal controllable dark red xanthene dye
  • Preparation method of fluorescein and rhodamine structures-fused optical signal controllable dark red xanthene dye
  • Preparation method of fluorescein and rhodamine structures-fused optical signal controllable dark red xanthene dye

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The preparation of embodiment 1, intermediate product 1, concrete method is as follows:

[0032] The preparation steps of xanthene intermediate product 1 are as follows:

[0033]

[0034] 1) Add 2-(2,4-dihydroxybenzoyl)benzoic acid (0.492g, 2mmol) and 1,5-dihydroxynaphthalene (0.427g, 2.6mmol) into 5mL methanesulfonic acid and stir, oil at 85°C The reaction was heated in the bath for 6-8h, and the product solution was obtained after cooling.

[0035] 2) Add 60 mL of water to the reaction solution obtained in the previous step, and add an appropriate amount of NaHCO 3 The solid neutralized the reaction solution, extracted with hot ethyl acetate to collect the organic phase, and washed with anhydrous Na 2 SO 4 After drying and filtering, the obtained solid crude product was separated by column chromatography through a silica gel column with dichloromethane and ethanol to obtain intermediate product 1, 0.471 g of powdery white solid powder, and the yield was 62%. Me...

Embodiment 2

[0037] Embodiment 2, the preparation of xanthene fluorescent dye molecule 2, the specific method is as follows:

[0038] The synthesis steps are as follows:

[0039]

[0040] 1) The intermediate product 1 (0.224g, 0.5mmol) obtained in the above-mentioned Example 1 and 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid (0.203g, 0.65mmol) were added to 5mL concentrated H 2 SO 4 Stir in medium, heat the reaction in an oil bath at 83°C for 6h, and obtain a product solution after cooling.

[0041] 2) Add 60 mL of water to the reaction solution obtained in the previous step, and add an appropriate amount of NaHCO 3 The solid neutralized the reaction solution, extracted with dichloromethane, collected the organic phase, and washed with anhydrous Na 2 SO 4 After drying and filtering, the obtained solid crude product was separated by column chromatography through a silica gel column with dichloromethane and ethanol to obtain xanthene fluorescent dye 2, 0.131 g of powdery white soli...

Embodiment 3

[0043] Embodiment 3, the determination of the optical properties of the xanthene dye 2:

[0044] The dye compound 2 was made into a concentration of 5×10 -3 mol / L DMF solution, keep away from light for future use.

[0045] 1) Determination of the optical properties of compound 2 in different solvents: Compound 2 was prepared in different solvents to 5×10 -6 mol / L of the liquid to be tested was 3mL, and its ultraviolet absorption spectrum and fluorescence emission spectrum were measured before and after adding 1% trifluoroacetic acid. The dyestuff was stable in the structure of spirolide in almost all organic solvents, but for Acid sensitive.

[0046] 2) Determination of the influence of pH on absorption spectrum or fluorescence spectrum: the dye compound 2 was prepared into 5×10 under different pH (1-14) conditions -6 mol / L of the test solution 3mL. The ultraviolet-visible absorption and emission spectra were measured at room temperature. The results are attached figure...

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Abstract

The invention discloses a preparation method of a fluorescein and rhodamine structures-fused optical signal controllable dark red xanthene dye. According to the preparation method, fluorescein and rhodamine structures are fused as a whole to form a six-membered ring condensed system with a double-spiro structure so as to enhance conjugated groups of the dye. As absorption and emission wavelength of the dye is within the dark red area, the dye has the possibility of being used in biological fluorescent label imaging. Meanwhile, optical signals of the dye are controllable. The double-spiro structure of the dye can switch between spiro-lacton and ring-opening carboxylic acid and carboxylic anion. Through spiro-structural conversion, the fluorophore xanthene rong conjugated system (a quinoid system forms or disappears) in the whole molecular structure is regulated and controlled to expand the absorption and emission wavelength so as to make optical signal intensity change correspondingly. The carboxyl location of spiro-lacton in the designed xanthene dye can be easily modified so as to obtain a fluorescence probe for cell imaging.

Description

technical field [0001] The present invention relates to the preparation of molecular fluorescent dyes in optical sensing imaging detection technology, and introduces a method that combines the structures of fluorescein and rhodamine to increase the conjugated groups of dyes, thereby regulating the absorption and emission wavelengths of dyes at deep Preparation of xanthene dyes in the red region. Background technique [0002] In recent years, the development of high-sensitivity and high-selectivity optical detection methods for the identification, detection and monitoring of some important substances in biology and the environment has become an important development direction of chemical sensors. Although some conventional detection methods such as: high-resolution liquid chromatography, mass spectrometry, atomic absorption spectroscopy, inductively coupled plasma atomic emission spectroscopy, electrochemical sensing and other methods have been used for the analysis of relate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B6/00C09K11/06
CPCC09B6/00C09K11/06C09K2211/1088
Inventor 曾宪顺王庆
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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