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Xanthene fluorescent dye with biofilm permeability potential and preparation method thereof

A technology for fluorescent dyes and xanthenes, which is applied in the field of preparation of xanthenes dyes, and can solve the problems of narrow application range and unreliable photostability

Inactive Publication Date: 2015-02-04
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But as far as we know, although the existing rhodafluor dyes have excellent optical properties, they still have limitations, such as their photostability needs to be improved, and the pH range is narrow, etc.

Method used

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  • Xanthene fluorescent dye with biofilm permeability potential and preparation method thereof
  • Xanthene fluorescent dye with biofilm permeability potential and preparation method thereof
  • Xanthene fluorescent dye with biofilm permeability potential and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of a novel pH-stable and membrane-permeable xanthene-based dye Compound 1 with potential for biorelevant applications:

[0032]

[0033] Add 3.133 g (10 mmol) of 2-(4-diethylamino)-2-hydroxybenzoyl)benzoic acid and 1.601 g (10 mmol) of 1,4-dihydroxynaphthalene into a 100 mL round bottom flask, stirring 10 ml of methanesulfonic acid was added dropwise, and the reaction was stopped at 85 °C for 4 h. Add 100 mL of water to the reaction solution, add appropriate amount of NaHCO 3 The solid neutralized the reaction solution, extracted with 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 recrystallized with 10 mL of methanol solution, and suction filtered to obtain 3.820 g of bright red solid powder, namely compound 1, with a yield of 87%. Melting point: 256 – 258 °C; HRMS (LC / MS) m / z: [M + H] + = 438.1705; 1 H NMR (400 MHz, DMSO-d 6 , ppm) δ 9.93 (S, 1H), 8.54...

Embodiment 2

[0035] Synthesis of a novel pH-stable and membrane-permeable xanthene-based dye Compound 1 with potential for biorelevant applications:

[0036]

[0037] Add 3.102 g (10 mmol) of 2-(4-diethylamino)-2-hydroxybenzoyl)benzoic acid and 1.605 g (10 mmol) of 1,4-dihydroxynaphthalene into a 100 mL round bottom flask, stirring 10 ml of methanesulfonic acid was added dropwise, and the reaction was stopped at 80 °C for 5 h. Add 100 mL of water to the reaction solution, add appropriate amount of NaHCO 3 The solid neutralized the reaction solution, extracted with 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 recrystallized with 12 mL of methanol solution, and suction filtered to obtain 3.732 g of bright red solid powder, namely compound 1, with a yield of 85%. Melting point: 256 – 258 °C; HRMS (LC / MS) m / z: [M + H] + = 438.1705; 1 H NMR (400 MHz, DMSO-d 6 , ppm) δ 9.93 (S, 1H), 8.54...

Embodiment 3

[0039] Synthesis of a novel pH-stable and membrane-permeable xanthene-based dye Compound 1 with potential for biorelevant applications:

[0040]

[0041] Add 2.998 g (10 mmol) of 2-(4-diethylamino)-2-hydroxybenzoyl)benzoic acid and 1.601 g (10 mmol) of 1,4-dihydroxynaphthalene into a 100 mL round bottom flask, stirring 10 ml of methanesulfonic acid was added dropwise, and the reaction was stopped at 83 °C for 4 h. Add 120 mL of water to the reaction solution, add appropriate amount of NaHCO 3 The solid neutralized the reaction solution, extracted with 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 recrystallized with 15 mL of methanol solution, and suction filtered to obtain 3.424 g of bright red solid powder, namely compound 1, with a yield of 78%. Melting point: 256 – 258 °C; HRMS (LC / MS) m / z: [M + H] + = 438.1705; 1 H NMR (400 MHz, DMSO-d 6 , ppm) δ 9.93 (S, 1H), 8.54...

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Abstract

The invention discloses a fluorescent dye, a synthesis method and application thereof. The structure of the fluorescent dye is shown as formula (1). The invention provides a novel PH stable membrane permeable xanthene dye with biologically relevant application potentials. The fluorescent dye has high synthesis yield, can keep fluorescence open in an aqueous phase with PH of 4-10, and has very good photophysical and chemical properties, and the hydroxyl position of xanthene and the carboxyl position of spiro lactone can easily be modified to generate biologically related tracers. After modification of the carboxyl position of spiro lactone by hydrazine, a derivative (i.e. compound 5) can achieve significant selective recognition on mercury (shown as the attached figure), thus being able to serve as a very good mercury detection fluorescent probe. In addition, benefiting from a very wide range of PH application and good film permeability, the dye can be applied to lysosomes and other acidic organelles to serve as a detection and recognition gene, thus having important application value. (formula 1).

Description

technical field [0001] The present invention relates to the preparation of molecular fluorescent dyes in optical sensing imaging detection technology, especially a preparation method of a novel xanthene dye with stable pH and permeable membrane, which has biological application potential, and applies the dye to In cell imaging experiments. Background technique [0002] The study of molecular fluorescent dyes is a hot topic in the fields of molecular sensing technology, molecular imaging technology and optoelectronic device research. Xanthene dyes (such as fluorescein and rhodamines and their derivatives) have been extensively studied and widely used in molecular biology and solar cells due to their large molar extinction coefficient, high quantum efficiency and good biocompatibility. field. However, the application of these existing dyes is limited due to the defects of their own photophysical properties. For example, fluorescein dyes will undergo irreversible photobleac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06C07D493/22
CPCC09B11/24C09K11/06C09K2211/1088
Inventor 曾宪顺焦晓洁
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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