Novel fluorescent dye capable of multifunctionalization, and preparation method and application thereof

A fluorescent dye, multi-functional technology, applied in the field of chemical biology, can solve problems such as cell death and harmful organisms

Inactive Publication Date: 2015-07-15
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The amount of active oxygen plays a beneficial role in the organism within a certain range, but when the organism is exposed to external ca

Method used

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  • Novel fluorescent dye capable of multifunctionalization, and preparation method and application thereof
  • Novel fluorescent dye capable of multifunctionalization, and preparation method and application thereof
  • Novel fluorescent dye capable of multifunctionalization, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Embodiment 1: the synthesis of compound 1

[0097] Benzoylmorpholine (11.64g, 0.061mol) and POCl 3 (7.0ml, 0.077mol) was sequentially added to the round bottom flask, stirred until completely dissolved, and reacted at room temperature until the reaction was complete; then pyrrole (4.2ml, 0.061mol) was slowly added dropwise to the reaction system to react; Completely, put the reaction system into an ice bath, add saturated Na to the reaction system dropwise 2 CO 3 solution until no bubbles were generated; extracted with dichloromethane, dried and then spin-dried to obtain 9.13 g of a white solid. Then the obtained white solid (2.91g, 0.017mol) was dissolved in acetonitrile and weighed CuCl 2 2H 2 O (6.02g, 0.035mol) was added to the reaction system, and after the reaction was complete, slowly drop H into the reaction system 2 SO 4 The solution was stirred evenly, extracted with dichloromethane, dried and spin-dried. Through silica gel column chromatography, 1.65 g...

Embodiment 2

[0098] Embodiment 2: the synthesis of compound 2

[0099] Weigh pyrrolealdehyde (0.95g, 0.01mol) and dissolve it in ethanol, then add propanedicyanide (0.73g, 0.011mol) into the above reaction system, wait for most of the solids to dissolve, then add a small amount of piperidine, The reaction temperature was refluxed at high temperature. After the reaction was complete, the reaction system was lowered to room temperature, and a solid was produced by washing with water to obtain a crude product, which was passed through a silica gel column to obtain 1.08 g of compound 2 as a yellow solid.

Embodiment 3

[0100] Embodiment 3: the synthesis of compound Cl-BODIPY-2CN

[0101] Compound 1 (0.206g, 0.001mol) was weighed and dissolved in dichloromethane, POCl3 (0.136ml, 0.0015mol) was added to the solution, and stirred at room temperature. Then compound 2 (0.172g, 0.0012mol) was dissolved in a small amount of dichloromethane and added to the above reaction system. Under the protection of inert gas, react for 12h. To complete the reaction, add saturated NaHCO 3 Adjust the pH of the solution to neutral, extract, spin dry after drying, dissolve the obtained product in an appropriate amount of dichloromethane, add Et 3 N (0.693ml, 0.005mol) was stirred, then BF was added dropwise 3 ·Et 2 O (0.631ml, 0.005mol), stirred overnight after the dropwise addition, after the reaction was complete, extracted, dried and then spin-dried. After going through a silica gel column chromatography, 0.176 g of the product cyan solid Cl-BODIPY-2CN was obtained; 1 HNMR (CDCl 3 ,400MHz):δ8.29(s,1H),7.6...

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Abstract

The invention belongs to the field of chemicobiology, and provides a novel fluorescent dye capable of multifunctionalization, and a preparation method and application thereof. The novel fluorescent dye capable of multifunctionalization is based on a BODIPY parent, and is prepared by carrying out Knoevenagel reaction on a raw material pyrrole aldehyde for synthesizing BODIPY and propyl dicyan. The modification of the Knoevenagel reaction is utilized to achieve the goal of regulating the spectrum property of the fluorescent dye. Cl-BODIPY-2CN active chlorine can quickly perform nucleophilic substitution reaction with multiple mercapto or amino compounds, and the optical properties of the fluorescent dye obviously change in the substitution process. The Cl-BODIPY-2CN is used for detecting ONOO-. The fluorescent dye provided by the invention has the advantages of high light stability and high reaction sensitivity, and can be subjected to functionalized application in many aspects. The preparation method has the advantages of simple and accessible raw materials, low cost, higher yield and high light stability.

Description

technical field [0001] The invention belongs to the field of chemical biology and relates to the construction of a highly modifiable and multifunctional novel fluorescent dye, in particular to a highly modifiable and multifunctional novel fluorescent dye and a preparation method and application thereof. Background technique [0002] Boron-dipyrromethene (BODIPY for short) fluorescent dyes complexed with boron fluoride is a new type of popular fluorescent dyes. BODIPY fluorescent dyes have excellent properties, such as high fluorescence quantum yield, high molar extinction coefficient, Good photostability has attracted the attention of many scientific researchers; because the structure of BODIPY fluorescent dyes is easy to modify, the current system of this type of fluorescent dyes has been rapidly expanded, making this type of fluorescent dyes extremely rich. Through the appropriate modification of the BODIPY structure, the photophysical properties of this type of fluorescen...

Claims

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Application Information

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IPC IPC(8): C09B23/04C07F5/02C09K11/06G01N21/64
Inventor 赵春常安建才费强王飞翼
Owner EAST CHINA UNIV OF SCI & TECH
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