Camphor-based enhanced fluorescent probe for detecting Fe2+ as well as preparation method and application of camphor-based enhanced fluorescent probe

A fluorescent probe and enhanced technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as interference and lack of selectivity, and achieve fast response, high sensitivity, and easy synthesis

Active Publication Date: 2021-04-06
NANJING FORESTRY UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This is mainly due to the labile redox nature of iron, making most fluorescent probes sensitive to Fe 2+ Lack of selectivity, especially by Fe 3+ interference

Method used

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  • Camphor-based enhanced fluorescent probe for detecting Fe2+ as well as preparation method and application of camphor-based enhanced fluorescent probe
  • Camphor-based enhanced fluorescent probe for detecting Fe2+ as well as preparation method and application of camphor-based enhanced fluorescent probe
  • Camphor-based enhanced fluorescent probe for detecting Fe2+ as well as preparation method and application of camphor-based enhanced fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] N,N-Dimethyl-4-(3-(4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-enyl)prop-1-en-1-yl) The synthesis of aniline oxide, reaction formula is as follows:

[0028]

[0029] Specific steps are as follows:

[0030] 1) Preparation of 3-(3-(4-(dimethylamino)phenyl)allylidene)-1,7,7-trimethylbicyclo[2.1.1]heptan-2-one:

[0031]Add 10mmol of camphor, 12mmol of 4-dimethylaminocinnamaldehyde, 30mL of tert-butanol and 20mmol of potassium tert-butoxide into a dry three-necked flask in sequence, and stir and reflux for 12h. After the reaction solution was distilled off under reduced pressure to remove the solvent tert-butanol, ethyl acetate was added, and then washed with saturated brine until neutral, and the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 3-(3-(4 -(Dimethylamino)phenyl)allylidene)-1,7,7-trimethylbicyclo[2.1.1]heptan-2-one crude product, recrystallized from anhydrous methanol to obtain orange-red powder 3-(3-(4-(dimethylam...

Embodiment 2

[0035] N, N-dimethyl-4-(3-(4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-enyl)prop-1-en-1-yl ) aniline oxide was dissolved in PBS / EtOH (v / v=8 / 2) buffer to prepare 1×10 -5 M concentration of the probe solution, the Fe 2+ Dissolved in PBS / EtOH (v / v=8 / 2) buffer solution to prepare concentration of 0, 1×10 -6 , 2×10 -6 , 3×10 -6 , 4×10 -6 , 5×10 -6 , 6×10 -6 , 7×10 -6 , 8×10 -6 , 9×10 -6 , 10×10 -6 , 11×10 -6 , 12×10 -6 , 13×10 -6 , 14×10 -6 , 15×10 -6 , 16×10 -6 , 17×10 -6 , 18×10 -6 , 19×10 -6 , 20×10 -6 M's solution. Different concentrations of Fe were measured by a standard titration method under a fluorescence spectrophotometer 2+ p-N,N-dimethyl-4-(3-(4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-enyl)prop-1-en-1-yl ) Fluorescence emission spectrum of aniline oxide, such as figure 1 shown. The results showed that within the concentration range of 0-20μM, with the Fe in the system 2+ As the concentration increased, the solution changed from colorless to red fl...

Embodiment 3

[0037] N, N-dimethyl-4-(3-(4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-enyl)prop-1-en-1-yl ) aniline oxide was dissolved in PBS / EtOH (v / v=8 / 2) buffer to prepare 1×10 -5 The probe solution of M concentration is prepared by dissolving different metal ions, anions and biologically relevant substances in PBS / EtOH (v / v=8 / 2) buffer solution to make 100×10 -6 M concentration solution, Fe 2+ Formulated to 20×10 -6 M concentration solution. Using standard titration method to measure the effect of different metal ions and biologically relevant species on N,N-dimethyl-4-(3-(4,7,7-trimethyl-3-oxobicyclo[ 2.2.1] The fluorescence emission spectrum of hept-2-enyl)prop-1-en-1-yl)aniline oxide, as figure 2 shown. The results showed that the addition of Fe to the probe solution 2+ After the red fluorescence is enhanced, and the addition of K + 、Na + , Mg 2+ , Ca 2+ 、Cu 2+ , Zn 2+ 、Al 3+ 、Ni + 、Cs 2+ , Sn 2+ 、Cr 3+ 、Cd 2+ , Mn 2+ , La 3+ 、Co 2+ , Hg 2+ 、Ag + , Pb 2+ 、Ce 4...

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Abstract

The invention discloses a camphor-based enhanced fluorescent probe for detecting Fe2+ as well as a preparation method and application of the camphor-based enhanced fluorescent probe. The fluorescent probe is N,N-Dimethyl-4-(3-(4,7,7-trimethyl-3-oxybicyclo[2.2.1]hept-2-enyl)prop-1-en-1-yl)aniline oxide. The preparation method comprises the following steps: taking camphor as a raw material, carrying out condensation reaction on camphor and 4-dimethylamino cinnamyl aldehyde to obtain 3-(3-(4-(dimethylamino)phenyl)allylidene)-1,7,7-trimethylbicyclo[2.1.1]heptan-2-one. carrying out oxidation reaction on 3-(3-(4-(dimethylamino)phenyl)allylidene)-1,7,7-trimethylbicyclo[2.1.1]heptan-2-one and m-chloroperoxybenzoic acid to obtain N,N-Dimethyl-4-(3-(4,7,7-trimethyl-3-oxybicyclo[2.2.1]hept-2-enyl)prop-1-en-1-yl)aniline oxide. The compound can specifically recognize Fe2+, and solution fluorescence is changed from colorless to red under 365nm ultraviolet light, so that the compound can be used as an enhanced fluorescent probe for detecting Fe2+, the detection limit reaches 8.3 nM, the response time is within 40s, and the compound has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a method for detecting Fe 2+ High selectivity, high sensitivity and fast response enhanced camphor-based fluorescent probe and its preparation method and application. Background technique [0002] Iron is the most abundant trace element in the human body and plays an important role in many life activities, such as oxygen binding and transport in the body, mitochondrial respiration, enzyme synthesis, electron transfer and redox, etc. The disorder of iron homeostasis will not only affect the occurrence and development of iron deficiency anemia, atherosclerosis, neurodegenerative diseases, etc., but also cause cell ferroptosis. Although intracellular iron has different binding forms and different ligands, it is currently believed that the unstable iron pool in the cytoplasm that can reflect the intracellular iron homeostasis has weaker binding force and higher redox ac...

Claims

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Application Information

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IPC IPC(8): C07C291/04C09K11/06G01N21/64
CPCC07C291/04C09K11/06G01N21/6428C07C2602/42C09K2211/1007C09K2211/1011
Inventor 王石发张燕王忠龙巩帅李明新高语杨益琴徐徐
Owner NANJING FORESTRY UNIV
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