One for detection of fe 2+ Camphor-based enhanced fluorescent probe and its preparation method and application

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

Active Publication Date: 2022-03-29
NANJING FORESTRY UNIV
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  • Summary
  • 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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  • One for detection of fe <sup>2+</sup> Camphor-based enhanced fluorescent probe and its preparation method and application
  • One for detection of fe <sup>2+</sup> Camphor-based enhanced fluorescent probe and its preparation method and application
  • One for detection of fe <sup>2+</sup> Camphor-based enhanced fluorescent probe and its preparation method and application

Examples

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 method for detecting Fe 2+ The camphor-based enhanced fluorescent probe and its preparation method and application. The fluorescent probe is N,N-dimethyl-4-(3-(4,7,7-trimethyl-3-oxybicyclo[2.2.1]hept-2-enyl)prop-1-ene ‑1‑yl) aniline oxide. The present invention utilizes camphor as raw material, carries out condensation reaction with 4-dimethylaminocinnamaldehyde, obtains 3-(3-(4-(dimethylamino)phenyl) allylidene)-1,7,7-trimethyl 3-(3-(4-(dimethylamino)phenyl)allylidene)-1,7,7-trimethylbicyclo[2.1.1] Heptyl-2-one is oxidized with m-chloroperoxybenzoic acid to obtain N,N-dimethyl-4-(3-(4,7,7-trimethyl-3-oxybicyclo[2.2.1] Hep-2-enyl)prop-1-en-1-yl)aniline oxide. The compound can specifically recognize Fe 2+ , under 365nm ultraviolet light, the fluorescence of the solution changes from colorless to red, so it can be used to detect Fe 2+ The enhanced fluorescent probe has a detection limit of 8.3nM and a response time of 40s, which 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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Patent Type & Authority Patents(China)
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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