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Fluorescent probe for specially identifying bivalent copper ions in water phase and application thereof

A technology of divalent copper ions and fluorescent probes, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, chemical instruments and methods, etc., and can solve the problems of low selectivity, low biological practicability, poor specificity or specificity, etc. , to achieve the effect of high fluorescence quantum yield

Inactive Publication Date: 2015-07-15
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the comprehensive analysis of current copper ion fluorescent probes mainly has the following shortcomings: First, in order to improve selectivity, most copper ion probes are detected in organic solvents or components containing organic solvents, which greatly improves the practicability of environmental detection. Second, most of the recognition mechanisms of copper ion probes detect copper ions under the mechanism of FRET, ICT, and PET, and the selectivity is not high, and the specificity or specificity is poor; third, the recognition of most copper ion probes is not reversible Sexuality, low biological availability

Method used

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  • Fluorescent probe for specially identifying bivalent copper ions in water phase and application thereof
  • Fluorescent probe for specially identifying bivalent copper ions in water phase and application thereof
  • Fluorescent probe for specially identifying bivalent copper ions in water phase and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 3-hydroxy-4-(1hydro-phenanthrenequinone[9,10-d]imidazol-2-ethyl)phenyl 4-hydroxyl (1):

[0026] Mix 0.21g (1mmol) of phenanthrenequinone, 0.276g (2mmol) of 2,4-dihydroxybenzaldehyde, 1.54g ammonium acetate and 10mL glacial acetic acid in a 50mL round-bottomed flask, heat and reflux for 1h under nitrogen protection, and react The system changed from brown to reddish brown. After the reaction was completed, cool to room temperature, pour the liquid into 100 mL of ice water, filter the precipitate, wash with water three times and dry it, and recrystallize with ethanol to obtain a white solid. Yield: 83%.

[0027] 1 H NMR (400MHz, d 6 -DMSO), δ(ppm): 0.75-0.76(d, J=8.0Hz, 2H), 6.37-6.47(m, 6H), 6.162-6.159(t, J=0.6Hz, 2H), 5.73(m, 1H).

[0028] Synthesis of 3-hydroxy-4-(1hydro-phenanthrenequinone[9,10-d]imidazol-2-ethyl)phenyl 4-oxopentanoate (2):

[0029] 0.20 g (0.6 mmol) of compound (1), 0.17 g (1.5 mmol) of levulinic acid, 0.24 (1.2 mmol) of DCC, 0.00...

Embodiment 2

[0032] Solvation Effect of 3-Hydroxy-4-(1H-phenanthrenequinone[9,10-d]imidazol-2-ethyl)phenyl 4-oxopentanoate (PI)

[0033] Prepare in advance 1 serving of 10 mL of 10 -3 The N,N-dimethylformamide solution of M probe PI, then take 10 μL and add it to six identical 5mL volumetric flasks, dilute to 5mL with DMF, acetonitrile, PBS, methanol, tetrahydrofuran, and chloroform respectively, and then perform fluorescence detection (λ Ex =365nm,λ Em =450nm), see the results figure 1 ;

Embodiment 3

[0035] Calculate the quantum yield of probe PI in each solvent according to the data in Example 2.

[0036] The above calculation formula is as follows:

[0037] Φ s = Φ r ( A r ( λ r ) A s ( λ s ) ) ( I ( λ r ) I ( λ ...

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Abstract

The invention discloses a fluorescent probe suitable for specially identifying bivalent copper ions in a water phase. The fluorescent probe is 3-hydroxy-4-(1H-phenanthrenequinone[9,10-d]imidazol-2-ethyl)phenyl-4-oxo-valerate (Pi for short) and has a chemical structural formula represented by a formula (1) (shown in the specification). The invention further discloses an application of the fluorescent probe for detecting whether water contains bivalent copper ions. An experiment proves that the copper ion fluorescent probe can be used for selectively detecting copper ions in the water phase based on an ESIPT (Excited-State Intramolecular Proton Transfer) mechanism and carrying out fluorescence quenching, and the fluorescence recovery is enhanced when meeting biological mercaptan. According to the characteristics of the fluorescent probe, the fluorescent probe has an outstanding advantage for detecting the heavy metal ion level in an environment and living bodies as well as a latent application value in the field of laser excitation fluorescence biomarkers.

Description

technical field [0001] The invention relates to a fluorescent probe for recognizing heavy metal copper ions and its application, in particular to a fluorescent probe for a phenanthrenequinone compound that specifically recognizes divalent copper ions in an aqueous phase and its application; it belongs to organic small molecule fluorescent probes field. Background technique [0002] Under normal circumstances, in addition to iron and zinc, copper ions are the third most abundant essential trace element in the human body. The total copper content in the adult body is generally 70-80 mg. [0003] Copper ions play an important role in various physiological processes. However, copper ions, as toxic heavy metal elements, can cause oxidative stress and neurological diseases, including Alzheimer's, Parkinson's, Menkes' and Wilson et al. Therefore, the detection of copper ions has aroused people's great attention. [0004] At present, the detection methods of copper ions are mainl...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D235/02G01N21/64
Inventor 林伟英刘勇孟芳芳石起慢
Owner UNIV OF JINAN
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