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A switch type ferric ion fluorescent probe and preparation method thereof

A technology of fluorescent probe and ferric iron, which is applied in the field of cation detection to achieve the effects of low detection concentration, simple operation and simple structure

Inactive Publication Date: 2015-08-12
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims to provide a switch-type ferric ion fluorescent probe and its preparation method. The technical problem to be solved is to select and synthesize a suitable fluorescent probe molecular structure to realize the real-time detection of ferric ion concentration, and It has the characteristics of specific selectivity, high sensitivity and low detection concentration

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  • A switch type ferric ion fluorescent probe and preparation method thereof
  • A switch type ferric ion fluorescent probe and preparation method thereof
  • A switch type ferric ion fluorescent probe and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of fluorescent probe molecule RD

[0026] 1. Synthesis of intermediate 1

[0027] Weigh 5g (11.22mmol) of rhodamine B and 0.67g (13.46mmol) of hydrazine hydrate into a round bottom flask, add 100mL of ethanol solvent, install a condenser, heat to reflux at 80°C, track with TLC until the reaction of the raw materials is complete, and stop the reaction . The solvent was spin-dried and recrystallized from ethanol to obtain 4.88 g (10.66 mmol) of intermediate 1 as a white solid with a yield of 95%.

[0028] 1 H NMR (CDCl 3 ,400MHz,ppm):δ:1.15(12H,t,J=7.02Hz),3.34(8H,q,J=7.00Hz),3.61(2H,s),6.45-6.29(6H,m),7.10( 1H,m),7.45(2H,m),7.93(1Hm). 13 C NMR (DMSO-d 6 ,100MHz,ppm),δ:12.41,43.64,64.71,97.35,105.4,107.73,122.12,123.47,127.68,132.36,148.06,151.85,152.99,165.26.

[0029] 2. Synthesis of Intermediate 2

[0030]Weigh 11.36g (3mmol) of the intermediate in a round-bottomed flask, add the solvent dichloromethane (10mL), and slowly add 0.76g o...

Embodiment 2

[0035] Embodiment 2: the selectivity of fluorescent probe molecule RD to ferric ion

[0036] Dissolve fluorescent probe molecules in methanol to prepare 1 mM mother solution, take 100 μL of the mother solution in a 10 mL volumetric flask, and then dilute to volume with HEPES aqueous solution (pH 7.0). When adding 40 times the equivalent (Na + ,Mg 2+ , Ca 2+ ) and 2 times the equivalent of various metal ions (Ag + ,Mn 2+ ,Cu 2+ ,Hg 2+ ,Pb 2+ , Fe 2+ ,Co 2+ , Ni 2+ ,Zn 2+ ,Cd 2+ ,Cr 3+ , Fe 3+ ), the fluorescent probe molecule is excited at 550nm to detect changes in the fluorescence spectrum. from Figure 4 It can be seen that the addition of various other metal ions will not cause the fluorescence change of the fluorescent probe. Only the ferric ion can affect the fluorescence change of the probe, and the chromium ion has a weak influence. Under the condition of co-existence, the fluorescent probe molecules are highly specific and selective to ferric ions.

Embodiment 3

[0037] Embodiment 3: the insensitivity of fluorescent probe molecule RD to pH

[0038] Using the response of the fluorescent probe molecule RD to pH, under the conditions of biological simulation, the pH of the fluorescent probe molecule is studied. At pH=6-9, the fluorescence intensity of the fluorescent probe molecule (RD) will not change with the pH while changing ( Figure 5 ), indicating that the fluorescent probe molecule of the present invention can be well applied in cell imaging.

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Abstract

The invention discloses a switch-type ferric ion fluorescence probe and a preparation method thereof. Rhodamine B is adopted as a matrix of the switch-type ferric ion fluorescence probe, and the structural formula of the switch-type ferric ion fluorescence probe is as follows (refer to the Specification). According to the invention, fluorescence probe molecules demonstrate higher selectivity and sensitivity in the concomitant system of ferric ions and other positive ions; a fluorescence development experiment shows that the fluorescence probe molecules have excellent cell penetrability, are nontoxic for cells, and can be used for detecting the concentration and distribution of ferric ions in cells.

Description

1. Technical field [0001] The invention relates to a fluorescent probe molecule and a preparation method thereof, in particular to a switch-type ferric ion fluorescent probe and a preparation method thereof, belonging to the technical field of cation detection. 2. Background technology [0002] The transition metal ion iron ion plays a vital role in the growth and evolution of life. However, when the concentration of ferric ion in the human body reaches a certain level, it is closely related to the incidence of cancer and the dysfunction of human organs, such as heart disease , pancreas and liver disease. Therefore, it is of great significance to detect the concentration of ferric ion in real time in the environment. [0003] Fluorescent probes are molecules that can change the fluorescent signal when a substance or a certain substance in a system changes in a certain system. The advantages of fluorescence spectroscopy are its convenience and sensitivity in trace detection....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC09B11/24C09K11/06C09K2211/1011C09K2211/1029C09K2211/1088C09K2211/187
Inventor 孟祥明叶维鹏蔡玉磊汪恕欣朱满洲冯燕
Owner ANHUI UNIVERSITY
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