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Near infrared fluorescent probe for detecting zinc ions in water phase and preparation method thereof

A fluorescent probe, near-infrared technology, applied in chemical instruments and methods, biological testing, luminescent materials, etc., can solve problems such as difficult large-scale application, high cost, and complicated operation

Active Publication Date: 2011-11-16
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The methods commonly used to determine trace zinc are: atomic absorption spectrometry, which belongs to the conventional elemental analysis method, but has low sensitivity and complicated operation for the determination of trace elements; Zeeman effect graphite atomic absorption spectrometry, which is an accurate and reliable method, but it is also complicated to operate, and the cost is high, so it is difficult to apply on a large scale
More importantly, these methods cannot be applied in biological systems without damaging living cells and living tissues.
It is even more impossible to detect changes in the concentration of zinc ions in living cells and living tissues of biological systems in real time
[0005] In the prior art, fluorescent molecular probe technology is applied to the detection of ions, which can realize in-situ detection. Since ordinary fluorescent molecular probes have poor solubility or poor selectivity in aqueous solution, it is necessary to design a Fluorescent molecular probes with good performance. At the same time, most of the fluorescent probe molecules that recognize zinc ions are in the short-wavelength region, which will cause damage to cells when excited, and the autofluorescence in organisms also seriously interferes with the detection. Its application is subject to certain restrictions

Method used

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  • Near infrared fluorescent probe for detecting zinc ions in water phase and preparation method thereof
  • Near infrared fluorescent probe for detecting zinc ions in water phase and preparation method thereof
  • Near infrared fluorescent probe for detecting zinc ions in water phase and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0035] Such as figure 1 As shown, 6.56g of 2-chloromethylpyridine hydrochloride (0.040 mol, M=164.03g / mol) was dissolved in 40 mL of water, and then 3.20g (0.080 mol, M=40.00 g / mol ) sodium hydroxide to give a red solution. Under sufficient stirring, 3.20 g of N-tert-butoxycarbonylethylenediamine (0.020 mol, M=160.21g / mol), 128 mg of phase transfer catalyst, 6.64 g of potassium iodide, and 40 mL of tetrahydrofuran were added. The reaction was carried out at room temperature for 2 days under the protection of argon. Extracted with dichloromethane, dried, and evaporated to remove the solvent to obtain a crude product. The intermediate product N`-tert-butoxycarbonyl-N,N-bis(2-chloromethylpyridine)ethylenediamine (4) was obtained as a colorless oil after separation on a silica gel column.

[0036]Dissolve 5.0g of N`-tert-butoxycarbonyl-N,N-bis(2-chloromethylpyridine)ethylenediamine (4) (0.0146mol, M=342.44g / mol) in 15mL of dichloromethane, place in an ice water bath. With su...

Embodiment 2

[0043] Fluorescent probe obtained in embodiment one 1 MTT cytotoxicity test: MTT colorimetry is a method for detecting cell survival and growth. The detection principle is that succinate dehydrogenase in the mitochondria of living cells can reduce exogenous MTT to water-insoluble blue-purple crystal formazan Zan (Formazan) and deposited in cells, but dead cells do not have this function. Dimethyl sulfoxide (DMSO) can dissolve formazan in cells, and its light absorption value is measured at a wavelength of 490nm with an enzyme-linked immunosorbent detector, which can indirectly reflect the number of living cells.

[0044] 1. Weigh 0.5 g of MTT, dissolve it in 100 ml of phosphate buffered solution (PBS), filter it with a 0.22 μm filter membrane to remove bacteria in the solution, prepare an MTT solution with a concentration of 5 mg / ml, and store it in the dark at 4°C.

[0045] 2. Cell inoculation: Collect KB cells in logarithmic phase, make a single cell suspension with culture...

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Abstract

The invention belongs to the field of small molecular fluorescent probes and particularly relates to a near infrared fluorescent probe for detecting zinc ions in a water phase and a preparation method thereof. The near infrared fluorescent probe for detecting the zinc ions in the water phase is structured in the specification. The fluorescent probe has the advantages of high selectivity and high sensitivity, as well as an emission peak of fluorescence spectrum in a near infrared area, low cytotoxicity, good membrane permeability and good water solubility. The fluorescent probe has a capability of detection of the zinc ions and fluorescence imaging in cells.

Description

technical field [0001] The invention belongs to the field of small molecule fluorescent probes, in particular to a near-infrared fluorescent probe for detecting zinc ions in water phase and a preparation method thereof. Background technique [0002] Zinc is one of the essential trace elements for the human body. Its content in the human body ranks second only to iron. It can be used as a cofactor to regulate the activity of proteins or enzymes. In addition, zinc ions also have the function of neuroregulation. It is true that zinc can cause nerve growth and development to be hindered, and it will cause sexual organ development retardation, manifested as hypoplasia of the prostate and seminal vesicles, and decreased sperm, resulting in decreased sexual physiological functions. [0003] Due to the zinc cation Zn 2+ The outermost electron distribution is 3d 10 4s 0 , does not show any spectral or magnetic signals, so commonly used ultraviolet spectroscopy, circular dichroism,...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D413/14G01N33/52
Inventor 路建美杨学波葛健锋徐庆锋李娜君王丽华
Owner SUZHOU UNIV
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