Near infrared fluorescent probe for detecting zinc ion in cell and its synthesis method and use

A fluorescent probe and synthesis method technology, applied in the fields of biological detection technology and clinical medical detection, can solve the problems of fluorescence interference, complex structure, expensive instruments, etc., achieve low permeability and side effects, high measurement sensitivity, and simple synthesis method Effect

Inactive Publication Date: 2006-10-11
SHANDONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Many existing methods, including atomic absorption spectrometry, electron paramagnetic resonance, Electron Probe Micronalysis, etc., have been used for the detection of metal ions in cells, but the instruments used in these methods are expensive, and they cannot perform real-time and original detection of metal ions in organisms. Bit dynamic detection, and the sample pretreatment is more complicated when these methods are determined, so the application is limited
[0004] At present, existing fluorescent probes that can detect cellular zinc ions mainly include the following categories: TSQ (Frederickson, C.J.; Kasarkis, E.J.; Ringo, D.; Frederickson, R.E.J.Neurosci.Methods, 1987,20,91- 103.), Zinquin ethyl ester (Tsuda, M.Neurosci., 17, 6678, 1997) dansylaminoethyl cyclamate (Koike, T.; Watanabe, T.; Aoki, S.; Kimura,...

Method used

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  • Near infrared fluorescent probe for detecting zinc ion in cell and its synthesis method and use
  • Near infrared fluorescent probe for detecting zinc ion in cell and its synthesis method and use
  • Near infrared fluorescent probe for detecting zinc ion in cell and its synthesis method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0042] Probe Synthesis

[0043]

[0044] In a 100ml three-necked flask, add 0.3 grams (5mmol) of propyl cyanine dye Cy.7 and 2 grams of bis(2-pyridylmethyl)amine with near-infrared fluorescence spectrum, add about 60ml of N,N-dimethyl form The amide was completely dissolved, and then reacted under nitrogen protection at 66°C for 4 hours, cooled to 15°C at room temperature, and then decompressed by a decompression oil pump and rotary evaporated at 35°C until evaporated to dryness. After cooling, it was dissolved with ether to form a solution. Then add 1.2 times the weight of water of diethyl ether and extract to layering at room temperature, get the extract I, and then add 0.8 times of the weight of the extract I to extract to layering with ethyl acetate, to obtain the extract II, and finally to Anhydrous magnesium sulfate was added to the extract II to dry it, and then it was decompressed by a vacuum oil pump and rotary evaporated at 35°C to remove ethyl acetate to obtain 0...

Embodiment 2

[0047] Replace two (2-pyridylmethyl) amines with quinoline sulfonamide, all the other are the same as in Example 1.

Embodiment 3

[0049] Replace bis(2-pyridylmethyl)amine with 4,7,10-trimethyl-1,4,7,10-tetraazacyclododecyl, and the rest are the same as in Example 1.

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Abstract

This invention is near-infrared fluorescent probe for intracellular zinc ion test. The syncetic process is as followings: A.mix cyanine dyes Cy.7 and complexing group in the weight propotion of 1:5-10, resolve the mix in N,N-dimethyl formamide, and react at 60-70deg C for 2-5 hours with the protection of inactive gas; B. Cool the production A to 10-20deg C, dry blowing with depression, resolve in aether, add water for extraction, the extraction liquor I obtained, then add acetic ester for extraction, the extraction liquor II obtained; C. Add anhydrous addex-magnesium in liquor II for desiccation, dry blowing with depression at 30-40deg C, get rid of acetic ester for the final production. The near-infrared fluorescent probe has a good cellular osmosis and little side effect. In particular, it's seligible for cellular zinc ion test.

Description

technical field [0001] The present invention relates to the fields of biological detection technology and clinical medical detection, in particular to a near-infrared fluorescent probe for detecting intracellular zinc ions; the present invention also relates to a synthesis method of the fluorescent probe; in addition, the present invention also relates to the fluorescent probe the use of. Background technique [0002] Zinc ions are the second most abundant transition metal in living organisms. A large number of zinc ions are concentrated in nerve tissue, such as the concentration in brain tissue is 0.1-0.5nM. Zinc ions are directly involved in the regulation of gene expression through metal regulatory proteins. For example, zinc, as a component of zinc finger proteins, can affect gene expression by changing the structure of chromatin or by interrupting DNA synthesis. Most of the zinc ions in organisms are tightly combined with proteins, and there are "free zinc pools" in s...

Claims

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Application Information

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IPC IPC(8): C07D401/14G01N33/52
Inventor 唐波黄辉徐克花陈蓁蓁李普明刘霞
Owner SHANDONG NORMAL UNIV
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