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A fluorescent probe for detecting fluoride ions in living cells and its preparation method

A technology of fluorescent probes and fluoride ions, which is applied in the field of fluorescent probes, can solve the problems of poor cell membrane penetration and limitation of fluorine ion fluorescence imaging, and achieve the effects of simple post-processing, simple synthesis methods, and high yields

Inactive Publication Date: 2019-08-20
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is well known that polymers have poor cell membrane penetration, which greatly limits the fluorescence imaging of fluoride ions in living cells.
So far, there have been few reports on small molecule probes suitable for the detection and imaging of fluoride ions in vivo

Method used

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  • A fluorescent probe for detecting fluoride ions in living cells and its preparation method
  • A fluorescent probe for detecting fluoride ions in living cells and its preparation method
  • A fluorescent probe for detecting fluoride ions in living cells and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of compound HPQF

[0026] Compound a (550.6 mg) and 2-aminobenzamide (177.3 mg) were dissolved in 40 mL of methanol, stirred at 0° C. for 10 minutes, and then refluxed for 30 minutes; then p-toluenesulfonamide (20 mg) was added and continued Reflux for 1 hour; after the reaction solution was cooled to room temperature, dichlorodicyanobenzoquinone (270.8 mg) was added, stirred overnight, and filtered with suction, the resulting filter residue was compound HPQF, with a yield of 70%.

[0027] 1 H NMR (300MHz, CDCl 3 )δ(ppm): 10.96(s, 1H), 8.53(d, J=6.99Hz, 1H), 8.29(d, J=7.86Hz, 1H), 7.77~7.70(m, 6H), 7.48~7.35( m, 8H), 7.20~7.13(m, 3H), 7.07(d, J=8.31Hz, 1H), 6.81(d, J=8.37Hz, 2H), 5.19(s, 2H), 1.11(s, 9H ). 13 C NMR (75MHz, CDCl 3 )δ(ppm):161.69,157.05,156.05,150.88,149.43,135.60,134.45,133.08,132.73,131.58,130.03,128.92,127.90,127.65,126.48,126.47,122.14,121.36,120.54,120.34,113.91,71.55, 26.57. ESI-HRMS C 37 h 34 N 2 o 3 Si[M+Na] ...

Embodiment 2

[0028] Embodiment 2: Compound HPQF detects fluoride ion in vitro

[0029] Dissolve the compound HPQF in DMSO, and prepare 1uL of solutions of different concentrations (20-200uM), then add fluoride ion solutions of different concentrations (0-2000uM) prepared from tetrabutylammonium fluoride (TABF), and wait After 0-10 minutes, set the excitation wavelength to 405nm, and collect the fluorescence signal intensity at the wavelength of 470-530nm. When the concentration of fluoride ion is 20uM, obvious fluorescence "turn-on" effect can be observed.

Embodiment 3

[0030] Example 3: Compound HPQF detects fluoride ions in living cells

[0031] Subculture HepG2 cells for 2-10 hours first, set the experimental group to add fluoride ion solution to co-culture for 1-6 hours, set the blank control group to co-culture with the control solution without fluoride ion for 1-6 hours; then use a large amount of PBS solution repeatedly The HepG2 cells were washed several times to fully remove free extracellular fluoride ions; the compound HPQF (20-200uM) was added to incubate for 0.5-3 hours, and the fluorescence intensity of the two groups of cells was observed by confocal laser microscopy. Experimental results such as image 3 As shown, compared with the blank control group, the fluorescence intensity of the field of view in the experimental group was significantly enhanced, indicating that the compound HPQF has good cell membrane penetration and can be applied to the dynamic monitoring of fluoride ion concentration in living cells.

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Abstract

The invention discloses a fluorescent probe for detecting fluorine ions in living cells and a method for preparing the fluorescent probe. The fluorescent probe is of a structure shown as a formula I. The fluorescent probe and the method have the advantages that the fluorescent probe is nearly free of optional fluorescent light, but Si-O bonds can be broken under induction of the fluorine ions, TBDPS (tert-butyl diphenyl silicon-based) protecting groups can be removed, phenolic hydroxy can be generated, HPQ (hydroxypiperaquine) can be released, accordingly, effects of transferring protons in excited-state molecules can be realized, phenomena of greatly enhancing fluorescent light can occur, and strategies for detecting the fluorine ions by means of fluorescent light 'turn-on' can be implemented; the phenomena of enhancing the fluorescent light of the probe can be observed by naked eyes under illumination of ultraviolet lamps when the fluorine ions have the low concentration of 20 micro-M, the fluorescent probe is excellent in biocompatibility, can be permeated through cell membranes and can be combined with laser confocal microscopes, and accordingly response of the fluorescent probe to the micromole-level fluorine ions in the living cells can be observed; the method for synthesizing the fluorescent probe is simple, post-treatment is simple and convenient, and ultimate products with high yields can be obtained without column chromatographic purification.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting fluorine ions in living cells and a preparation method thereof, belonging to the field of fluorescent probes. Background technique [0002] Anions play an important role in various physiological processes in organisms. In particular, fluoride ion is an indispensable trace ion in human life activities. The effect of fluoride ion on the human body is a double-edged sword: it is a necessary trace ion in proper amount, but it has toxic effect in excessive amount. For example: an appropriate amount of fluoride can be used for the treatment of osteoporosis and dental care; however, excessive fluoride ions can easily lead to dental fluorosis, bone fluorosis, lower IQ, inactivation of enzymes, and even cause kidney, gastrointestinal, and damage to the immune system. In addition, fluoride can also cause changes in collagen and mucopolysaccharide metabolism and so on. Although the chemical structure ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C09K11/06G01N21/64
Inventor 毛伍祥徐小为
Owner HUBEI UNIV
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