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Method for detecting aluminum ions in cells by long wave emission fluorescence imaging

A technology of fluorescence imaging and aluminum ions, applied in fluorescence/phosphorescence, measurement devices, material excitation analysis, etc., can solve the problems of poor cell permeability, photodamage of cells or living biological samples, short emission wavelength, etc., and achieve high selectivity, The separation and purification process is easy and the effect of good sensitivity

Active Publication Date: 2019-01-01
BOHAI UNIV
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Problems solved by technology

[0003] In recent years, based on the identification of Al 3+ There are many designs of fluorescent probe molecules, for example, Biosens Bioelectron (2015), 68, 749-756; Spectrochim Acta A Mol Biomol Spectrosc (2018), 19, 2257-2262; Sensors and Actuators B: Chemical (2017), 247, 451-460 ; Biosens Bioelectron (2017), 77, 530-536; Sensors and Actuators B: Chemical (2018), 266, 95-105; Anal Chim Acta (2016), 942, 104-111; Tetrahedron Letters (2016), 57 (8), 953- 958; these documents are all for the detection of multiple cations, and have not realized the detection of Al 3+ Specific recognition of Sensors and Actuators B: Chemical (2016), 229, 138-144; Spectrochim Acta A Mol Biomol Spectrosc (2018), 201, 185-192; Analytical Methods (2012), 4 (7), 1906; Sensors and Actuators B: Chemical (2017), 240, 916-925; Journal of Photochemistry and Photobiology A: Chemistry (2017), 332, 101-111; Sensors and Actuators B: Chemical (2017), 238, 128-137; Sensors and Actuators B: Chemical (2018), 264,304-311; although these literatures can specifically identify Al 3+ , but the emission wavelength is short and cannot be detected in the long-wavelength range. It is easy to cause light damage to cells or biological samples, and to a certain extent causes background fluorescence self-interference, and most cells have poor permeability, so they cannot be used to identify Al in cells. 3+ , therefore, the design and synthesis of better Al 3+ Fluorescent probes are important

Method used

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  • Method for detecting aluminum ions in cells by long wave emission fluorescence imaging
  • Method for detecting aluminum ions in cells by long wave emission fluorescence imaging
  • Method for detecting aluminum ions in cells by long wave emission fluorescence imaging

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Embodiment 1

[0032] Compound 1,4-diethyl-7-hydroxytetrahydroquinoxaline-6-carbaldehyde (234 mg, 1 mmol) and salicyl hydrazide (152 mg, 1 mmol) were dissolved in ethanol and refluxed for 8 h, cooled to room temperature, and a yellow color was precipitated The solid was purified by recrystallization from ethanol to obtain 237 mg of a yellow solid, which was the acceptor L, and the yield was 64.3%. Fluorescent Probe L 1 H NMR spectrum, 13 The C NMR spectrum and mass spectrum are shown in Figure 1-3 shown.

[0033] 1 H NMR (400MHz, DMSO-d 6 )δ12.07(s, 1H), 11.77(s, 1H), 10.75(s, 1H), 8.46(s, 1H), 7.90(d, J=7.7Hz, 1H), 7.44(t, J=7.6 Hz, 1H), 6.96(t, J=8.1Hz, 2H), 6.54(s, 1H), 6.08(s, 1H), 3.41(s, 2H), 3.34(d, J=7.0Hz, 2H), 3.27–3.17(m, 2H), 3.11(s, 2H), 1.09(td, J=6.6, 2.9Hz, 6H).

[0034] 13 C NMR (101MHz, DMSO-d 6)δ164.26,159.74,153.26,151.39,140.10,134.09,128.53,128.32,119.27,117.72,115.77,111.26,97.42,47.11,45.12,10.68,10.15.

[0035] HRMS(ESI + )calcd for C 20 H 24 N 4 O 3 ...

Embodiment 2

[0037] Compound 1,4-diethyl-7-hydroxytetrahydroquinoxaline-6-carbaldehyde (234 mg, 1 mmol) and salicyl hydrazide (304 mg, 2 mmol) were dissolved in ethanol and refluxed for 10 h, cooled to room temperature, and a yellow color was precipitated The solid was purified by recrystallization from ethanol to obtain 257 mg of red solid, which was the fluorescent probe L, and the yield was 69.8%. Fluorescent Probe L 1 H NMR spectrum, 13 The C NMR spectrum and mass spectrum are shown in Figure 1-3 shown.

Embodiment 3

[0039] Compound 1,4-diethyl-7-hydroxytetrahydroquinoxaline-6-carbaldehyde (234 mg, 1 mmol) and salicyl hydrazide (456 mg, 3 mmol) were dissolved in ethanol and refluxed for 12 h, cooled to room temperature, and a yellow color was precipitated The solid was purified by recrystallization from ethanol to obtain 267 mg of red solid, which was the acceptor L, and the yield was 72.5%. Fluorescent Probe L 1 H NMR spectrum, 13 The C NMR spectrum and mass spectrum are shown in Figure 1-3 shown.

[0040] Fluorescent probe L detects Al in cells 3+ :

[0041] Detection of trace amounts of Al in cells by long-wavelength emission fluorescence imaging 3+ When , firstly use 5 μmol / L-10 μmol / L fluorescent probe L solution (the solvent is PBS buffer) to incubate the cells to make the fluorescent probe L enter the active cells, and then mix the active cells with the fluorescent probe L with Al 3+ Incubate to make probes with Al 3+ Reacts in active cells to generate compounds that emit fl...

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Abstract

The invention relates to a method for detecting aluminum ions in cells by long wave emission fluorescence imaging. A fluorescent probe L is adopted as a fluorescent imaging probe for detecting trace Al<3+> in cells by fluorescent imaging, trace Al<3+> in cells is detected by long wave emission fluorescence imaging, and the chemical structural formula of the fluorescent probe L is shown in the formula. The formula is shown in the description. During detection, a fluorescent probe L solution is first used for culturing cells, so that the fluorescent probe L gets into the active cells, the activecells with the fluorescent probe L are then cultured along with Al<3+>, so that the probe reacts with Al<3+> in the active cells to produce a compound which can emit fluorescence with a characteristic wavelength, realizing the imaging of Al<3+> ions dyed by the probe in the active cells, and a laser confocal fluorescence microscope is used for observing the fluorescence image of the cultured active cells. The method has the advantages that: the method has high selectivity and good sensitivity, trace Al<3+> in cells can be detected by fluorescence imaging under a long emitted wavelength, moreover, the tissue-penetrating capability is high, and light-induced injury and background fluorescence self-interference are prevented.

Description

technical field [0001] The invention relates to a method for detecting aluminum ions in cells by long-wave emission fluorescence imaging. Background technique [0002] It is well known that the development of chemical sensors for detecting metal ions has received extensive attention due to their important roles in medicine, living systems, and the environment. Aluminum (Al) is the third most ubiquitous and abundant metallic element in the earth's crust, and people are widely exposed to aluminum as it is dispersed in areas such as water treatment, food additives, storage tools or cooking utensils, pharmaceuticals, and light alloys. At the same time, Al 3+ It is also an essential element in the life system, but excessive intake of Al 3+ It will affect the absorption of calcium in the intestine, causing the bones to soften, shrink or even deform, and affect the absorption of iron in the blood, causing anemia. In addition, Al 3+ Its toxicity causes damage to the central nerv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64
CPCG01N21/6402G01N21/6428G01N21/6458G01N2021/6439
Inventor 钟克利汤立军曲秀莉侯淑华任欢欢朱文慧李秋莹徐永霞邓隆隆
Owner BOHAI UNIV
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