Mitochondria-targeted double-signal turn-on formaldehyde fluorescent nano-probe, and preparation and application of same

A technology of fluorescent nanoprobes and formaldehyde, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, and can solve problems such as affecting mitochondrial function, inaccurate detection results of a single signal, and reducing mitochondrial membrane potential. To achieve the effect of improving accuracy

Active Publication Date: 2017-12-22
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, excessive formaldehyde will reduce the mitochondrial membrane potential and affect mitochondrial function
At present, there is no relevant literature to study the concentration of formaldehyde in mitochondria. Therefore, it is urgent to develop formaldehyde probes targeting mitochondria in cells.
[0004] 3. Fluorescent probes have attracted attention due to their advantages of high sensitivity and real-time detection, but most of the current probes only have the characteristics of single-signal turn-on output when detecting analytes, but a single signal is easily affected by external factors. The impact of the environment can not accurately detect the results

Method used

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  • Mitochondria-targeted double-signal turn-on formaldehyde fluorescent nano-probe, and preparation and application of same
  • Mitochondria-targeted double-signal turn-on formaldehyde fluorescent nano-probe, and preparation and application of same
  • Mitochondria-targeted double-signal turn-on formaldehyde fluorescent nano-probe, and preparation and application of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The preparation of embodiment 1 (1) compound (II)

[0055] Dissolve 1.22g of p-hydroxybenzaldehyde (10mmol) in 50mL of acetone solution, then add 2.07g of potassium carbonate (15mmol), react at 60-70°C for half an hour, then add 2.37g of 3-bromopropyne (20mmol), 60 The reaction was stopped after 2 hours at -70°C, and the solvent was distilled off under reduced pressure. Add water to the mixture, extract with ethyl acetate, combine the organic phases, wash with water and saturated brine several times, dry over anhydrous sodium sulfate, filter, spin to dry the solvent, and separate by column chromatography (ethyl acetate:petroleum ether=1: 10 is the eluent) to obtain white solid compound (II) (1.53 g, 95% yield). 1 H NMR (500MHz, CDCl 3 )δ9.88(s,1H),7.95–7.75(m,2H),7.18–6.98(m,2H),4.77(d,J=2.4Hz,2H),2.58(t,J=2.4Hz,1H ). 13 CNMR (126MHz, CDCl 3 )δ190.69, 162.30, 131.81, 130.51, 115.11, 77.51, 76.35, 55.87.ESIcalcd.for C 10 h 8 o 2 [M+H] + 161.05, found 161.18.

...

Embodiment 2

[0067] Example 2 The nanoprobe nano-MTDF was tested for particle size by dynamic light diffraction under the condition of DMSO / water buffer (pH=7.4, v / v=1 / 99) and nanoparticle imaging by transmission electron microscope.

[0068] Accurately weigh a certain amount of compound (I) prepared in Example 1, prepare a probe mother solution with a concentration of 0.1mM with DMSO, pipette 0.02mL into 1.98mL water, ultrasonicate for several minutes, and then shake vigorously to obtain nano Probe nano-MTDF, and then use nano-zs90particle analyzer to measure the particle size of nano-MTDF in water. At the same time, take the above mixed liquid droplet on the copper grid, and dry it at 37°C for transmission electron microscope imaging. The results are shown in image 3 .

[0069] see image 3 (a) It can be found that the result obtained by the dynamic light diffraction test is that the average particle diameter of the particles is 161.9 nm, and the polydispersity coefficient PDI index is...

Embodiment 3

[0070] Example 3 Fluorescence spectrum detection of nanoprobe nano-MTDF (1 μM) at different DMSO / water ratios.

[0071] Accurately weigh a certain amount of compound (I) prepared in Example 1, use dimethyl sulfoxide to prepare a probe mother solution with a concentration of 0.1mM, pipette 0.02mL and add to 1.98mL different DMSO / water ratios (DMSO 1%, 5%, 10%, 20%, 40%, 60%, 70%, 80%, 90%), ultrasonic for several minutes, then violently shake, and then measure the fluorescence spectrum of compound (I).

[0072] The experimental results show that as the ratio of DMSO increases, the fluorescence of compound (I) increases, which proves that with the reduction of the ratio of DMSO, the aggregation effect of compound (I) is enhanced, and the fluorescence at different excitation wavelengths is weakened, indicating that Rodan Bright B fluorescence is quenched due to aggregation. At the same time, it can also be observed that regardless of the ratio of DMSO, the probe has only one emi...

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Abstract

The invention discloses a preparation method and an application of a mitochondria-targeted double-signal turn-on formaldehyde fluorescent nano-probe. The formaldehyde fluorescent nano-probe is based on both fluorescent resonance energy transfer and self-assembly effect. The nano-probe hardly has fluorescence in water; when the nano-probe is reacted with formaldehyde, two free fluorescent compounds are generated, thus achieving double-turn-on effect and further improving the accuracy of a detection result. The nano-probe has excellent specificity on the formaldehyde. A confocal fluorescence microscope test proves that the nano-probe can permeate through a cell membrane and enters mitochondria in a cell, and can detect the change of concentration of formaldehyde in the cell. The nano-probe is a novel tool for researching the metabolic mechanism of the formaldehyde in mitochondria and has great prospect in the field of biology.

Description

technical field [0001] The invention relates to a mitochondria-targeted dual-signal turn-on formaldehyde fluorescent nanometer probe, a preparation method and application thereof. Background technique [0002] 1. Activated carbon clusters are a class of compounds with one or more carbonyl groups, which play a key role in human physiological processes. Formaldehyde, a recognized carcinogen, is the smallest molecule in activated carbon clusters. On the one hand, formaldehyde can come from industrial production, building materials, leather, fuel, and even food. On the other hand, formaldehyde comes from endogenous metabolites produced by intracellular oxidase and demethylase, and the formaldehyde concentration in normal cells can reach about 0.4mM. Excessive formaldehyde in the body can cause neurodegenerative diseases, Alzheimer's disease and various cancers, etc. Most of the formaldehyde detection methods at this stage cannot monitor the formaldehyde concentration in cells...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C09K11/06G01N21/64
CPCC07D405/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088G01N21/6486
Inventor 朱勍谢振达方红梨朱伸赵成艳
Owner ZHEJIANG UNIV OF TECH
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