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Preparation method of ratio type acidic pH fluorescent probe

A fluorescent probe, ratio-type technology, applied in the field of fluorescent probes, to achieve the effect of improving accuracy

Active Publication Date: 2020-08-25
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the determination of intracellular extreme acidic pH remains a great challenge due to the lack of suitable probes

Method used

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  • Preparation method of ratio type acidic pH fluorescent probe
  • Preparation method of ratio type acidic pH fluorescent probe
  • Preparation method of ratio type acidic pH fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of fluorescent probes

[0035] Synthetic route such as figure 1 . In a 250mL round bottom flask, dissolve 7-diethylaminocoumarin-3-aldehyde (200mg, 0.82mmol) and 4-methylquinoline (141mg, 0.98mmol) in 10ml DMF, add p-trimethyl Chlorosilane (1.1mL, 8.2mmol), wrap the bottle with aluminum foil to avoid light. in N 2 Protect and heat and stir at 100°C for 24h. Stop the reaction, after cooling to room temperature, add 100ml of water, use 1.0M Na 2 CO 3 The solution was adjusted to a solution pH of 8. Then use 100ml of dichloromethane to extract three times, collect the organic layer, and add 3g of anhydrous Na 2 SO 4 dry. The solvent was spun off, and the crude product was purified by silica gel column chromatography using petroleum ether and ethyl acetate with a volume ratio of 2:1 as the eluent, and a reddish-brown solid (100 mg, 32.9%) was obtained after purification and separation, which was the probe Molecular compound JS-1. 1 H NMR (400MHz, CDCl ...

Embodiment 2

[0037] Preparation of fluorescent probes and different pH solutions;

[0038] 1. Take an appropriate amount of probe molecule JS-1 and dissolve it in chromatographically pure acetonitrile to prepare a 1.0 mM fluorescent probe molecule stock solution.

[0039] 2. Weigh an appropriate amount of KH 2 PO 4 、Na 2 HPO 4 , NaCl, and KCl were fixed to volume with distilled water to obtain a phosphate buffer solution with a concentration of 0.01M and pH=7.4;

[0040] 3. Use 1.0M hydrochloric acid or 1.0M sodium hydroxide solution to adjust the pH of the phosphate buffer solution to obtain phosphate buffer solutions of various pHs; and according to the volume ratio of acetonitrile:PBS=4:6, prepare Acetonitrile / PBS detection solution with different pH;

[0041] 4. Add the fluorescent probe molecule stock solution in step 1 to the detection solution obtained in step 3 to obtain a mixed test solution, the concentration of the fluorescent probe molecules in the mixed test solution is 1...

Embodiment 3

[0043] UV-visible absorption spectrum determination of fluorescent probes interacting with different pH;

[0044] figure 2 It is the ultraviolet-visible absorption spectrum of the fluorescent probe JS-1 (10 μM) in response to different pH (2.1-8.4). The instrument used for the determination of ultraviolet-visible absorption spectrum is Shimadzu UV-2600 ultraviolet-visible spectrophotometer. Such as figure 2 As shown, when the pH is 8.4, the probe has a strong absorption at 432nm; as the pH decreases from 8.4 to 2.1, the maximum absorption wavelength of the probe red shifts to 520nm. This is due to the protonation of the N atom in the quinoline group. The color of the solution changed from light yellow (pH=8.4) to pink (pH=2.1), and the color change was obvious, which could be observed with naked eyes.

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Abstract

The invention belongs to the technical field of fluorescent probes, and particularly relates to a preparation method and application of a ratio type acidic pH fluorescent probe. The invention providesa preparation method for synthesizing a fluorescent probe from 4-methylquinoline and 7-diethylaminocoumarin-3-aldehyde under the action of trimethylchlorosilane. The ratio type acidic pH fluorescentprobe prepared by the method has good selectivity on pH, and is high in sensitivity and rapid in response; the probe is respectively used for detecting pH in living cells, escherichia coli or zebra fish bodies, and a satisfactory result is obtained.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to the preparation of a ratio-type acidic pH fluorescent probe and its application in detection of pH in living cells, Escherichia coli or zebrafish for non-diagnostic and therapeutic purposes. Background technique [0002] pH plays an important regulatory role in various cell behaviors, such as enzyme activity, cell proliferation and apoptosis, information transmission and drug resistance, etc., and is an important parameter affecting cell behavior. Under normal circumstances, H in human extracellular fluid and blood + The concentration is 40nM, the pH is 7.4, and the fluctuation does not exceed 5nM. However, when the pH value in the body is abnormal, it will lead to abnormal functions of cells and tissues, which will lead to various diseases, such as inflammation, tumors, cardiopulmonary or nervous system diseases (such as Alzheimer's disease) and cystic fi...

Claims

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Application Information

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IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06G01N21/6428G01N21/6458C09K2211/1029C09K2211/1088G01N2021/6432Y02A50/30
Inventor 姜舒韩志湘许海董良欢代晓婷
Owner JIANGSU UNIV
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