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A kind of ratiometric pH probe with organelle or protein targeting function and its application

An organelle and protein technology, applied in the fields of instruments, organic chemistry, scientific instruments, etc., can solve problems such as increasing the difficulty of synthesis, and achieve the effects of excellent protein targeting, easy functional modification, and excellent organelle localization.

Inactive Publication Date: 2021-09-21
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional ratiometric pH probes achieve organelle targeting by introducing additional corresponding Tag groups, which increases the difficulty of synthesis

Method used

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  • A kind of ratiometric pH probe with organelle or protein targeting function and its application
  • A kind of ratiometric pH probe with organelle or protein targeting function and its application
  • A kind of ratiometric pH probe with organelle or protein targeting function and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] The first step of the Click reaction to synthesize compound TB1: under argon, copper sulfate pentahydrate (515mg, 2.14mmol), sodium ascorbate (566mg, 2.86mmol), compound T (695mg, 2.86mmol) and compound B1 (460mg, 1.43 mmol) was dissolved in 10 mL of N,N-dimethylformamide, reacted at room temperature for 2 h, and determined the end point by TLC. The reaction solution was diluted with 100 mL of dichloromethane, washed 3 times with 30 mL of saturated brine, the organic phase was dried over anhydrous sodium sulfate, filtered with suction, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain compound TB1 (412 mg, 51%) . The structure of the product was identified by HRMS, HRMS [M]: 565.2069.

[0027] The second step is the Click reaction to synthesize the compound TB1R1: under argon protection, copper sulfate pentahydrate (141mg, 587.51μmol), sodium ascorbate (233mg, 1.18mmol), TB...

Embodiment 2

[0030]

[0031] The synthesis method refers to Example 1, and the compound Tag2 is used instead of Tag1, and the product structure is identified by HRMS, HRMS [M+H] + : 1287.5095.

Embodiment 3

[0033]

[0034] The synthesis method refers to Example 1, and the compound Tag3 is used instead of Tag1, and the product structure is identified by HRMS, HRMS [M+H] + : 1328.4534.

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Abstract

A kind of ratio-type pH probe with cell organelle or protein targeting function and its application belongs to the field of fine chemical industry. In the field of biological imaging, the visualization of cell activities is of great significance. Ratio pH probes located in organelles mainly achieve organelle targeting by connecting specific Tags, such as introducing morpholine to achieve lysosome positioning, introducing triphenylphosphine to achieve mitochondrial targeting, and using Hoechst to achieve DNA targeting, etc. . The introduction of Tag sites directly on the basis of ratiometric pH probes often has a series of problems such as increased synthesis steps and increased separation difficulty, so it is very important to develop a general platform. BODIPY and rhodamine have the advantages of high molar extinction coefficient and fluorescence quantum yield, narrow spectrum, and spectral matching, which are very suitable for the construction of ratiometric pH probes with FRET mechanism. These compounds have high biocompatibility and can specifically bind to ratiometric pH. , and also has the function of organelle targeting.

Description

technical field [0001] The invention relates to a kind of ratio-type pH probe with cell organelle or protein targeting function and its application, which belongs to the field of fine chemical industry. Background technique [0002] Organelles play different roles in maintaining the normal physiological activities of cells. However, their normal physiological functions need to be performed within a certain pH range. Abnormal pH often leads to a series of physiological diseases. For example, the pH of lysosomes is about Between 4 and 6, this is a necessary condition to ensure the activity of various enzymes, and it plays a vital role in degrading aging organelles and various substances in cells. Once the pH is abnormal, the activity of hydrolytic enzymes is reduced or even inactivated. Corresponding physiological functions will be destroyed. [0003] In the biological field, the visual study of organelle pH is of great significance for cell activities. Traditional ratiometr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C07F9/6561C09K11/06G01N21/64
CPCC07F5/022C07F9/65615C09K11/06G01N21/6428C09K2211/1044C09K2211/1059C09K2211/1055C09K2211/1037C09K2211/1014C09K2211/1033C09K2211/1062C09K2211/1074C09K2211/1066C09B11/24C09B23/04
Inventor 肖义闫宇张新富陈令成
Owner DALIAN UNIV OF TECH
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