Application of hydrophilic tetra-cation cyclophane constructed based on TPE

A cationic and hydrophilic technology, applied in the direction of medical preparations containing active ingredients, organic active ingredients, instruments, etc., to achieve the effect of improving antioxidant capacity

Active Publication Date: 2022-03-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many TPE-based cationic cyclopanes have been used for host-guest recognition, there are few examples of hydrophilic TPE cationic cyclopanes recognizing biomolecules in aqueous media

Method used

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  • Application of hydrophilic tetra-cation cyclophane constructed based on TPE
  • Application of hydrophilic tetra-cation cyclophane constructed based on TPE
  • Application of hydrophilic tetra-cation cyclophane constructed based on TPE

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the synthesis of compound 3

[0042]at 0°C, N 2 Under atmosphere, 37.1 mL of n-butyllithium (1.6M) was added to a solution of compound 1 (10 g, 59.4 mmol) in THF (100 mL), and the resulting orange-red solution was stirred at 0° C. for 30 min. Then, compound 2 (6.3g, 29.7mmol) was dissolved in THF (20mL) to obtain a THF solution of compound 2, and then the solution of compound 2 was added dropwise to the mixed solution of compound 1 and n-butyllithium, and the mixed solution was heated To room temperature, continue to stir for 6h. The reaction was quenched with 60 mL of saturated aqueous ammonium chloride. Extract the organic phase with DCM and anhydrous Na 2 SO 4 dry. The resulting crude product was dissolved in 20 mL of toluene, a catalytic amount of p-toluenesulfonic acid (342 mg, 1.8 mmol) was added, and the reaction was refluxed at 90 ° C for 5 h. Molecular sieve dehydration unit separates the generated water. With mass fraction 10% NaHCO 3 Wa...

Embodiment 2

[0043] Embodiment 2: the synthesis of compound 4

[0044] in N 2 Under atmosphere, compound 3 (1.1g, 2.83mmol) was dissolved in CCl 4 (20mL), then NBS (1.5g, 8.49mmol) and dibenzoyl peroxide (50mg, 0.2mmol) were added, and finally the mixture was heated to reflux at 70°C for 12h. After the reaction, the mixture was filtered to remove solid impurities. Extraction with DCM, organic phase with anhydrous Na 2 SO 4 dry. The solvent was removed by rotary evaporation, and the resulting crude product was purified by column chromatography (silica gel; the volume ratio of petroleum ether to ethyl acetate was 10:1 as the eluent), and the eluate containing the target compound was collected, spin-dried, and then 50°C After vacuum drying for 12 h, compound 4 (0.9 g, yield 60%) was obtained.

Embodiment 3

[0045] Embodiment 3: the synthesis of compound 5,

[0046] 4,4'-bipyridine (2.0 g, 12.8 mmol) was dissolved in 20 mL of acetonitrile, and heated to reflux at 75°C. A solution of compound 4 (1.2 mg, 2.3 mmol) in acetonitrile (5 mL) was then added dropwise to the bipyridine solution. Reflux at 75°C for 3 days. The reacted mixture was filtered, and the filter cake was washed 3 times with acetonitrile. After vacuum drying at 50° C. for 12 h, compound 5 (1.7 g, yield 90%) was obtained.

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Abstract

The invention relates to application of hydrophilic TPE (thermoplastic elastomer)-based tetra-cation cyclophane in NADPH (nicotinamide adenine dinucleotide phosphate) recognition and cell imaging. According to the material, TPE and a 4, 4 '-dipyridyl unit are used as construction units. Due to electrostatic interaction and pi-pi accumulation, TPE-cyc can specifically recognize NADPH and compound the NADPH in a mode of 1: 1. After TPE-cyc is internalized by tumor cells, NADPH in the cells can be captured, and the balance of NADPH generation reaction from NADH + NADP + to NADPH + NAD + is broken, so that the balance of the NADPH participating in the redox process is broken, and the antioxidant capacity is improved to remove ROS. Meanwhile, high-concentration GSH in tumor cells can reduce a 4, 4 '-dipyridyl (MV) unit of TPE-cyc to a free radical cation state and destroy a photoinduced electron transfer (PET) effect between electron-rich TPE and an electron-deficient dipyridyl unit, so that fluorescence of a TPE unit is recovered, and the tumor cells are lightened. Therefore, TPE-cyc, as a GSH-responsive fluorescent switch, displays image cells at high resolution.

Description

technical field [0001] The invention relates to the application of a hydrophilic tetracationic cyclopan based on TPE in biomolecular recognition. Background technique [0002] Understanding the importance of molecular recognition in the complex biological processes involved in various nucleic acids, enzymes, and nucleotides helps chemists develop smart structures with specific responses. In recent years, artificial molecular receptors have received increasing attention for their potential applications in medicine and biology. Nicotinamide adenine dinucleotide phosphate (NADPH), a major cellular reducer, plays an important role in maintaining GSH, the reduced form of glutathione. GSH eliminates reactive oxygen species (ROS) in cells, thereby preventing cellular oxidative damage. Although the possible mechanisms of NADPH's involvement in physiological processes have been proposed, due to the complexity and uncertainty of the existing mechanisms, more in-depth mechanistic stu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4375A61P35/00C07D471/22C09K11/06G01N21/64
CPCA61K31/4375C07D471/22A61P35/00C09K11/06G01N21/6428G01N21/6458C09K2211/1074C09K2211/1007G01N2021/6432Y02A50/30
Inventor 吴丹张占魁李昕玥
Owner ZHEJIANG UNIV OF TECH
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