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Synthesis method of spiropyrane small-molecule fluorescent probe with extreme acid/extreme alkaline switch response and application of spiropyrane small-molecule fluorescent probe

A technology of fluorescent probes and spiropyrans, applied in the field of molecular fluorescent probes, to achieve the effects of fast pH response, excellent biocompatibility, and good biocompatibility

Active Publication Date: 2015-02-18
BEIJING UNIV OF CHEM TECH
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Furthermore, fluorescent probes responding in the two pH ranges of the extremely acidic and alkaline intervals are of great interest due to their widespread demand in gastric disease treatment and smart materials and the few reports and developments of such pH probes. become very precious

Method used

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  • Synthesis method of spiropyrane small-molecule fluorescent probe with extreme acid/extreme alkaline switch response and application of spiropyrane small-molecule fluorescent probe
  • Synthesis method of spiropyrane small-molecule fluorescent probe with extreme acid/extreme alkaline switch response and application of spiropyrane small-molecule fluorescent probe
  • Synthesis method of spiropyrane small-molecule fluorescent probe with extreme acid/extreme alkaline switch response and application of spiropyrane small-molecule fluorescent probe

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Embodiment 1

[0029] 1) Slowly add 43.3mmol of phosphorus oxychloride dropwise to 1.5mL of dimethylformamide in an ice bath, remove the ice bath, stir at room temperature for 30 minutes under a nitrogen atmosphere, then drop in 10mL of 2,7-dimethoxy The dichloromethane solution of dimethoxynaphthalene, in which 2,7-dimethoxynaphthalene is 5.3mmol, reacted at room temperature for 10h; after the reaction was completed, the reaction liquid was added dropwise into the ice-water mixture, hydrolyzed for 3h, extracted with dichloromethane, and then The solvent dichloromethane was evaporated to dryness, and finally recrystallized with methanol to obtain white needle-like crystals of 2,7-dimethoxy-1-aldehyde naphthalene, denoted as AO, with a yield of 78%;

[0030] 1 H NMR (CDCl 3,400MHz,ppm):δ10.90(s,1H,CHO),8.85(d,1H,ArH),7.98(d,1H,ArH),7.66(d,1H,ArH),7.12(d,1H, ArH),7.07(dd,1H,ArH),4.08(s,3H,OCH 3 ),3.98(s,3H,OCH 3 ). 13 C NMR (101MHz, CDCl 3 ): δ192.07, 164.86, 161.52, 137.37, 133.52, 129....

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Abstract

The invention discloses a synthesis method of a spiropyrane small-molecule fluorescent probe with extreme acid / extreme alkaline switch response and an application of the spiropyrane small-molecule fluorescent probe. By virtue of the synthesis method, naphthalene nucleus spiropyrane with two carboxyl groups and a phenolic hydroxyl group is synthesized by carrying out modification on three loca of spiropyrane, wherein the naphthalene nucleus spiropyrane has the characteristic of reversible switch type response on pH values of extreme acid / extreme alkaline; when the pH value is smaller than 1.0, red fluorescence is represented; when the pH value is 1.0-12.0, fluorescence is represented; when the pH value is greater than 12.0, blue-green fluorescence is represented. The synthesized spiropyrane small-molecule fluorescent probe also has the characteristics of being high in optical, thermal and chemical stability and structural designability, and excellent in biocompatibility and cell labeling property; meanwhile, the synthesized spiropyrane small-molecule fluorescent probe is safe and low in low toxicity, and is capable of smoothly entering bacteria for bio-labeling, implementing the pH response of extreme acid / extreme alkaline as same as that of solutions in organisms; furthermore, the synthesized spiropyrane small-molecule fluorescent probe can be used as a multifunctional cell fluorescence labeling dye and can be applied to scientific research and gene diagnosis in the field of biological medicines.

Description

technical field [0001] The invention belongs to the technical field of molecular fluorescent probes, and in particular relates to a synthesis method and application of a spiropyran small-molecule fluorescent probe with extreme acid / extreme base switch response. Background technique [0002] The human body usually has a certain pH due to the presence of body fluids. The pH value in the human body is generally in a relatively stable state, but when a person is affected by pathology or the like, the pH value in the body will change accordingly. By measuring the pH value of the human body, it is very convenient to detect the human health index in real time, which also makes the pH value measurement very important in the biological field. At present, the commonly used pH measurement methods are mainly glass electrodes and fluorescent probes, and fluorescent probes have received more and more attention in recent years because of their faster response than glass electrodes, safety...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
Inventor 尹梅贞万树林沈杰郑洋
Owner BEIJING UNIV OF CHEM TECH
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