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Hypochlorous acid fluorescent probe as well as preparation method and application thereof

A fluorescent probe, hypochlorous acid technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc.

Inactive Publication Date: 2018-08-21
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no report on the use of natural sesquiterpenes as raw materials to synthesize fluorescent probes for the detection of hypochlorous acid

Method used

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  • Hypochlorous acid fluorescent probe as well as preparation method and application thereof
  • Hypochlorous acid fluorescent probe as well as preparation method and application thereof
  • Hypochlorous acid fluorescent probe as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The synthesis process of the novel hypochlorous acid fluorescent probe is as follows:

[0033]

[0034] Specific steps are as follows:

[0035] 1) Preparation of 7-(4'-diethylaminobenzylidene) isolongifanone:

[0036] Add 8mmol isolongifolanone, 10mmol p-diethylaminobenzaldehyde, 8mmol sodium ethoxide and 30mL ethanol in sequence to a three-necked flask equipped with a stirrer, thermometer and reflux condenser, and heat to reflux at 80-90°C for reaction , react for about 5 hours until the conversion rate of isolongifolanone reaches over 95% (GC tracking detection). The reactant was extracted 3 times with 30 mL of ethyl acetate, the organic phases were combined, and washed several times with saturated brine until neutral; the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to recover the solvent to obtain 7-(4′-di The crude product of ethylaminobenzylidene) isolongifolanone is recrystallized with ethanol-ethyl acetate to obtain colorl...

Embodiment 2

[0048] 1-(((4-(4′-(diethylamino)phenyl)-6,6,10,10-tetramethyl-5,7,8,9,10,10α-hexahydro-6H- 6α,9-Methylenebenzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol was dissolved in PBS buffer solution (pH=7.4, 10mM, 50% (v / v ) ethanol), prepared into a solution with a concentration of 10 μM, and also active oxygen and anions such as H 2 o 2 、ONOO - , O 2 - , NO 2 - , F - , Cl - 、Br - , NO 3 - 、HSO 3 - , SO 3 2- , SO 4 2- 、HS - 、HCO 3 - , CO 3 2- 、CN - 、SCN - , ClO 2 - , ClO 4 - , ClO -Dissolve in PBS buffer solution to make a solution with a concentration of 1mM. Different reactive oxygen species and anion pairs were measured for 1-(((4-(4′-(diethylamino)phenyl)-6,6,10,10-tetramethyl-5,7,8,9,10 , the fluorescence spectrum of 10α-hexahydro-6H-6α,9-methanobenzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol, such as figure 1 shown. The results showed that compared with other reactive oxygen species and anions, only hypochlorous acid could cause significant ch...

Embodiment 3

[0050] 1-(((4-(4′-(diethylamino)phenyl)-6,6,10,10-tetramethyl-5,7,8,9,10,10α-hexahydro-6H- 6α,9-Methylenebenzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol was dissolved in PBS buffer solution (pH=7.4, 10mM, 50% (v / v ) ethanol) to prepare a solution with a concentration of 10 μM, and also dissolve hypochlorous acid in PBS buffer solution to prepare a concentration of 0, 2, 4, 6, 8, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40 μM solutions. 1-(((4-(4'-(diethylamino)phenyl)-6,6,10,10-tetramethyl-5,7,8,9,10 ,10α-hexahydro-6H-6α,9-methanobenzo[h]-2-quinolyl)imino)methyl)naphthalene-2-ol UV absorption spectrum, such as figure 2 shown. The results showed that the ultraviolet absorption of the compound around 430-450nm decreased significantly, indicating that the compound could react with hypochlorous acid.

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Abstract

The invention discloses a hypochlorous acid fluorescent probe as well as a preparation method and an application thereof. Iso-longitolanone as a derivative of longifolene which is a natural renewableresource is taken as a raw material and subjected to condensation with 4-diethylaminobenzaldehyde, and 7-(4'-diethylaminobenzylidene) iso-longitolanone is generated; 7-(4'-diethylaminobenzylidene) iso-longitolanone and guanidine hydrochloride are subjected to condensation and cyclization, 4-(4'-diethylaminophenyl)-6,6,10,10-tetramethyl-6,7,8,9,10,10-hexahydro-5H-methenobenzo-2-quinolinamine is obtained and subjected to condensation with 2-hydroxy-1-naphthaldehyde, and a fluorescent probe compound is obtained. The compound only can be subjected to a specific reaction with hypochlorous acid, emits blue fluorescence under irradiation of 365 nm ultraviolet rays, can serve as the fluorescent probe for detecting hypochlorous acid and has good application prospect.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a novel hypochlorous acid fluorescent probe as well as its preparation method and application. Background technique [0002] Hypochlorous acid (HClO) is an important weakly acidic reactive oxygen species in living systems and plays a very important role in various physiological processes. In leukocytes including monocytes, neutrophils and macrophages, under the catalysis of myeloperoxidase (MPO), hydrogen peroxide oxidizes chloride ions to generate endogenous hypochlorous acid. However, excessive hypochlorous acid can lead to tissue damage and various diseases such as neuronal degeneration and necrosis, cardiovascular disease, rheumatoid arthritis, asthma and atherosclerosis. Because hypochlorous acid is so important in biology, real-time monitoring of the dynamic distribution of hypochlorous acid in cells is of great significance to the medical diagnosis neighborho...

Claims

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Application Information

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IPC IPC(8): C07D239/70C09K11/06G01N21/64
CPCC07D239/70C09K11/06C09K2211/1044G01N21/6428G01N21/6486
Inventor 王石发王忠龙张燕徐徐杨益琴徐海军李明新谷文姜倩
Owner NANJING FORESTRY UNIV
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