2-(10-buty1-2-methoxy-10H-phenothiazin-3-yl)-7-(diethylamino)chromenylium perchlorate derivative as well as preparation method and application thereof

A technology of phenothiazine derivatives and benzopyrylium, which is applied in the field of chemical synthesis, can solve problems such as high detection limit, poor water solubility, and inability to realize real-time quantitative detection of HClO

Active Publication Date: 2021-02-12
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, many fluorescent probes for detecting changes in intracellular HClO levels have been developed (Chem 2020, 6, 832–866; Chem. Rev. 2019, 119, 10403-10519; Chem. Soc. Rev. 2016, 45, 2976 -3016), but they have defects such as long response time to HClO, high detection limit, poor water solubility, etc., and they cannot realize the real-time quantitative detection of HClO in the process of ferroptosis

Method used

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  • 2-(10-buty1-2-methoxy-10H-phenothiazin-3-yl)-7-(diethylamino)chromenylium perchlorate derivative as well as preparation method and application thereof
  • 2-(10-buty1-2-methoxy-10H-phenothiazin-3-yl)-7-(diethylamino)chromenylium perchlorate derivative as well as preparation method and application thereof
  • 2-(10-buty1-2-methoxy-10H-phenothiazin-3-yl)-7-(diethylamino)chromenylium perchlorate derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 Synthesis of benzopyrylium-phenothiazine derivatives

[0055] (1) Synthesis of 10-n-butyl-2-methoxyphenothiazine

[0056]

[0057] Under argon atmosphere, 2-methoxyphenothiazine (5 mmol, 1.145 g), bromobutane (10 mmol, 1.36 g), sodium hydroxide (10 mmol, 0.4 g) and potassium iodide (0.072 mmol, 12 mg) was added to dimethyl sulfoxide (10 mL), the reaction system was reacted at 95 °C for 6 h, cooled to room temperature, quenched by adding 100 mL of water, followed by extraction with dichloromethane, the organic phase was collected and washed with anhydrous Drying over sodium sulfate, removing the organic solvent under reduced pressure, the resulting sample was separated by column chromatography (petroleum ether as the eluent) to obtain 10-n-butyl-2-methoxyphenothiazine (compound 1) as a colorless oily liquid, producing The rate is 89%.

[0058] (2) Synthesis of 1-(10-n-butyl-2-methoxy-phenothiazin-3-yl)ethanone

[0059]

[0060] Under ice bath, compound...

Embodiment 2

[0067] Example 2 Detection of HClO by Benzopyrylium-Phenothiazine Derivative PTC in Aqueous Phase System

[0068] Add 2.98mL PBS (10 mM, pH = 7.4) buffer solution and 10 μL benzopyrylium-phenothiazine derivative PTC (3 mM) to a series of fluorescence cuvettes successively, then add HClO, ONOO - , HO • , H 2 o 2 , O 2 −• , t -BuOOH,NO, Cys, Hcy, GSH, L-Ser, DL-Met, L-Phe, L-Lys, L-Leu, L-Pro, L-His,S 2- , NO 3 - ,NO 2 - , HSO 3 - , OAc - , SO 4 2- , PO 4 3- , K + , Zn 2+ , Cu 2+ , Na + (30 mM), if the fluorescence intensity of benzopyrylium-phenothiazine derivative PTC in PBS buffer at 627nm is significantly enhanced, indicating that HClO is added; if benzopyrylium-phenothiazine derivative PTC The fluorescence intensity of the PBS buffer solution at 627nm did not change significantly, indicating that it was not HClO that was added.

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Abstract

The invention provides a 2-(10-buty1-2-methoxy-10H-phenothiazin-3-yl)-7-(diethylamino)chromenylium perchlorate derivative as well as a preparation method and application thereof. The 2-(10-buty1-2-methoxy-10H-phenothiazin-3-yl)-7-(diethylamino)chromenylium perchlorate derivative for real-time quantitative detection of HClO provided by the invention is simple and convenient to synthesize, cheap andeasily available in raw materials and good in water solubility, shows the advantages of high sensitivity, good selectivity and instantaneous response to HClO detection and can realize real-time quantitative detection of hypochlorous acid in a water phase system and living cells, and detection and quantification of HClO in the living cell and zebra fish in-vivo ferroptosis process are realized forthe first time, and the derivative has clinical application values.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and biosensing technology, and specifically relates to a benzopyrylium-phenothiazine derivative and its preparation method and application; the invention also relates to a benzopyrylium-phenothiazine derivative The application of detecting hypochlorous acid in an aqueous phase system; the present invention also relates to the application of benzopyrylium-phenothiazine derivatives in detecting living cells and the application of hypochlorous acid in the process of ferroptosis. Background technique [0002] Hypochlorous acid (HClO) in the body is mainly produced by the myeloperoxidase (MPO) secreted by immune cells when the inflammatory response catalyzes the peroxidation reaction of chloride ions, and it can also be produced by exogenous stimuli (such as lipopolysaccharide and phorbol). ester) induced. As an important reactive oxygen species in cells, HClO plays an important role in resisting the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04G01N21/64
CPCC07D417/04G01N21/6428Y02A50/30
Inventor 包霞珍霍聪德袁勇
Owner NORTHWEST NORMAL UNIVERSITY
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