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Reagent and method for detecting biological endogenous oxidants

A technology of compound and composition, applied in the detection reagent and field of biological endogenous oxidant

Inactive Publication Date: 2014-12-10
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for highly oxidizing species (including ClO - and HO · ) is still a problem with the high selectivity

Method used

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  • Reagent and method for detecting biological endogenous oxidants
  • Reagent and method for detecting biological endogenous oxidants
  • Reagent and method for detecting biological endogenous oxidants

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0128] Embodiment 1: the preparation of compound 1

[0129]

[0130] 100mg (0.45mmol) of 6-nitro-7-fluoro-4-methylcoumarin, 56mg of m-methoxyphenol (0.45mmol) and 62mg of potassium carbonate (0.45mmol) were added to 20ml of acetonitrile, reflux Stir overnight, then filter with suction, spin the filtrate to dry the solvent under reduced pressure, and separate the product with a chromatographic column, eluting with a mixed solvent of petroleum ether / ethyl acetate (2:1, V / V), to obtain 82 mg of a yellow solid, with a yield of 60 %.

[0131] Take 210 mg (0.64 mmol) of the compound obtained in the previous step into a reaction flask, add a catalytic amount of 5% Pd / C, and methanol as a solvent, put it in a hydrogenation reduction device and react for 6 hours, suction filter after the reaction, and depressurize the filtrate The solvent was spin-dried, and the product was filtered off Pd / C with a very short chromatographic column, and then recrystallized with dichloromethane to o...

Embodiment 2

[0135] Embodiment 2: the preparation of compound 2

[0136]

[0137] 6-nitro-7-fluoro-4-methylcoumarin 650mg (2.91mmol) and 870mg of 4-chloro-3-hydroxy p-toluenesulfonate (2.91mmol) and 415mg of potassium carbonate (3.00mmol ) was added to 40ml of acetonitrile, refluxed and stirred overnight, then suction filtered, the filtrate was spin-dried under reduced pressure, the product was separated by chromatographic column, and the eluent was petroleum ether / ethyl acetate mixed solvent (15:4, V / V) , to obtain 320mg of yellow solid, yield 22%.

[0138] Take 200mg (0.40mmol) of the compound obtained in the previous step into a reaction flask, add a catalytic amount of 5% Pd / C, and methanol as a solvent, put it in a hydrogenation reduction device and react for 6 hours, suction filter after the reaction, and depressurize the filtrate The solvent was spin-dried, and the product was filtered off Pd / C with a very short chromatographic column, and then recrystallized with ethyl acetate / ...

Embodiment 3

[0141] Embodiment 3: the preparation of compound 3

[0142]

[0143] 100mg (0.45mmol) of 6-nitro-7-fluoro-4-methylcoumarin, 56mg of m-methoxyphenol (0.45mmol) and 62mg of potassium carbonate (0.45mmol) were added to 20ml of acetonitrile, reflux Stir overnight, then filter with suction, spin the filtrate to dry the solvent under reduced pressure, the product is separated by a chromatographic column, and the eluent is a mixed solvent of petroleum ether / ethyl acetate (2:1, V / V), and 82 mg of a yellow solid is obtained, with a yield of 60 %.

[0144] Take 210 mg (0.64 mmol) of the compound obtained in the previous step into a reaction flask, add a catalytic amount of 5% Pd / C, and methanol as a solvent, put it in a hydrogenation reduction device and react for 6 hours, suction filter after the reaction, and depressurize the filtrate The solvent was spin-dried, and the product was filtered off Pd / C with a very short chromatographic column, and then recrystallized with dichlorometha...

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Abstract

The invention relates to a chemical reagent and a method for detecting biological endogenous oxidants, in particular to a compound shown as a general formula I or II and a method for detecting the biological endogenous oxidants such as reactive oxygen species (ROS) and reactive nitrogen species (RNS) by using the compound. The compound has high selectivity particularly for peroxynitrous acid (ONOO-) and hypochlorous acid (ClO-) and can be applied to a cell microscopic imaging experiment, a fluorescent dye can be generated, and a sensitive, proportional and multi-channel fluorescent signal can be sent.

Description

technical field [0001] The invention relates to a chemical reagent and a detection method for detecting biological endogenous oxidants. Background technique [0002] Reactive oxygen species (ROS) and reactive nitrogen species (RNS) are usually considered as very small inorganic or organic molecules with strong oxidizing properties. There are various forms of ROS and RNS, including free radicals such as superoxide radicals, hydroxyl radicals, nitric oxide, nitrogen dioxide, and organic hydroperoxide radicals, as well as non-radical species such as hydrogen peroxide, Singlet oxygen, ozone, nitrous acid, peroxynitrite, and hypochlorous acid. ROS and RNS are by-products of cellular respiration. Under normal conditions, ROS and RNS are present at very low levels and play important roles in cell signaling. Whereas during oxidative stress, the levels of ROS and RNS are dramatically increased, which can cause severe damage to various biomolecules such as proteins, lipids and DNA....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C07D498/04G01N21/64G01N33/52
Inventor 杨有军张泉娟钱旭红
Owner EAST CHINA UNIV OF SCI & TECH
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