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具有自旋捕获性质的新型杂芳基硝酮的合成与评价

Synthesis and evaluation of new heteroaryl nitrones with spin trap properties.

作者信息

Barriga-González G, Aliaga C, Chamorro E, Olea-Azar C, Norambuena E, Porcal W, González M, Cerecetto H

机构信息

Departamento de Química, Facultad de Ciencias Básicas, Universidad Metropolitana de Ciencias de la Educación Av. José Pedro Alessandri 774, Ñuñoa Santiago Chile

Facultad de Química y Biología, Universidad de Santiago de Chile Av. Bernardo O'Higgins 3363 Santiago Chile.

出版信息

RSC Adv. 2020 Nov 4;10(66):40127-40135. doi: 10.1039/d0ra07720h. eCollection 2020 Nov 2.

DOI:10.1039/d0ra07720h
PMID:35520832
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9057510/
Abstract

A new series of heteroaryl nitrones were synthesized and evaluated as free radical traps due to the results showed in our previous report. The physicochemical characterization of these new nitrones by electron spin resonance (ESR) demonstrated their high capability to trap and stabilize different atom centered free radicals generated by the Fenton reaction. Additionally, we intensely studied them in terms of their physicochemical properties. Kinetic studies, including the use of a method based on competition and the hydroxyl adduct decay, gave the corresponding rate constants and half-lives at the physiological pH of these newly synthesized nitrones. New nitrones derived from quinoxaline 1,4-dioxide heterocycles were more suitable than DMPO to trap hydroxyl free radicals with a half-life longer than two hours. We explain some of the results using computational chemistry through density functional theory (DFT).

摘要

由于我们之前报告中显示的结果，合成了一系列新的杂芳基硝酮并将其作为自由基捕获剂进行评估。通过电子自旋共振（ESR）对这些新硝酮进行的物理化学表征表明，它们具有捕获和稳定由芬顿反应产生的不同原子中心自由基的高能力。此外，我们深入研究了它们的物理化学性质。动力学研究，包括使用基于竞争和羟基加合物衰变的方法，给出了这些新合成硝酮在生理pH下的相应速率常数和半衰期。源自喹喔啉1,4-二氧化物杂环的新硝酮比DMPO更适合捕获羟基自由基，其半衰期超过两小时。我们通过密度泛函理论（DFT）使用计算化学来解释一些结果。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/96df/9057510/6960c6277f45/d0ra07720h-f12.jpg
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本文引用的文献

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New heteroaryl nitrones with spin trap properties: Identification of a 4-furoxanyl derivative with excellent properties to be used in biological systems.具有自旋捕获特性的新型杂芳基硝酮：鉴定出一种 4-呋喃基衍生物，具有在生物体系中应用的优异性能。
Bioorg Med Chem. 2010 Jan 15;18(2):795-802. doi: 10.1016/j.bmc.2009.11.053. Epub 2009 Nov 27.
2
Heteroarylnitrones as drugs for neurodegenerative diseases: synthesis, neuroprotective properties, and free radical scavenger properties.杂芳基硝酮作为神经退行性疾病的药物：合成、神经保护特性及自由基清除特性
J Med Chem. 2008 Oct 9;51(19):6150-9. doi: 10.1021/jm8006432. Epub 2008 Sep 13.
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Synthesis and characterization of a practically better DEPMPO-type spin trap, 5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO).
一种实际性能更优的DEPMPO型自旋捕获剂5-(2,2-二甲基-1,3-丙氧基环磷酰基)-5-甲基-1-吡咯啉N-氧化物（CYPMPO）的合成与表征
Free Radic Res. 2006 Nov;40(11):1166-72. doi: 10.1080/10715760600883254.
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Applications of electron spin resonance and spin trapping in tropical parasitic diseases.电子自旋共振和自旋捕获技术在热带寄生虫病中的应用。
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