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Iron-binding and anti-fenton properties of novel amino acid-derived cyclic imide dioximes
Mravljak, Janez (Author), Jakopin, Žiga (Author)

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Abstract
We present a novel route for the preparation of amino acid-derived cyclic imide dioxime derivatives. Readily accessible amino acids were conveniently converted to their corresponding cyclic imide dioximes in simple synthetic steps. The aim of this work was to describe and compare the iron-chelating and antioxidant properties of synthesized compounds in relation to their molecular structure, and in particular, which of those features are essential for iron(II)-chelating ability. The glutarimide dioxime moiety has been established as an iron(II)-binding motif and imparts potent anti-Fenton properties to the compounds. Compound 3 was shown to strongly suppress hydroxyl radical formation by preventing iron cycling via Fe-complexation. These findings provide insights into the structural requirements for achieving anti-Fenton activity and highlight the potential use of glutarimide dioximes as antioxidants.

Language:English
Keywords:amino acid, building block, iron(II)-chelating agents, cyclic imide dioxime, antioxidant, Fenton reaction, anti-Fenton
Work type:Article (dk_c)
Tipology:1.01 - Original Scientific Article
Organization:FFA - Faculty of Pharmacy
Year:2019
Number of pages:Str. 1-12
Numbering:Vol. 8, iss. 10, art. 473
UDC:547.466:615.4:54
ISSN on article:2076-3921
DOI:10.3390/antiox8100473 This link opens in a new window
COBISS.SI-ID:4819569 This link opens in a new window
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Downloads:63
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Record is a part of a journal

Title:Antioxidants
Shortened title:Antioxidants
Publisher:MDPI
ISSN:2076-3921
COBISS.SI-ID:522976025 This link opens in a new window

Document is financed by a project

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije (ARRS)
Project no.:P1-0208
Name:Farmacevtska kemija: načrtovanje, sinteza in vrednotenje učinkovin

Licences

License:CC BY 4.0, Creative Commons Attribution 4.0 International
Link:http://creativecommons.org/licenses/by/4.0/
Description:This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
Licensing start date:12.03.2021

Secondary language

Language:Slovenian
Keywords:aminokisline, antioksidanti, Fentonova reakcija, ciklični dioksimi

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