Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
The potential of nitrones (N-oxides) as therapeutic antioxidants is due to their ability to counteract oxidative stress, mainly attributed to their action as radical scavengers toward C- and O-centered radicals. Among them, nitrones from the amidinoquinoxaline series resulted in interesting derivati...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-07-01
|
| Series: | Antioxidants |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2076-3921/10/8/1185 |
| _version_ | 1827686059711922176 |
|---|---|
| author | Nadia Gruber Liliana Orelli Cristina Minnelli Luca Mangano Emiliano Laudadio Giovanna Mobbili Pierluigi Stipa |
| author_facet | Nadia Gruber Liliana Orelli Cristina Minnelli Luca Mangano Emiliano Laudadio Giovanna Mobbili Pierluigi Stipa |
| author_sort | Nadia Gruber |
| collection | DOAJ |
| description | The potential of nitrones (N-oxides) as therapeutic antioxidants is due to their ability to counteract oxidative stress, mainly attributed to their action as radical scavengers toward C- and O-centered radicals. Among them, nitrones from the amidinoquinoxaline series resulted in interesting derivatives, due to the ease with which it is possible to introduce proper substituents within their structure in order to modulate their lipophilicity. The goal is to obtain lipophilic antioxidants that are able to interact with cell membranes and, at the same time, enough hydrophilic to neutralize those radicals present in a water compartment. In this work, the antioxidant efficacy of a series of amidinoquinoxaline nitrones has been evaluated regarding the oxidation of 2-deoxyribose and lipid peroxidation. The results have been rationalized on the basis of the different possible mechanisms involved, depending on some of their properties, such as lipophilicity, the ability to scavenge free radicals, and to undergo single electron transfer (SET) reactions. |
| first_indexed | 2024-03-10T09:03:07Z |
| format | Article |
| id | doaj.art-3332e27b54e244e1b3218823badbaf23 |
| institution | Directory Open Access Journal |
| issn | 2076-3921 |
| language | English |
| last_indexed | 2024-03-10T09:03:07Z |
| publishDate | 2021-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antioxidants |
| spelling | doaj.art-3332e27b54e244e1b3218823badbaf232023-11-22T06:35:21ZengMDPI AGAntioxidants2076-39212021-07-01108118510.3390/antiox10081185Amidinoquinoxaline-Based Nitrones as Lipophilic AntioxidantsNadia Gruber0Liliana Orelli1Cristina Minnelli2Luca Mangano3Emiliano Laudadio4Giovanna Mobbili5Pierluigi Stipa6Química Ogánica II, Departamento de Ciencias Químicas, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, CONICET, Junín 956, Buenos Aires 1113, ArgentinaQuímica Ogánica II, Departamento de Ciencias Químicas, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, CONICET, Junín 956, Buenos Aires 1113, ArgentinaDipartimento di Scienze della Vita e dell’Ambiente (DISVA), Università Politecnica delle Marche, via Brecce Bianche, 60131 Ancona, ItalyF. Hoffmann-La Roche AG, Grenzacherstrasse 124, 4070 Basel, SwitzerlandDipartimento di Scienze e Ingegneria della Materia, dell’Ambiente ed Urbanistica (SIMAU), Università Politecnica delle Marche, via Brecce Bianche, 60131 Ancona, ItalyDipartimento di Scienze della Vita e dell’Ambiente (DISVA), Università Politecnica delle Marche, via Brecce Bianche, 60131 Ancona, ItalyDipartimento di Scienze e Ingegneria della Materia, dell’Ambiente ed Urbanistica (SIMAU), Università Politecnica delle Marche, via Brecce Bianche, 60131 Ancona, ItalyThe potential of nitrones (N-oxides) as therapeutic antioxidants is due to their ability to counteract oxidative stress, mainly attributed to their action as radical scavengers toward C- and O-centered radicals. Among them, nitrones from the amidinoquinoxaline series resulted in interesting derivatives, due to the ease with which it is possible to introduce proper substituents within their structure in order to modulate their lipophilicity. The goal is to obtain lipophilic antioxidants that are able to interact with cell membranes and, at the same time, enough hydrophilic to neutralize those radicals present in a water compartment. In this work, the antioxidant efficacy of a series of amidinoquinoxaline nitrones has been evaluated regarding the oxidation of 2-deoxyribose and lipid peroxidation. The results have been rationalized on the basis of the different possible mechanisms involved, depending on some of their properties, such as lipophilicity, the ability to scavenge free radicals, and to undergo single electron transfer (SET) reactions.https://www.mdpi.com/2076-3921/10/8/1185antioxidantsnitronesspin trappingreactive oxygen speciesdensity functional theory (DFT)free radicals |
| spellingShingle | Nadia Gruber Liliana Orelli Cristina Minnelli Luca Mangano Emiliano Laudadio Giovanna Mobbili Pierluigi Stipa Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants Antioxidants antioxidants nitrones spin trapping reactive oxygen species density functional theory (DFT) free radicals |
| title | Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants |
| title_full | Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants |
| title_fullStr | Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants |
| title_full_unstemmed | Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants |
| title_short | Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants |
| title_sort | amidinoquinoxaline based nitrones as lipophilic antioxidants |
| topic | antioxidants nitrones spin trapping reactive oxygen species density functional theory (DFT) free radicals |
| url | https://www.mdpi.com/2076-3921/10/8/1185 |
| work_keys_str_mv | AT nadiagruber amidinoquinoxalinebasednitronesaslipophilicantioxidants AT lilianaorelli amidinoquinoxalinebasednitronesaslipophilicantioxidants AT cristinaminnelli amidinoquinoxalinebasednitronesaslipophilicantioxidants AT lucamangano amidinoquinoxalinebasednitronesaslipophilicantioxidants AT emilianolaudadio amidinoquinoxalinebasednitronesaslipophilicantioxidants AT giovannamobbili amidinoquinoxalinebasednitronesaslipophilicantioxidants AT pierluigistipa amidinoquinoxalinebasednitronesaslipophilicantioxidants |