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Antioxidant Activity, Stability in Aqueous Medium and Molecular Docking/Dynamics Study of 6-Amino- and N-Methyl-6-amino-L-ascorbic Acid

The antioxidant activity and chemical stability of 6-amino-6-deoxy-L-ascorbic acid (D1) and N-methyl-6-amino-6-deoxy-L-ascorbic acid (D2) were examined with ABTS and DPPH assays and compared with the reference L-ascorbic acid (AA). In addition, the optimal storing conditions, as well as the pH at wh...

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Autores principales: Saftić Martinović, Lara, Birkic, Nada, Miletić, Vedran, Antolović, Roberto, Štanfel, Danijela, Wittine, Karlo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9862502/
https://www.ncbi.nlm.nih.gov/pubmed/36674926
http://dx.doi.org/10.3390/ijms24021410
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author Saftić Martinović, Lara
Birkic, Nada
Miletić, Vedran
Antolović, Roberto
Štanfel, Danijela
Wittine, Karlo
author_facet Saftić Martinović, Lara
Birkic, Nada
Miletić, Vedran
Antolović, Roberto
Štanfel, Danijela
Wittine, Karlo
author_sort Saftić Martinović, Lara
collection PubMed
description The antioxidant activity and chemical stability of 6-amino-6-deoxy-L-ascorbic acid (D1) and N-methyl-6-amino-6-deoxy-L-ascorbic acid (D2) were examined with ABTS and DPPH assays and compared with the reference L-ascorbic acid (AA). In addition, the optimal storing conditions, as well as the pH at which the amino derivatives maintain stability, were determined using mass spectrometry. Comparable antioxidant activities were observed for NH-bioisosteres and AA. Moreover, D1 showed higher stability in an acidic medium than the parent AA. In addition, AA, D1, and D2 share the same docking profile, with wild-type human peroxiredoxin as a model system. Their docking scores are similar to those of dithiothreitol (DTT). This suggests a similar binding affinity to the human peroxiredoxin binding site.
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spelling pubmed-98625022023-01-22 Antioxidant Activity, Stability in Aqueous Medium and Molecular Docking/Dynamics Study of 6-Amino- and N-Methyl-6-amino-L-ascorbic Acid Saftić Martinović, Lara Birkic, Nada Miletić, Vedran Antolović, Roberto Štanfel, Danijela Wittine, Karlo Int J Mol Sci Article The antioxidant activity and chemical stability of 6-amino-6-deoxy-L-ascorbic acid (D1) and N-methyl-6-amino-6-deoxy-L-ascorbic acid (D2) were examined with ABTS and DPPH assays and compared with the reference L-ascorbic acid (AA). In addition, the optimal storing conditions, as well as the pH at which the amino derivatives maintain stability, were determined using mass spectrometry. Comparable antioxidant activities were observed for NH-bioisosteres and AA. Moreover, D1 showed higher stability in an acidic medium than the parent AA. In addition, AA, D1, and D2 share the same docking profile, with wild-type human peroxiredoxin as a model system. Their docking scores are similar to those of dithiothreitol (DTT). This suggests a similar binding affinity to the human peroxiredoxin binding site. MDPI 2023-01-11 /pmc/articles/PMC9862502/ /pubmed/36674926 http://dx.doi.org/10.3390/ijms24021410 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Saftić Martinović, Lara
Birkic, Nada
Miletić, Vedran
Antolović, Roberto
Štanfel, Danijela
Wittine, Karlo
Antioxidant Activity, Stability in Aqueous Medium and Molecular Docking/Dynamics Study of 6-Amino- and N-Methyl-6-amino-L-ascorbic Acid
title Antioxidant Activity, Stability in Aqueous Medium and Molecular Docking/Dynamics Study of 6-Amino- and N-Methyl-6-amino-L-ascorbic Acid
title_full Antioxidant Activity, Stability in Aqueous Medium and Molecular Docking/Dynamics Study of 6-Amino- and N-Methyl-6-amino-L-ascorbic Acid
title_fullStr Antioxidant Activity, Stability in Aqueous Medium and Molecular Docking/Dynamics Study of 6-Amino- and N-Methyl-6-amino-L-ascorbic Acid
title_full_unstemmed Antioxidant Activity, Stability in Aqueous Medium and Molecular Docking/Dynamics Study of 6-Amino- and N-Methyl-6-amino-L-ascorbic Acid
title_short Antioxidant Activity, Stability in Aqueous Medium and Molecular Docking/Dynamics Study of 6-Amino- and N-Methyl-6-amino-L-ascorbic Acid
title_sort antioxidant activity, stability in aqueous medium and molecular docking/dynamics study of 6-amino- and n-methyl-6-amino-l-ascorbic acid
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9862502/
https://www.ncbi.nlm.nih.gov/pubmed/36674926
http://dx.doi.org/10.3390/ijms24021410
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