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

Lara Saftić Martinović; Nada Birkic; Vedran Miletić; Roberto Antolović; Danijela Štanfel; Karlo Wittine

doi:10.3390/ijms24021410

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

Int J Mol Sci. 2023 Jan 11;24(2):1410. doi: 10.3390/ijms24021410.

Authors

Lara Saftić Martinović¹, Nada Birkic¹, Vedran Miletić², Roberto Antolović³, Danijela Štanfel⁴, Karlo Wittine⁵

Affiliations

¹ Department of Biotechnology, University of Rijeka, Radmile Matejčić 2, 51000 Rijeka, Croatia.
² Group for Applications and Services on Exascale Research Infrastructure, Faculty of Informatics and Digital Technologies, University of Rijeka, Radmile Matejčić 2, 51000 Rijeka, Croatia.
³ Department of Nursing, School of Medicine, Catholic University of Croatia, Ilica 242, 10000 Zagreb, Croatia.
⁴ Jadran-Galenski Laboratorij d.d., Svilno 20, 51000 Rijeka, Croatia.
⁵ Selvita Ltd., Prilaz Baruna Filipovića 29, 10000 Zagreb, Croatia.

Abstract

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.

Keywords: ABTS; DPPH; MS/MS; antioxidant; ascorbic acid; molecular docking/dynamics; peroxiredoxin; stability.

MeSH terms

Antioxidants*
Ascorbic Acid* / chemistry
Humans
Molecular Docking Simulation

Substances

Antioxidants
Ascorbic Acid

Grants and funding

We are grateful to the project “Research infrastructure for campus-based laboratories at the University of Rijeka”, co-financed by the European Regional Development Fund (ERDF). We would also like to acknowledge the financial support of Selvita Ltd.