Format

Send to

Choose Destination
Bioorg Chem. 2017 Oct;74:201-211. doi: 10.1016/j.bioorg.2017.08.001. Epub 2017 Aug 10.

Structure-activity relationships and molecular docking of thirteen synthesized flavonoids as horseradish peroxidase inhibitors.

Author information

1
Laboratoire des Sciences fondamentales, Université Amar Telidji, Laghouat BP37G, Laghouat, Algeria; Laboratoire des Sciences chimiques et physiques appliquées, ENS de Laghouat, BP 4033 Laghouat, Algeria.
2
Laboratoire des Sciences fondamentales, Université Amar Telidji, Laghouat BP37G, Laghouat, Algeria; Laboratoire des Sciences chimiques et physiques appliquées, ENS de Laghouat, BP 4033 Laghouat, Algeria. Electronic address: amardjeridane@yahoo.fr.
3
Laboratoire des Sciences fondamentales, Université Amar Telidji, Laghouat BP37G, Laghouat, Algeria.
4
Laboratoire de Recherche en Systèmes Chimiques Complexes, Faculté des Sciences et Technique de Saint-Jérôme, Université Paul Cézanne, Marseille, France.

Abstract

For the first time, the structure-activity relationships of thirteen synthesized flavonoids have been investigated by evaluating their ability to modulate horseradish peroxidase (HRP) catalytic activity. Indeed, a modified spectrophotometrically method was carried out and optimized using 4-methylcatechol (4-MC) as peroxidase co-substrate. The results show that these flavonoids exhibit a great capacity to inhibit peroxidase with Ki values ranged from 0.14±0.01 to 65±0.04mM. Molecular docking has been achieved using Auto Dock Vina program to discuss the nature of interactions and the mechanism of inhibition. According to the docking results, all the flavonoids have shown great binding affinity to peroxidase. These molecular modeling studies suggested that pyran-4-one cycle acts as an inhibition key for peroxidase. Therefore, potent peroxidase inhibitors are flavonoids with these structural requirements: the presence of the hydroxyl (OH) group in 7, 5 and 4' positions and the absence of the methoxy (O-CH3) group. Apigenin contributed better in HRP inhibitory activity. The present study has shown that the studied flavonoids could be promising HRP inhibitors, which can help in developing new molecules to control thyroid diseases.

KEYWORDS:

Flavones; Flavonols; Horseradish peroxidase inhibitor; Molecular docking; Structure-relationship

PMID:
28843840
DOI:
10.1016/j.bioorg.2017.08.001
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Elsevier Science
Loading ...
Support Center