Unknown

Dataset Information

0

Design, synthesis, in vitro, and in silico evaluations of kojic acid derivatives linked to amino pyridine moiety as potent tyrosinase inhibitors.

ABSTRACT: In the present study, novel series of kojic acid derivatives conjugated to amino pyridine moiety were designed and synthesized to explore their inhibitory activity against tyrosinase. To this end, the structure of all derivatives was characterized by 1H NMR, 13C NMR, FT-IR, and elemental analysis. Next, all derivatives were evaluated against tyrosinase compared to the kojic acid as positive control and exhibited different inhibitory potencies. Furthermore, the antioxidant potential of all derivatives was determined. The kinetic analysis of the most active agent revealed that 3-hydroxy-6-(hydroxymethyl)-2-((3-nitrophenyl)(pyridin-2-ylamino)methyl)-4H-pyran-4-one (4h) binds to the enzyme in the uncompetitive mode of action. The docking analysis and molecular dynamic simulations showed considerable binding affinity and significant interactions with tyrosinase enzyme to target the melanogenesis pathway, proposing them as potent candidates to control hyperpigmentation in the future.

SUBMITTER: Rezapour Niri D 

PROVIDER: S-EPMC10682633 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Design, synthesis, <i>in vitro</i>, and <i>in silico</i> evaluations of kojic acid derivatives linked to amino pyridine moiety as potent tyrosinase inhibitors.

Rezapour Niri Davood D   Sayahi Mohammad Hosein MH   Behrouz Somayeh S   Moazzam Ali A   Rasekh Fatemeh F   Tanideh Nader N   Irajie Cambyz C   Seif Nezhad Mohammad M   Larijani Bagher B   Iraji Aida A   Mahdavi Mohammad M  

Heliyon 20231103 11

In the present study, novel series of kojic acid derivatives conjugated to amino pyridine moiety were designed and synthesized to explore their inhibitory activity against tyrosinase. To this end, the structure of all derivatives was characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, FT-IR, and elemental analysis. Next, all derivatives were evaluated against tyrosinase compared to the kojic acid as positive control and exhibited different inhibitory potencies. Furthermore, the antioxidant p  ...[more]

Similar Datasets

Unknown Tyrosinase inhibitory mechanism and anti-browning properties of novel kojic acid derivatives bearing aromatic aldehyde moiety.
| S-EPMC9807860 | biostudies-literature
Unknown Nitrophenylpiperazine derivatives as novel tyrosinase inhibitors: design, synthesis, and in silico evaluations.
| S-EPMC10998383 | biostudies-literature
Unknown In vitro and in silico studies of the inhibitory effects of some novel kojic acid derivatives on tyrosinase enzyme.
| S-EPMC4818360 | biostudies-literature
Unknown Analysis of Kojic Acid Derivatives as Competitive Inhibitors of Tyrosinase: A Molecular Modeling Approach.
| S-EPMC8152073 | biostudies-literature
Unknown Urolithin and Reduced Urolithin Derivatives as Potent Inhibitors of Tyrosinase and Melanogenesis: Importance of the 4-Substituted Resorcinol Moiety.
| S-EPMC8199067 | biostudies-literature
Unknown Design, synthesis, and molecular dynamics simulation studies of some novel kojic acid fused 2-amino-3-cyano-4H-pyran derivatives as tyrosinase inhibitors.
| S-EPMC10885651 | biostudies-literature
Unknown Synthesis, anti-browning effect and mechanism research of kojic acid-coumarin derivatives as anti-tyrosinase inhibitors.
| S-EPMC10826612 | biostudies-literature
Unknown Synthesis, Anticancer Screening, and In Silico Evaluations of Thieno[2,3-<i>c</i>]pyridine Derivatives as Hsp90 Inhibitors.
| S-EPMC11858597 | biostudies-literature
Unknown Kinetic and computational molecular docking simulation study of novel kojic acid derivatives as anti-tyrosinase and antioxidant agents.
| S-EPMC6522964 | biostudies-literature
Unknown Kojic Acid Peptide: A New Compound with Anti-Tyrosinase Potential.
| S-EPMC5064183 | biostudies-literature