ArticlePloS one2017
Carvacrol derivatives as mushroom tyrosinase inhibitors; synthesis, kinetics mechanism and molecular docking studies.
Article in PloS one, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 70 citations in OpenAlex.
- Mechanistic profiling and optimized production of Altenusin, a fungal carboxy-biphenyl scaffold for tyrosinase inhibition.RSC advances · 2026Article
- Biological activities of Centaurium erythraea and its main chemotypes: menthol, carvacrol, and tricosane.AMB Express · 2025Article
- Natural Tyrosinase Inhibitors fromMolecules (Basel, Switzerland) · 2025Article
- Chemical Composition, Anti-Tyrosinase and Antioxidant Potential of Essential Oils fromMolecules (Basel, Switzerland) · 2025Article
- Tyrosinase Inhibition and Antimelanogenic Effects of Resorcinol-Containing Compounds.ChemMedChem · 2024Review
- Anilino-1,4-naphthoquinones as potent mushroom tyrosinase inhibitors:Journal of enzyme inhibition and medicinal chemistry · 2024Article
- Phytochemical characterization and multifaceted bioactivity assessment of essential oil fromHeliyon · 2024Article
- Synthesis,Journal of enzyme inhibition and medicinal chemistry · 2023Article
- Exploring Major Flavonoid Phytochemicals fromInternational journal of molecular sciences · 2023Article
- Naturally-Occurring Tyrosinase Inhibitors Classified by Enzyme Kinetics and Copper Chelation.International journal of molecular sciences · 2023Review
- Tyrosinase Inhibitors Naturally Present in Plants and Synthetic Modifications of These Natural Products as Anti-Melanogenic Agents: A Review.Molecules (Basel, Switzerland) · 2023Review
- Preparation of Spice Extracts: Evaluation of Their Phytochemical, Antioxidant, Antityrosinase, and Anti-BioMed research international · 2022Article
- Identification of (Z)-2-benzylidene-dihydroimidazothiazolone derivatives as tyrosinase inhibitors: Anti-melanogenic effects andComputational and structural biotechnology journal · 2022Article
- Review
- Natural and synthetic flavonoid derivatives as new potential tyrosinase inhibitors: a systematic review.RSC advances · 2021Review
- Synthesis, Kinetics, Binding Conformations and Structure-activity Relationship of Potent Tyrosinase Inhibitors: Aralkylated 2-aminothiazole-ethyltriazole Hybrids.Iranian journal of pharmaceutical research : IJPR · 2021Article
- (Molecules (Basel, Switzerland) · 2020Article
- Enzyme Inhibitory Kinetics and Molecular Docking Studies of Halo-Substituted Mixed Ester/Amide-Based Derivatives as Jack Bean Urease Inhibitors.BioMed research international · 2020Article
- Synthesis, computational studies, tyrosinase inhibitory kinetics and antimelanogenic activity of hydroxy substituted 2-[(4-acetylphenyl)amino]-2-oxoethyl derivatives.Journal of enzyme inhibition and medicinal chemistry · 2019Article
- A comprehensive review on tyrosinase inhibitors.Journal of enzyme inhibition and medicinal chemistry · 2019Review
Corrections and comments
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Authors and funding
8 authors at 6 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The present work describesthe development of highly potent mushroom tyrosinase inhibitor better than the standard kojic acid. Carvacrol derivatives 4a-f and 6a-d having substituted benzoic acid and cinnamic acidresidues were synthesized with the aim to possess potent tyrosinase inhibitory activity.The structures of the synthesized compounds were ascertained by their spectroscopic data (FTIR, 1HNMR, 13CNMR and Mass Spectroscopy).Mushroom tyrosinase inhibitory activity of synthesized compounds was determined and it was found that one of the derivative 6c possess higher activity (IC50 0.0167μM) than standard kojic acid (IC50 16.69μM). The derivatives 4c and 6b also showed good tyrosinase inhibitory activity with (IC50 16.69μM) and (IC50 16.69μM) respectively.Lineweaver-Burk and Dixon plots were used for the determination of kinetic mechanism of the compounds 4c and 6b and 6c. The kinetic analysis revealed that compounds 4c and 6b showed mixed-type inhibition while 6c is a non-competitive inhibitor having Ki values19 μM, 10 μM, and 0.05 μMrespectively. The enzyme inhibitory kinetics further showed thatcompounds 6b and 6c formed irreversible enzyme inhibitor complex while 4c bind reversibly with mushroom tyrosinase.The docking studies showed that compound 6c have maximum binding affinity against mushroom tyrosinase (PDBID: 2Y9X) with binding energy value (-7.90 kcal/mol) as compared to others.The 2-hydroxy group in compound 6c interacts with amino acid HIS85 which is present in active binding site. The wet lab results are in good agreement with the dry lab findings.Based upon our investigation we may propose that the compound 6c is promising candidate for the development of safe cosmetic agent.
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