Combined Kinetic Studies and Computational Analysis on Kojic Acid Analogs as Tyrosinase Inhibitors

Background: The use of tyrosinase has confirmed to be the best means of recognizing safe, effective, and potent tyrosinase inhibitors for whitening skin. Twenty-four 2-phenoxy(thiomethyl)pyridotriazolopyrimidines were synthesized and characterized in our previous studies. Objective: The present work aimed to evaluate their cytotoxicity against HepG2 (hepatocellular carcinoma), A549 (pulmonary adenocarcinoma), MCF-7 (breast adenocarcinoma) and WRL 68 (embryonic liver) cell lines. Methods: MTT assay was employed to investigate the cytotoxicity, and a tyrosinase inhibitor screening kit was used to evaluate the Tyrosinase (TYR) inhibitory activity of the targets. Results: The tested compounds exhibited no considerable cytotoxicity, and nine of them were selected for a tyrosinase inhibitory test. Compounds 2b, 2m, and 5a showed good inhibitory percentages against TYR compared to that of kojic acid (reference substance). Molecular docking was performed to rationalize the Structure-Activity Relationship (SAR) of the target pyridotriazolopyrimidines and analyze the binding between the docked-selected compounds and the amino acid residues in the active site of tyrosinase. Conclusion: The target pyridotriazolopyrimidines were identified as a new class of tyrosinase inhibitors.

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Synthesis of Novel Compounds as New Potent Tyrosinase Inhibitors

BioMed Research International ◽

10.1155/2013/207181 ◽

2013 ◽

Vol 2013 ◽

pp. 1-7 ◽

Cited By ~ 8

Author(s):

Hooshang Hamidian

Keyword(s):

Kojic Acid ◽

Azo Compounds ◽

The Novel ◽

Mushroom Tyrosinase ◽

Reference Standard ◽

Tyrosinase Inhibition ◽

H Nmr ◽

Ft Ir ◽

Tyrosinase Inhibitors ◽

C Nmr

In the present paper, we report the synthesis and pharmacological evaluation of a new series of azo compounds with different groups (1-naphthol, 2-naphthol, andN,N-dimethylaniline) and trifluoromethoxy and fluoro substituents in the scaffold. All synthesized compounds (5a–5f) showed the most potent mushroom tyrosinase inhibition (IC50values in the range of 4.39 ± 0.76–1.71 ± 0.49 µM), comparable to the kojic acid, as reference standard inhibitor. All the novel compounds were characterized by FT-IR,1H NMR,13C NMR, and elemental analysis.

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Flavones as tyrosinase inhibitors: kinetic studies in vitro and in silico

Phytochemical Analysis ◽

10.1002/pca.2897 ◽

2020 ◽

Vol 31 (3) ◽

pp. 314-321 ◽

Cited By ~ 4

Author(s):

Randolph R.J. Arroo ◽

Suat Sari ◽

Burak Barut ◽

Arzu Özel ◽

Ketan C. Ruparelia ◽

...

Keyword(s):

In Silico ◽

Kinetic Studies ◽

Tyrosinase Inhibitors

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Isoprenylated Phenolic Compounds from Morus macroura as Potent Tyrosinase Inhibitors

Planta Medica ◽

10.1055/s-0043-121698 ◽

2017 ◽

Vol 84 (05) ◽

pp. 336-343 ◽

Cited By ~ 7

Author(s):

Yifan Wang ◽

Liangjin Xu ◽

Wen Gao ◽

Lixin Niu ◽

Chunyue Huang ◽

...

Keyword(s):

Kojic Acid ◽

Positive Control ◽

Diels Alder ◽

Extensive Analysis ◽

Ic50 Value ◽

Ic50 Values ◽

Tyrosinase Inhibitors ◽

Inhibitory Activities ◽

New Compounds

AbstractThree new Diels-Alder adducts, macrourins E – G (1–3), one new 2-arylbenzofuran, macrourin H (4), and eight known Diels-Alder adducts (5–12) were isolated from Morus macroura. Their structures were elucidated through extensive analysis of spectroscopic data. The 1H NMR and ECD trends in the determination of the configurations of these Diels-Alder adducts were summarized. The tyrosinase inhibitory activities of all compounds isolated were evaluated, and the new compounds (1–4) as well as the eight known compounds (5–12) were found to be potent with IC50 values ranging from 0.39 to 4.54 µM. Among them, 1 showed the best tyrosinase inhibitory activity with an IC50 value of 0.39 µM, approximately 50 times stronger than the positive control, kojic acid.

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Kojic acid–natural product conjugates as mushroom tyrosinase inhibitors

European Journal of Medicinal Chemistry ◽

10.1016/j.ejmech.2020.112480 ◽

2020 ◽

Vol 201 ◽

pp. 112480

Author(s):

Morteza Ashooriha ◽

Mehdi Khoshneviszadeh ◽

Mahsima Khoshneviszadeh ◽

Alireza Rafiei ◽

Mostafa Kardan ◽

...

Keyword(s):

Natural Product ◽

Kojic Acid ◽

Mushroom Tyrosinase ◽

Tyrosinase Inhibitors

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Synthesis and Biological Evaluation of Kojic acid Derivatives as Tyrosinase Inhibitors

Bulletin of the Korean Chemical Society ◽

10.5012/bkcs.2014.35.12.3647 ◽

2014 ◽

Vol 35 (12) ◽

pp. 3647-3650 ◽

Cited By ~ 4

Author(s):

Yeong Jin Choi ◽

Ho Sik Rho ◽

Heung Soo Baek ◽

Yong Deog Hong ◽

Yung Hyup Joo ◽

...

Keyword(s):

Kojic Acid ◽

Biological Evaluation ◽

Tyrosinase Inhibitors ◽

Synthesis And Biological Evaluation

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Phosphonic and Phosphinic Acid Derivatives as Novel Tyrosinase Inhibitors: Kinetic Studies and Molecular Docking

Chemistry & Biodiversity ◽

10.1002/cbdv.201900167 ◽

2019 ◽

Vol 16 (7) ◽

Cited By ~ 2

Author(s):

Ewa Wolińska ◽

Katarzyna Hałdys ◽

Jerzy Góra ◽

Tomasz K. Olszewski ◽

Bogdan Boduszek ◽

...

Keyword(s):

Molecular Docking ◽

Phosphinic Acid ◽

Kinetic Studies ◽

Tyrosinase Inhibitors

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Electrochemical Screening and Evaluation of Lamiaceae Plant Species from South Africa with Potential Tyrosinase Activity

Sensors ◽

10.3390/s19051035 ◽

2019 ◽

Vol 19 (5) ◽

pp. 1035 ◽

Cited By ~ 1

Author(s):

Ninon Etsassala ◽

Tesfaye Waryo ◽

Olugbenga Popoola ◽

Adewale Adeloye ◽

Emmanuel Iwuoha ◽

...

Keyword(s):

South Africa ◽

South African ◽

Kojic Acid ◽

Screening Method ◽

Tyrosinase Activity ◽

Minimum Concentration ◽

Methanolic Extracts ◽

Fast Screening ◽

African Flora ◽

Tyrosinase Inhibitors

South Africa is a country with a wide variety of plants that may contain excellent anti-tyrosinase inhibitors. With wide applications in cosmetics, pharmaceuticals and food products, tyrosinase inhibitors have received very special attention in the recent past as a way of preventing the overproduction of melanin in epidermal layers which often over time brings detrimental effects on human skin. In this present study, a fast screening method using a cyclic voltammetry technique was applied in the evaluation of methanolic extracts of twenty-five species of plants from the Lamiaceae family for anti-tyrosinase activity. Among these plants, those that showed a fast current inhibition rate at a minimum concentration when compared to a kojic acid standard were classified as having the greatest anti-tyrosinase activity. These include Salvia chamelaeagnea, S. dolomitica, Plectranthus ecklonii, P. namaensis, and P. zuluensis. The results presented herein focused in particular on providng firsthand information for further extensive research and exploration of natural product materials with anti-tyrosinase activity from South African flora for use in cosmetics, skin care and medicinal treatments.

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