Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase

Xie, Wei; Zhang, Huilin; He, Jingjing; Zhang, Jingai; Yu, Qiuyan; Luo, Chunxiang; Li, Shangru

doi:10.1016/j.bmcl.2016.12.027

Cited by 74 publications

(17 citation statements)

References 12 publications

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“…The inhibitory effect of compounds 1a and 1d on diphenolase activity of mushroom tyrosinase activity is reversible. These findings support the previous proposal that kojic acid modification is a promising strategy for developing new potential tyrosinase inhibitors 30,31…”

Section: Discussionsupporting

confidence: 91%

Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity

Singh

Chen

Xie

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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In an attempt to synthesise new tyrosinase inhibitors, we designed and synthesised a series of chalconehydroxypyridinone hybrids as potential tyrosinase inhibitors adopting strategic modifications of kojic acid. All the newly synthesised compounds were characterised by NMR and mass spectrometry. Initial screening of the target compounds demonstrated that compounds 1a, 1d, and 1n had relatively strong inhibitory activities against tyrosinase monophenolase, with IC 50 values of 3.07 ± 0.85, 2.25 ± 0.8 and 2.75 ± 1.19 lM, respectively. The inhibitory activity against monophenolase was 6-to 8-fold higher than that of kojic acid. Compounds 1a, 1d, and 1n also showed inhibition of diphenolase, with IC 50 values of 17.05 ± 0.07, 11.70 ± 0.03 and 19.3 ± 0.28 lM, respectively. The inhibition kinetics of diphenolase indicates that compounds 1a and 1d induce reversible inhibition on tyrosinase. Finally, we found that copper coordination should be one of the important inhibitory mechanism of these compounds in tyrosinase.

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Section: Discussionsupporting

confidence: 91%

Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity

Singh

Chen

Xie

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…When DL-DOPA, norepinephrine and dopamine are oxidised by tyrosinase, Kojic acid inhibits effectively the rate of formation of pigmented product(s) and of oxygen uptake 411 . Furthermore, several of its derivatives have demonstrated a potent tyrosinase inhibitory activity 361 , 412–418 . Noh et al.…”

Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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471

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Tyrosinase is a multi-copper enzyme which is widely distributed in different organisms and plays an important role in the melanogenesis and enzymatic browning. Therefore, its inhibitors can be attractive in cosmetics and medicinal industries as depigmentation agents and also in food and agriculture industries as antibrowning compounds. For this purpose, many natural, semi-synthetic and synthetic inhibitors have been developed by different screening methods to date. This review has focused on the tyrosinase inhibitors discovered from all sources and biochemically characterised in the last four decades.

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“…By far, some natural and synthetic tyrosinase inhibitors have been reported, for example, hydroquinone, ascorbic acid, arbutin, kojic acid, aromatic aldehydes, aromatic acids, aromatic alcohols, tropolone, and polyphenols . However, only few compounds such as kojic acid, arbutin, tropolone, and 1‐phenyl‐2‐thiourea (PTU) have been used as cosmetic products and therapeutic agents . Moreover, it has been reported that arbutin decomposes at room temperature (10% decomposition at 20°C for 15 days) .…”

Section: Introductionmentioning

confidence: 99%

Microwave‐assisted synthesis and biological evaluation of new thiazolylhydrazone derivatives as tyrosinase inhibitors and antioxidants

Yan

Liu

2020

Journal of Heterocyclic Chem

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In this work, we have synthesized a series of 2‐thiazolylhydrazone derivatives (1–27) and investigated their biological activities as tyrosinase inhibitors and antioxidants. Some compounds showed potent tyrosinase inhibitory activities and 4‐(2‐(2‐(1‐(4‐Aminophenyl)ethylidene)‐hydrazinyl)thiazol‐4‐yl) phenol (26) showed more potent inhibitory effect than the standard tyrosinase inhibitor kojic acid (IC50: 9.8 μM vs. 23.6 μM). Compounds 2, 14, and 26 exhibited high antioxidant activities in 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and 2,2′‐azinobis (3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS) assays. The structure–activity relationship (SAR) indicated that the substitutions of bromine, hydroxyl group, and amino groups cause great effect to the inhibition effect against tyrosinase. The mechanism and kinetic studies demonstrated that the inhibitory effect of compound 26 on the tyrosinase by acting as the reversible and uncompetitive inhibitor. Docking studies suggests that compound 26 interacts strongly with mushroom tyrosinase via hydrogen bonding.

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Synthesis and biological evaluation of novel hydroxybenzaldehyde-based kojic acid analogues as inhibitors of mushroom tyrosinase

Cited by 74 publications

References 12 publications

Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity

Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity

A comprehensive review on tyrosinase inhibitors

Microwave‐assisted synthesis and biological evaluation of new thiazolylhydrazone derivatives as tyrosinase inhibitors and antioxidants

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