Improved TLC Bioautographic Assay for Qualitative and Quantitative Estimation of Tyrosinase Inhibitors in Natural Products

Zhou, Jianhua; Tang, Qingjiu; Wu, Tao; Cheng, Zhihong

doi:10.1002/pca.2666

Cited by 26 publications

(9 citation statements)

References 19 publications

(32 reference statements)

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“…IC 50 values of the tested molecules and kojic acid are given in Table . In many studies, inhibition activity of standard inhibitor kojic acid has been determined and the results were similar to ours. Enzyme inhibition activities of phthalocyanines were also investigated in a few studies .…”

Section: Resultssupporting

confidence: 84%

Synthesis, Photophysical and Biological Properties of New Phthalocyanines Bearing Peripherally 4‐(Trifluoromethoxy)phenoxy Groups

et al. 2019

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In this study, a novel phthalonitrile derivative namely 4-(4-(trifluoromethoxy)phenoxy) phthalonitrile (2) was introduced and characterized. A number of peripherally tetra-substituted phthalocyanines (H 2 Pc, CuPc and PdPc) were obtained by cyclotetramerization of 2 in suitable high-boiling solvents. Characterization of the resulting phthalocyanines has been performed by diverse techniques such as NMR, FTIR and UV/Vis spectroscopy. Organic solvents like acetone, N,N-Dimethylformamide (DMF) and dichloromethane (DCM) were utilized to investigate the influence of solvent nature on aggregation behavior of CuPc. In addition, the aggregation properties of the CuPc were studied in tetrahydrofuran (THF) and DCM at different concentrations ranging from 4 × 10 À 6 to 14 × 10 À 6 m. Fluorescence quantum yields of H 2 Pc and PdPc were determined in DMF. Fluorescence lifetime for H 2 Pc was calculated 2.07 ns, as well. The fluorescence quenching feature of H 2 Pc was explored by adding different concentrations of benzoquinone in DMF. The values of K sv and k q for H 2 Pc were obtained 59.01 m À 1 and 28.51 m À 1 ns À 1 , respectively. Moreover, tyrosinase inhibition and antioxidant activities of the phthalocyanines were studied by using TLC dot -blot technique and spectrophotometric assay. CuPc exhibited the highest inhibitory activity on tyrosinase enzyme. All tested molecules showed moderate antioxidant activity.

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Section: Resultssupporting

confidence: 84%

Synthesis, Photophysical and Biological Properties of New Phthalocyanines Bearing Peripherally 4‐(Trifluoromethoxy)phenoxy Groups

et al. 2019

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“…A different approach is based on thin layer chromatography (TLC) bioautographic assay, with the reported advantages of a low cost and sensitive methodology [225], whereas ultrafiltration coupled with HPLC has been proposed as a strategy for identification of specific inhibitors of the enzyme [226].…”

Section: New Trends In the Search For Tyrosinase Inhibitorsmentioning

confidence: 99%

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

2019

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One of the most common approaches for control of skin pigmentation involves the inhibition of tyrosinase, a copper-containing enzyme which catalyzes the key steps of melanogenesis. This review focuses on the tyrosinase inhibition properties of a series of natural and synthetic, bioinspired phenolic compounds that have appeared in the literature in the last five years. Both mushroom and human tyrosinase inhibitors have been considered. Among the first class, flavonoids, in particular chalcones, occupy a prominent role as natural inhibitors, followed by hydroxystilbenes (mainly resveratrol derivatives). A series of more complex phenolic compounds from a variety of sources, first of all belonging to the Moraceae family, have also been described as potent tyrosinase inhibitors. As to the synthetic compounds, hydroxycinnamic acids and chalcones again appear as the most exploited scaffolds. Several inhibition mechanisms have been reported for the described inhibitors, pointing to copper chelating and/or hydrophobic moieties as key structural requirements to achieve good inhibition properties. Emerging trends in the search for novel skin depigmenting agents, including the development of assays that could distinguish between inhibitors and potentially toxic substrates of the enzyme as well as of formulations aimed at improving the bioavailability and hence the effectiveness of well-known inhibitors, have also been addressed.

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“…In other words, sensitive and correct assay methods for screening and development of effective tyrosinase inhibitors are of great importance. For this purpose, several spectrophotometric 6–10 , chromatographic 11–17 , electrophoretic 18–22 , radiometric 23 , 24 and electrochemical 25–27 assays have been applied and developed by researchers so far. Recently, a novel fluorescent biosensor 28 and tyrosinase-based thin-layer chromatography-autography have been suggested for tyrosinase inhibitor screening 29 .…”

Section: Introductionmentioning

confidence: 99%

A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

758

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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Improved TLC Bioautographic Assay for Qualitative and Quantitative Estimation of Tyrosinase Inhibitors in Natural Products

Abstract: Our improved assay is a relatively low-cost, sensitive, and quantitative method compared to the reported TLC bioautographic assays. Copyright © 2016 John Wiley & Sons, Ltd.

Cited by 26 publications

References 19 publications

Synthesis, Photophysical and Biological Properties of New Phthalocyanines Bearing Peripherally 4‐(Trifluoromethoxy)phenoxy Groups

Synthesis, Photophysical and Biological Properties of New Phthalocyanines Bearing Peripherally 4‐(Trifluoromethoxy)phenoxy Groups

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

A comprehensive review on tyrosinase inhibitors

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