Kojic acid–natural product conjugates as mushroom tyrosinase inhibitors

Ashooriha, Morteza; Khoshneviszadeh, Mehdi; Khoshneviszadeh, Mahsima; Rafiei, Alireza; Kardan, Mostafa; Yazdian‐Robati, Rezvan; Emami, Saeed

doi:10.1016/j.ejmech.2020.112480

Cited by 50 publications

(27 citation statements)

References 28 publications

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“…<1% Approved [121,122] Over the past few decades, increasing attempts have been devoted to identifying effective TYR inhibitors from natural products and synthetic compounds through in vitro and in silico procedures. Generally speaking, spectrophotometry is the most commonly used in the determination of TYR activity [30,112,123]. Most inhibitors are assessed by dopachrome formation using L-tyrosine or L-DOPA as substrates.…”

Section: <1%mentioning

confidence: 99%

Spectrophotometric Assays for Sensing Tyrosinase Activity and Their Applications

et al. 2021

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Tyrosinase (TYR, E.C. 1.14.18.1), a critical enzyme participating in melanogenesis, catalyzes the first two steps in melanin biosynthesis including the ortho-hydroxylation of L-tyrosine and the oxidation of L-DOPA. Previous pharmacological investigations have revealed that an abnormal level of TYR is tightly associated with various dermatoses, including albinism, age spots, and malignant melanoma. TYR inhibitors can partially block the formation of pigment, which are always used for improving skin tone and treating dermatoses. The practical and reliable assays for monitoring TYR activity levels are very useful for both disease diagnosis and drug discovery. This review comprehensively summarizes structural and enzymatic characteristics, catalytic mechanism and substrate preference of TYR, as well as the recent advances in biochemical assays for sensing TYR activity and their biomedical applications. The design strategies of various TYR substrates, alongside with several lists of all reported biochemical assays for sensing TYR including analytical conditions and kinetic parameters, are presented for the first time. Additionally, the biomedical applications and future perspectives of these optical assays are also highlighted. The information and knowledge presented in this review offer a group of practical and reliable assays and imaging tools for sensing TYR activities in complex biological systems, which strongly facilitates high-throughput screening TYR inhibitors and further investigations on the relevance of TYR to human diseases.

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Section: <1%mentioning

confidence: 99%

Spectrophotometric Assays for Sensing Tyrosinase Activity and Their Applications

et al. 2021

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“…To choose potent derivatives for cell-based in vitro of anti-tyrosinase and melanogenicinhibitory activity, we synthesized 13 (Z)-2-(substituted benzylidene)benzimidazothiazolone derivatives 1-13, which were determined using mushroom tyrosinase and kojic acid (as a potent tyrosinase inhibitor) [43,44]. The inhibitory potential of compounds 1-13 against tyrosinase was assessed using L-tyrosine as the substrate, and the results were described as the IC 50 values determined with linear regression analysis (Table 2).…”

Section: Inhibitory Activities Of (Z)-2-(substituted Benzylidene)benzimidazothiazolone Derivatives 1-13 Against Mushroom Tyrosinasementioning

confidence: 99%

New Benzimidazothiazolone Derivatives as Tyrosinase Inhibitors with Potential Anti-Melanogenesis and Reactive Oxygen Species Scavenging Activities

et al. 2021

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Thirteen (Z)-2-(substituted benzylidene)benzimidazothiazolone analogs were synthesized and evaluated for their inhibitory activity against mushroom tyrosinase. Among the compounds synthesized, compounds 1–3 showed greater inhibitory activity than kojic acid (IC50 = 18.27 ± 0.89 μM); IC50 = 3.70 ± 0.51 μM for 1; IC50 = 3.05 ± 0.95 μM for 2; and IC50 = 5.00 ± 0.38 μM for 3, and found to be competitive tyrosinase inhibitors. In silico molecular docking simulations demonstrated that compounds 1–3 could bind to the catalytic sites of tyrosinase. Compounds 1–3 inhibited melanin production and cellular tyrosinase activity in a concentration-dependent manner. Notably, compound 2 dose-dependently scavenged ROS in B16F10 cells. Furthermore, compound 2 downregulated the protein kinase A (PKA)/cAMP response element-binding protein (CREB) and mitogen-activated protein kinase (MAPK) signaling pathways, which led to a reduction in microphthalmia-associated transcription factor (MITF) expression, and decreased tyrosinase, tyrosinase related protein 1 (TRP1), and TRP2 expression, resulting in anti-melanogenesis activity. Hence, compound 2 may serve as an anti-melanogenic agent against hyperpigmentation diseases.

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“…For this reason, in recent years, the direction of the γ-pyrones chemistry devoted to the preparation of conjugates of kojic acid or other derivatives functionalized at C 6 OH groups has been developed [12][13][14][15][16][17][18]. Among the new effective tyrosinase inhibitors, it is worth noting a number of hybrid molecules combining a kojic acid residue and an aryl/hetaryl moiety -for example, Mannich base 2 [18], 1,2,3-triazole derivatives 3 [19,20], substituted thiophenol 4 [21] or 4-amino-1,2,4-triazoles 5 [22] (Scheme 1). In addition, a number of hybrid structures with a kojic acid motif are known, demonstrating a different spectrum of biological action.…”

Section: Doi: 101134/s107036322109005xmentioning

confidence: 99%

Synthesis and Some Properties of New 5-Hydroxy-2-[(hetarylthio)methyl]-4H-pyran-4-ones

et al. 2021

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Kojic acid–natural product conjugates as mushroom tyrosinase inhibitors

Cited by 50 publications

References 28 publications

Spectrophotometric Assays for Sensing Tyrosinase Activity and Their Applications

Spectrophotometric Assays for Sensing Tyrosinase Activity and Their Applications

New Benzimidazothiazolone Derivatives as Tyrosinase Inhibitors with Potential Anti-Melanogenesis and Reactive Oxygen Species Scavenging Activities

Synthesis and Some Properties of New 5-Hydroxy-2-[(hetarylthio)methyl]-4H-pyran-4-ones

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