Inhibitory effects of iron-based carbonaceous nanocomposites on mushroom tyrosinase activity: molecular aspects and mechanistic insights

Barros, Marcela Rodrigues; Menezes, Thaís Meira; Garcia, Yarima Sanchez; Neves, Jorge Luiz

doi:10.1039/d3nj00882g

Cited by 4 publications

(3 citation statements)

References 59 publications

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“…In the organism, melanin acts crucial roles to protect the skin from UV radiation ( Lu et al, 2023a ; Znajafi et al, 2023 ). But, excessive elevated melanin content leads to lots of pigmentation disorders, including age spots and melanoma ( Broulier et al, 2023 ; De Barros et al, 2023 ; Xue et al, 2023 ). Inhibition of tyrosinase activity would reduce melanin generation, thence, the finding on novel tyrosinase inhibitors is attracting more attention due to their potential application in medicine and cosmetics fields ( Wang and Mu, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Inhibition mechanism investigation of quercetagetin as a potential tyrosinase inhibitor

Liang

2024

Front. Chem.

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Tyrosinase is one important rate limiting enzyme in melanin synthesis, directly affecting the melanin synthesis. Quercetagetin is one active ingredient from marigold. Thence, the inhibition effects of quercetagetin against tyrosinase were investigated. The results showed quercetagetin could inhibit tyrosinase activity with IC50 value of 0.19 ± 0.01 mM and the inhibition type was a reversible mixed-type. Results of fluorescence quenching showed quercetagetin could quench tyrosinase fluorescence in static process. CD and 3D fluorescence results showed the interaction of quercetagetin to tyrosinase could change tyrosinase conformation to inhibit activity. Moreover, docking revealed details of quercetagetin’s interactions with tyrosinase.

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Section: Introductionmentioning

confidence: 99%

Inhibition mechanism investigation of quercetagetin as a potential tyrosinase inhibitor

Liang

2024

Front. Chem.

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“…Tyrosinase plays crucial roles in mediating the production of melanin pigment via two steps [ 4 , 5 , 6 , 7 , 8 ]. In the melanin process, tyrosinase monophenolase firstly catalyzes the hydroxylation of L-tyrosine to yield L-DOPA, which is further oxidized into o -dopaquinone by tyrosinase diphenolase ( Figure 1 ) [ 9 , 10 , 11 , 12 ]. The produced melanin is distributed in the keratinocytes of human skin and hair; it is very important for human health [ 13 , 14 , 15 , 16 , 17 ], due to the effects of melanin in protecting human skin and eyes from damage against UV light [ 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anti-Tyrosinase Activity, and Spectroscopic Inhibition Mechanism of Cinnamic Acid–Eugenol Esters

Min

Zheng

et al. 2023

Molecules

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Tyrosinase plays crucial roles in mediating the production of melanin pigment; thus, its inhibitors could be useful in preventing melanin-related diseases. To find potential tyrosinase inhibitors, a series of cinnamic acid–eugenol esters (c1~c29) was synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR, HRMS, and FT-IR, respectively. The biological evaluation results showed that all compounds c1~c29 exhibited definite tyrosinase inhibitory activity; especially, compound c27 was the strongest tyrosinase inhibitor (IC50: 3.07 ± 0.26 μM), being ~4.6-fold stronger than the positive control, kojic acid (IC50: 14.15 ± 0.46 μM). Inhibition kinetic studies validated compound c27 as a reversible mixed-type inhibitor against tyrosinase. Three-dimensional fluorescence and circular dichroism (CD) spectra results indicated that compound c27 could change the conformation and secondary structure of tyrosinase. Fluorescence-quenching results showed that compound c27 quenched tyrosinase fluorescence in the static manner with one binding site. Molecular docking results also revealed the binding interactions between compound c27 and tyrosinase. Therefore, cinnamic acid–eugenol esters, especially c27, could be used as lead compounds to find potential tyrosinase inhibitors.

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“…In the process of melanin production, tyrosinase modulates the first two steps by the catalytic oxidation of L-tyrosine to dopaquinone [14]. In the first step, tyrosinase catalyzes L-tyrosine to convert it into 3,4-dihydroxyphenylalanine (L-DOPA), and in the second step, tyrosinase further oxidizes L-DOPA to dopaquinone, which is the important intermediate in melanin biosynthesis and is converted to melanin pigments by subsequent related chemical reactions [15][16][17]. Therefore, inhibiting tyrosinase activity is essential for the reduction in melanin synthesis [18].…”

Section: Introductionmentioning

confidence: 99%

In Vitro and In Vivo Biological Evaluation of Indole-thiazolidine-2,4-dione Derivatives as Tyrosinase Inhibitors

Lu,

Hu,

Min

et al. 2023

Molecules

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Tyrosinase is an important rate-limiting enzyme in melanin biosynthesis. To find potential tyrosinase inhibitors with anti-melanogenic activity, a series of indole-thiazolidine-2,4-dione derivatives 5a~5z were synthesized by incorporating indole with thiazolidine-2,4-dione into one compound and assayed for their biological activities. All compounds displayed tyrosinase inhibitory activities and 5w had the highest anti-tyrosinase inhibitory activity with an IC50 value of 11.2 μM. Inhibition kinetics revealed 5w as a mixed-type tyrosinase inhibitor. Fluorescence quenching results indicated that 5w quenched tyrosinase fluorescence in a static process. CD spectra and 3D fluorescence spectra results suggested that the binding of 5w with tyrosinase could change the conformation and microenvironment of tyrosinase. Molecular docking also represented the binding between 5w and tyrosinase. Moreover, 5w could inhibit tyrosinase activity and melanogenesis both in B16F10 cells and the zebrafish model. Therefore, compound 5w could serve as a tyrosinase inhibitor with anti-melanogenic activity.

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Inhibitory effects of iron-based carbonaceous nanocomposites on mushroom tyrosinase activity: molecular aspects and mechanistic insights

Abstract: Tyrosinase (Tyr) is a key enzyme in melanin biosynthesis, being its overexpression related to several skin disorders, including melanomas and hyperpigmentation. Based on this relevant role, molecules have been studied...

Cited by 4 publications

References 59 publications

Inhibition mechanism investigation of quercetagetin as a potential tyrosinase inhibitor

Inhibition mechanism investigation of quercetagetin as a potential tyrosinase inhibitor

Synthesis, Anti-Tyrosinase Activity, and Spectroscopic Inhibition Mechanism of Cinnamic Acid–Eugenol Esters

In Vitro and In Vivo Biological Evaluation of Indole-thiazolidine-2,4-dione Derivatives as Tyrosinase Inhibitors

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