Synthesis, computational molecular docking analysis and effectiveness on tyrosinase inhibition of kojic acid derivatives

Karakaya, Gülşah; Türe, Aslı; Ercan, Ayşe; Öncül, Selin; Aytemir, Mutlu Dilsiz

doi:10.1016/j.bioorg.2019.102950

Cited by 52 publications

(43 citation statements)

References 23 publications

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“…Kojic acid (KA) is a natural compound widely studied as a competitive inhibitor of tyrosinase [ 18 , 19 ]. KA prevents the formation of melanin in human melanocytes due to the reversible inhibition of tyrosinase, but it has some side effects, such as skin irritability and instability [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Analysis of Kojic Acid Derivatives as Competitive Inhibitors of Tyrosinase: A Molecular Modeling Approach

et al. 2021

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Tyrosinases belong to the functional copper-containing proteins family, and their structure contains two copper atoms, in the active site, which are coordinated by three histidine residues. The biosynthesis of melanin in melanocytes has two stages depending on the actions of the natural substrates L-DOPA and L-tyrosine. The dysregulation of tyrosinase is involved in skin cancer initiation. In the present study, using molecular modeling tools, we analyzed the inhibition activity of tyrosinase activity using kojic acid (KA) derivatives designed from aromatic aldehydes and malononitrile. All derivatives showed conformational affinity to the enzyme active site, and a favorable distance to chelate the copper ion, which is essential for enzyme function. Molecular dynamics simulations revealed that the derivatives formed promising complexes, presenting stable conformations with deviations between 0.2 and 0.35 Å. In addition, the investigated KA derivatives showed favorable binding free energies. The most stable KA derivatives showed the following binding free energies: −17.65 kcal mol−1 (D6), −18.07 kcal mol−1 (D2), −18.13 (D5) kcal mol−1, and −10.31 kcal mol−1 (D4). Our results suggest that these derivatives could be potent competitive inhibitors of the natural substrates of L-DOPA (−12.84 kcal mol−1) and L-tyrosine (−9.04 kcal mol−1) in melanogenesis.

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Section: Introductionmentioning

confidence: 99%

Analysis of Kojic Acid Derivatives as Competitive Inhibitors of Tyrosinase: A Molecular Modeling Approach

et al. 2021

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“…For the second target compound, hydroxycinnamoil moiety was combined with a heterocyclic amine, pyrrolidine. Other chemical constituents bearing morpholine and pyrrolidine moieties, such as tetrazole (Łukowska-Chojnacka et al, 2019), pyridazinone (Kamble et al, 2017), pyrazolidine (Surendra Kumar et al, 2017), and kojic acid derivatives (Karakaya et al, 2019), have been obtained and have showed moderate-to-high biological activities, such as antifungal, antioxidant, antimicrobial, cytotoxic, and tyrosinase inhibitory activities.…”

Section: Introductionmentioning

confidence: 99%

Novel hydroxycinnamamide from morpholine and pyrrolidine: Synthesis, characterization, docking study, and anticancer activity against P388 leukemia murine cells

Firdaus¹,

Hariani²,

Firdausiah³

et al. 2020

J Appl Pharm Sci

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“…Unfortunately, no such activities were observed. The core unsaturated pyran ring of 1 was structurally similar to kojic acid (Figure 2A) [22], which was probably the reason for the tyrosinase inhibition activity of 1. Structure differences between 1 and kojic acid were the functionalities substituted on the core ring.…”

Section: Bioactivity Evaluation Of Compounds 1-8mentioning

confidence: 90%

“…Kojic acid is a well-known tyrosinase inhibitor produced by Aspergillus and Penicillium fungi [19,20], that has been widely used in the cosmetic industries as a skin lightning/depigmenting agent [21]. Due to the metabolic instability of kojic acid, many efforts have been devoted to finding more powerful tyrosinase inhibitors [22][23][24][25]. However, attempts to discover tyrosinase inhibitors from Arctic-derived microbes are rarely found in the literature [26,27].…”

Section: Introductionmentioning

confidence: 99%

Cylindromicin from Arctic-Derived Fungus Tolypocladium sp. SCSIO 40433

et al. 2021

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The fungus strain SCSIO 40433 was isolated from an Arctic-derived glacier sediment sample and characterized as Tolypocladium cylindrosporum. A new compound, cylindromicin (1), and seven known secondary metabolites (2–8) were isolated from this strain. The chemical structures of these compounds were elucidated by comprehensive spectroscopic analyses. Cylindromicin (1) featured a 3,4-dihydro-2H-pyran skeleton. The absolute configuration of compound 1 was assigned via interpretation of key Nuclear Overhauser Effect Spectroscopy (NOESY) correlations and Electronic Circular Dichroism (ECD) calculation. Cylindromicin (1) exhibited significant tyrosinase inhibition activity. This study highlights Polar fungi as a potential resource for new bioactive natural products.

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Synthesis, computational molecular docking analysis and effectiveness on tyrosinase inhibition of kojic acid derivatives

Cited by 52 publications

References 23 publications

Analysis of Kojic Acid Derivatives as Competitive Inhibitors of Tyrosinase: A Molecular Modeling Approach

Analysis of Kojic Acid Derivatives as Competitive Inhibitors of Tyrosinase: A Molecular Modeling Approach

Novel hydroxycinnamamide from morpholine and pyrrolidine: Synthesis, characterization, docking study, and anticancer activity against P388 leukemia murine cells

Cylindromicin from Arctic-Derived Fungus Tolypocladium sp. SCSIO 40433

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