Synthesis, biological evaluation, and molecular docking analysis of novel 1, 3, 4-thiadiazole -based kojic acid derivatives as tyrosinase inhibitors

Talebi, Meysam; Majidi, Kiarash; Bassam, Kiana; Abdi, Movahed; Daneshvar, Maryam I.; Moayedi, Seyedeh Sara; Pourhesabi, Saba; Attarroshan, Mahshid; Boumi, Shahin; Kabiri, Maryam; Hosseini, Faezeh Sadat; Khoshneviszadeh, Mehdi; Amanlou, Massoud

doi:10.1016/j.molstruc.2022.133707

Cited by 11 publications

(7 citation statements)

References 26 publications

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“…Thus, the identification of novel tyrosinase inhibitors was crucial to the development of new therapeutic agents that may be used to treat diseases associated with skin-pathological disorders. Many active compounds, including kojic acid, vitamin C, hydroquinone, and arbutin, are reported to exhibit inhibition of tyrosinase and are extensively used in pharmacology, clinical research, and similar fields [ 66 ]. However, due to their lack of safety, unsatisfactory efficacy, and cytotoxicity, further studies for proper use are exclusively necessary.…”

Section: Resultsmentioning

confidence: 99%

Phytochemical Analysis, Biological Activities, and Molecular Docking Studies of Root Extracts from Paeonia Species in Serbia

Batinić,

Jovanović,

Stojković

et al. 2024

Pharmaceuticals

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Without being aware of their chemical composition, many cultures have used herbaceous peony roots for medicinal purposes. Modern phytopreparations intended for use in human therapy require specific knowledge about the chemistry of peony roots and their biological activities. In this study, ethanol–water extracts were prepared by maceration and microwave- and ultrasound-assisted extractions (MAE and UAE, respectively) in order to obtain bioactive molecules from the roots of Paeonia tenuifolia L., Paeonia peregrina Mill., and Paeonia officinalis L. wild growing in Serbia. Chemical characterization; polyphenol and flavonoid content; antioxidant, multianti-enzymatic, and antibacterial activities of extracts; and in vitro gastrointestinal digestion (GID) of hot water extracts were performed. The strongest anti-cholinesterase activity was observed in PT extracts. The highest anti-ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) radical potential was observed in PP extracts, whereas against DPPH (2,2-diphenyl-1-picrylhydrazyl radicals), the best results were achieved with PO extracts. Regarding antibacterial activity, extracts were strongly potent against Bacillus cereus. A molecular docking simulation was conducted to gather insights into the binding affinity and interactions of polyphenols and other Paeonia-specific molecules in the active sites of tested enzymes. In vitro GID of Paeonia teas showed a different recovery and behavior of the individual bioactives, with an increased recovery of methyl gallate and digallate and a decreased recovery of paeoniflorin and its derivatives. PT (Gulenovci) and PP (Pirot) extracts obtained by UAE and M were more efficient in the majority of the bioactivity assays. This study represents an initial step toward the possible application of Paeonia root extracts in pharmacy, medicine, and food technologies.

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Section: Resultsmentioning

confidence: 99%

Phytochemical Analysis, Biological Activities, and Molecular Docking Studies of Root Extracts from Paeonia Species in Serbia

Batinić,

Jovanović,

Stojković

et al. 2024

Pharmaceuticals

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“…Molecular docking is an indispensable tool for designing or discovering novel chemical compounds with promising or potential biological properties, which has led to the identification of promising inhibitors targeting tyrosinase [ 14 , 55 , 56 , 57 , 58 , 59 ]. Typically, docking predicts the binding pose(s) of compounds into a binding site using a scoring function to rank the best of them [ 60 ].…”

Section: Resultsmentioning

confidence: 99%

Coumarin-Based Compounds as Inhibitors of Tyrosinase/Tyrosine Hydroxylase: Synthesis, Kinetic Studies, and In Silico Approaches

Nunes

Araújo

Silva

et al. 2023

IJMS

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Cancer represents the main cause of morbidity and mortality worldwide, constituting a serious health problem. In this context, melanoma represents the most aggressive and fatal type of skin cancer, with death rates increasing every year. Scientific efforts have been addressed to the development of inhibitors targeting the tyrosinase enzyme as potential anti-melanoma agents due to the importance of this enzyme in melanogenesis biosynthesis. Coumarin-based compounds have shown potential activity as anti-melanoma agents and tyrosinase inhibitors. In this study, coumarin-based derivatives were designed, synthesized, and experimentally evaluated upon tyrosinase. Compound FN-19, a coumarin–thiosemicarbazone analog, exhibited potent anti-tyrosinase activity, with an IC50 value of 42.16 ± 5.16 µM, being more active than ascorbic acid and kojic acid, both reference inhibitors. The kinetic study showed that FN-19 acts as a mixed inhibitor. Still, for this compound, molecular dynamics (MD) simulations were performed to determine the stability of the complex with tyrosinase, generating RMSD, RMSF, and interaction plots. Additionally, docking studies were performed to elucidate the binding pose at the tyrosinase, suggesting that the hydroxyl group of coumarin derivative performs coordinate bonds (bidentate) with the copper(II) ions at distances ranging from 2.09 to 2.61 Å. Then, MM/PBSA calculations revealed that van der Waals interactions are the most relevant intermolecular forces for complex stabilization. Furthermore, it was observed that FN-19 has a binding energy (ΔEMM) value similar to tropolone, a tyrosinase inhibitor. Therefore, the data obtained in this study will be useful for designing and developing novel coumarin-based analogs targeting the tyrosinase enzyme.

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“…12 However, several widely recognized brightening substances i.e., kojic acid and hydroquinone, are regarded as dangerous agents attributable to the undesired adverse effects i.e., neurological disorders, dermatological cancer, skin irritation, and cytotoxicity. [13][14][15][16] The exploration of novel, manageable and harm-less tyrosinase inhibitors has become a matter of grave concern.…”

Section: Introductionmentioning

confidence: 99%

“…, neurological disorders, dermatological cancer, skin irritation, and cytotoxicity. 13–16 The exploration of novel, manageable and harm-less tyrosinase inhibitors has become a matter of grave concern.…”

Section: Introductionmentioning

confidence: 99%

Discovery of novel 1,2,4-triazole tethered β-hydroxy sulfides as bacterial tyrosinase inhibitors: synthesis and biophysical evaluation through in vitro and in silico approaches

Saeed,

Saif,

Zahoor

et al. 2024

RSC Adv.

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Synthesis, biological evaluation, and molecular docking analysis of novel 1, 3, 4-thiadiazole -based kojic acid derivatives as tyrosinase inhibitors

Cited by 11 publications

References 26 publications

Phytochemical Analysis, Biological Activities, and Molecular Docking Studies of Root Extracts from Paeonia Species in Serbia

Phytochemical Analysis, Biological Activities, and Molecular Docking Studies of Root Extracts from Paeonia Species in Serbia

Coumarin-Based Compounds as Inhibitors of Tyrosinase/Tyrosine Hydroxylase: Synthesis, Kinetic Studies, and In Silico Approaches

Discovery of novel 1,2,4-triazole tethered β-hydroxy sulfides as bacterial tyrosinase inhibitors: synthesis and biophysical evaluation through in vitro and in silico approaches

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