Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluation

Lu, Li; Zhang, Xin; Kang, Yu; Xiong, Zhuang; Zhang, Kun; Xu, Xuetao; Bai, Liping; Li, Hongguang

doi:10.1016/j.arabjc.2023.104724

Cited by 13 publications

(9 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 1r, which has 9-methyl and 7-hydroxy groups with anthraquinone-connected to coumarins, was less active in antioxidant and antibacterial activities, and highly active in tyrosinase inhibition. In a previous study, compound 1r displayed lower tyrosinase inhibition activity than that of other coumarin derivatives [ 49 ]. Compound 1t, with 9-hydroxy and 7-methyl groups with anthraquinone-connected coumarins, had lower antioxidant and tyrosinase inhibitory activities, and highly active in antibacterial activity.…”

Section: Resultsmentioning

confidence: 99%

“…Coumarin and anthraquinone derivatives are multitarget compounds with antibacterial activity, particularly against E. coli and S. aureus, etc [ [30] , [31] , [32] , [33] ]. Based on the above selection, coumarin and anthraquinone derivatives were screened for antibacterial activity in current work, these multi-target compounds of coumarin and anthraquinone derivatives also act as antioxidants and have tyrosinase activity, according to previously reported literature [ [34] , [35] , [36] , [37] , [38] ]. In cosmetic products, tyrosinase inhibitors are being utilized more often to preserve skin whiteness.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies

Loganathan,

Ahamed,

Radhakrishnan

et al. 2024

Heliyon

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies

Loganathan,

Ahamed,

Radhakrishnan

et al. 2024

Heliyon

View full text Add to dashboard Cite

“…The 3D fluorescence spectra of tyrosinase-compound c27 mixture was measured according to previous reports [ 55 ]. To 3 mL of tyrosinase solution (final concentration: 168 μM) in PBS, 10 µL of compound c27 (2 mM) was added and incubated for 5 min.…”

Section: Methodsmentioning

confidence: 99%

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

Min

Zheng

et al. 2023

Molecules

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…The in vitro cytotoxicity of compound 11 against hepatocytes LO2 cells was assayed using the MTT method [ 44 , 45 ]. LO2 cells were cultured in DMEM containing 10% FBS, 100 IU/mL penicillin, and 100 IU/mL streptomycin at 37 °C under 5% CO2.…”

Section: Methodsmentioning

confidence: 99%

Anti-α-Glucosidase, SAR Analysis, and Mechanism Investigation of Indolo[1,2-b]isoquinoline Derivatives

Liu

et al. 2023

Molecules

Self Cite

View full text Add to dashboard Cite

To find potential α-glucosidase inhibitors, indolo[1,2-b]isoquinoline derivatives (1–20) were screened for their α-glucosidase inhibitory effects. All derivatives presented potential α-glucosidase inhibitory effects with IC50 values of 3.44 ± 0.36~41.24 ± 0.26 μM compared to the positive control acarbose (IC50 value: 640.57 ± 5.13 μM). In particular, compound 11 displayed the strongest anti-α-glucosidase activity, being ~186 times stronger than acarbose. Kinetic studies found that compounds 9, 11, 13, 18, and 19 were all reversible mix-type inhibitors. The 3D fluorescence spectra and CD spectra results revealed that the interaction between compounds 9, 11, 13, 18, and 19 and α-glucosidase changed the conformational changes of α-glucosidase. Molecular docking and molecular dynamics simulation results indicated the interaction between compounds and α-glucosidase. In addition, cell cytotoxicity and drug-like properties of compound 11 were also investigated.

show abstract

Novel coumarin derivatives as potential tyrosinase inhibitors: Synthesis, binding analysis and biological evaluation

Cited by 13 publications

References 44 publications

Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies

Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies

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

Anti-α-Glucosidase, SAR Analysis, and Mechanism Investigation of Indolo[1,2-b]isoquinoline Derivatives

Contact Info

Product

Resources

About