Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors

Ghafary, Shahrzad; Ranjbar, Sara; Larijani, Bagher; Amini, Mohsen; Biglar, Mahmood; Mahdavi, Mohammad; Bakhshaei, Maryam; Khoshneviszadeh, Mahsima; Sakhteman, Amirhossein; Khoshneviszadeh, Mehdi

doi:10.1016/j.ijbiomac.2019.05.201

Cited by 22 publications

(11 citation statements)

References 31 publications

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“…The search for new tyrosinase inhibitors is of interest in medicinal, cosmetic, agricultural, and food industries [6,19]. Tyrosinase catalyzes the reactions that produce dihydroxyphenylalanine and dopaquinone in the initial steps of melanogenesis [20].…”

Section: Discussionmentioning

confidence: 99%

The Guanidine Pseudoalkaloids 10-Methoxy-Leonurine and Leonurine Act as Competitive Inhibitors of Tyrosinase

Kim

Leem

Lee³

2020

Biomolecules

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Tyrosinase plays a key role in the production of melanin. A variety of industrial fields have shown interest in the development of tyrosinase inhibitors from plants. In this study, compounds 1–5 derived from Leonurus japonicas were evaluated to determine their ability to inhibit tyrosinase. Of these, 10-methoxy-leonurine (1) and leonurine (2) exhibited IC50 values of 7.4 ± 0.4 and 12.4 ± 0.8 μM, respectively, and acted as competitive inhibitors of tyrosinase, with Ki values in the micromolar range. In silico modeling revealed a guanidine group located in the inner cavity and a benzene ring docked within the active site of these compounds. These guanidine pseudoalkaloids show potential not only as tyrosinase inhibitors but also as lead compounds in new scaffolds for the development of novel inhibitors.

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Section: Discussionmentioning

confidence: 99%

The Guanidine Pseudoalkaloids 10-Methoxy-Leonurine and Leonurine Act as Competitive Inhibitors of Tyrosinase

Kim

Leem

Lee³

2020

Biomolecules

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“…Mushroom tyrosinase was assayed as reported in our previous studies. [ 36–38 ] l ‐DOPA was used as the substrate and enzyme activity was checked by detecting dopachrome formation at 475 nm. All test samples were dissolved in DMSO at 40 mM and diluted to the required concentrations.…”

Section: Methodsmentioning

confidence: 99%

1,2,3‐Triazole‐linked 5‐benzylidene (thio)barbiturates as novel tyrosinase inhibitors and free‐radical scavengers

Ranjbar

Shahvaran

Edraki

et al. 2020

Archiv der Pharmazie

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In this study, benzyl-1,2,3-triazole-linked 5-benzylidene (thio)barbiturate derivatives 7a-d and 8a-h were designed as potential tyrosinase inhibitors and free-radical scavengers. The twelve derivatives were synthesized via the [3+2] cycloaddition reaction of the corresponding benzyl azide as a dipole and the corresponding alkyne as a dipolarophile in the presence of copper(I) species, generated in situ from copper (II)/ascorbate. The thiobarbiturate derivative 8h and the barbiturate derivative 8b bearing 4-fluoro and 4-bromo groups on the benzyl-triazole moiety were found to be the most potent tyrosinase inhibitors with IC 50 values of 24.6 ± 0.9 and 26.8 ± 0.8 μM, respectively. Almost all the compounds showed a good radical scavenging activity with EC 50 values in the range of 29.9-324.9 μM. Derivatives 7a, 8f, and 8h were the most potent free-radical scavengers with EC 50 values of 29.9 ± 0.8, 36.8 ± 0.9, and 39.2 ± 1.1 μM, respectively. The kinetic analysis revealed that compound 8h was a mixed-type tyrosinase inhibitor. The molecular docking analysis indicated that 8b and 8h were well accommodated in the active site of the tyrosinase enzyme and possessed the most negative binding energy values of −8.55 and −8.81 kcal/mol, respectively. Moreover, it was found that the two residues, Asn81 and Glu322, played a significant role in forming stable enzyme-inhibitor complexes.

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“…Tyrosinase from mushroom (EC number 1.14.18.1, Sigma T3824-25KU, 2680 units/mg solid) applied for the bioassay of KA-SLN 3 and KA solution according to previous studies with slight modifications by M. Khoshneviszadeh et al [36,37]. Mushroom tyrosinase inhibitory activity was evaluated using L-DOPA as a substrate and the formation of dopachrome was observed at 475 nm [38,39].…”

Section: Determination Of Mushroom Tyrosinase Activitymentioning

confidence: 99%

An emerging technology in lipid research for targeting hydrophilic drugs to the skin in the treatment of hyperpigmentation disorders: kojic acid-solid lipid nanoparticles

Khezri

Saeedi

Morteza‐Semnani

et al. 2020

Artificial Cells, Nanomedicine, and Biotechnology

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Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors

Cited by 22 publications

References 31 publications

The Guanidine Pseudoalkaloids 10-Methoxy-Leonurine and Leonurine Act as Competitive Inhibitors of Tyrosinase

The Guanidine Pseudoalkaloids 10-Methoxy-Leonurine and Leonurine Act as Competitive Inhibitors of Tyrosinase

1,2,3‐Triazole‐linked 5‐benzylidene (thio)barbiturates as novel tyrosinase inhibitors and free‐radical scavengers

An emerging technology in lipid research for targeting hydrophilic drugs to the skin in the treatment of hyperpigmentation disorders: kojic acid-solid lipid nanoparticles

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