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Identification of two novel thiazolidin-2-imines as tyrosinase inhibitors: synthesis, crystal structure, molecular docking and DFT studies

Summary

Scientists created two new chemical compounds that are much better at slowing down the enzyme tyrosinase, which is responsible for skin darkening and browning of foods. These compounds were tested both in the lab and using computer models, and they worked about 14 times better than kojic acid, a commonly used anti-darkening ingredient. The research suggests these new compounds could be useful in cosmetics, food preservation, and treating skin conditions like unwanted pigmentation.

Background

N- and S-containing 5-membered heterocycles such as thiazolidin-2-imines are biologically active organic compounds found in many marketed drugs. Tyrosinase inhibitors are attractive in medicinal, cosmetic, food and agricultural industries as depigmentation and anti-browning agents due to their role in controlling melanin production.

Objective

To develop an efficient three-component one-pot synthesis of novel thiazolidine-2-imines using aldimine, alkyne and isothiocyanates with Zn(II) catalyst, and to evaluate their inhibitory activity against tyrosinase enzyme.

Results

The optimized synthesis yielded 90% and 95% for compounds 4a and 4b respectively. Both compounds showed superior tyrosinase inhibition activity (IC₅₀ = 1.151 ± 1.25 and 2.079 ± 0.87 μM) compared to kojic acid standard (IC₅₀ = 16.031 ± 1.27 μM). Molecular docking revealed strong hydrogen bonding, arene-π, and π-π interactions with key amino acids in the tyrosinase active site.

Conclusion

Two novel thiazolidine-2-imines were successfully synthesized and demonstrated excellent tyrosinase inhibitory activity superior to the standard kojic acid. The binding mechanisms were elucidated through molecular docking, supporting their potential as potent anti-browning and depigmentation agents for clinical, cosmetic, and agricultural applications.
  • Published in:Heliyon,
  • Study Type:Chemical Synthesis and Bioassay Study,
  • Source: PMID: 36046526, DOI: 10.1016/j.heliyon.2022.e10098
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