Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors.

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ID: 1952
2019
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Ranked #10 of 200 articles by views in International journal of biological macromolecules

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Abstract
Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. Hence, tyrosinase inhibitors are important in the fields of medicine, cosmetics and agriculture. In this study, novel N-(2-morpholinoethyl)cinnamamide derivatives bearing different substituents on phenyl ring were designed, synthesized and evaluated for their tyrosinase diphenolase inhibitory activity. The compounds were found to be better tyrosinase inhibitors (ICs were in micro molar range) than cinnamic acid. (E)-3-(3-chlorophenyl)-N-(2-morpholinoethyl)acrylamide (B6) exhibited the highest inhibition with IC value of 15.2 ± 0.6 μM which was comparable to that of kojic acid. The inhibition kinetic analysis of B6 indicated that the compound was a mixed-type tyrosinase inhibitor. In silico ADME prediction indicated that B6 might show more skin penetration than kojic acid. Molecular docking analysis confirmed that the active inhibitors well accommodated in the mushroom tyrosinase active site and it was also revealed that B6 formed the most stable drug-receptor complex with the target protein. Therefore, cinnamamide B6 could be introduced as a potent tyrosinase inhibitor that might be a promising lead in cosmetics, medicine and food industry.
Reference Key
ghafary2019novelinternational Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Ghafary, Shahrzad;Ranjbar, Sara;Larijani, Bagher;Amini, Mohsen;Biglar, Mahmood;Mahdavi, Mohammad;Bakhshaei, Maryam;Khoshneviszadeh, Mahsima;Sakhteman, Amirhossein;Khoshneviszadeh, Mehdi;
Journal International journal of biological macromolecules
Year 2019
DOI
S0141-8130(19)32555-3
URL
Keywords Keywords not found

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