Development of Stilbenoid and Chalconoid Analogues as Potent Tyrosinase Modulators and Antioxidant Agents
A number of stilbenoid and chalconoid derivatives were prepared by straightforward methods, and their ability to modulate tyrosinase activity and to scavenge free radicals were evaluated in vitro. The cell-free in vitro evaluation revealed two diarylpropanes, <b>24</b> and <b>25<...
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MDPI AG,
2022-08-01T00:00:00Z.
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| LEADER | 00000 am a22000003u 4500 | ||
|---|---|---|---|
| 001 | doaj_9c5d96933c874fb19f8eece6ae9d9ba5 | ||
| 042 | |a dc | ||
| 100 | 1 | 0 | |a Argyro Vontzalidou |e author |
| 700 | 1 | 0 | |a Sapfo-Maria Dimitrakoudi |e author |
| 700 | 1 | 0 | |a Konstantinos Tsoukalas |e author |
| 700 | 1 | 0 | |a Grigoris Zoidis |e author |
| 700 | 1 | 0 | |a Eliza Chaita |e author |
| 700 | 1 | 0 | |a Evanthia Dina |e author |
| 700 | 1 | 0 | |a Christina Cheimonidi |e author |
| 700 | 1 | 0 | |a Ioannis P. Trougakos |e author |
| 700 | 1 | 0 | |a George Lambrinidis |e author |
| 700 | 1 | 0 | |a Alexios-Leandros Skaltsounis |e author |
| 700 | 1 | 0 | |a Emmanuel Mikros |e author |
| 700 | 1 | 0 | |a Nektarios Aligiannis |e author |
| 245 | 0 | 0 | |a Development of Stilbenoid and Chalconoid Analogues as Potent Tyrosinase Modulators and Antioxidant Agents |
| 260 | |b MDPI AG, |c 2022-08-01T00:00:00Z. | ||
| 500 | |a 10.3390/antiox11081593 | ||
| 500 | |a 2076-3921 | ||
| 520 | |a A number of stilbenoid and chalconoid derivatives were prepared by straightforward methods, and their ability to modulate tyrosinase activity and to scavenge free radicals were evaluated in vitro. The cell-free in vitro evaluation revealed two diarylpropanes, <b>24</b> and <b>25</b>, as potent tyrosinase inhibitors, whereas diarylpropenoic acids seemed to enhance the enzymatic activity. An in silico evaluation of the binding affinity of the selected compounds with the crystal structure of tyrosinase was also conducted in order to obtain better insight into the mechanism. Representative synthetic compounds with inhibitory and activating properties were further evaluated in melanoma cell lines B16F1 and B16F10 for their ability to moderate tyrosinase activity and affect melanin production. Dihydrostilbene analogues <b>I</b> and <b>II</b>, exhibited a stronger anti-melanogenic effect than kojic acid through the inhibition of cellular tyrosinase activity and melanin formation, while diarylpropanoic acid <b>44</b> proved to be a potent melanogenic factor, inducing cellular tyrosinase activity and melanin formation. Moreover, the antioxidant evaluation disclosed two analogues (<b>29</b> and <b>11</b>) with significant free-radical-scavenging activity (12.4 and 20.3 μM), which were 10- and 6-fold more potent than ascorbic acid (122.1 μΜ), respectively. | ||
| 546 | |a EN | ||
| 690 | |a tyrosinase inhibition | ||
| 690 | |a tyrosinase activation | ||
| 690 | |a free-radical-scavenging activity | ||
| 690 | |a diarylpropanes | ||
| 690 | |a diarylpropenoic acids | ||
| 690 | |a dihydrostilbenes | ||
| 690 | |a Therapeutics. Pharmacology | ||
| 690 | |a RM1-950 | ||
| 655 | 7 | |a article |2 local | |
| 786 | 0 | |n Antioxidants, Vol 11, Iss 8, p 1593 (2022) | |
| 787 | 0 | |n https://www.mdpi.com/2076-3921/11/8/1593 | |
| 787 | 0 | |n https://doaj.org/toc/2076-3921 | |
| 856 | 4 | 1 | |u https://doaj.org/article/9c5d96933c874fb19f8eece6ae9d9ba5 |z Connect to this object online. |