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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| Format: | Article |
| Language: | English |
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MDPI AG
2022-08-01
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| Series: | Antioxidants |
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| Online Access: | https://www.mdpi.com/2076-3921/11/8/1593 |
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| author | Argyro Vontzalidou Sapfo-Maria Dimitrakoudi Konstantinos Tsoukalas Grigoris Zoidis Eliza Chaita Evanthia Dina Christina Cheimonidi Ioannis P. Trougakos George Lambrinidis Alexios-Leandros Skaltsounis Emmanuel Mikros Nektarios Aligiannis |
| author_facet | Argyro Vontzalidou Sapfo-Maria Dimitrakoudi Konstantinos Tsoukalas Grigoris Zoidis Eliza Chaita Evanthia Dina Christina Cheimonidi Ioannis P. Trougakos George Lambrinidis Alexios-Leandros Skaltsounis Emmanuel Mikros Nektarios Aligiannis |
| author_sort | Argyro Vontzalidou |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-09T10:02:41Z |
| format | Article |
| id | doaj.art-9c5d96933c874fb19f8eece6ae9d9ba5 |
| institution | Directory Open Access Journal |
| issn | 2076-3921 |
| language | English |
| last_indexed | 2024-03-09T10:02:41Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antioxidants |
| spelling | doaj.art-9c5d96933c874fb19f8eece6ae9d9ba52023-12-01T23:20:27ZengMDPI AGAntioxidants2076-39212022-08-01118159310.3390/antiox11081593Development of Stilbenoid and Chalconoid Analogues as Potent Tyrosinase Modulators and Antioxidant AgentsArgyro Vontzalidou0Sapfo-Maria Dimitrakoudi1Konstantinos Tsoukalas2Grigoris Zoidis3Eliza Chaita4Evanthia Dina5Christina Cheimonidi6Ioannis P. Trougakos7George Lambrinidis8Alexios-Leandros Skaltsounis9Emmanuel Mikros10Nektarios Aligiannis11Division of Pharmacognosy and Natural Product Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceDivision of Pharmacognosy and Natural Product Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceDivision of Pharmacognosy and Natural Product Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceDivision of Pharmaceutical Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceDivision of Pharmacognosy and Natural Product Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceDivision of Pharmacognosy and Natural Product Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceDepartment of Cell Biology and Biophysics, Faculty of Biology, National & Kapodistrian University of Athens, GR-15784 Athens, GreeceDepartment of Cell Biology and Biophysics, Faculty of Biology, National & Kapodistrian University of Athens, GR-15784 Athens, GreeceDivision of Pharmaceutical Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceDivision of Pharmacognosy and Natural Product Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceDivision of Pharmaceutical Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceDivision of Pharmacognosy and Natural Product Chemistry, Department of Pharmacy, National & Kapodistrian University of Athens, Panepistimiopolis Zografou, GR-15771 Athens, GreeceA 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.https://www.mdpi.com/2076-3921/11/8/1593tyrosinase inhibitiontyrosinase activationfree-radical-scavenging activitydiarylpropanesdiarylpropenoic acidsdihydrostilbenes |
| spellingShingle | Argyro Vontzalidou Sapfo-Maria Dimitrakoudi Konstantinos Tsoukalas Grigoris Zoidis Eliza Chaita Evanthia Dina Christina Cheimonidi Ioannis P. Trougakos George Lambrinidis Alexios-Leandros Skaltsounis Emmanuel Mikros Nektarios Aligiannis Development of Stilbenoid and Chalconoid Analogues as Potent Tyrosinase Modulators and Antioxidant Agents Antioxidants tyrosinase inhibition tyrosinase activation free-radical-scavenging activity diarylpropanes diarylpropenoic acids dihydrostilbenes |
| title | Development of Stilbenoid and Chalconoid Analogues as Potent Tyrosinase Modulators and Antioxidant Agents |
| title_full | Development of Stilbenoid and Chalconoid Analogues as Potent Tyrosinase Modulators and Antioxidant Agents |
| title_fullStr | Development of Stilbenoid and Chalconoid Analogues as Potent Tyrosinase Modulators and Antioxidant Agents |
| title_full_unstemmed | Development of Stilbenoid and Chalconoid Analogues as Potent Tyrosinase Modulators and Antioxidant Agents |
| title_short | Development of Stilbenoid and Chalconoid Analogues as Potent Tyrosinase Modulators and Antioxidant Agents |
| title_sort | development of stilbenoid and chalconoid analogues as potent tyrosinase modulators and antioxidant agents |
| topic | tyrosinase inhibition tyrosinase activation free-radical-scavenging activity diarylpropanes diarylpropenoic acids dihydrostilbenes |
| url | https://www.mdpi.com/2076-3921/11/8/1593 |
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