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Research in Pharmaceutical Sciences، جلد ۱۶، شماره ۴، صفحات ۴۲۵-۴۳۵
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| عنوان فارسی |
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| چکیده فارسی مقاله |
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| کلیدواژه‌های فارسی مقاله |
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| عنوان انگلیسی |
Benzylidene-6-hydroxy-3,4-dihydronaphthalenone chalconoids as potent tyrosinase inhibitors |
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| چکیده انگلیسی مقاله |
Background and purpose: Tyrosinase enzyme has a key role in melanin biosynthesis by converting tyrosine into dopaquinone. It also participates in the enzymatic browning of vegetables by polyphenol oxidation. Therefore, tyrosinase inhibitors are useful in the fields of medicine, cosmetics, and agriculture. Many tyrosinase inhibitors having drawbacks have been reported to date; so, finding new inhibitors is a great need. Experimental approach: A variety of 6-hydroxy-3,4-dihydronaphthalenone chalcone-like analogs ( C1 - C10 ) have been synthesized by aldol condensation of 6-hydroxy tetralone and differently substituted benzaldehydes. The compounds were evaluated for their inhibitory effect on mushroom tyrosinase by a spectrophotometric method. Moreover, the inhibition manner of the most active compound was determined by Lineweaver-Burk plots. Docking study was done using AutoDock 4.2. The drug-likeness scores and ADME features of the active derivatives were also predicted. Results/Findings: Most of the compounds showed remarkable inhibitory activity against the tyrosinase enzyme. 6-Hydroxy-2-(3,4,5-trimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one ( C2 ) was the most potent derivative amongst the series with an IC 50 value of 8.8 μM which was slightly more favorable to that of the reference kojic acid (IC 50 = 9.7 μM). Inhibitory kinetic studies revealed that C2 behaves as a competitive inhibitor. According to the docking results, compound C2 formed the most stable enzyme-inhibitor complex, mainly via establishing interactions with the two copper ions in the active site. I n silico drug-likeness and pharmacokinetics predictions for the proposed tyrosinase inhibitors revealed that most of the compounds including C2 have proper drug-likeness scores and pharmacokinetic properties. Conclusion and implications: Therefore, C2 could be suggested as a promising tyrosinase inhibitor that might be a good lead compound in medicine, cosmetics, and the food industry, and further drug development of this compound might be of great interest. |
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| کلیدواژه‌های انگلیسی مقاله |
Keywords, Anti-tyrosinase activity,Chalcones,Drug-likeness,Kinetic studies,Molecular docking,Tyrosinase inhibitor. |
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| نویسندگان مقاله |
| Sara Ranjbar
2Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, I.R. Iran.
| Mehraneh Mohammadabadi Kamarei
3Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, I.R. Iran.
| Mahsima Khoshneviszadeh
2Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, I.R. Iran.
| Hona Hosseinpoor
3Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, I.R. Iran.
| Najmeh Edraki
2Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, I.R. Iran.
3Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, I.R. Iran.
| Mehdi Khoshneviszadeh
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| نشانی اینترنتی |
http://rps.mui.ac.ir/index.php/jrps/article/view/2078 |
| فایل مقاله |
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| کد مقاله (doi) |
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| زبان مقاله منتشر شده |
en |
| موضوعات مقاله منتشر شده |
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| نوع مقاله منتشر شده |
Original Article |
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