Synthesis, Biological Evaluation, Molecular Docking, Md Simulation and Dft Analysis of New 3-Hydroxypyridine-4-One Derivatives As Anti-Tyrosinase and Antioxidant Agents

Synthesis, Biological Evaluation, Molecular Docking, Md Simulation and Dft Analysis of New 3-Hydroxypyridine-4-One Derivatives As Anti-Tyrosinase and Antioxidant Agents Publisher

Sadeghian S¹ ; Zare F^{1, 2} ; Khoshneviszadeh M¹ ; Hafshejani AF¹ ; Salahshour F¹ ; Khodabakhshloo A¹ ; Saghaie L³ ; Goshtasbi G¹ ; Sarikhani Z¹ ; Poustforoosh A⁴ ; Sabet R¹ ; Sadeghpour H¹

Show Affiliations

1. Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
2. Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
3. Department of Medicinal Chemistry, Faculty of Pharmacy, Isfahan University of Medical Sciences, Isfahan, Iran
4. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

Source: Heliyon Published:2024

Abstract

In the present study, ten new substituted 3-hydroxypyridine-4-one derivatives were synthesized in a four-step method, and their chemical structures were confirmed using various spectroscopic techniques. Subsequently, the inhibitory activities of these derivatives against tyrosinase enzyme and their antioxidant activities were evaluated. Amongest the synthesized compounds, 6b bearing a 4-OH-3-OCH3 substitution was found to be a promising tyrosinase inhibitor with an IC50 value of 25.82 μM, which is comparable to the activity of kojic acid as control drug. Kinetic study indicated that compound 6b is a competitive inhibitor of tyrosinase enzyme, which was confirmed by molecular docking results. The molecular docking study and MD simulation showed that compound 6b was properly placed within the tyrosinase binding pocket and interacted with key residues, which is consistent with its biological activity. The DFT analysis demonstrated that compound 6b is kinetically more stable than the other compounds. In addition, compounds 6a and 6b exhibited the best antioxidant activities. The findings indicate that compound 6b could be a promising lead for further studies. © 2024 The Authors

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Style	Citing Format
MLA	Sadeghian S, et al.. "Synthesis, Biological Evaluation, Molecular Docking, Md Simulation and Dft Analysis of New 3-Hydroxypyridine-4-One Derivatives As Anti-Tyrosinase and Antioxidant Agents." Heliyon, vol. 10, no. 15, 2024, pp. -.
APA	Sadeghian S, Zare F, Khoshneviszadeh M, Hafshejani AF, Salahshour F, Khodabakhshloo A, Saghaie L, Goshtasbi G, Sarikhani Z, Poustforoosh A, Sabet R, Sadeghpour H (2024). Synthesis, Biological Evaluation, Molecular Docking, Md Simulation and Dft Analysis of New 3-Hydroxypyridine-4-One Derivatives As Anti-Tyrosinase and Antioxidant Agents. Heliyon, 10(15), -.
Chicago	Sadeghian S, Zare F, Khoshneviszadeh M, Hafshejani AF, Salahshour F, Khodabakhshloo A, Saghaie L, et al.. "Synthesis, Biological Evaluation, Molecular Docking, Md Simulation and Dft Analysis of New 3-Hydroxypyridine-4-One Derivatives As Anti-Tyrosinase and Antioxidant Agents." Heliyon 10, no. 15 (2024): -.
Harvard	Sadeghian S et al. (2024) 'Synthesis, Biological Evaluation, Molecular Docking, Md Simulation and Dft Analysis of New 3-Hydroxypyridine-4-One Derivatives As Anti-Tyrosinase and Antioxidant Agents', Heliyon, 10(15), pp. -.
Vancouver	Sadeghian S, Zare F, Khoshneviszadeh M, Hafshejani AF, Salahshour F, Khodabakhshloo A, et al.. Synthesis, Biological Evaluation, Molecular Docking, Md Simulation and Dft Analysis of New 3-Hydroxypyridine-4-One Derivatives As Anti-Tyrosinase and Antioxidant Agents. Heliyon. 2024;10(15):-.
BibTex	@article{ author = {Sadeghian S and Zare F and Khoshneviszadeh M and Hafshejani AF and Salahshour F and Khodabakhshloo A and Saghaie L and Goshtasbi G and Sarikhani Z and Poustforoosh A and Sabet R and Sadeghpour H}, title = {Synthesis, Biological Evaluation, Molecular Docking, Md Simulation and Dft Analysis of New 3-Hydroxypyridine-4-One Derivatives As Anti-Tyrosinase and Antioxidant Agents}, journal = {Heliyon}, volume = {10}, number = {15}, pages = {-}, year = {2024} }
RIS	TY - JOUR AU - Sadeghian S AU - Zare F AU - Khoshneviszadeh M AU - Hafshejani AF AU - Salahshour F AU - Khodabakhshloo A AU - Saghaie L AU - Goshtasbi G AU - Sarikhani Z AU - Poustforoosh A AU - Sabet R AU - Sadeghpour H TI - Synthesis, Biological Evaluation, Molecular Docking, Md Simulation and Dft Analysis of New 3-Hydroxypyridine-4-One Derivatives As Anti-Tyrosinase and Antioxidant Agents JO - Heliyon VL - 10 IS - 15 SP - EP - PY - 2024 ER -

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