Assessment of Anti-tyrosinase and Antioxidant Activities along with Molecular Docking Studies, and in silico ADME of Some 3-Hydroxypyridin-4-one Derivatives

1.    Song Y, Chen S, Li L, Zeng Y, Hu X. The Hypopigmentation Mechanism of Tyrosinase Inhibitory Peptides Derived from Food Proteins: An Overview. Molecules. 2022 Apr 22;27(9):2710. doi: 10.3390/molecules27092710. 
2.    Peng Z, Wang G, He Y, Wang JJ, Zhao Y. Tyrosinase inhibitory mechanism and anti-browning properties of novel kojic acid derivatives bearing aromatic aldehyde moiety. Curr Res Food Sci. 2022 Dec 22;6:100421. doi: 10.1016/j.crfs.2022.100421. 
3.    Xu H, Li X, Mo L, Zou Y, Zhao G. Tyrosinase inhibitory mechanism and the anti-browning properties of piceid and its ester. Food Chem. 2022 Oct 1;390:133207. doi: 10.1016/j.foodchem.2022.133207.
4.    Ashooriha M, Khoshneviszadeh M, Khoshneviszadeh M, Rafiei A, Kardan M, Yazdian-Robati R, et al. Kojic acid-natural product conjugates as mushroom tyrosinase inhibitors. Eur J Med Chem. 2020 Sep 1;201:112480. doi: 10.1016/j.ejmech.2020.112480. 
5.    Sepehri N, Iraji A, Yavari A, Asgari MS, Zamani S, Hosseini S, et al. The natural-based optimization of kojic acid conjugated to different thio-quinazolinones as potential anti-melanogenesis agents with tyrosinase inhibitory activity. Bioorg Med Chem. 2021 Apr 15;36:116044. doi: 10.1016/j.bmc.2021.116044. 
6.    He M, Fan M, Yang W, Peng Z, Wang G. Novel kojic acid-1,2,4-triazine hybrids as anti-tyrosinase agents: Synthesis, biological evaluation, mode of action, and anti-browning studies. Food Chem. 2023 Sep 1;419:136047. doi: 10.1016/j.foodchem.2023.136047. 
7.    Wang G, He M, Huang Y, Peng Z. Synthesis and biological evaluation of new kojic acid-1,3,4-oxadiazole hybrids as tyrosinase inhibitors and their application in the anti-browning of fresh-cut mushrooms. Food Chem. 2023 May 30;409:135275. doi: 10.1016/j.foodchem.2022.135275. 
8.    Zhao DY, Zhang MX, Dong XW, Hu YZ, Dai XY, Wei X, et al. Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors. Bioorg Med Chem Lett. 2016 Jul 1;26(13):3103-3108. doi: 10.1016/j.bmcl.2016.05.006. 
9.    Dai, X.-Y., et al., Novel multifunctional hydroxypyridinone derivatives as potential shrimp preservatives. Food Bioprocess Tech. 2016. 9: p. 1079-1088.
10.    Zhu YZ, Chen K, Chen YL, Zhang C, Xie YY, Hider RC, et al. Design and synthesis of novel stilbene-hydroxypyridinone hybrids as tyrosinase inhibitors and their application in the anti-browning of freshly-cut apples. Food Chem. 2022 Aug 15;385:132730. doi: 10.1016/j.foodchem.2022.132730. 
11.    Li DF, Hu PP, Liu MS, Kong XL, Zhang JC, Hider RC, et al. Design and synthesis of hydroxypyridinone-L-phenylalanine conjugates as potential tyrosinase inhibitors. J Agric Food Chem. 2013 Jul 10;61(27):6597-603. doi: 10.1021/jf401585f. 
12.    Shao LL, Wang XL, Chen K, Dong XW, Kong LM, Zhao DY, et al. Novel hydroxypyridinone derivatives containing an oxime ether moiety: Synthesis, inhibition on mushroom tyrosinase and application in anti-browning of fresh-cut apples. Food Chem. 2018 Mar 1;242:174-181. doi: 10.1016/j.foodchem.2017.09.054. 
13.    Zhang X, Wu YT, Wei XY, Xie YY, Zhou T. Preparation, antioxidant and tyrosinase inhibitory activities of chitosan oligosaccharide-hydroxypyridinone conjugates. Food Chem. 2023 Sep 15;420:136093. doi: 10.1016/j.foodchem.2023.136093. 
14.    Singh LR, Chen YL, Xie YY, Xia W, Gong XW, Hider RC, et al. Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity. J Enzyme Inhib Med Chem. 2020 Dec;35(1):1562-1567. doi: 10.1080/14756366.2020.1801669. 
15.    Fazel R, Hassani B, Zare F, Jokar Darzi H, Khoshneviszadeh M, Poustforoosh A, et al. Design, synthesis, in silico ADME, DFT, molecular dynamics simulation, anti-tyrosinase, and antioxidant activity of some of the 3-hydroxypyridin-4-one hybrids in combination with acylhydrazone derivatives. J Biomol Struct Dyn. 2023 Sep 7:1-11. doi: 10.1080/07391102.2023.2252087. 
16.    Hassani B, Zare F, Emami L, Khoshneviszadeh M, Fazel R, Kave N, et al. Synthesis of 3-hydroxypyridin-4-one derivatives bearing benzyl hydrazide substitutions towards anti-tyrosinase and free radical scavenging activities. RSC Adv. 2023 Nov 7;13(46):32433-32443. doi: 10.1039/d3ra06490e. 
17.    Sabet R, Fassihi A, Hemmateenejad B, Saghaei L, Miri R, Gholami M. Computer-aided design of novel antibacterial 3-hydroxypyridine-4-ones: application of QSAR methods based on the MOLMAP approach. J Comput Aided Mol Des. 2012 Mar;26(3):349-61. doi: 10.1007/s10822-012-9561-2. 
18.    Sabet R, Behjati M, Vahabpour R, Memarnejadian A, Rostami M, Fassihi A, et al. Iron chelation afforded cardioprotection against H2O2-induced H9C2 cell injury: application of novel 3-hydroxy pyridine-4-one derivatives. Int J Cardiol. 2012 Dec 15;162(1):60-3. doi: 10.1016/j.ijcard.2011.11.067. 
19.    Sabet R, Behjati M, Vahabpour R, Memarnejadian A, Rostami M, Fassihi A, et al. Iron chelation afforded cardioprotection against H2O2-induced H9C2 cell injury: application of novel 3-hydroxy pyridine-4-one derivatives. Int J Cardiol. 2012 Dec 15;162(1):60-3. doi: 10.1016/j.ijcard.2011.11.067. 
20.    Saad HM, Tan CH, Lim SH, Manickam S, Sim KS. Evaluation of anti-melanogenesis and free radical scavenging activities of five Artocarpus species for cosmeceutical applications. Ind Crops Prod. 2021; 161: p. 113184.
21.    Zare F, Solhjoo A, Sadeghpour H, Sakhteman A, Dehshahri A. Structure-based virtual screening, molecular docking, molecular dynamics simulation and MM/PBSA calculations towards identification of steroidal and non-steroidal selective glucocorticoid receptor modulators. J Biomol Struct Dyn. 2023 Sep-Oct;41(16):7640-7650. 
22.    Taslimi P. Evaluation of in vitro inhibitory effects of some natural compounds on tyrosinase activity and molecular docking study: Antimelanogenesis potential. J Biochem Mol Toxicol. 2020 Nov;34(11):e22566. doi: 10.1002/jbt.22566. 
23.    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 Jul 26;10(15):e35281. doi: 10.1016/j.heliyon.2024.e35281. 
24.    Shehzadi SA, Saeed A, Perveen F, Channar PA, Arshad I, Abbas Q, et al. Identification of two novel thiazolidin-2-imines as tyrosinase inhibitors: synthesis, crystal structure, molecular docking and DFT studies. Heliyon. 2022 Aug 11;8(8):e10098. doi: 10.1016/j.heliyon.2022.e10098. 
25.    Chorfi Z, Aggoun D, Houchi S, Messasma Z, Abd El-Maksoud MS, Fernández-Garcĩa M, et al. Interaction of a novel inorganic nickel complex with tyrosinase as potential inhibitor: Synthesis, spectroscopic, DFT, NBO, docking and ADMET properties. J Mol Struct. 2023; 1280: p. 134998.‏
26.    Sabet R, Behjati M, Vahabpour R, Memarnejadian A, Rostami M, Fassihi A, et al. Iron chelation afforded cardioprotection against H2O2-induced H9C2 cell injury: application of novel 3-hydroxy pyridine-4-one derivatives. Int J Cardiol. 2012 Dec 15;162(1):60-3. doi: 10.1016/j.ijcard.2011.11.067.
27.    Iraji A, Khoshneviszadeh M, Bakhshizadeh P, Edraki N, Khoshneviszadeh M. Structure-Based Design, Synthesis, Biological Evaluation and Molecular Docking Study of 4-Hydroxy-N'-methylenebenzohydrazide Derivatives Acting as Tyrosinase Inhibitors with Potentiate Anti-Melanogenesis Activities. Med Chem. 2020;16(7):892-902. doi: 10.2174/1573406415666190724142951. 
28.    Emami L, Zare F, Zomorodian K, Agha MSN, Sabet R. Evaluation of Antimicrobial Activity of Some Hybrids of Pyrimidine-Azole Derivatives along with Molecular Docking Study. TIPS. 2023; 9(3):183-190.
29.    Zare F, Hashemi H, Hassani B, Fazel R, Miri R, Sadeghpour H. Synthesis, Biological Evaluation, in silico ADMET and Molecular Docking of new 1, 4‐Dihydropyridine Derivatives Bearing Ether Substitution as Calcium Channel Blockers. Chem Select. 2023; 8(21), e202204515
30.    Purwanto BT, Siswandono S, Kesuma D, Widiandani T,  Siswanto I. Molecular modeling, admet prediction, synthesis and the cytotoxic activity from the novel n-(4-tert-butylphenylcarbamoyl) benzamide against hela. RJC. 2021. 14(2): p. 1341-1350.