Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach

References

• Jakimiuk K, Wink M, Tomczyk M. Flavonoids of the Caryophyllaceae. Phytochem Rev 2021;20:1–40.
   Google Scholar
• García-Sosa AR, Maran U. Improving the use of ranking in virtual screening against HIV-1 integrase with triangular numbers and including ligand profiling with antitargets. J Chem Inf Model 2014;54:3172–85.
   PubMed Web of Science ®Google Scholar
• Glisic S, Sencanski M, Perovic V, et al. Arginase flavonoid anti-leishmanial in silico inhibitors flagged against anti-targets. Molecules 2016;21:589–14.
   PubMed Web of Science ®Google Scholar
• Flurkey WH, Inlow JK. Proteolytic processing of polyphenol oxidase from plants and fungi. J Inorg Biochem 2008;102:2160–70.
   PubMed Web of Science ®Google Scholar
• Ismaya WT, Rozeboom HJ, Weijn A, et al. Crystal structure of Agaricus bisporus mushroom tyrosinase: identity of the tetramer subunits and interaction with tropolone. Biochem 2011;50:5477–86.
   PubMed Web of Science ®Google Scholar
• Klabunde T, Eicken C, Sacchettini JC, Krebs B. Crystal structure of a plant catechol oxidase containing a dicopper center. Nat Struct Mo. Biol 1998;5:1084–90.
   Google Scholar
• Zolghadri S, Bahrami A, Hassan Khan MT, et al. A comprehensive review on tyrosinase inhibitors. J Enzyme Inhib Med Chem 2019;34:279–309.
   PubMed Web of Science ®Google Scholar
• Hazes B, Magnus K, Bonaventura C, et al. Crystal structure of deoxygenated Limulus polyphemus subunit II hemocyanin at 2.18 A resolution: clues for a mechanism for allosteric regulation. Protein Sci 1993;2:597–619.
   PubMed Web of Science ®Google Scholar
• Ferro S, Deri B, Germanò MP, et al. Targeting tyrosinase: development and structural insights of novel inhibitors bearing arylpiperidine and arylpiperazine fragments. J Med Chem 2018;61:3908–17.
   PubMed Web of Science ®Google Scholar
• Lai X, Wichers HJ, Soler-Lopez M, Dijkstra BW. Structure and function of human tyrosinase and tyrosinase-related proteins. Chem–An Eur J 2018;24:47–55.
   PubMed Web of Science ®Google Scholar
• Şöhretoğlu D, Sari S, Barut B, Özel A. Tyrosinase inhibition by some flavonoids: inhibitory activity, mechanism by in vitro and in silico studies. Bioorg Chem 2018;81:168–74.
   PubMed Web of Science ®Google Scholar
• Isidorov V, Szoka L, Nazaruk J. Cytotoxicity of white birch bud extracts: perspectives for therapy of tumours. PLoS One 2018;13:e0201949–10.
   PubMed Web of Science ®Google Scholar
• Nazaruk J, Jakoniuk P. Flavonoid composition and antimicrobial activity of Cirsium rivulare (Jacq.) all flowers. J Ethnopharmacol 2005;102:208–12.
   PubMed Web of Science ®Google Scholar
• Tomczyk M, Gudej J. Quercetin and kaempferol glycosides from Ficaria verna flowers and their structure studied by 2D NMR spectroscopy. Pol J Chem 2002;76:1601–5.
   Google Scholar
• Strawa J, Wajs-Bonikowska A, Jakimiuk K, et al. Phytochemical examination of woolly burdock Arctium tomentosum leaves and flower heads. Chem Nat Compd 2020;56:345–7.
   Web of Science ®Google Scholar
• Juszczak AM, Czarnomysy R, Strawa JW, et al. In vitro anticancer potential of Jasione montana and its main components against human amelanotic melanoma cells. Int J Mol Sci 2021;22:1–25.
   Web of Science ®Google Scholar
• Strawa J, Galanty A, Jakimiuk K, Grabowska K, Podolak I, Tomczyk M. Cytotoxic effect on human melanoma cell lines and tyrosinase inhibition of Hottonia palustris. Poster session presented at: 69th International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research; 5-9 September 2021; Bonn, Germany; Virtual Conference.
   Google Scholar
• Jakimiuk K, Strawa JW, Granica S, Tomczyk M. New flavone C-glycosides from Scleranthus perennis and their anti-collagenase activity. Molecules 2021;26:5631–10.
   PubMed Web of Science ®Google Scholar
• Tomczyk M. Secondary metabolites from Potentilla recta L. and Drymocallis rupestris (L.) Soják (syn. Potentilla rupestris L.) (Rosaceae). Biochem Syst Ecol 2011;39:893–6.
   Web of Science ®Google Scholar
• Gudej J, Tomczyk M. Polyphenolic compounds from flowers of Ficaria verna Huds. Acta Pol Pharm 1999;56:475–6.
   Google Scholar
• Ciganović P, Jakimiuk K, Tomczyk M, Zovko-Končić M. Glycerolic licorice extracts as active cosmeceutical ingredients: extraction optimization, chemical characterization, and biological activity. Antioxidants 2019;8:445–14.
   Web of Science ®Google Scholar
• Yoshino M, Murakami K. A graphical method for determining inhibition constants. J Enzyme Inhib Med Chem 2009;24:1288–90.
   PubMed Web of Science ®Google Scholar
• Butt ARS, Abbasi MA, Rehman AA, et al. Synthesis and structure-activity relationship of tyrosinase inhibiting novel bi-heterocyclic acetamides: mechanistic insights through enzyme inhibition, kinetics and computational studies. Bioorg Chem 2019;86:459–72.
   PubMed Web of Science ®Google Scholar
• Lu C, Wu C, Ghoreishi D, et al. OPLS4: improving force field accuracy on challenging regimes of chemical space. J Chem Theory Comput 2021;17:4291–300.
   PubMed Web of Science ®Google Scholar
• Berman HM, Westbrook J, Feng Z, et al. The protein data bank. Nucleic Acids Res 2000;28:3908–17.
   Web of Science ®Google Scholar
• Sastry GM, Adzhigirey M, Day T, et al. Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments. J Comput Aided Mol Des 2013;27:221–34.
   PubMed Web of Science ®Google Scholar
• Friesner RA, Murphy RB, Repasky MP, et al. Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. J Med Chem 2006;49:6177–96.
   PubMed Web of Science ®Google Scholar
• Jacob V, Hagai T, Soliman K. Structure-activity relationships of flavonoids. Curr Org Chem 2011;15:2641–57.
   Web of Science ®Google Scholar
• Cos P, Ying L, Calomme M, et al. Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J Nat Prod 1998;61:71–6.
   PubMed Web of Science ®Google Scholar
• Jakimiuk K, Gesek J, Atanasov AG, Tomczyk M. Flavonoids as inhibitors of human neutrophil elastase. J Enzyme Inhib Med Chem 2021;36:1016–28.
   PubMed Web of Science ®Google Scholar
• Zhang L, Zhao X, Tao G-J, et al. Investigating the inhibitory activity and mechanism differences between norartocarpetin and luteolin for tyrosinase: a combinatory kinetic study and computational simulation analysis. Food Chem 2017;223:40–8.
   PubMed Web of Science ®Google Scholar
• Fan M, Zhang G, Hu X, et al. Quercetin as a tyrosinase inhibitor: inhibitory activity, conformational change and mechanism. Food Res Int 2017;100:226–33.
   PubMed Web of Science ®Google Scholar
• Lu Y, Chen J, Wei D, et al. Tyrosinase inhibitory effect and inhibitory mechanism of tiliroside from raspberry. J Enzyme Inhib Med Chem 2009;24:1154–60.
   PubMed Web of Science ®Google Scholar
• Atanasov AG, Zotchev SB, Dirsch VM, Supuran CT. Natural products in drug discovery: advances and opportunities. Nat Rev Drug Discov 2021;20:200–16.
   PubMed Web of Science ®Google Scholar