Evaluation of novel pyrimidine derivatives as a new class of mushroom tyrosinase inhibitor

References

• Rezaei M, Mohammadi HT, Mahdavi A, Shourian M, Ghafouri H. Evaluation of thiazolidinone derivatives as a new class of mushroom tyrosinase inhibitors. Int J Biol Macromol. 2018;108:205–213. doi:10.1016/j.ijbiomac.2017.11.14729180052
   PubMed Web of Science ®Google Scholar
• Yun HY, Do Hyun Kim SS, Ullah S, et al. Design, synthesis, and anti-melanogenic effects of (E)-2-benzoyl-3-(substituted phenyl) acrylonitriles. Drug Des Devel Ther. 2015;9:4259.
   PubMed Web of Science ®Google Scholar
• Ramsden CA, Riley PA. Tyrosinase: the four oxidation states of the active site and their relevance to enzymatic activation, oxidation and inactivation. Bioorg Med Chem. 2014;22(8):2388–2395. doi:10.1016/j.bmc.2014.02.04824656803
   PubMed Web of Science ®Google Scholar
• Thanigaimalai P, Le Hoang TA, Lee K-C, et al. Structural requirement (s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells. Bioorg Med Chem Lett. 2010;20(9):2991–2993. doi:10.1016/j.bmcl.2010.02.06720359890
   PubMed Web of Science ®Google Scholar
• Al-Amin M, Cao J, Naeem M, et al. Increased therapeutic efficacy of a newly synthesized tyrosinase inhibitor by solid lipid nanoparticles in the topical treatment of hyperpigmentation. Drug Des Devel Ther. 2016;10:3947. doi:10.2147/DDDT.S123759
   PubMed Web of Science ®Google Scholar
• Abbas Q, Ashraf Z, Hassan M, et al. Development of highly potent melanogenesis inhibitor by in vitro, in vivo and computational studies. Drug Des Devel Ther. 2017;11:2029. doi:10.2147/DDDT.S137550
   PubMed Web of Science ®Google Scholar
• Harris Z, Donovan MG, Branco GM, Limesand KH, Burd R. Quercetin as an emerging anti-melanoma agent: a four-focus area therapeutic development strategy. Front Nutr. 2016;3:48. doi:10.3389/fnut.2016.0004827843913
   PubMed Web of Science ®Google Scholar
• Loizzo M, Tundis R, Menichini F. Natural and synthetic tyrosinase inhibitors as antibrowning agents: an update. Compr Rev Food Sci Food Saf. 2012;11(4):378–398. doi:10.1111/j.1541-4337.2012.00191.x
   Web of Science ®Google Scholar
• Do Hyun Kim SJK, Ullah S, Yun HY, Chun P, Moon HR. Design, synthesis, and antimelanogenic effects of (2-substituted phenyl-1, 3-dithiolan-4-yl) methanol derivatives. Drug Des Devel Ther. 2017;11:827. doi:10.2147/DDDT.S131538
   PubMed Web of Science ®Google Scholar
• Sugumaran M, Barek H. Critical analysis of the melanogenic pathway in insects and higher animals. Int J Mol Sci. 2016;17(10):1753. doi:10.3390/ijms17101753
   PubMed Web of Science ®Google Scholar
• Gorman MJ, Arakane Y. Tyrosine hydroxylase is required for cuticle sclerotization and pigmentation in Tribolium castaneum. Insect Biochem Mol Biol. 2010;40(3):267–273. doi:10.1016/j.ibmb.2010.01.00420080183
   PubMed Web of Science ®Google Scholar
• Battaini G, Monzani E, Casella L, Santagostini L, Pagliarin R. Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid. JBIC J Bio Inorg Chemistry. 2000;5(2):262–268.
   PubMed Web of Science ®Google Scholar
• Zhu Y-J, Zhou H-T, Hu Y-H, et al. Antityrosinase and antimicrobial activities of 2-phenylethanol, 2-phenylacetaldehyde and 2-phenylacetic acid. Food Chem. 2011;124(1):298–302. doi:10.1016/j.foodchem.2010.06.036
   Web of Science ®Google Scholar
• GąSowska B, Kafarski P, Wojtasek H. Interaction of mushroom tyrosinase with aromatic amines, o-diamines and o-aminophenols. Biochim Et Biophys Acta (Bba)-Gen Subj. 2004;1673(3):170–177. doi:10.1016/j.bbagen.2004.04.013
   PubMed Web of Science ®Google Scholar
• Bhat AR. Biological activity of pyrimidine derivativies: a review. Org Med Chem IJ. 2017;2(2):1–4.
   Google Scholar
• Dansena H, Dhongade H, Chandrakar K. Pharmacological potentials of pyrimidine derivative: a review. Asian J Pharm Clin Res. 2015;8(4):171–177.
   Google Scholar
• Bae SJ, Ha YM, Park YJ, et al. Design, synthesis, and evaluation of (E)-N-substituted benzylidene–aniline derivatives as tyrosinase inhibitors. Eur J Med Chem. 2012;57:383–390. doi:10.1016/j.ejmech.2012.09.02623149255
   PubMed Web of Science ®Google Scholar
• Mohammadi A, Ghafoori H, Ghalami-Choobar B, Rohinejad R. Synthesis, solvatochromic properties and biological evaluation of some novel azo-hydrazone tautomeric dyes. J Mol Liq. 2014;198:44–50. doi:10.1016/j.molliq.2014.07.005
   Web of Science ®Google Scholar
• Jimenez-Cervantes C, Valverde P, García-Borrón JC, Solano F, Lozano JA. Improved tyrosinase activity stains in polyacrylamide electrophoresis gels. Pigm Cell Res. 1993;6(6):394–399.
   PubMedGoogle 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. Biochemistry. 2011;50(24):5477–5486. doi:10.1021/bi200395t21598903
   PubMed Web of Science ®Google Scholar
• Word JM, Lovell SC, Richardson JS, Richardson DC. Asparagine and glutamine: using hydrogen atom contacts in the choice of side-chain amide orientation. J Mol Biol. 1999;285(4):1735–1747. doi:10.1006/jmbi.1998.24019917408
   PubMed Web of Science ®Google Scholar
• Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem. 2010;31(2):455–461. doi:10.1002/jcc.2133419499576
   PubMed Web of Science ®Google Scholar
• Sanner MF. Python: a programming language for software integration and development. J Mol Graph Model. 1999;17(1):57–61.10660911
   PubMed Web of Science ®Google Scholar
• ColemanWF, ArumainayagamCR. HyperChem 5 (By Hypercube, Inc.). J Chem Educ. 1998;75:4. https://doi.org/10.1021/ed075p416
   Google Scholar
• Grosdidier A, Zoete V, Michielin O. EADock: docking of small molecules into protein active sites with a multiobjective evolutionary optimization. Proteins. 2007;67(4):1010–1025. doi:10.1002/prot.2136717380512
   PubMed Web of Science ®Google Scholar
• Wallace AC, Laskowski RA, Thornton JM. LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions. Protein Eng Des Sel. 1995;8(2):127–134. doi:10.1093/protein/8.2.127
   Web of Science ®Google Scholar
• Parvez S, Kang M, Chung HS, Bae H. Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries. Phytother Res. 2007;21(9):805–816. doi:10.1002/ptr.218417605157
   PubMed Web of Science ®Google Scholar
• Liu P, Shu C, Liu L, Huang Q, Peng Y. Design and synthesis of thiourea derivatives with sulfur-containing heterocyclic scaffolds as potential tyrosinase inhibitors. Bioorg Med Chem. 2016;24(8):1866–1871. doi:10.1016/j.bmc.2016.03.01326972919
   PubMed Web of Science ®Google Scholar
• Pillaiyar T, Manickam M, Namasivayam V. Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors. J Enzyme Inhib Med Chem. 2017;32(1):403–425. doi:10.1080/14756366.2016.125688228097901
   PubMed Web of Science ®Google Scholar