Potent inhibitory effects of benzyl and p-xylidine-bis dithiocarbamate sodium salts on activities of mushroom tyrosinase

References

• Yoruk R, Marshall MR. Physicochemical properties and function of plant polyphenol oxidase: a review. J Food Biochem 2003;27:361–422.
   Web of Science ®Google Scholar
• Seo SY, Sharma VK, Sharma N. Mushroom tyrosinase: recent prospects. J Agric Food Chem 2003;51:2837–53.
   PubMed Web of Science ®Google Scholar
• Van Gelder CWG, Flurkey WH, Wichers HJ. Sequence and structural features of plant and fungal tyrosinases. Phytochemistry 1997;45:1309–23.
   PubMed Web of Science ®Google Scholar
• Halaouli S, Asther M, Sigoillot J-C, Hamdi M, Lomascolo A. Fungal tyrosinases: new prospects in molecular characteristics, bio-engineering and biotechnological applications. J Appl Microbiol 2006;100:219–32.
   PubMed Web of Science ®Google Scholar
• Mayer AM. Polyphenol oxidases in plants and fungi: going places? A review. Phytochemistry 2006;67:2318–31.
   PubMed Web of Science ®Google Scholar
• Robb DA. Copper Proteins and Copper Enzymes. Boca Raton: CRC Press, 1984.
   Google Scholar
• Riley PA. Tyrosinase kinetics: a semi-quantitative model of the mechanism of oxidation of monohydric and dihydric phenolic substrates. J Theor Biol 2000;203:1–12.
   PubMed Web of Science ®Google Scholar
• Fenoll LG, Rodriguez-Lopez JN, Garcia-Sevilla F, Tudela J, Garcia-Ruiz PA, Varon R. Oxidation by mushroom tyrosinase of monophenols generating slightly unstable oquinones. Eur J Biochem 2000;267:5865–78.
   PubMedGoogle Scholar
• Nylander K, Bourdon J-C, Bray SE, Gibbs NK, Kay R, Hart I, et al. Transcriptional activation of tyrosinase and TRP-1 by p53 links UV irradiation to the protective tanning response. J Pathol 2000;190:39–46.
   PubMed Web of Science ®Google Scholar
• Jaenicke E, Decker H. Tyrosinases from crustaceans form hexamers. Biochem J 2003;371:515–23.
   PubMed Web of Science ®Google Scholar
• Jacobson ES. Pathogenic roles for fungal melanins. Clin Microbiol Rev 2000;13:708–17.
   PubMed Web of Science ®Google Scholar
• Barrett FM. Wound-healing phenoloxidase in larval cuticle of Calpodes ethulius (Lepidoptera: Hesperiidae). Can J Zool 1984;62:834–8.
   Web of Science ®Google Scholar
• Sugumaran M. Molecular mechanism for culticular sclerotization. Adv Insect Physiol 1988;21:179–231.
   Google Scholar
• Sugumaran M. Molecular mechanisms for mammalian melanogenesis. Comparison with insect cuticular sclerotization. FEBS Lett 1991;295: 233–9.
   PubMed Web of Science ®Google Scholar
• Goding CR. Melanocytes: the new black. Int J Biochem Cell Biol 2007;39:275–9.
   PubMed Web of Science ®Google Scholar
• Spritz RA. The genetics of generalized vitiligo and associated autoimmune diseases. J Dermatol Sci 2006;41:3–10.
   PubMed Web of Science ®Google Scholar
• Strothkemp KG, Jolley RL, Mason HS. Quaternary structure of mushroom tyrosinase. Biochem Biophys Res Commun 1976;70:519–24.
   PubMed Web of Science ®Google Scholar
• Decker H, Schweikardt T, Tuczek F. The first crystal structure of tyrosinase: all questions answered?Angew Chem Int Ed Engl 2006;45:4546–50.
   PubMed Web of Science ®Google Scholar
• Sanchez-Ferrer A, RodriGuez-Lopez JN, Garcia-Canovas F, Garcia-Carmona F. Tyrosinase: a comprehensive review of its mechanism. Biochim Biophys Acta 1995;1247:1–11.
   PubMed Web of Science ®Google Scholar
• Fenoll LG, Rodriguez-Lopez JN, Garcia-Sevilla F, Garcia-Ruiz PA, Varo NR, Garcia-Canovas F, et al. Analysis and interpretation of the action mechanism of mushroom tyrosinase on monophenols and diphenols generating highly unstable o-quinone. Biochim Biophys Acta 2001;1548:1–22.
   PubMed Web of Science ®Google Scholar
• Rajarathnam S, Shashirekha MN, Rashmi S. Biochemical changes associated with mushroom browning in Agaricus bisporus (Lange) Imbach and Pleurotus florida (Block and Tsao): commercial implications. J Sci Food Agric 2003;83:1531–7.
   Web of Science ®Google Scholar
• Friedman M. Food browning and its prevention: an overview. J Agric Food Chem 1996;44:631–53.
   Web of Science ®Google Scholar
• Rescigno A, Sollai F, Pisu B, Rinaldi A, Sanjust E. Tyrosinase inhibition: general and applied aspects. J Enzyme Inhib Med Chem 2002;17:207–18.
   PubMed Web of Science ®Google Scholar
• Kenji O, Minako K, Yoshihide S, Seiichi K, Yuki M, Yoshinori N, et al. Inhibitory effects of whisky congeners on melanogenesis in mouse B16 melanoma cells. Biosci Biotech Biochem 2008;72:1107–10.
   PubMed Web of Science ®Google Scholar
• Palumbo A, Ischia M, Misuraca G, Prota G. Mechanism of inhibition of melanogenesis by hydroquinone. Biochim Biophys Acta 1991;1073: 85–90.
   PubMed Web of Science ®Google Scholar
• Maeda K, Fukuda M. In vitro effectiveness of several whitening cosmetic components in human melanocytes. J Soc Cosmet Chem 1991;42: 361–8.
   Web of Science ®Google Scholar
• Riely PA, Sawyer B, Wolff MA. The melanocytotoxic effect of 4-hydroxyanisole. J Invest Dermatol 1975;64:86–9.
   PubMed Web of Science ®Google Scholar
• Kim Y-J, Uyama H. Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 2005;62:1707–23.
   PubMed Web of Science ®Google Scholar
• Naish S, Holden JL, Cooksey CJ, Riely PA. The major primary cytotoxic product of 4-hydroxyanisole oxidation by mushroom tyrosinase is 4-methoxy ortho benzoquinone. Pigment Cell Res 1988;1:382–5.
   PubMedGoogle Scholar
• Riely PA. Melanogenesis: a realistic target for antimelanoma therapy. Eur J Cancer 1991;27:1172–7.
   PubMed Web of Science ®Google Scholar
• Badria FA, Gayyar MA. A new type of tyrosinase inhibitors from natural products as potential treatments for hyperpigmentation. Boll Chim Farma 2001;140:267–71.
   PubMedGoogle Scholar
• Kubo I, Kinst-Hori I. Tyrosinase inhibitors from anise oil. J Agric Food Chem 1998;46:1268–71.
   Web of Science ®Google Scholar
• Kubo I, Kinst-Hori I. Tyrosinase inhibitors from cumin. J Agric Food Chem 1998;46:5338–41.
   Web of Science ®Google Scholar
• Kubo I, Kinst-Hori I. Tyrosinase inhibitory activity of the olive oil flavor compounds. J Agric Food Chem 1999;47:4574–8.
   PubMed Web of Science ®Google Scholar
• Kubo I, Kinst-Hori I. 2-Hydroxy-4-methoxy benzaldehyde: a potent tyrosinase inhibitor from African medicinal plants. Planta Med 1999;65:19–22.
   PubMed Web of Science ®Google Scholar
• Jimenez M, Chazarra S, Escribano J, Cabanes J, Garcia-Carmona F. Competitive inhibition of mushroom tyrosinase by 4-substituted benzaldehydes. J Agric Food Chem 2001;49:4060–3.
   PubMed Web of Science ®Google Scholar
• Espin JC, Wichers HG. Effect of captopril on mushroom tyrosinase activity in vivo. Biochim Biophys Acta 2001;1554:289–300.
   Web of Science ®Google Scholar
• Andrawis A, Khan V. Effect of methimazole on the activity of mushroom tyrosinase. Biochem J 1996;35:91–6.
   Google Scholar
• Ferrar PH, Walker JRI. Inhibition of diphenoloxidases: a comparative study. J Food Biochem 1996;20:15–30.
   Web of Science ®Google Scholar
• Lee KH, Koketsu M, Choi SY, Lee KJ, Lee P, Ishihara H, et al. Potent inhibitory effects of N-aryl S-alkylthiocarbamate derivatives on the dopa oxidase activity of mushroom tyrosinase. Chem Pharm Bull 2005;53:747–9.
   PubMed Web of Science ®Google Scholar
• Seiji M, Yashida T, Itakura H, Irimajiri T. Inhibition of melanin formation by sulfhydryl compounds. J Invest Dermatol 1969;52:280–6.
   PubMed Web of Science ®Google Scholar
• Kasraee B, Hügin A, Tran C, Sorg O, Saurat J-H. Methimazole is an inhibitor of melanin synthesis in cultured B16 melanocytes. J Invest Dermatol 2004;122:1338–41.
   PubMed Web of Science ®Google Scholar
• Anderson JW. Extraction of enzyme and sub cellular organelles from plant tissues. Phytochemistry 1968;7:1973–88.
   Web of Science ®Google Scholar
• Palmer JK, Robbert JB. Inhibition of banana polyphenol oxidase by 2-mercaptobenzothiazole. Science 1967;157:200–1.
   PubMed Web of Science ®Google Scholar
• Ronconi L, Maccato C, Barreca D, Saini R, Zancato M, Fregona D. Gold (III) dithiocarbamate derivatives of N-methylglycine: an experimental and theoretical investigation. Polyhedron 2005;24:521–31.
   Web of Science ®Google Scholar
• Faraglia G, Sitran S, Montagner D. Pyrrolidine dithiocarbamates of Pd (II). Inorg Chim Acta 2005;358:971–80.
   Web of Science ®Google Scholar
• Kim I, Kim CH, Kim JH, Lee J, Choi JJ, Chen ZA, et al. Pyrrolidine dithiocarbamate and zinc inhibit proteasome-dependent proteolysis. Exp Cell Res 2004;298:229–38.
   PubMed Web of Science ®Google Scholar
• Gheibi N, Saboury AA, Mansury-Torshizy H, Haghbeen K, Moosavi-Movahedi AA. The inhibition effect of some n-alkyl dithio- carbamates on mushroom tyrosinase. J Enzyme Inhib Med Chem 2004;20:393–9.
   Web of Science ®Google Scholar
• Alijanianzadeh M, Saboury AA, Mansouri-Torshizi H, Haghbeen K, Moosavi-Movahedi AA. The inhibitory effect of some new synthesized xanthates on mushroom tyrosinase activities. J Enzyme Inhib Med Chem 2007;22:239–46.
   PubMed Web of Science ®Google Scholar
• Mansouri-Torshizi H, Islami-Moghaddam M, Divsalar A, Saboury AA. 2,2’-Bipyridinebutyldithiocarbamatoplatinum (II) and palladium (II) complexes: synthesis, characterization, cytotoxicity, and rich DNA-binding studies. Bioorg Med Chem 2008;16:9616–25.
   PubMed Web of Science ®Google Scholar
• Cabanes J, Garcia-Canovas F, Lozano JA, Garcia-Carmona F. A kinetic study of the melanization pathway between L-tyrosine and dopachrome. Biochim Biophys Acta 1987;790:101–7.
   Web of Science ®Google Scholar
• Chen QX, Kubo I. Kinetics of mushroom tyrosinase inhibition by quercetin. J Agric Food Chem 2002;50:4108–12.
   PubMed Web of Science ®Google Scholar
• Marangoni AG. Enzyme Kinetics: A Modern Approach. New York: John Wiley & Sons, 2002.
   Google Scholar
• Tellinghuisen J. Stupid statistics! Methods Cell Biol 2008;84:739–80.
   PubMed Web of Science ®Google Scholar
• Tellinghuisen J. Least squares in calibration: weights, nonlinearity, and other nuisances. Methods Enzymol 2009;454:259–85.
   PubMed Web of Science ®Google Scholar
• Cortes A, Cascante M, Cardenas M, Cornish-Bowden A. Relationships between inhibition constants, inhibitor concentrations for 50% inhibition and types of inhibition: new ways of analyzing data. Biochem J 2001;357:263–8.
   PubMed Web of Science ®Google Scholar
• Atkins P, DePaula J. Physical Chemistry, 7th ed. New York: WH Freeman & Company, 2002: Ch. 9.
   Google Scholar
• Perozzo R, Folkers G, Scapozza L. Thermodynamics of protein–ligand interactions: history, presence, and future aspects. J Recept Signal Transduct Res 2004;24:1–52.
   PubMed Web of Science ®Google Scholar
• Hanlon DP, Shuman S. Copper ion binding and enzyme inhibitory properties of the anti thyroid drug methimazole. Experientia 1975;31:1005–6.
   PubMedGoogle Scholar
• Saboury AA, Zolghadri S, Haghbeen K, Moosavi-Movahedi AA. The inhibitory effect of benzenethiol on the cresolase and catecholase activities of mushroom tyrosinase. J Enzyme Inhib Med Chem 2006;21:711–17.
   PubMed Web of Science ®Google Scholar
• Shi Y, Chen QX, Wang Q, Song KK, Qiu L. Inhibitory effects of cinnamic acid and its derivatives on the diphenolase activity of mushroom (Agaricus bisporus) tyrosinase. Food Chem 2005;92:707–12.
   Web of Science ®Google Scholar
• Park KH, Lee JR, Hahn HS, Kim YH, Bae CD, Yang JM, et al. Inhibitory effect of ammonium tetrathiotungstate on tyrosinase and its kinetic mechanism. Chem Pharm Bull 2006;54:1266–70.
   PubMed Web of Science ®Google Scholar
• Liu J, Yi W, Wan Y, Ma L, Song H. 1-(1-Arylethylidene)thiosemicarbazide derivatives: a new class of tyrosinase inhibitors. Bioorg Med Chem 2008;16:1096–102.
   PubMed Web of Science ®Google Scholar
• Karbassi F, Saboury AA, Hassan Khan MT, Iqbal Choudhary M, Saifi ZS. Mushroom tyrosinase inhibition by two potent uncompetitive inhibitors. J Enzyme Inhib Med Chem 2004;19:349–53.
   PubMed Web of Science ®Google Scholar
• Liu J, Cao R, Yi W, Ma C, Wan Y, Zhou B, et al. A class of potent tyrosinase inhibitors: alkylidenethiosemicarbazide compounds. Eur J Med Chem 2009;44:1773–8.
   PubMed Web of Science ®Google Scholar