The role of alkyl chain length in the inhibitory effect n-alkyl xanthates on mushroom tyrosinase activities
Languages of publication
Sodium salts of four n-alkyl xanthate compounds, C2H5OCS2Na (I), C3H7OCS2Na (II), C4H9OCS2Na (III), and C6H13OCS2Na (IV) were synthesized and examined for inhibition of both cresolase and catecholase activities of mushroom tyrosinase (MT) in 10 mM sodium phosphate buffer, pH 6.8, at 293 K using UV spectrophotemetry. 4-[(4-methylbenzo)azo]-1,2-benzendiol (MeBACat) and 4-[(4-methylphenyl)azo]-phenol (MePAPh) were used as synthetic substrates for the enzyme for catecholase and cresolase reactions, respectively. Lineweaver-Burk plots showed different patterns of mixed, competitive or uncompetitive inhibition for the four xanthates. For the cresolase activity, I and II showed uncompetitive inhibition but III and IV showed competitive inhibition pattern. For the catecholase activity, I and II showed mixed inhibition but III and IV showed competitive inhibition. The synthesized compounds can be classified as potent inhibitors of MT due to their Ki values of 13.8, 11, 8 and 5 µM for the cresolase activity, and 1.4, 5, 13 and 25 µM for the catecholase activity for I, II, III and IV, respectively. For the catecholase activity both substrate and inhibitor can be bound to the enzyme with negative cooperativity between the binding sites (α > 1) and this negative cooperativity increases with increasing length of the aliphatic tail of these compounds. The length of the hydrophobic tail of the xanthates has a stronger effect on the Ki values for catecholase inhibition than for cresolase inhibition. Increasing the length of the hydrophobic tail leads to a decrease of the Ki values for cresolase inhibition and an increase of the Ki values for catecholase inhibition.
- Institute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran
- Institute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran
- Department of Chemistry, University of Sistan and Baluchestan, Zahedan, Iran
- Andrawis A, Kahn V (1996) Effect of methimazole on the activity of mushroom tyrosinase. Biochem J 235: 91-96.
- Atkins P, dePaula J (2002) Physical Chemistry, 7th edn, chapter 9. W. H. Freeman & Company, NewYork.
- Barrett FM (1984) Wound-healing phenoloxidase in larval cuticle of Calpodes ethlius (Lepidoptera: Hesperiidae). Can J Zool 62: 834-838.
- Battaini G, Monzani E, Casella L, Santagostini L, Pagliarin R (2000) Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid. J Biol Inorg Chem 5: 262-268.
- Cabanes J, Chazarra S, Garcia-Carmona F (1994) Kojic acid, a cosmetic skin agent, is a slow-binding inhibitor of catecholase activity of tyrosinase. J Pharm Pharmacol 46: 982-985.
- Chen JS, Wei C, Marshall MR (1991a) Inhibition mechanism of kojic acid on polyphenol oxidase. J Agric Food Chem 39: 1897-1901.
- Chen JS, Wei C, Rolle RS, Otwell WS, Balban MO, Marshall MR (1991b) Inhibitory effect of kojic acid on some plant and crustacean polyphenol oxidases. J Agric Food Chem 39: 1396-1401.
- Chen QX, Kubo I (2002) Kinetics of mushroom tyrosinase inhibition by quercetin. J Agric Food Chem 50: 4108-4112.
- Espin JC, Wichers HG (2001) Effect of captopril on mushroom tyrosinase activity in vivo. Biochim Biophys Acta 1544: 289-300.
- Fackler JP Jr, William CS (1969) Sulfur ligand complexes. IX. Reactions of metal xanthates and their derivatives. The formation of biophosphine-dithiocarbonate and -trithiocarbonate complexes of palladium (II) and platinum (II). Inorg Chem 8: 1631-1639.
- Ferrar PH, Walker JRI (1996) Inhibition of diphenoloxidases: a comparative study. J Food Biochem 20: 15-30.
- Gheibi N, Saboury AA, Haghbeen K, Moosavi-Movahedi AA (2005) Activity and structural changes of mushroom tyrosinase induced by n-alkyl sulfates. Colloids Surf B Biointerfaces 45: 104-107.
- Gheibi N, Saboury AA, Mansury-Torshizy H, Haghbeen K, Moosavi-Movahedi AA (2004) The inhibition effect of some n-alkyl dithiocarbamates on mushroom tyrosinase. J Enzyme Inhib Med Chem 20: 393-399.
- Goetghebeur M, Kermasha S (1996) Inhibition of polyphenol oxidase by copper-metallothionein from Aspergillus niger. Phytochemistry 42: 935-940.
- Haghbeen K, Saboury AA, Karbassi F (2004) Substrate share in the suicide inactivation of mushroom tyrosinase. Biochim Biophys Acta 1675: 139-146.
- Haghbeen K, Tan EW (1998) Facile synthesis of catechol azo dyes. J Org Chem 63: 4503-4505.
- Hanlon DP, Shuman S (1975) Copper ion binding and enzyme inhibitory properties of the antithyroid drug methimazole. Experientia 31: 1005-1006.
- Hepp AF, Himmelwright RS, Eickman NC, Solomon EI (1979) Ligand displacement reactions of oxyhemocyanin: comparison of reactivities of arthropods and mollusks. Biochem Biophys Res Commun 89: 1050-1057.
- Himmelwright RS, Eickman NC, Solomon EI (1979) Reactions and interconversion of met and dimer hemocyanin. Biochem Biophys Res Commun 86: 628-634.
- Himmelwright RS, Eickman NC, Lubein CD, Solomon EI (1980) Chemical and spectroscopic comparison of the binuclear copper active site of ollusk and arthropod hemocyanins. J Am Chem Soc 102: 5378-5388.
- Jackman MP, Hajnal A, Lerch K (1991) Albino mutants of Streptomyces glaucescens tyrosinase. Biochem J 274: 707-713.
- Kahn V (1995) Title! In Enzymatic Browning and its Prevention (Lee CY, Whitaker JR, eds) pp 277-294, American Chemical Society, Washington DC.
- Kahn V, Ben-Shalom N, Zakin V (1997) Effect of kojic acid on the oxidation of N-acetyldopamine by mushroom tyrosinase. J Agric Food Chem 45: 4460-4465.
- Karbassi F, Haghbeen K, Saboury AA, Ranjbar B, Moosavi-Movahedi AA (2003) Activity, structural and stability changes of mushroom tyrosinase by sodium dodecyl sulfate. Colloids Surf B Biointerfaces 32: 137-143.
- Karbassi F, Haghbeen K, Saboury AA, Ranjbar B, Moosavi-Movahedi AA, Farzami B (2004a) Stability, structural and suicide inactivation changes of mushroom tyrosinase after acetylation by N-acetylimidazole. Int J Biol Macromol 34: 257-262.
- Karbassi F, Saboury AA, Hassan Khan MT, Iqbal Choudhary M, Saifi ZS (2004b) Mushroom tyrosinase inhibition by two potent uncompetitive inhibitors. J Enzyme Inhib Med Chem 19: 349-353.
- Katsoulos GA, Tsipis CA (1984) Synthesis of some novel Pt (II) and Pd (II) n-alkyliminodithiocarbonato complexes and investigation of the mechanism of their formation by CNDO/2 quantum chemical calculations. Inorg Chim Acta 84: 89-94.
- Kim YM, Yun J, Lee CK, Lee H, Min KR, Kim Y (2002) Oxyresveratrol and hydroxystilbene compounds: inhibitory effect on tyrosinase and mechanism of action. J Biol Chem 277: 16340-16344.
- Kim YJ, Chung JE, Kurisawa M, Uyama H, Kobayashi S (2004) New tyrosinase inhibitors, (+)-catechin-aldehyde polycondensates. Biomacromolecules 5: 474-479.
- Kubo I, Kinst-Hori I (1988) Tyrosinase inhibitors from cumin. J Agric Food Chem 46: 5338-5341.
- Kubo I, Kinst-Hori I, Ishiguro K, Chaudhuri SK, Sanchez Y, Ogura T (1994) Tyrosinase inhibitory flovonoids from Heterotheca inuloides and their structural functions. Bioorg Med Chem Lett 4: 1443-1446.
- Kubo I, Kinst-Hori I (1999) Flovonols from saffron flower: tyrosinase inhibitory activity and inhibition mechanism. J Agric Food Chem 47: 4121-4125.
- Kubo I, Kinst-Hori I, Chaudhuri SK, Kubo Y, Sanchez Y, Ogura T (2000) Flovonols from Heterothesca inuloides: tyrosinase inhibitory activity and structural criteria. Bioorg Med Chem 8: 1749-1755.
- Lee HS (2002) Tyrosinase inbibitors of pulsatilla cernua root-derived materials. J Agric Food Chem 50: 1400-1403.
- Lee SE, Kim MK, Lee SG, Ahn YJ, Lee HS (2000) Inhibition effects of cinnamomum cassia bark-derived materials on mushroom tyrosinase. Food Sci Biotechnol 9: 330-333.
- Lerch K (1981) In Metal Ions in Biological Systems (Sigel H, ed) pp 143-186, Marcel Dekker, New York.
- Liangli YU (2003) Inhibitory effects of (S)- and I-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acids on tyrosinase activity. J Agric Food Chem 51: 2344-2347.
- Lim JT (1999) Treatment of melasma using kojic acid in a gel containing hydroquinone and glycolic acid. Dermatol Surg 25: 282-284.
- Maeda K, Fukuda M (1991) In vitro effectiveness of several whitening cosmetic components in human melanocytes. J Soc Cosmet Chem 42: 361-368
- Martinez MV, Whitaker JR (1995) The biochemistry and control of enzymatic browning. Trends Food Sci Technol 6: 195-200.
- Mohamed AA, Kani I, Ramirez AO, Fackler JP (2004) Synthesis, characterization and luminescent properties of dinuclear gold(I) xanthate complexes: X-ray structure of [Au2(n-Bu-xanthate)2]. Inorg Chem 43: 3833-3839.
- Mosher DB, Pathak MA, Fitzpatric TB eds (1983) Update: dermatology in general medicine. pp 205-225; McGraw Hill, New York.
- Pawelek JM, Korner AM (1982) The biosynthesis of mammalian melanin. Am Sci 70: 136-145.
- Saboury AA, Zolghadri S, Haghbeen K, Moosavi-Movahedi AA (2006) The inhibitory effect of benzenethiol on the cresolase and catecholase activities of mushroom tyrosinase. J Enzyme Inhib Med Chem 21: 711-717.
- Sanchez-Ferrer A, Rodriguez-Lopez JN, Garcia-Canovas F, Garcia-Carmona F (1995) Tyrosinase: a comprehensive review of its mechanism. Biochim Biophys Acta 1247: 1-11.
- Schoot Uiterkamp AJM (1972) Monomer and magnetic dipole-coupled Cu+2 EPR signals in nitrosylhemocyanin. FEBS Lett 20: 93-96.
- Shareefi Borojerdi S, Haghbeen K, Karkhane AA, Fazli M, Saboury AA (2004) Successful resonance Raman study of cresolase activity of mushroom tyrosinase. Biochem Biophys Res Commun 314: 925-930.
- Strothkemp KJ, Jolley RL, Mason Hs (1976) Quaternary structure of mushroom tyrosinase. Biochem Biophys Res Commun 70: 519-524.
- Sugumaran M (1988) Molecular mechanism for cuticular sclerotization. Adv Insect Physiol 21: 179-231.
- Whitaker JR (1995) Polyphenol oxidase. In Food enzymes: structure and mechanism (Wong DWS, ed) pp 271-307, Chapman & Hall, New York.
- Wilcox DE, Porras AG, Hwang YT, Lerch K, Winkler ME, Solomon E8I (1985) Substrate analogue binding to the coupled binuclear copper active site in tyrosinase. J Am Chem Soc 107: 4015-4027.
- Xie LP, Chen QX, Huang H, Wang HZ, Zhang RQ (2003) Inhibitory effects of some flavonoids on the activity of mushroom tyrosinase. Biochemistry (Mosc) 68: 487-491.
- Xu Y, Stokes AH, Freeman WM, Kumer SC, Vogt BA, Vrana KE (1997) Tyrosinase mRNA is expressed in human substantia nigra. Mol Brain Res 45: 159-162.
- Yong G, Leone C, Strothkemp KJ (1990) Agricus bisporus metapotyrosinase: preparation, characterization, and conversion to mixed-metal derivatives of the binuclear site. Biochemistry 29: 9684-9690.
- Zawistowski J, Biliaderis CG, Eskin NAM (1991) Polyphenol oxidase. In Oxidative enzymes in foods (Robinson DS, Eskin NAM, eds) pp 217-273, Elsevier Applied Science: New York.
Publication order reference