Evaluation of p-phenylene-bis and phenyl dithiocarbamate sodium salts and inhibitors of mushroom tyrosinase

• Autorzy: Amin E. , Saboury A. A. , Mansouri-Torshizi H. , Zolghadri S. , Bordbar A.-K.
• Języki publikacji: EN

Abstrakty

EN

 Two structurally related compounds, phenyl dithiocarbamate sodium salt (I) and p-phenylene-bis (dithiocarbamate) sodium salt (II) were prepared by reaction of the parent aniline and p-phenylenediamine with CS2 in the presence of sodium hydroxide. These water soluble compounds were characterized by spectroscopic techniques, IR, 1H NMR and elemental analysis. The inhibitory effects of both compounds on both activities of mushroom tyrosinase (MT) from Agricus bisporus were studied at two temperatures, 27ºC and 37ºC. L-3, 4-dihydroxyphenylalanine (L-DOPA), and l-tyrosine were used as natural substrates for the catecholase and cresolase enzyme reactions, respectively. Kinetic analysis confirmed noncompetitive inhibition mode of I and mixed type of II on both activities of MT; I and II inhibit MT with inhibition constants (KI) of 300 μM and 4 μM, respectively. Analysis of thermodynamic parameters indicated predominant involvement of hydrophobic interactions in binding of I and electrostatic ones in binding of II to MT. It seems that II is a more potent MT inhibitor due to its two charged head groups able to chelate copper ions in the enzyme active site. Intrinsic fluorescence studies as a function of concentrations of both compounds showed unexpectedly quenching of emission intensity without any shift of emission maximum. Extrinsic ANS-fluorescence indicated that only binding of I induces limited changes in the tertiary structure of MT, in agreement with the postulated hydrophobic nature of the binding mechanism.

Słowa kluczowe

EN

p-phenylene-bis zob.dithiocarbamate; dithiocarbamate; phenyl dithiocarbamate; sodium salt; inhibitor; mushroom tyrosinase; melanin; organosulphur compound; chemical property; Agaricus bisporus; biological activity

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2010
• Tom: 57
• Numer: 3
• Opis fizyczny: p.277-283,fig.,ref.

Twórcy

autor

Amin E.

• Institute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran

autor

Saboury A. A.

autor

Mansouri-Torshizi H.

autor

Zolghadri S.

autor

Bordbar A.-K.

Bibliografia

• Alijanianzadeh M, Saboury AA (2007) Temperature dependence of activation and inhibition of mushroom tyrosinase by ethyl xanthate. Bull Korean Chem Soc 28: 758-762.
• Alijanianzadeh M, Saboury AA, Mansuri-Torshizi H, Haghbeen K, Moosavi-Movahedi AA (2007) The inhibitory effect of some new synthesized xanthates on mushroom tyrosinase activities. J Enzyme Inhib Med Chem 22: 239-246. 
• Amin E, Saboury AA, Mansoori-Torshizi H, Moosavi-Movahedi AA (2009) Potent inhibitory effects of benzyl and p-xylidine-bis dithiocarbamate sodium salts on activities of mushroom tyrosinase. J Enzyme Inhib Med Chem (In press). 
• Artes F, Castaner M, Gil MI (1998) Review: Enzymatic browning in minimally processed fruit and vegetables. Food Sci Technol Int 4: 377-389.
• Bittner S (2006) When quinones meet amino acids: chemical, physical and biological consequences. Amino Acids 30: 205-224. 
• Briganti S, Camera E, Picardo M (2003) Chemical and instrumental approaches to treat hyperpigmentation. Pigment Cell Res 16: 101-110. 
• Criton M, Mellay-Hamon VL (2008) Analogues of N-hydroxy-N'-phenylthiourea and N-hydroxy-N'-phenylurea as inhibitors of tyrosinase and melanin formation. Bioorg Med Chem Lett 18: 3607-3610. 
• Decker H, Schweikardt T, Tuczek F (2006) The first crystal structure of tyrosinase: All questions answered? Angew Chem Int Ed Engl 45: 4546-4550. 
• Desai RM, Shah MK, Shah VH (2006) Preparation and antimicrobial screening of Cu(II), Ni(II), Zn(II) and Cd(II) complexes. Eur J Chem 3: 137-141.
• Espin JC, Wichers HJ (2001) Effect of captopril on mushroom tyrosinase activity in vitro. Biochim Biophys Acta 1544: 289-300. 
• Fenoll LG, Rodriguez-Lopez JN, Garcia-Sevilla F, Garcia-Ruiz PA, Varon R, Garcia-Canovas F, Tudela J (2001) Analysis and interpretation of the action mechanism of mushroom tyrosinase on monophenols and diphenols generating highly unstable o-quinones. Biochim Biophys Acta 1548: 1-22. 
• Fraignier MP, Marques L, Fleuriet A, Macheix JJ (1995) Biochemical and immunochemical characteristics of polyphenol oxidases from different fruits of Prunus. J Agric Food Chem 43: 2375-2380.
• Garcia-Molina F, Hiner AN, Fenoll LG, Rodriguez-Lopez JN, Garcia-Ruiz PA, Garcia-Canovas F, Tudela J (2005) Mushroom tyrosinase: catalase activity, inhibition, and suicide inactivation. J Agric Food Chem 53: 3702-3709. 
• García-Molina F, Muñoz JL, Varón R, Rodríguez-López JN, García-Cánovas F, Tudela J (2007) A review on spectrophotometric methods for measuring the monophenolase and diphenolase activities of tyrosinase. J Agric Food Chem 55: 9739-9749. 
• Gasymov OK, Glasgow BJ (2007) ANS fluorescence: potential to augment the identification of the external binding sites of proteins. Biochim Biophys Acta 1774: 403-411. 
• Gheibi N, Saboury AA, Mansuri-Torshizi H, Haghbeen K, Moosavi-Movahedi AA (2005) The inhibition effect of some n-alkyl dithiocarbamates on mushroom tyrosinase. J Enzyme Inhib Med Chem 20: 393-399. 
• Givseppina F, Sergio S, Diego M (2005) Pyrrolidine dithiocarbamates of Pd(II). Inorg Chim Acta 358: 971-980.
• Halaouli S, Asther M, Sigoillot JC, Hamdi M, Lomascolo A (2006) Fungal tyrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications. J Appl Microbiol 100: 219-232. 
• Holm RH, Kennepohl P, Solomon EI (1996) Structural and functional aspects of metal sites in biology. Chem Rev 96: 2239-2314. 
• Jolley RL, Nelson RM (1969) The multiple forms of mushroom tyrosinase. Structural studies on the isoenzymes. J Biol Chem 244: 3251-3257. 
• Khwaja SS, Shahab AAN, Lutfullah C, Yonas C (2006) Template synthesis of symmetrical transition metal dithiocarbamates. J Braz Chem Soc 17: 107-112.
• Kim YJ, Uyama H (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 62: 1707-1723. 
• Lee KH, Koketsu M, Choi SY, Lee KJ, Lee P, Ishihara H, Kim SY (2005) Potent inhibitory effects of N-aryl s-alkylthiocarbamate derivatives on the Dopa oxidase activity of mushroom tyrosinase. Chem Pharm Bull (Tokyo) 53: 747-749. 
• Liu J, Cao R, Yi W, Ma C, Wan Y, Zhou B, Ma L, Song H (2009) A class of potent tyrosinase inhibitors: alkylidenethiosemicarbazide compounds. Eur J Med Chem 44: 1773-1778. 
• Manav N, Mishra AK, Kaushik NK (2006) In vitro antitumour and antibacterial studies of some Pt(IV) dithiocarbamate complexes. Spectrochim Acta A Mol Biomol Spectrosc 65: 32-35. 
• Matoba Y, Kumagai T, Yamamoto A, Yoshitsu H, Sugiyama M (2006) Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis. J Biol Chem 281: 8981-8990. 
• Nakamura T, Sho S, Ogura Y (1966) On the purification and properties of mushroom tyrosinase. J Biochem 59: 481-486. 
• Park KH, Lee JR, Hahn HS, Kim YH, Bae CD, Yang JM, Oh S, Bae YJ, Kim DE, Hahn M-J (2006) Inhibitory effect of ammonium tetrathiotungstate on tyrosinase and its kinetic mechanism. Chem Pharm Bull (Tokyo) 54: 1266-1270. 
• Parvez S, Kang M, Chung HS, Cho C, Hong MC, Shin MK, Bae H (2006) Survey and mechanism of skin depigmenting and lightening agents. Phytother Res 20: 921-934. 
• Perozzo R, Folkers G, Scapozza L (2004) Thermodynamics of protein-ligand interactions: history, presence, and future aspects. J Recept Signal Transduct Res 24: 1-52. 
• Rescigno A, Sollai F, Pisu B, Rinaldi A, Sanjust E (2002) Tyrosinase inhibition: General and applied aspects. J Enzyme Inhib Med Chem 17: 207-218. 
• Ronconi L, Maccato C, Barreca D, Saini R, Zancato MDF (2005) Gold (III) dithiocarbamate derivatives of N-methylglycine: an experimental and theoretical investigation. Polyhedron 24: 521-531.
• Saboury AA, Alijanianzadeh M, Mansoori-Torshizi H (2007) The role of alkyl chain length in the inhibitory effect n-alkyl xanthates on mushroom tyrosinase activities. Acta Biochim Pol 54: 183-191. 
• Saboury AA (2009) Enzyme inhibition and activation: a general theory. J Iran Chem Soc 6: 219-229.
• 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-Cortes S, Vasina M, Francioso O, Garcia-Ramos JV (1998) Raman and surface enhanced Raman spectroscopy of dithiocarbamate fungicides. Vib Spectrosc 17: 133-144.
• Seo SY, Sharma VK, Sharma N (2003) Mushroom tyrosinase: recent prospects. J Agric Food Chem 51: 2837-2853. 
• Siddiqi KS, Sadaf K, Shahab AAN, El-ajaily MM (2007) Polynuclear transition metal complexes with thiocarbohydrazide and dithiocarbamates. Spectrochim Acta A Mol Biomol Spectrosc 67: 995-1002. 
• Strothkamp KG, Jolley RL, Mason HS (1976) Quaternary structure of mushroom tyrosinase. Biochem Biophys Res Commun 70: 519-524. 
• Vaneet KS, Aulakh SJ, Malik AK (2005) Fourth derivative spectrophotometric determination of fungicide thiram (tetramethyldithiocarbamate) using sodium molybdate and its application. Talanta 65: 375-379.