Mechanistic studies of the inactivation of tyrosinase by resorcinol

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 5, 2013, Pages 1166-1173

  Stratford, Michael R L ^a   Ramsden, Christopher A ^b   Riley, Patrick A ^c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b KEELE UNIVERSITY   (United Kingdom)

^c Totteridge Institute for Advanced Studies   (United Kingdom)

Author keywords

Oximetry; Quinones; Quintox mechanism; Resorcinols; Tyrosinase

Indexed keywords

2 CHLORORESORCINOL; 2 FLUORORESORCINOL; 2 METHYLRESORCINOL; 2,4 DIFLUORORESORCINOL; 2,4,6 TRICHLORORESORCINOL; 2,5 DIFLUORORESORCINOL; 2,5 DIMETHYLRESORCINOL; 4 ETHYLRESORCINOL; 4 FLUORORESORCINOL; 4,6 DICHLORORESORCINOL; 4,6 DIMETHYLRESORCINOL; 5 FLUORORESORCINOL; 5 HYDROXYRESORCINOL; 5 METHOXYRESORCINOL; COPPER ION; MONOPHENOL MONOOXYGENASE; ORCINOL; RESORCINOL; RESORCINOL DERIVATIVE; TETRAFLUORORESORCINOL; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME INACTIVATION; ENZYME MECHANISM; ENZYME METABOLISM; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SPECTROPHOTOMETRY; SUBSTITUTION REACTION;

CATALYTIC DOMAIN; CATECHOLS; COPPER; KINETICS; MONOPHENOL MONOOXYGENASE; OXIDATION-REDUCTION; OXIMETRY; PROTEIN BINDING; RESORCINOLS; SPECTROPHOTOMETRY;

EID: 84873708098     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.12.031     Document Type: Article

References (39)

1. C.A. Ramsden, M.R.L. Stratford, and P.A. Riley Org. Biomol. Chem. 7 2009 3388
2. M.R.L. Stratford, C.A. Ramsden, and P.A. Riley Bioorg. Med. Chem. 20 2012 4364
3. G. Prota Melanins and Melanogenesis 1992 Academic Press San Diego
4. J. Borovansky, and P.A. Riley and Melanosomes: Biosynthesis, Biogenesis, Physiological, and Pathological Functions 2011 Wiley-VCH Weinheim
5. F. Artés, M. Castañer, and M.I. Gil Food Sci. Technol. Int. 4 1998 377
6. E.J. Land, C.A. Ramsden, and P.A. Riley Tohoku J. Exp. Med. 212 2007 341
7. C.A. Ramsden, and P.A. Riley Arkivoc x 2010 248
8. C.A. Ramsden, and P.A. Riley Arkivoc i 2010 260
9. E.J. Land, C.A. Ramsden, P.A. Riley, and M.R.L. Stratford Tohoku J. Exp. Med. 216 2008 231
10. C. Dietler, and K. Lerch Reaction Inactivation of Tyrosinase T.E. King, H.S. Mason, M. Morrison, Oxidases and Related Redox Systems 1982 Pergamon Press New York 305
11. T.C. Wong, B.S. Luh, and J.R. Whitaker Plant Physiol. 48 1971 24
12. K. Tasaka, C. Kamei, S. Nakano, Y. Takeuchi, and M. Yamato Methods Finds Exp. Clin. Pharmacol. 20 1998 99
13. K. Shimizu, R. Kondo, and K. Sakai Planta Med. 66 2000 11
14. O. Nerya, J. Vaya, R. Musa, S. Izrael, R. Ben-Arie, and S. Tamir J. Agric. Food Chem. 51 2003 1201
15. S.Y. Seo, V.K. Sharma, and N. Sharma J. Agric. Food Chem. 51 2003 2837
16. O. Nerya, R. Musa, S. Khatib, S. Tamir, and J. Vaya Phytochemistry 65 2004 1389
17. D.S. Kim, S.Y. Kim, S.H. Park, Y.G. Choi, S.B. Kwon, M.K. Kim, J.I. Na, S.W. Youn, and K.C. Park Biol. Pharm. Bull. 28 2005 2216
18. S. Khatib, O. Nerya, R. Musa, M. Shmuel, S. Tamir, and J. Vaya Bioorg. Med. Chem. 13 2005 433
19. N. Jun, G. Hong, and K. Jun Bioorg. Med. Chem. 15 2007 2396
20. K.K. Song, H. Huang, P. Han, C.L. Zhang, Y. Shi, and Q.X. Chen Biochem. Biophys. Res. Commun. 342 2006 1147
21. Y.M. Kim, J. Yun, C.K. Lee, H. Lee, K.R. Min, and Y. Kim J. Biol. Chem. 277 2002 16340
22. Q.X. Chen, and I. Kubo J. Agric. Food Chem. 50 2002 4108
23. D.E. Wilcox, A.G. Porras, Y.T. Hwang, K. Lerch, M.E. Winkler, and E.I. Solomon J. Am. Chem. Soc. 107 1985 4015
24. S. Khatib, O. Nerya, R. Musa, S. Tamir, T. Peter, and J. Vaya J. Med. Chem. 50 2007 2676
25. W.-C. Sun, K.R. Gee, D.H. Klaubert, and R.P. Haugland J. Org. Chem. 62 1997 6469
26. D.J. Cram, and F.W. Cranz J. Am. Chem. Soc. 72 1950 595
27. J.H. James, M.E. Peach, and C.R. Williams J. Fluorine Chem. 27 1985 91
28. T. Umemoto, M. Nagayoshi, K. Adachi, and G. Tomizawa J. Org. Chem. 63 1998 3379
29. V.L. Heasley, R.E. Renfrow, L.C. Sator, J.L. Boerneke, and D.F. Shellhamer Res. J. Chem. Environ. 11 2007 13
30. C.J. Cooksey, P.J. Garratt, E.J. Land, S. Pavel, C.A. Ramsden, P.A. Riley, and N.P.M. Smit J. Biol. Chem. 272 1997 26226
31. M.R. Stratford, P.A. Riley, and C.A. Ramsden Chem. Res. Toxicol. 24 2011 350
32. W. Dürckheimer, and E.F. Paulus Angew. Chem., Int. Ed. Engl. 24 1985 224
33. H. Kubinyi The Free-Wilson method and its relationship to the extrathermodynamic approach C.A. Ramsden, Comprehensive Medicinal Chemistry Vol. 4 1990 Pergamon Press Oxford 589
34. A. Kovács, I. Macsári, and I. Hargittai J. Phys. Chem. A 103 1999 3110
35. S. Naish-Byfield, and P.A. Riley Pigment Cell Res. 11 1998 94
36. S. Naish-Byfield, and P.A. Riley Pigment Cell Res. 11 1998 127
37. E.J. Land, C.A. Ramsden, and P.A. Riley Acc. Chem. Res. 36 2003 300
38. O. Crescenzi, A. Napolitano, G. Prota, and M.G. Peter Tetrahedron 47 1991 6243
39. J.R. Ros, J.N. Rodriguez-López, and F. García- Cánovas Biochem. J. 295 1993 309