3D-QSAR analysis and molecular docking of thiosemicarbazone analogues as a potent tyrosinase inhibitor

Bulletin of the Korean Chemical Society

Volumn 32, Issue 4, 2011, Pages 1241-1248

  Park, Joonho ^a   Sung, Nack Do ^b  

^a QUEEN S UNIVERSITY   (Canada)

^b Chungnam National University   (South Korea)

Author keywords

3D QSAR; CoMFA; CoMSIA; Molecular Docking; Thiosemicarbazone analogues; Tyrosinase inhibitor

Indexed keywords

3D-QSAR; COMFA; COMSIA; MOLECULAR DOCKING; THIOSEMICARBAZONES; TYROSINASE INHIBITOR;

COMPUTATIONAL CHEMISTRY; MOLECULAR MODELING; MOLECULES; OPTIMIZATION; SUBSTRATES; THREE DIMENSIONAL;

ENZYME INHIBITION;

EID: 79954619896     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2011.32.4.1241     Document Type: Article

References (49)

1. Chase, M. R.; Raina, K.; Bruno, J.; Sugumaran, M. Insect. Biochem. Molec. 2000, 30, 953.
2. (a) Chen, Q. X.; Liu, X. D.; Huang, H. Biochemistry-Moscow 2003, 68, 644.
3. (b) Olivares, C.; Cervantes, C. J.; Lozano, J. A.; Solano, F.; Garcia-Borron, J. C. Biochem. J. 2001, 354, 131.
4. Sptitz, R. A.; Hearing, V. J., Jr. Adv. Hum. Genet. 1994, 22, 1.
5. Martinez, M. V.; Whitaker, J. R. Trends Food Sci. Technol. 1995, 6, 195.
6. (a) Matoba, Y.; Kumagai, T.; Yamamoto, A.; Yoshitsu, H.; Sugiyama, M. J. Biol. Chem. 2006, 281, 8981.
7. (b) Jackman, M. O.; Hajnal, A.; Lerch, K. Biochem. J. 1991, 274, 707.
8. (a) Kim, Y. J.; Uyama, H. Cell. Mol. Life Sci. 2005, 62, 1707.
9. (b) Wilcox, D. E.; Porras, A. G.; Hwang, Y. T.; Lerch, K.; Winkler, M. E.; Solomon, E. I. J. Am. Chem. Soc. 1985, 107, 4015.
10. (c) Sanjust, E.; Cecchini, G.; Sollai, F.; Curreli, N.; Mescigno, A. Arch. Biochem. Biophys. 2003, 412, 272.
11. Khan, K. M.; Maharvi, G. M.; Khan, M. T. H.; Shaikh, A. J.; Perveen, S.; Begaum, S.; Choudhary, M. I. Bioorg. Med. Chem. 2006, 14, 344.
12. Parvez, S.; Kang, M.; Chung, H. S.; Bae, H. Phytother. Res. 2007, 21, 805.
13. Khan, M. T. H. Pure Appl. Chem. 2007, 79, 2277.
14. Khan, M. T. H. Topics Heterocyclic Chem. 2007, 9, 119.
15. (a) Xue, C. B.; Zhang, L.; Luo, W. C.; Xie, X. Y.; Jiang, L.; Xiao, T. Bioorg. Med. Chem. 2007, 15, 2006.
16. (b) Pasha, F. A.; Muddassar, M.; Beg, Y.; Cho, S. J. Chem. Biol. Drug. Des. 2008, 71, 483.
17. (c) Yi, W.; Cao, R. H.; Chen, Z. Y.; Yu, L.; Ma, L.; Song, H. C. Chem. Pharm. Bull. 2009, 57, 1273.
18. (d) Liu, J.; Yi, W.; Wan, Y.; Ma, L.; Song, H. Bioorg. Med. Chem. 2008, 16, 1096.
19. (e) Yi, W.; Cao, R.; Chen, Z.; Yu, L.; Wen, H.; Yan, Q.; Ma, L.; Song, H. Chem. Pharm. Bull. 2010, 58, 752.
20. Xue, C. B.; Luo, W. C.; Ding, Q.; Liu, S. Z.; Gao, X. X. J. Comput. Aided Mol. Des. 2008, 22, 290.
21. Chung, S. W.; Ha, Y. M.; Kim, Y. J.; Song, S.; Lee, H.; Suh, H.; Chung, H. Y. Arch. Pharm. Res. 2009, 32, 289.
22. Chen, Y. R.; Chiou, R. Y.; Lin, T. Y.; Huang, C. P.; Tang, W. C.; Chen, S. T.; Lin, S. B. J. Agri. Food Chem. 2009, 57, 2200.
23. Sung, J. H.; Park, S. H.; Seo, D. H.; Lee, J. H.; Hong, S. W.; Hong, S. S. Biosci. Biotechol. Biochem. 2009, 73, 552.
24. Sung, N. D.; Jung, H. S.; Kim, S. J. J. Soc. Cosmet. Scientists Korea 2004, 30, 491.
25. Sung, N. D.; Chung, Y. H.; Jang, S. C.; Kim, S. J. J. Appl. Biol. Chem. 2007, 50, 52.
26. Kim, S. J.; Kim, S. G.; Sung, N. D. J. Soc. Cosmet. Scientists Korea 2008, 34, 109.
27. (a) Akamatsu, M. Curr. Topics Med. Chem. 2002, 2, 1381.
28. (b) Cramer, R. D., III.; Patterson, D. E.; Bunce, J. E. J. Am. Chem. Soc. 1988, 110, 5959.
29. (c) Klebe, G.; Abraham, U.; Mietzner, T. J. Med. Chem. 1994, 37, 4130.
30. Tripos Inc., Sybyl molecular modeling and QSAR software on CD-Rom, (Ver.8.1.1) Theory and manual., St. Louis, Missouri. 2008.
31. (a) Soung, M. G.; Kim, J. H.; Kwon, B. M.; Sung, N. D. Bull. Korean Chem. Soc. 2010, 31, 1335.
32. (b) Soung, M. G.; Park, K. Y.; Sung, N. D. Bull. Korean Chem. Soc. 2010, 31, 1469.
33. (c) Soung, M. G.; Kil, M. J.; Sung, N. D. Bull. Korean Chem. Soc. 2009, 30, 2749.
34. Kerr, R. Biophys. J. 1994, 67, 1501.
35. Cramer, R. D.; Bunce, J. D.; Patterson, D. E. Quant. Struct. Act. Relat. 1988, 7, 18.
36. Clark, R. D.; Fox, P. C. J. Comput. -Aided. Mol. Des. 2004, 18, 563.
37. Quian, L.; Brian, M.; Karl, S.; Julian, S. J. Med. Chem. 2007, 50, 5392.
38. (a) Jain, A. N. J. Med. Chem. 2003, 46, 499.
39. (b) Patrick, A. H.; Jonathan, B. C.; John, O. T. J. Chem. Inf. Model. 2008, 48, 1602.
40. Jain, A. N. J. Comp. -Aided Mole. Des. 1996, 10, 427.
41. (a) Clark, R. D.; Fox, P. C. J. Comput. -Aided. Mol. Des. 2003, 17, 1.
42. (b) Clark, R. D.; Sprous, D. G.; Leonard, J. M. Validating Models Based on Large Data Sets; Prous Science: Barcelona, 2001; p 475.
43. Kahn, V., Ben-Shalom, N.; Zakin, V. J. Agric. Food Chem. 1997, 45, 4460.
44. Briganti, S.; Camera, E.; Picardo, M. Pigment. Cell. Res. 2003, 16, 101.
45. (a) Smith, C. M.; Hotchkiss, S. A. M. Allergic Contact Dermatitis: Chemical and Metabolic Mechanisms; Taylor and Francis: London, 2001.
46. (b) Jowsey, I. R; Basketter, D. A.; Westmoreland, C.; Kimber, I. A. J. Appl. Toxicol. 2006, 6, 341.
47. (c) Natsch, A.; Wmter, R.; Ellis, G. Toxicol. Sci. 2009, 107, 106.
48. (a) Himmelwright, R. S.; Eickman, N. C.; Lubein, C. D.; Solomon E. I.; Lerch, K. J. Am. Chem. Soc. 1980, 102, 2563.
49. (b) Kim, Y. J.; Chung, J. E.; Kurisawa, M.; Uyama, H.; Kobayashi, S. Biomacromol. 2004, 5, 474.