Synthesis, characterization and biological evaluation of paeonol thiosemicarbazone analogues as mushroom tyrosinase inhibitors

International Journal of Biological Macromolecules

Volumn 62, Issue , 2013, Pages 589-595

  Zhu, Tian Hua ^a   Cao, Shu Wen ^a   Yu, Yan Ying ^a  

^a NANCHANG UNIVERSITY   (China)

Author keywords

Anti tyrosinase; Copper ions chelation; Fluorescence quenching; Inhibition kinetics; Paeonol thiosemicarbazone

Indexed keywords

2 HYDROXY 4 METHOXYACETOPHENONE 4 METHYL 3 THIOSEMICARBAZONE; 2 HYDROXY 4 METHOXYACETOPHENONE 4 PHENYL 3 THIOSEMICARBAZONE; 2 HYDROXY ACETOPHENONE 4 METHYL 3 THIOSEMICARBAZONE; 2 HYDROXY ACETOPHENONE 4 PHENYL 3 THIOSEMICARBAZONE; 2,4 DIHYDROXY ACETOPHENONE 4 PHENYL 3 THIOSEMICARBAZONE; 2,4 DIHYDROXYACETOPHENONE 4 METHYL 3 THIOSEMICARBAZONE; 4 METHOXY ACETOPHENONE 4 METHYL 3 THIOSEMICARBAZONE; 4 METHOXY ACETOPHENONE 4 PHENYL 3 THIOSEMICARBAZONE; ACETOPHENONE 4 METHYL 3 THIOSEMICARBAZONE; ACETOPHENONE 4 PHENYL 3 THIOSEMICARBAZONE; OXYGENASE INHIBITOR; UNCLASSIFIED DRUG;

BINDING AFFINITY; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BINDING; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; FLUORESCENCE ANALYSIS; INHIBITION KINETICS; REVIEW; SPECTROFLUOROMETRY; STRUCTURE ACTIVITY RELATION;

BASIDIOMYCOTA;

ANTI-TYROSINASE; COPPER IONS CHELATION; FLUORESCENCE QUENCHING; INHIBITION KINETICS; PAEONOL THIOSEMICARBAZONE;

ACETOPHENONES; AGARICALES; CHELATING AGENTS; COPPER; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MONOPHENOL MONOOXYGENASE; THIOSEMICARBAZONES;

EID: 84887223351     PISSN: 01418130     EISSN: 18790003     Source Type: Journal    
DOI: 10.1016/j.ijbiomac.2013.09.056     Document Type: Review

References (36)

1. Yoon J., Fujii S., Solomon E.I. Proc. Natl. Acad. Sci. U. S. A. 2009, 106:6585-6590.
2. Li Y., Wang Y., Jiang H., Deng J. Proc. Natl. Acad. Sci. U. S. A. 2009, 106:17002-17006.
3. Pham-Huy L.A., He H.C. Pham-Huy, Int. J. Biomed. Sci. 2008, 4:89-96.
4. Valko M., Leibfritz D., Moncol J., Cronin M.T.D., Mazur M., Telser J. Int. J. Biochem. Cell Biol. 2007, 39:44-84.
5. Guevara I.L., Pandya A.G. Int. J. Dermatol. 2008, 40:212-215.
6. Kanost M.R., Jiang H.B., Yu X.Q. Immunol. Rev. 2004, 198:97-105.
7. Lunadei L., Galleguillo P., Diezma B., Lleo L., Ruiz-Garcia L. Postharvest Biol. Technol. 2011, 60:225-234.
8. Guerrero A., Rosell G. Curr. Med. Chem. 2005, 12:461-469.
9. Garcia A., Fulton J.E. Dermatol. Surg. 1996, 22:443-447.
10. Kameyama K., Sakai C., Kondoh S., Yonemoto K., Nishiyama S., Tagawa M., Murata T., Ohnuma T., Quigley J., Dorsky A., Bucks D., Blanock K. J. Am. Acad. Dermatol. 1996, 34:29-33.
11. Nakajima M., Shinoda I., Fukuwatari Y., Hayasawa H. Pigment Cell Res. 1998, 11:12-17.
12. Cabanes J., Chazarra S., Garcia-Carmona F. J. Pharm. Pharmacol. 1994, 46:982-985.
13. Jimenez M., Chazarra S., Escribano J., Cabanes J., Garcia-Carmona F. J. Agric. Food Chem. 2001, 49:4060-4063.
14. Chen Q.X., Song K.K., Wang Q., Huang H. J. Enzyme Inhib. Med. Chem. 2003, 18:491-496.
15. Chen Q.X., Song K.K., Qiu L., Liu X.D., Huang H., Guo H.Y. Food Chem. 2005, 91:269-274.
16. Si Y.X., Yin S.J., Park D., Chung H.Y., Yan L., Lü Z.R., Zhou H.M., Yang J.M., Qian G.Y., Parka Y.D. Int. J. Biol. Macromol. 2011, 48:700-704.
17. Liu S.H., Pan I.H., Chu I.M. Biol. Pharm. Bull. 2007, 30:1135-1139.
18. Zhu Y.J., Zhou H.T., Hu Y.H., Tang J.Y., Su M.X., Guo Y.J., Chen Q.X., Liu B. Food Chem. 2011, 124:298-302.
19. Valero E., Garcia-Moreno M., Varon R., Garcia-Carmona F. J. Agric. Food Chem. 1991, 39:1043-1046.
20. Franco D.C.Z., de Carvalho G.S.G., Rocha P.R., Teixeira R.D., da Silva A.D., Raposo N.R.B. Molecules 2012, 17:11816-11825.
21. Lima L.L., Lima R.M., da Silva A.F., do Carmo A.M.R., da Silva A.D., Raposo N.R.B. Sci. World J. 2013, 2013:274643-274649.
22. Pham-Huy L.A., He H., Pham-Huy C. Int. J. Biomed. Sci. 2008, 4:89-96.
23. Zhu Y.J., Song K.K., Li Z.C., Pan Z.Z., Guo Y.J., Zhou J.J., Wang Q., Liu B., Chen Q.X. J. Agric. Food Chem. 2009, 57:5518-5523.
24. Lee K.C., Thanigaimalai P., Sharma V.K., Kim M.S., Roh E., Hwang B.Y., Kim Y., Jung S.H. Bioorg. Med. Chem. Lett. 2010, 20:6794-6796.
25. Thanigaimalai P., Eeda Venkateswara Rao, Lee K.C., Sharma V.K., Roh E., Kim Y., Jung S.H. Bioorg. Med. Chem. Lett. 2012, 22:886-889.
26. Lv P.C., Zhou C.F., Chen J., Liu P.G., Wang K.R., Mao W.J., Li H.Q., Yang Y., Xiong J., Zhu H.L. Bioorg. Med. Chem. 2010, 18:314-319.
27. Gong S.Z., Cheng J., Yang Z.R. Acta Pharm. Sin. 2006, 41:561-564.
28. Fang Y.T., Chen Y.Z., Feng G.F., Ma L. Bioorg. Med. Chem. 2011, 19:1167-1171.
29. Si Y.X., Wang Z.J., Park D., Chung H.Y., Wang S.F., Yan L., Yang J.M., Qian G.Y., Yin S.J., Park Y.D. Int. J. Biol. Macromol. 2012, 50:257-262.
30. Karikari A.S., Mather B.D., Long T.E. Biomacromolecules 2007, 8:302-308.
31. Eftink M.R., Ghiron C.A. Anal. Biochem. 1981, 114:199-227.
32. Xue C.B., Zhang L., Luo W.C., Xie X.Y., Jiang L., Xiao T. Bioorg. Med. Chem. 2007, 15:2006-2015.
33. Shimizu K., Kondo R., Sakai K., Takeda N., Nagahata T., Oniki T. Lipids 2001, 36:1321-1326.
34. Khatib S., Nerya O., Musa R., Shmuel M., Tamir S., Vaya J. Bioorg. Med. Chem. 2005, 13:433-441.
35. Kubo I., Hinst-Hori I. J. Agric. Food Chem. 1998, 46:5338-5341.
36. Sekher Pannala A., Chan T.S., O'Brien P.J., Rice-Evans C.A. Biochem. Biophys. Res. Commun. 2001, 282:1161-1168.