Inhibition of horseradish peroxidase catalytic activity by new 3-phenylcoumarin derivatives: Synthesis and structure-activity relationships

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 3, 2007, Pages 1516-1524

  Kabeya, Luciana M ^a   de Marchi, Anderson A ^a   Kanashiro, Alexandre ^a   Lopes, Norberto P ^a   da Silva, Carlos H T P ^a   Pupo, Mônica T ^a   Lucisano Valim, Yara M ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Catechol; Coumarin; Docking; Horseradish peroxidase

Indexed keywords

3 PHENYLCOUMARIN; 6 ACETOXY 3 (2' ACETOXYPHENYL)COUMARIN; 6 ACETOXY 3 (3' ACETOXYPHENYL)COUMARIN; 6 ACETOXY 3 (3',4' DIACETOXYPHENYL)COUMARIN; 6 ACETOXY 3 PHENYLCOUMARIN; 6 HYDROXY 3 (2' HYDROXYPHENYL)COUMARIN; 6 HYDROXY 3 (3' HYDROXYPHENYL)COUMARIN; 6 HYDROXY 3 (3',4' DIHYDROXYPHENYL)COUMARIN; 6 HYDROXY 3 (4' HYDROXYPHENYL)COUMARIN; 6 HYDROXY 3 PHENYLCOUMARIN; 6,7 DIACETOXY 3 (3',4' DIACETOXYPHENYL)COUMARIN; 6,7 DIACETOXY 3 (3',4' METHYLENEDIOXYPHENYL)COUMARIN; 6,7 DIHYDROXY 3 (3',4' DIHYDROXYPHENYL)COUMARIN; 6,7 DIHYDROXY 3 (3',4' METHYLENEDIOXYPHENYL)COUMARIN; CATECHOL; COUMARIN DERIVATIVE; FLAVONOID; GALANGIN; HORSERADISH PEROXIDASE; KAEMPFEROL; MYRICETIN; QUERCETIN; SCAVENGER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG ACTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROXYLATION; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; STRUCTURE ACTIVITY RELATION;

COUMARINS; ENZYME INHIBITORS; FREE RADICAL SCAVENGERS; HORSERADISH PEROXIDASE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

ARMORACIA RUSTICANA;

EID: 33845933196     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.10.068     Document Type: Article

References (39)

1. Everse J., Everse K.E., and Grisham M.B. Peroxidases in Chemistry and Biology (1991), CRC Press, Boca Raton, FL
2. Poulos T.L., and Fenna R.E. In: Siegel H. (Ed). Metals in Biological Systems Vol. 30 (1994), Marcel Dekker, New York 25-75
3. Keilin D., and Hartree E.F. Biochem. J. 49 (1951) 88
4. Nakajima R., and Yamazaki I. J. Biol. Chem. 262 (1987) 2576
5. Acosta M., Arnao M.B., Hernandez-Ruiz J., and Garcia-Canovas F. In: Welinder K.G., Rassmussen S.K., Penel C., and Greppin H. (Eds). Plant Peroxidases: Biochemistry and Physiology (1993), University of Geneva, Geneva 201-205
6. Hernandez-Ruiz J., Arnao M.B., Hiner A.N.P., Garcia-Canovas F., and Acosta M. Biochem. J. 354 (2001) 107
7. George P. Nature 169 (1952) 612-613
8. Poulos T.L., and Kraut J. J. Biol. Chem. 255 (1980) 8199
9. Takahama U., and Yoshitama K. J. Plant Res. 111 (1998) 97
10. Hiraga S., Sasaki K., Ito H., Ohashi Y., and Matsui H. Plant Cell Physiol. 42 (2001) 462
11. Babior B.M. Am. J. Med. 109 (2000) 33
12. Zhang R., Brennan M.-L., Shen Z., MacPherson J.C., Schmitt D., Molenda C.E., and Hazen S.L. J. Biol. Chem. 277 (2002) 46116
13. Klebanoff S.J. J. Leukocyte Biol. 77 (2005) 598
14. Obinger C. Arch. Biochem. Biophys. 445 (2006) 197
15. Middleton Jr. E., Kandaswami C., and Theoharides T.C. Pharmacol. Rev. 52 (2000) 673
16. Hoult J.R.S., and Payá M. Gen. Pharmacol. 27 (1996) 713
17. García-Argáez A.N., Apan T.O.R., Delgado H.P., Velázquez G., and Martínez-Vázquez M. Planta Med. 66 (2000) 279
18. Veitch N.C. Phytochemistry 65 (2004) 249
19. Dure L.S., and Cormier M.J. J. Biol. Chem. 239 (1964) 2351
20. Marquele F.D., Di Mambro V.M., Georgetti S.R., Casagrande R., Lucisano-Valim Y.M., and Fonseca M.J.V. J. Pharm. Biomed. Anal. 39 (2005) 455
21. Kanashiro A., Kabeya L.M., Grael C.F.F., Jordao C.O., Azzolini A.E.C.S., Lopes J.L.C., and Lucisano-Valim Y.M. J. Pharm. Pharmacol. 58 (2006) 853
22. Kumar A., Singh B.K., Tyagi R., Jain S.K., Sharma S.K., Prasad A.K., Raj H.G., Rastogi R.C., Watterson A.C., and Parmar V.S. Bioorg. Med. Chem. 13 (2005) 4300
23. Raj H.G., Parmar V.S., Jain S.C., Priyadarsini K.I., Mittal J.P., Goel S., Das S.K., Sharma S.K., Olsen C.E., and Wengel J. Bioorg. Med. Chem. 7 (1999) 2091
24. Gobbo-Neto L., Santos M.D., Kanashiro A., Almeida M.C., Lucisano-Valim Y.M., Lopes J.L.C., Souza G.E.P., and Lopes N.P. Planta Med. 71 (2005) 3
25. Kabeya L.M., Kanashiro A., Azzolini A.E.C.S., Soriani F.M., Lopes J.L.C., and Lucisano-Valim Y.M. Res. Commun. Mol. Pathol. Pharmacol. 111 (2002) 103
26. Moreira M.R., Polizello A.C.M., Kabeya L.M., Kanashiro A., and Lucisano-Valim Y.M. Braz. J. Pharm. Sci. 39 (2003) 87 4th Congress of Pharmaceutical Sciences, Ribeirão Preto, Brazil, June 29th-July 2nd, 2003. University of São Paulo: São Paulo, SP, 2003
27. de Marchi A.A., Castilho M.S., Nascimento P.G.B., Archanjo F.C., Del Ponte G., Oliva G., and Pupo M.T. Bioorg. Med. Chem. 12 (2004) 4823
28. Berglund G.I., Carlsson G.H., Smith A.T., Szoke H., Henriksen A., and Hadju J. Nature 417 (2002) 463
29. Henriksen A., Schuller D.J., Meno K., Smith A.T., Welinder K.G., and Gajhede M. Biochemistry 37 (1998) 8054
30. Rodri{dotless}guez-Lopez J.N., Lowe D.J., Hernandez-Ruiz J., Hiner A.N.P., Garci{dotless}a-Canovas F., and Thorneley R.N.F. J. Am. Chem. Soc. 123 (2001) 11838
31. Navas Díaz A., García Sánches F., and González García J.A. J. Biolumin. Chemilumin 13 (1998) 75
32. Bors W., Heller W., Michel C., and Saran M. Methods Enzymol. 186 (1990) 343
33. Corbett M.D., and Corbett B.R. Chem. Biol. Interact. 63 (1987) 249
34. Crotti A.E.M., Vessecchi R., Lopes J.L.C., and Lopes N.P. Quím. Nova 29 (2006) 287
35. Krol W., Czuba Z., Scheller S., Paradowski Z., and Shani J. J. Ethnopharmacol. 41 (1994) 121
36. Blois M.S. Nature 181 (1958) 1199
37. Verdonk M.L., Cole J.C., Hartshorn M.J., Murray C.W., and Taylor R.D. Proteins 52 (2003) 609
38. Insight II user guide, v. 2000, Accelrys, CA, USA, 2000.
39. Spartan '04 full, v.1.0.3; Tutorial and User's Guide; Wavefunction, Inc., USA, 2005.