In vitro study of isoflavones and isoflavans as potent inhibitors of human 12- and 15-lipoxygenases

Chemical Biology and Drug Design

Volumn 82, Issue 3, 2013, Pages 317-325

  Mascayano, Carolina ^a   Espinosa, Victoria ^a   Sepúlveda Boza, Silvia ^a   Hoobler, Eric K ^b   Perry, Steve ^b  

^a UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Docking and scavenger properties; Human lipoxygenase assay; Isoflavonoids

Indexed keywords

5 HYDROXY 7 BENZYL 4' NITROISOFLAVONE; 5,7 DIHYDROXY 4' NITROISOFLAVONE; 6,7 DIHYDROXY 3' CHLOROISOFLAVONE; 6,7 DIHYDROXY 4' CHLOROISOFLAVONE; 6,7 DIHYDROXY 4' NITROISOFLAVONE; 7 BENZYL 4' METHOXYISOFLAVONE; 7 HYDROXY 8 METHYL 3' TRIFLUOROMETHYLISOFLAVONE; 7 HYDROXY 8 METHYL 4' CHLOROISOFLAVAN; 7 HYDROXY 8 METHYL 4' NITROISOFLAVONE; 7 HYDROXY 8,4' DIMETHYLISOFLAVONE; 7 HYDROXYISOFLAVONE; 7,4' DIHYDROXY 8 METHYLISOFLAVONE; 7,4' DIHYDROXYISOFLAVONE; 7,8 DIHYDROXY 3' METHYLISOFLAVAN; 7,8 DIHYDROXY 4' METHYLISOFLAVAN; ARACHIDONATE 12 LIPOXYGENASE; ARACHIDONATE 15 LIPOXYGENASE; BAICALEIN; CATECHOL DERIVATIVE; FLAVONE DERIVATIVE; ISOFLAVAN DERIVATIVE; ISOFLAVONE DERIVATIVE; LIPOXYGENASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG INHIBITION; DRUG POTENCY; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; IC 50; IN VITRO STUDY; KINETICS; MEASUREMENT; MOLECULAR DOCKING; PRIORITY JOURNAL; SCAVENGING SYSTEM;

DOCKING AND SCAVENGER PROPERTIES; HUMAN LIPOXYGENASE ASSAY; ISOFLAVONOIDS;

ANTIOXIDANTS; ARACHIDONATE 12-LIPOXYGENASE; ARACHIDONATE 15-LIPOXYGENASE; BINDING SITES; HUMANS; ISOFLAVONES; KINETICS; LIPOXYGENASE INHIBITORS; MOLECULAR DOCKING SIMULATION; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84882832502     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12157     Document Type: Article

References (42)

1. Yamamoto S. (1992) Mammalian lipoxygenases: molecular structures and functions. Biochim Biophys Acta;1128:117-131.
2. Brash A.R. (1999) Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate. J Biol Chem;274:23679-23682.
3. Kuhn H., Thiele B.J. (1999) The diversity of the lipoxygenase family. Many sequence data but little information on biological significance. FEBS Lett;449:7-11.
4. Pontiki E., Hadjipavlou-Litina D. (2008) Lipoxygenase inhibitors: a comparative QSAR study review and evaluation of new QSARs. Med Res Rev;28:39-117.
5. Kamitani H., Geller M., Eling T. (1998) Expression of 15-lipoxygenase by human colorectal carcinoma Caco-2 cell lines during apoptosis and cell differentiation. J Biol Chem;273:21569-21577.
6. Kelavkar U., Glasgow W., Eling T.E. (2002) The effect of 15-lipoxygenase-1 expression on cancer cells. Curr Urol Rep;3:207-214.
7. Ding X.Z., Iversen P., Cluck M.W., Knezetic J.A., Adrian T.E. (1999) Lipoxygenase inhibitors abolish proliferation of human pancreatic cancer cells. Biochem Biophys Res Commun;261:218-223.
8. Connolly J.M., Rose D.P. (1998) Enhanced angiogenesis and growth of 12-lipoxygenase gene-transfected MCF-7 human breast cancer cells in athymic nude mice. Cancer Lett;132:107-112.
9. Natarajan R., Nadler J. (1998) Role of lipoxygenases in breast cancer. Front Biosci;3:81-88.
10. Nie D., Hillman G.G., Geddes T., Tang K., Pierson C., Grignon D.J., Honn K.V. (1998) Platelet-type 12-lipoxygenase in a human prostate carcinoma stimulates angiogenesis and tumor growth. Cancer Res;58:4047-4051.
11. Shappell S.B., Manning S., Boeglin W.E., Guan Y.F., Roberts R.L., Davis L., Olson S.J., Jack G.S., Coffey C.S., Wheeler T.M., Breyer M.D., Brash A.R. (2001) Alterations in lipoxygenase and cyclooxygenase-2 catalytic activity and mRNA expression in prostate carcinoma. Neoplasia;3:287-303.
12. Tang S., Bhatia B., Maldonado C.J., Yang P., Newman R.A., Liu J., Chandra D., Traag J., Klein R.D., Fischer S.M., Chopra D., Shen J., Zhau H.E., Chung L.W., Tang D.G. (2002) Evidence that arachidonate 15-lipoxygenase 2 is a negative cell cycle regulator in normal prostate epithelial cells. J Biol Chem;277:16189-16201.
13. Hagmann W., Borgers S. (1997) Requirement for epidermal growth factor receptor tyrosine kinase and for 12-lipoxygenase activity in the expression of 12-lipoxygenase in human epidermoid carcinoma cells. Biochem Pharmacol;53:937-942.
14. Cichewicz R.H., Kenyon V.A., Whitman S., Morales N.M., Arguello J.F., Holman T.R., Crews P. (2004) Redox inactivation of human 15-lipoxygenase by marine-derived meroditerpenes and synthetic chromanes: archetypes for a unique class of selective and recyclable inhibitors. J Am Chem Soc;126:14910-14920.
15. Moiseyev N., Rucker J., Glickman M.H. (1997) Reduction of ferric iron could serve as an electron sink to drive hydrogen tunneling in the lipoxygenase reaction. J Am Chem Soc;119:3853-3860.
16. Nelson M.J., Batt D.G., Thompson J.S., Wright S.W. (1991) Reduction of the active site iron by potent inhibitors of lipoxygenases. J Biol Chem;266:8225-8229.
17. Butovich I.A., Lukyanova S.M. (2008) Inhibition of lipoxygenases and cyclooxygenases by linoleyl hydroxamic acid: comparative in vitro studies. J Lipid Res;49:1284-1294.
18. Suzuki H., Ueda T., Juranek I., Yamamoto S., Katoh T., Node M., Suzuki T. (2000) Hinokitiol, a selective inhibitor of the platelet-type isozyme of arachidonate 12-lipoxygenase. Biochem Biophys Res Commun;275:885-889.
19. Kemal C., Louis-Flamberg P., Krupinski-Olsen R., Shorter A.L. (1987) Reductive inactivation of soybean lipoxygenase 1 by catechols: a possible mechanism for regulation of lipoxygenase activity. Biochemistry;26:7064-7072.
20. Sadik C.D., Sies H., Schewe T. (2003) Inhibition of 15-lipoxygenases by flavonoids: structure-activity relations and mode of action. Biochem Pharmacol;65:773-781.
21. Sekiya K., Okuda H., Arichi S. (1982) Selective Inhibition of platelet lipoxygenase by esculetin. Biochim Biophys Acta;713:68-72.
22. Gutierrez-Lugo M.T., Deschamps J.D., Holman T.R., Suarez E., Timmermann B.N. (2004) Lipoxygenase inhibition by anadanthoflavone, a new flavonoid from the aerial parts of Anadenanthera colubrina. Planta Med;70:263-265.
23. Deschamps J.D., Kenyon V.A., Holman T.R. (2006) Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases. Bioorg Med Chem;14:4295-4301.
24. Ueda H., Yamazaki C., Yamazaki M. (2002) Luteolin as an anti-inflammatory and anti-allergic constituent of Perilla frutescens. Biol Pharm Bull;25:1197-1202.
25. Sepúlveda-Boza S., Walizei G.H., Caroli-Rezende M., Vásquez Y., Mascayano C., Mejías L. (2001) The preparation of new isoflavones. Synth Commun;31:1933-1940.
26. Vasquez-Martinez Y., Ohri R.V., Kenyon V., Holman T.R., Sepúlveda-Boza S. (2007) Structure-activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2. Bioorg Med Chem;15:7408-7425.
27. Albert A.I., Zilliken F.W. (1989) U.S. Patent 4 814, 346.
28. Heaton A., Husband A. (2005) U.S.Patent 7 601 855.
29. Chang C.Y., Nair G.M., Santell C.R., Helferich W.G. (1994) Microwave-mediated synthesis of anticarcinogenic isoflavones from soybeans. J Agric Food Chem;42:1869-1871.
30. Singh H., Pratap R. (2006) A convenient one-pot synthesis of 7-hydroxy-isoflavones from resorcinol with substituted phenylacetic acids. Tetrahedron Lett;47:8161-8163.
31. Amagata T., Whitman S., Johnson T.A., Stessman C.C., Loo C.P., Lobkovsky E., Clardy J., Crews P., Holman T.R. (2003) Exploring sponge-derived terpenoids for their potency and selectivity against 12-human, 15-human, and 15-soybean lipoxygenases. J Nat Prod;66:230-235.
32. Holman T.R., Zhou J., Solomon E.I. (1998) Spectroscopic and functional characterization of a ligand coordination mutant of soybean lipoxygenase: first coordination sphere analogue of human 15-lipoxygenase. J Am Chem Soc;120:12564-12572.
33. Deschamps J.D., Gautschi J.T., Whitman S., Johnson T.A., Gassner N.C., Crews P., Holman T.R. (2007) Discovery of platelet-type 12-human lipoxygenase selective inhibitors by high-throughput screening of structurally diverse libraries. Bioorg Med Chem;15:6900-6908.
34. Carroll J., Jonsson E.N., Ebel R., Hartman M.S., Holman T.R., Crews P.J. (2001) Probing sponge-derived terpenoids for human 15-lipoxygenase inhibitors. J Org Chem;66:6847-6851.
35. i) and the concentration of inhibitor which causes 50 per cent inhibition (IC50) of an enzymatic reaction. Biochem Pharmacol;22:3099-3108.
36. Miliauskas G., Venskutonis P.R., van Beek T.A. (2004) Screening of radical scavenging activity of some medicinal and aromatic plant extracts. Food Chem;85:231-237.
37. Mascayano C., Nunez G., Acevedo W., Caroli Rezende M. (2010) Binding of arachidonic acid and two flavonoid inhibitors to human 12-and 15-lipoxygenases: a steered molecular dynamics study. J Mol Model;16:1039-1045.
38. Borbulevych O.Y., Jankun J., Selman S.H., Skrzypczak-Jankun E. (2004) Lipoxygenase interactions with natural flavonoid, quercetin, reveal a complex with protocatechuic acid in its X-ray structure at 2.1 Å resolutions. Proteins;54:13-19.
39. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., Olson A.J.J. (1998) Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function. Comput Chem;19:1639-1662.
40. Sadeghian H., Attaran N., Jafari Z., Saberi M.R., Pordel M., Riazi M.M. (2009) Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them. Bioorg Med Chem;17:2327-2335.
41. Kozak K.R., Gupta R.A., Moody J.S., Ji C., Boeglin W.E., DuBois R.N., Brash A.R., Marnett L.J. (2002) 15-Lipoxygenase metabolism of 2-arachidonylglycerol: generation of a PPARalpha agonist. J Biol Chem;277:23278-23286.
42. Gan Q.F., Browner M.F., Sloane D.L., Sigal E. (1996) Defining the arachidonic acid binding site of human 15-lipoxygenase. Molecular modeling and mutagenesis. J Biol Chem;271:25412-25418.