Chemoprotective and toxic potentials of synthetic and natural chalcones and dihydrochalcones in vitro

Toxicology

Volumn 208, Issue 1, 2005, Pages 81-93

  Forejtníková, Hana ^a   Lunerová, Kamila ^a   Kubínová, Renata ^a   Jankovská, Dagmar ^a   Marek, Radek ^b   Kareš, Radovan ^b   Suchý, Václav ^a   Vondráček, Jan ^c   Machala, Miroslav ^c  

^a UNIVERSITY OF VETERINARY AND PHARMACEUTICAL SCIENCES   (Czech Republic)

^b MASARYK UNIVERSITY   (Czech Republic)

^c VETERINARY RESEARCH INSTITUTE   (Czech Republic)

Author keywords

Chalcones; Cytochrome P450; Gap junctional intercellular communication; Lipid peroxidation

Indexed keywords

ALPHA NAPHTHOFLAVONE; BUTYLCRESOL; CHALCONE DERIVATIVE; CYTOCHROME P450 1A; ETHOXYRESORUFIN; FLAVONOID; FLUORANTHENE; HYDROXYL GROUP; IRON; NATURAL PRODUCT; QUERCETIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RESORUFIN DERIVATIVE;

AMINO ACID SUBSTITUTION; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CELLULAR DISTRIBUTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DERIVATIZATION; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; ENZYME ACTIVITY; ENZYME INHIBITION; GAP JUNCTION; HYDROXYLATION; IN VITRO STUDY; LIPID PEROXIDATION; LIVER MICROSOME; NONHUMAN; PRIORITY JOURNAL; RAT; SUBSTITUTION REACTION; TOXICOLOGY;

ANIMALS; CARCINOGENS; CELL COMMUNICATION; CELL LINE; CHALCONES; CYTOCHROME P-450 ENZYME SYSTEM; DOSE-RESPONSE RELATIONSHIP, DRUG; EPITHELIAL CELLS; GAP JUNCTIONS; LIPID PEROXIDATION; LIVER; MALE; MICROSOMES, LIVER; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 12444332632     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2004.11.011     Document Type: Article

References (52)

1. I.S. Arty, H. Timmerman, M. Samhoedi, S. Sastrohamidjojo, and H. van der Goot Synthesis of benzylideneacetophenones and their inhibition of lipid peroxidation Eur. J. Med. 35 2000 449 457
2. D.G. Batt, R. Goodman, D.G. Jones, J.S. Kerr, L.R. Mantegna, C. McAllister, R.C. Newton, S. Nurnberg, P.K. Welch, and M.B. Covington 2′-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis J. Med. Chem. 36 1993 1434 1442
3. R.A. Bunce, and H.D. Reeves Amberlyst-15 catalyzed addition of phenols to alpha,beta-unsaturated ketones Synth. Commun. 19 1989 1109 1118
4. G. Cao, E. Sofic, and R.L. Prior Antioxidant and prooxidant behaviour of flavonoids: structure-activity relationships Free Rad. Biol. Med. 22 1997 749 760
5. Y.-H. Chae, C.B. Marcus, D.K. Ho, J.M. Cassady, and W.M. Baird Effect of synthetic and naturally occuring flavonoids on benzo[a]pyrene metabolism by hepatic microsomes prepared from rats treated with cytochrome P-450 inducers Cancer Lett. 60 1991 15 24
6. J.D. Chambers, J. Crawford, H.W.R. Williams, C. Dufresne, J. Schneigetz, M.A. Bernstein, and C.K. Lau Reactions of 2-phenyl-4H-1,3,2-benzodioxaborin, a stable ortho-quinone methide precursor Can. J. Chem. 70 1992 1717 1732
7. P. Chiba, G. Ecker, D. Schmidt, J. Drach, B. Tell, S. Goldenberg, and V. Gekeler Structural requirements for activity of propafenone-type modulators in p-glycoprotein-mediated multidrug resistance Mol. Pharmacol. 49 1996 1122 1130
8. C. Cimarelli, and G. Palmieri Alkylation of dianions derived from 2-(1-iminoalkyl) phenols: synthesis of functionalized 2-acyl phenols Tetrahedron 54 1998 15711 15720
9. A.R. Collins, J. Cadet, L. Moller, H.E. Poulsen, and J. Vina Are we sure we know how to measure 8-oxo-7,8-dihydroguanine in DNA from human cells? Arch. Biochem. Biophys. 423 2004 57 65
10. T.P. Dalton, H.G. Shertzer, and A. Puga Regulation of gene expression by reactive oxygen Annu. Rev. Pharmacol. Toxicol. 39 1999 67 70
11. F.A. Davis, and B.C. Chen Enantioselective synthesis of (+)-O-trimethylsappanone-B and (+)-O-trimethylbrazilin J. Org. Chem. 58 1993 1751 1753
12. R. De Vincenzo, G. Scambia, P. Benedetti Panici, F.O. Ranelletti, G. Bonanno, A. Ercoli, F. Delle Monache, F. Ferrari, M. Piantelli, and S. Mancuso Effect of synthetic and naturally occuring chalcones on ovarian cancer cell growth: structure-activity relationships Anti-Cancer Drug Des. 10 1995 481 490
13. G. Di Carlo, N. Mascolo, A.A. Izzo, and F. Capasso Flavonoids: old and new aspects of a class of natural therapeutic drugs Life Sci. 65 1999 337 353
14. J.R. Dimmock, D.W. Elias, M.A. Beazely, and N.M. Kandepu Bioactivities of chalcones Curr. Med. Chem. 6 1999 1125 1149
15. A.T. Dinkova-Kostova, C. Abeygunawardana, and P. Talalay Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers J. Med. Chem. 41 1998 5287 5296
16. R. Edenharder, I. von Petersdorff, and R. Rauscher Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ) and other heterocyclic amine mutagens from cooked food Mutat. Res. 287 1993 261 274
17. M.H. El-Fouly, J.E. Trosko, and C.C. Chang Scrape-loading and dye transfer, a rapid and simple technique to study gap junctional intercellular communication Exp. Cell Res. 168 1987 422 430
18. P. Figueiredo, J.C. Lima, H. Santos, M.-C. Wigand, and R. Brouillard Photochromism of the synthetic 4′,7-dihydroxyflavylium chloride J. Am. Chem. Soc. 116 1994 1249 1254
19. P.W. Freeman, S.T. Murphy, J.E. Nemorin, and W.C. Taylor The constituents of Australian Pimelea species. 2. The isolation of unusual flavones from Pinelea-Simplex and Pimelea-Decora Aust. J. Chem. 34 1981 1779 1784
20. A.G. Gonzáles, F. León, L. Sánchez-Pinto, J.I. Padrón, and J. Bermejo Phenolic compounds of Dragon's blood from Dracaena draco J. Nat. Prod. 63 2000 1297 1299
21. F.P. Guengerich, and T. Shimada Activation of procarcinogens by human cytochrome P450 enzymes Mutat. Res. 400 1998 201 213
22. B. Halliwell, R. Aeschbach, J. Loliger, and I.O. Aruoma The characterization of antioxidants Food Chem. Toxicol. 33 1995 601 617
23. H.K. Hsieh, T.H. Lee, J.P. Wang, J.J. Wang, and C.N. Lin Synthesis and anti-inflammatory effect of chalcones and related compounds Pharm. Res. 15 1998 39 46
24. S. Kirchiakarian, H.G. Tongo, J. Bastide, P. Bastide, and M.M. Grenie Synthesis and angioprotective, antiallergic and antihistaminic activities of 3-benzyl-chromones (homoisoflavones) Eur. J. Med. Chem. 24 1989 541 546
25. H.H. Ko, L.T. Tsao, K.L. Yu, C.T. Liu, J.P. Wang, and C.N. Lin Structure-activity relationship studies on chalcone derivates: The potent inhibition of chemical mediators release Bioorgan. Med. Chem. 11 2003 105 111
26. J.-C. Le Bail, C. Pouget, C. Fagnere, J.-P. Basly, A.-J. Chulia, and G. Habrioux Chalcones are potent inhibitors of aromatase and 17β- hydroxysteroid dehydrogenase activities Life Sci. 68 2001 751 761
27. Y.N. Lee, H.I. Yeh, T.Y. Tian, W.W. Lu, Y.S. Ko, and C.H. Tsai 2′,5′-Dihydrochalcone down-regulates endothelial connexin43 gap junctions and affects MAP kinase activation Toxicology 179 2002 51 60
28. M. Machala, L. Blaha, J. Vondracek, J.E. Trosko, J. Scott, and B.L. Upham Inhibition of gap junctional intercellular communication by noncoplanar polychlorinated biphenyls: Inhibitory potencies and screening for potential mode(s) of action Toxicol. Sci. 76 2003 102 111
29. M. Machala, R. Kubínová, P. Horavová, and V. Suchý Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity Phytother. Res. 15 2001 114 118
30. R. Marek, J. Toušek, J. Dostál, J. Slavík, R. Dommisse, and V. Sklenář H-1 and C-13 NMR study of quaternary benzo[c]phenanthridine alkaloids Magn. Reson. Chem. 37 1999 781 787
31. B.M. Markaverich, R.R. Gregory, M. Alejandro, F.S. Kittrell, D. Medina, J.H. Clark, M. Varma, and R.S. Varma Methyl p-hydroxyphenyllacetate and nuclear type-II binding-sites in malignant-cells: metabolic-fate and mammary-tumor growth Cancer Res. 50 1990 1470 1478
32. T. Mosmann Rapid colorimetric assay for cellular growth and survival - application to proliferation and cytotoxicity assays J. Immunol. Meth. 65 1983 55 63
33. W.S. Murphy, and S. Wattanasin Reactions of aryl cyclopropyl ketones - a new synthesis of aryl tetralones J. Chem. Soc., Perkin Trans. 1 1980 1567 1577
34. D.V. Parke, C. Ioannides, and D.F.V. Lewis Computer modeling and in vitro tests in the safety evaluation of chemicals - strategic implications Toxicol. In Vitro 4 1990 680 685
35. R.A. Prough, M.D. Burke, and R.T. Mayer Direct fluorometric methods for measuring mixed-function oxidase activity Meth. Enzymol. 52 1978 372 377
36. R.A. Roberts, D.V. Nebert, J.A. Hickman, J.H. Richburg, and T.L. Goldsworthy Perturbation of the mitosis/apoptosis balance: a fundamental mechanims in toxicology Fundam. Appl. Toxicol. 38 1997 107 115
37. H.S. Rosenkrantz, N. Pollack, and A.R. Cunningham Exploring the relationship between the inhibition of gap junctional intercellular communication and other biological phenomena Carcinogenesis 21 2000 1007 1011
38. T. Saitoh, H. Noguchi, and S. Shibata A new isoflavone and the corresponding isoflavone of Licorice root Chem. Pharm. Bull. 28 1978 144 147
39. P. Sečkářová, R. Marek, J. Dostál, R. Dommisse, and E.L. Esmans Structural studies of benzophenanthridine alkaloid free bases by NMR spectroscopy Magn. Reson. Chem. 40 2002 147 152
40. F. Severi, S. Benvenuti, L. Constantino, G. Vampa, M. Melegari, and L. Antolini Synthesis and activity of a new series of chalcones as aldose reductase inhibitors Eur. J. Med. Chem. Chim. Ther. 33 1998 859 866
41. F. Severi, L. Constantino, S. Benvenuti, G. Vampa, and A. Mucci Synthesis and description of chalcone-like compounds, inhibitors of aldose reductase Med. Chem. Res. 6 1996 128 136
42. S. Shibata Anti-tumorigenic chalcones Stem Cells 12 1994 44 52
43. M.-H. Siess, J. Leclerc, M.-C. Canivenc-Lavier, P. Rat, and M. Suschetet Heterogenous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes Toxicol. Appl. Pharmacol. 130 1995 73 78
44. S. Sogawa, Y. Nihro, H. Ueda, T. Miki, H. Matsumoto, and T. Satoh Protective effects of hydroxychalcones on free radical-induced cell damage Biol. Pharm. Bull. 17 1994 251 256
45. S. Sogawa, Y. Nihro, H. Ueda, A. Izumi, T. Miki, H. Matsumoto, and T. Satoh 3,4-Dihydroxychalcones as potent 5-lipooxygenase and cyclooxygenase inhibitors J. Med. Chem. 36 1993 3904 3909
46. F.A. Tomas-Barberen, and M.N. Clifford Flavanones, chalcones and dihydrochalcones: nature, occurrence and dietary burden J. Sci. Food Agric. 80 2000 1073 1080
47. J.E. Trosko, and R.J. Ruch Gap junctions as targets for cancer chemoprevention and chemotherapy Curr. Drug Targets 3 2002 465 482
48. J.E. Trosko, and R.J. Ruch Cell-cell communication in carcinogenesis Front. Biosci. 3 1998 208 236
49. M.S. Tsao, J.D. Smith, K.G. Nelson, and J.W. Grisham A diploid epithelial cell line from normal adult rat liver with phenotypic properties of 'oval' cells Exp. Cell Res. 154 1984 38 52
50. M. Uchiyama, and M. Mihara Determination of malonaldehyde precursor in tissues by thiobarbituric acid test Anal. Biochem. 92 1978 271 278
51. L.W. Wattenberg Chemoprevention of cancer Cancer Res. 45 1985 1 8
52. L.W. Wattenberg, J.B. Coccia, and A.R. Galbraith Inhibition of carcinogen-induced pulmonary and mammary carcinogenesis by chalcone administered subsequent to carcinogen exposure Cancer Lett. 83 1994 165 169