Biological evaluation of morin and its new oxovanadium(IV) complex as antio-xidant and specific anti-cancer agents

Chemico-Biological Interactions

Volumn 206, Issue 2, 2013, Pages 289-301

  Naso, Luciana G ^a   Lezama, Luis ^b   Rojo, Teófilo ^b   Etcheverry, Susana B ^a   Valcarcel, María ^c   Roura, Meritxell ^c   Salado, Clarisa ^c   Ferrer, Evelina G ^a   Williams, Patricia A M ^a  

^a FACULTAD DE CIENCIAS EXACTAS   (Argentina)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^c Innoprot SL   (Spain)

Author keywords

Natural antioxidant morin; Oxovanadium(IV) complex; Radical scavengers; Tumor specificity

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); ANTINEOPLASTIC AGENT; ANTIOXIDANT; CASPASE 3; CASPASE 7; HYDROXYL RADICAL; MORIN; MORIN OXOVANADIUM COMPLEX; OXYGEN RADICAL; PEROXY RADICAL; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; VANADIUM DERIVATIVE;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BREAST EPITHELIUM; BREAST TUMOR; CANCER CELL CULTURE; CELL DAMAGE; CELL STRAIN SKBR3; CELL STRAIN T47D; COMPLEX FORMATION; CONTROLLED STUDY; DRUG EFFICACY; DRUG SCREENING; DRUG SENSITIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; EPITHELIUM CELL; HUMAN; HUMAN CELL; MITOCHONDRIAL MEMBRANE POTENTIAL; MOUSE; NONHUMAN; OSTEOBLAST; PHYSICAL CHEMISTRY; RAT;

1,1-DIPHENYL-2-PICRYLHYDRAZYL RADICAL; 2,2′-AZINOBIS(3-ETHYLBENZOTHIAZOLINE-6-SULFONIC ACID) DIAMMONIUM SALT; 2,2-AZOBIS(2-AMIDINOPROPANE) DIHYDROCHLORIDE; 3-(4,5-METHYL-THIAZOL-2-YL)-2,5DIPHENYL-TETRAZOLIUM BROMIDE; 4′,6′-DIAMIDINO-2-PHENYLINDOLE; 5-(AND-6)-CHLOROMETHYL-2,7,DICHLORODIHYDROFLUORESCEIN DIACETATE ACETYL ESTER; 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID; [VO(MOR)(2)H(2)O]·5H(2)O; AAPH; ABTS; CM-H2DCFDA; DAPI; DHR123; DIHYDRORHODAMINE 123; DIMETHYL SULFOXIDE; DMEM; DMSO; DPPH(); DULBECCO'S MODIFIED EAGLE'S MEDIUM; FBS; FETAL BOVINE SERUM; H2AX; LACTATE DEHYDROGENASE; LDH; MTT; NATURAL ANTIOXIDANT MORIN; NBT; NITROBLUE TETRAZOLIUM; OXOVANADIUM(IV) COMPLEX; PBS; PHOSPHATE-BUFFERED SALINE; RADICAL SCAVENGERS; REACTIVE OXYGEN SPECIES; REGIONS-OF-INTEREST; ROI; ROS; SOD; SUBTYPE OF H2A HISTONE; SUPEROXIDE DISMUTASE; TEAC; TETRAMETHYL RHODAMINE METHYL ESTER; TMRM; TROLOX; TROLOX EQUIVALENT ANTIOXIDANT COEFFICIENT; TUMOR SPECIFICITY; VOMOR;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CASPASE 3; CASPASE 7; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; COORDINATION COMPLEXES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FLAVONOIDS; HUMANS; MICE; RATS; REACTIVE OXYGEN SPECIES; VANADIUM;

MAMMALIA;

EID: 84886056869     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2013.10.006     Document Type: Article

References (51)

1. S.A. Aherne, and N.M. O'Brien Dietary flavonols: chemistry Food Content Metab. Nutr. 18 2002 75 81
2. N.C. Cook, and S. Samman Flavonoids-chemistry, metabolism, cardioprotective effects, and dietary sources J. Nutr. Biochem. 7 1996 66 76 (Pubitemid 26086316)
3. J.W. Kim, J.H. Lee, B.Y. Hwang, S.H. Mun, N.Y. Ko, D.K. Kim, B. Kim, H.S. Kim, Y.M. Kim, and W.S. Choi Morin inhibits Fyn kinase in mast cells and IgE-mediated type I hypersensitivity response in vivo Biochem. Pharmacol. 77 2009 1506 1512
4. W. Liu, and R. Guo Effects of Triton X-100 nanoaggregates on dimerization and antioxidant activity of morin Mol. Pharm. 5 2008 588 597
5. V. Sivaramakrishnan, P.N.M. Shilpa, V.R.P. Kumar, and S.N. Devaraj Attenuation of N-nitrosodiethylamine-induced hepatocellular carcinogenesis by a novel flavonol-Morin Chem. Biol. Interact. 171 2008 79 88 (Pubitemid 350191846)
6. C.S. Yang, J.M. Landau, M.T. Huang, and H.L. Newmark Inhibition of carcinogenesis by dietary polyphenolic compounds Annu. Rev. Nutr. 21 2001 381 406 (Pubitemid 32695277)
7. P.C.H. Holiman, M.G.L. Hertog, and M.B. Katan Analysis and health effects of flavonoids Food Chem. 57 1996 43 46 (Pubitemid 26345073)
8. S. Subash, and P. Subramanian Effect of morin on the levels of circulatory liver markers and redox status in experimental chronic hyperammonaemic rats Singapore Med. 49 2008 650 655
9. A. Evangelou, S. Karkabounas, G. Kalpouzos, M. Malamas, R. Liasko, D. Stefanou, A.T. Vlaho, and T.A. Kabanos Comparison of the therapeutic effects of two vanadium complexes administered at low doses on benzo[α]pyrene-induced malignant tumors in rats Cancer Lett. 119 1997 221 225 (Pubitemid 27478107)
10. T. Chakraborty, A. Chatterjee, A. Rana, D. Dhachinamoorthi, A. Kumar, and M. Chatterjee Carcinogen-induced early molecular events and its implication in the initiation of chemical hepatocarcinogenesis in rats: chemopreventive role of vanadium on this process Biochim. Biophys. Acta 1772 2007 48 59 (Pubitemid 44960731)
11. P. Villani, E. Cordelli, P. Leopardi, E. Siniscalchi, E. Veschetti, A.M. Fresegna, and R. Crebelli Evaluation of genotoxicity of oral exposure to tetravalent vanadium in vivo Toxicol. Lett. 170 2007 11 18 (Pubitemid 46498902)
12. D.X. Nguyen, P.D. Bos, and J. Massagué Metastasis: from dissemination to organ-specific colonization Nat. Rev. Cancer 9 2009 274 284
13. M. Badea, R. Olar, D. Marinescu, V. Uivarosi, V. Aldea, and T.O. Nicolescu Thermal stability of new vanadyl complexes with flavonoid derivatives as potential insulin-mimetic agents J. Therm. Anal. Calorim. 99 2010 823 827
14. M. Onishi Photometric Determination of Traces of Metals fourth ed. 1998 Wiley New York Part II
15. M.S. Islas, T. Rojo, L. Lezama, M. Griera Merino, M.A. Cortes, M. Rodriguez Puyol, E.G. Ferrer, and P.A.M. Williams Improvement of the antihypertensive capacity of candesartan and trityl candesartan by their SOD mimetic copper(II) complexes J. Inorg. Biochem. 123 2013 23 33
16. A.M. Cortizo, and S.B. Etcheverry Vanadium derivatives act as growth factor-mimetic compounds upon differentiation and proliferation of osteoblast-like UMR106 cells Mol. Cell. Biochem. 145 1995 97 102
17. C.M. Krejsa, S.G. Nadler, J.M. Esselstyn, T.J. Kavanagh, J.A. Ledbetter, and G.L. Schieven Role of oxidative stress in the action of vanadium phosphotyrosine phosphatase inhibitors. Redox independent activation of NF-kappaB J. Biol. Chem. 272 1997 11541 11549 (Pubitemid 27184165)
18. M.M. Bradford A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 1976 248 254
19. V.C. Sálice, A.M. Cortizo, C.L. Gómez Dumm, and S.B. Etcheverry Tyrosine phosphorylation and morphological transformation induced by four vanadium compounds on MC3T3E1 cells Mol. Cell. Biochem. 198 1999 119 128 (Pubitemid 29414530)
20. J.C. Cornard, and J.C. Merlin Spectroscopic and structural study of complexes of quercetin with Al(III) J. Inorg. Biochem. 92 2002 19 27 (Pubitemid 35291959)
21. E.G. Ferrer, M.V. Salinas, M.J. Correa, L. Naso, D.A. Barrio, S.B. Etcheverry, L. Lezama, T. Rojo, and P.A.M. Williams Synthesis, characterization, antitumoral and osteogenic activities of quercetin vanadyl(IV) complexes J. Biol. Inorg. Chem. 11 2006 791 801 (Pubitemid 44100473)
22. Q.K. Panhwar, S. Memon, and M.I. Bhanger Synthesis, characterization, spectroscopic and antioxidation studies of Cu(II)-morin complex J. Mol. Struct. 967 2010 47 53
23. S.B. Bukhari, S. Memon, M. Mahroof-Tahir, and M.I. Bhanger Synthesis, characterization and antioxidant activity copper-quercetin complex Spectrochim. Acta A 71 2009 1901 1906
24. N.D. Chasteen L.J. Berliner, J. Reuben, Biological Magnetic Resonance vol. 3 1981 Plenum New York
25. L. Naso, E.G. Ferrer, L. Lezama, T. Rojo, S.B. Etcheverry, and P.A.M. Williams Role of oxidative stress in the antitumoral action of a new vanadyl(IV) complex with the flavonoid chrysin in two osteoblast cell lines: relationship with the radical scavenger activity J. Biol. Inorg. Chem. 15 2010 889 902
26. M. Musialik, R. Kuzmicz, T.S. Pawlowski, and G. Litwinienko Acidity of hydroxyl groups: an overlooked influence on antiradical properties of flavonoids J. Org. Chem. 74 2009 2699 2709
27. M.W. Makinen, and M.J. Brady Structual origins of the insulin-mimetic activity of bis(acetylacetonato)oxovanadium(IV) J. Biol. Chem. 277 2002 12215 12220 (Pubitemid 34952788)
28. S.B. Etcheverry, E.G. Ferrer, L.G. Naso, J. Rivadeneira, V. Salinas, and P.A.M. Williams Antioxidant effects of the VO(IV) hesperidin complex and its role in cancer chemoprevention J. Biol. Inorg. Chem. 13 2008 435 447
29. P.C. Moorhouse, M. Grootveld, B. Halliwell, J.G. QuinIan, and J.M.C. Guttetidge Allopurinol and oxypurinol are hydroxyl radical scavengers FEBS Lett. 213 1987 23 28 (Pubitemid 17036125)
30. O. Potterat Antioxidant and free radical scavengers of natural origin Curr. Org. Chem. 1 1997 415 440 (Pubitemid 127681644)
31. X. Shi, H. Jiang, Y. Mao, J. Ye, and U. Saffiotti Vanadium(IV)-mediated free radical generation and related 2′-deoxyguanosine hydroxylation and DNA damage Toxicology 106 1996 27 38
32. 2 generation Cell. Biol. Toxicol. 23 2007 413 420
33. K. Lemanska, H. Szymusiak, B. Tyrakowska, R. Zielínskians, A.E.M.F. Soffers, and I.M.C.M. Rietjens The influence of pH on the antioxidant properties and the mechanisms of antioxidant action of hydroxyflavones Free Radical Biol. Med. 31 2001 869 881 (Pubitemid 32925084)
34. J.M. Herrero-Martínez, C. Repollés, E. Bosch, M. Rosés, and C. Ráfols Potentiometric determination of aqueous dissociation constants of flavonols sparingly soluble in water Talanta 74 2008 1008 1013
35. R.H. Holm, P. Kennepohl, and E.I. Solomon Structural and functional aspects of metal sites in biology Chem. Rev. 96 1996 2239 2314 (Pubitemid 126641104)
36. E. Wóznicka, M. Kopacz, M. Umbreit, and J. Kłos New complexes of La(III), Ce(III), Pr(III), Nd(III), Sm(III), Eu(III) and Gd(III) ions with morin J. Inorg. Biochem. 101 2007 774 782
37. P. Cos, L. Ying, M. Calomme, J.P. Hu, K. Cimanga, B. Van Poel, L. Pieters, A.J. Vlietinck, and D. Vanden Berghe Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers J. Nat. Prod. 61 1998 71 76 (Pubitemid 28086977)
38. Q. Khan Panhwar, S. Memon, and M.I. Bhanger Synthesis, characterization, spectroscopic and antioxidation studies of Cu(II)-morin complex J. Mol. Struct. 967 2010 47 53
39. A.M. Mendoza-Wilson, H. Santacruz-Ortega, and R.R. Balandrán- Quintana Relationship between structure, properties, and the radical scavenging activity of morin J. Mol. Struct. 995 2011 134 141
40. S. Tachakittirungrod, F. Ikegami, and S. Okonogi Antioxidant active principles isolated from Psidium guajava grown in Thailand Sci. Pharm. 75 2007 179 193
41. D. Villaño, M.S. Fernández-Pachón, M.L. Moyá, A.M. Troncoso, and M.C. García-Parrilla Radical scavenging ability of polyphenolic compounds towards DPPH free radical Talanta 71 2007 230 235 (Pubitemid 46038394)
42. A. Rice-Evans, N.J. Miller, and G. Paganga Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Biol. Med. 20 1996 933 956 (Pubitemid 26157509)
43. K.G. Lee, T. Shibamoto, G.R. Takeoka, S.E. Lee, J.H. Kim, and B.S. Park Inhibitory effects of plant-derived flavonoids and phenolic acids on malonaldehyde formation from ethyl arachidonate J. Agric. Food. Chem. 51 2003 7203 7207
44. R. Apak, K. Güçlü, B. Demirata, M. Özyürek, S.E. Çelik, B. Bektaşoǧlu, K.I. Berker, and D. Özyurt Comparative evaluation of various total antioxidant capacity assays applied to phenolic compounds with the CUPRAC assay Molecules 12 2007 1496 1547
45. + assay J. Agric. Food Chem. 52 2004 4669 4674
46. D. Villaño, M.S. Fernández-Pachón, A.M. Troncoso, and M.C. García-Parrilla Comparison of antioxidant activity of wine phenolic compounds and metabolites in vitro Anal. Chim. Acta 538 2005 391 398 (Pubitemid 40591903)
47. Z. Cheng, J. Ren, Y. Li, W. Chang, and Z. Chen Study on the multiple mechansims underlying the reaction between hydroxyl radical and phenolic compounds by qualitative structure and activity relationship Bioorg. Med. Chem. 10 2002 4067 4073 (Pubitemid 36164707)
48. K.E. Heim, A.R. Tagliaferro, and D.J. Bobilya Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships J. Nutr. Biochem. 13 2002 572 584 (Pubitemid 35246546)
49. C.D. Hapner, P. Deuster, and Y. Chen Inhibition of oxidative hemolysis by quercetin, but not other antioxidants Chem. Biol. Interact. 186 2012 275 279
50. A. Chowdhury, K. Kishino, R. Satoh, K. Hashimoto, H. Kikuchi, H. Nishikawa, Y. Shirataki, and H. Sakagami Tumor-specificity and apoptosis-inducing activity of stilbenes and flavonoids Anticancer Res. 25 2005 2055 2064
51. Z. Qi, W. Liufang, L. Xiang, L. Shuben, and H. Fengying Synthesis, characterization and antitumour properties of metal(II) solid complexes with Morin Transition Met. Chem. 21 1996 23 27