Synthesis, characterization and biological evaluation of Rutin-zinc(II) flavonoid -metal complex

Chemico-Biological Interactions

Volumn 239, Issue , 2015, Pages 184-191

  Ikeda, Norma Estefania Andrades ^a   Novak, Estela Maria ^b   Maria, Durvanei Augusto ^c   Velosa, Adélia Segin ^a   Pereira, Regina Mara Silva ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FUNDAÇÃO PRÓ SANGUE HEMOCENTRO DE SÃO PAULO   (Brazil)

^c INSTITUTO BUTANTAN   (Brazil)

Author keywords

Antitumor; Flavonoids; Metal complex; Rutin

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIOXIDANT; ASCORBIC ACID; DNA; METAL COMPLEX; PACLITAXEL; RUTIN ZINC COMPLEX; RUTOSIDE; UNCLASSIFIED DRUG; COORDINATION COMPOUND; ZINC;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; B16F10 CELL LINE; CELL CYCLE PROGRESSION; CELL SPECIFICITY; CHEMICAL ANALYSIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA FRAGMENTATION; DPPH RADICAL SCAVENGING ASSAY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; EHRLICH ASCITES TUMOR; ELEMENTAL ANALYSIS; FEMALE; FIBROBLAST; FREE RADICAL SCAVENGING ASSAY; GENE EXPRESSION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INFRARED SPECTROSCOPY; JURKAT CELL LINE; K562 CELL LINE; KG1 CELL LINE; LEUKEMIA CELL LINE; MELANOMA CELL LINE; MITOCHONDRIAL MEMBRANE POTENTIAL; MOUSE; MULTIPLE MYELOMA CELL LINE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; RPMI8226 CELL LINE; SK MEL 28 CELL LINE; SUPEROXIDE RADICAL SCAVENGING ASSAY; TREATMENT DURATION; TUMOR VASCULARIZATION; ULTRAVIOLET SPECTROSCOPY; UMBILICAL VEIN ENDOTHELIAL CELL; ANIMAL; BAGG ALBINO MOUSE; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; GENE EXPRESSION REGULATION; GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TOXICITY TESTING;

MUS;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTINEOPLASTIC COMBINED CHEMOTHERAPY PROTOCOLS; APOPTOSIS; CELL LINE; CHEMISTRY TECHNIQUES, SYNTHETIC; COORDINATION COMPLEXES; FEMALE; GENE EXPRESSION REGULATION; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANE POTENTIAL, MITOCHONDRIAL; MICE, INBRED BALB C; MOLECULAR STRUCTURE; PACLITAXEL; RUTIN; TOXICITY TESTS, SUBCHRONIC; XENOGRAFT MODEL ANTITUMOR ASSAYS; ZINC;

EID: 84938099921     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2015.06.011     Document Type: Article

References (39)

1. M.J. Balunas, and A.D. Kinghorn Drug discovery from medicinal plants Life Sci. 78 5 2005 431 441
2. E. Middleton The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer Pharmacol. Rev. 52 4 2000 673 751
3. R.J. Nijveldt, E. van Nood, D.E. van Hoorn, P.G. Boelens, K. van Norren, and P.A. van Leeuwen Flavonoids: a review of probable mechanisms of action and potential applications Am. J. Clin. Nutr. 74 2001 418 425
4. S. Martens, and A. Mithöfer Flavones and flavone synthases Phytochemistry 20 2005 2399 2407
5. L. Le Marchand Cancer preventive effects of flavonoids:a review Biomed. Pharmacother. 56 2002 296 301
6. C. Kandaswami, L.T. Lee, P.P. Lee, J.J. Hwang, F.C. Ke, Y.T. Huang, and M.T. Lee The antitumor activities of flavonoids In Vivo 5 2005 895 909
7. M.K. Chahar, N. Sharma, M.P. Dobhal, and Y.C. Joshi Flavonoids: a versatile source of anticancer drugs Pharmacog. Rev. 9 2001 1 12
8. I.B. Afanas'ev, E.A. Ostrakhovitch, E.V. Mikhal'chik, G.A. Ibragimova, and L.G. Korkina Enhancement of antioxidant and anti-inflammatory activities of bioflavonoid rutin by complexation with transition metals Biochem. Pharmacol. 61 6 2001 677 684
9. Y. Yang, H. Lin, K. Su, C. Chen, Y. Yu, C. Lin, S. Yu, H. Yan, K. Su, and Y.S. Chen "Rutin, a flavonoid that is a main component of saussurea involucrata, attenuates the senescence effect in d-Galactose aging mouse model Evid. Based Complement. Altern. Med. 2012 2012 1 10
10. J.C.T. Carvalho, J.A.A. Sertie, and M.V.J. Barbosa Anti-inflammatory activity of the crude extract from the fruits of Pterodon emarginatus Vog J. Ethnopharmacol. 64 2 1999 127 133
11. L. Yu, K. Zhou, and J.W. Parry Inhibitory effects of wheat bran extracts on human LDL oxidation and free radicals LWT Swiss Soc. Food Sci. Technol. 38 5 2005 463 470
12. M. Nikishimi, N. Rao, and K. Yagi The occurrence of superoxide anion in the reaction of reduced phenazine methosulfate and molecular oxygen Biochem. Biophys. Res. Commun. 46 2 1972 849 854
13. T. Mossman Rapid colorimetric assay for cellular growth and survival: application to proliferative and citotoxicity assays J. Immunol. Methods 65 1-2 1983 55 63
14. A.M. Boldi Libraries from natural product-like scaffolds Curr. Opin. Chem. Biol. 8 3 2004 281 286
15. S. Shang, and D.S. Tan Advancing chemistry and biology through diversity-oriented synthesis of natural product-like libraries Curr. Opin. Chem. Biol. 9 3 2005 248 258
16. V.A. Kostyuk, A.I. Potapovich, T.V. Kostyuk, and M.G. Cherian Metal complexes of dietary flavonoids: evaluation of radical scavenger properties and protective activity against oxidative stress in vivo Cell. Mol. Biol. (Noisy-le-Grand) 53 1 2007 62 69
17. S.R. Maxwell Prospects for the use of antioxidant therapies Drugs 49 3 1995 345 361
18. A. Braca, C. Sortino, M. Politi, I. Morelli, and J. Mendez Antioxidant activity of flavonoids from Licania licaniaeflora J. Ethnopharmacol. 79 3 2002 379 381
19. D. Malesev, and V. Kuntic Investigation of metal-flavonoid chelates and the determination of flavonoids via metal-flavonoid complexing reactions J. Serbian Chem. Soc. 72 10 2007 921 939
20. J. Tan, B. Wang, and L. Zhu DNA binding, cytotoxicity, apoptotic inducing activity, and molecular modeling study of quercetin zinc(II) complex Bioorg. Med. Chem. 17 2009 614 620
21. S. Yamasaki, K. Sakata-Sogawa, A. Hasegawa, T. Suzuki, K. Kabu, E. Sato, T. Kurosaki, S. Yamashita, M. Tokunaga, K. Nishida, and T. Hirano Zinc is a novel intracellular second messenger J. Cell Biol. 177 4 2007 637 645
22. M. Murakami, and T. Hirano Intracellular zinc homeostasis and zinc signaling Cancer Sci. 99 8 2008 1515 1522
23. T. Sliwinski, A. Czechowska, M. Kolodziejczak, J. Jajte, M. Wisniewska-Jarosinska, and J. Blasiak Zinc salts differentially modulate DNA damage in normal and cancer cells Cell Biol. Int. 33 4 2009 542 547
24. L.C. Costello, and R.B. Franklin Cytotoxic/tumor suppressor role of zinc for the treatment of cancer: an enigma and an opportunity Expert Rev. Anticancer Ther. 12 1 2012 121 128
25. S.B. Ere, C. Karaalp, E. Bedir, H. Kaehlig, S. Glasl, S. Khan, and L. Krenn Secondary metabolites of Centaurea calolepis and evaluation of cnicin for anti-inflammatory, antioxidant, and cytotoxic activities Pharm. Biol. 49 8 2011 840 849
26. A. Ravi, M. Alvala, V. Sam, A.M. Kalle, V.K. Irlapati, and B.M. Reddy Anticancer activity of Pupalia lappacea on chronic myeloid leukemia K562 cells Daru: J. Facul. Pharm. 20 1 2012 86
27. Y. Cong, J. Guo, T. Wang, M. Li, K. Li, and J. Wang Q. Li.Chemical constituents and antitumor activity on leukemia K562 cell of Leonurus heterophyllus Zhongguo Zhong Yao Za Zhi 34 14 2009 1816 1818
28. L.G. Menon, R. Kuttan, and G. Kuttan Inhibition of lung metastasis in mice induced by B16F10 melanoma cells by polyphenolic compounds Cancer Lett. 95 1-2 1995 221 225
29. C. Martínez Conesa, V. Vicente Ortega, M.J. Yáñez Gascón, M. Alcaraz Baños, M. Canteras Jordana, O. Benavente-García, and J. Castillo Treatment of metastatic melanoma B16F10 by the flavonoids tangeretin, rutin, and diosmin J. Agric. Food Chem. 53 17 2005 6791 6797
30. M. Matsuo, N. Sasaki, K. Saga, and T. Kaneko Cytotoxicity of Flavonoids toward Cultured Normal Human Cells Biol. Pharm. Bull. 28 2 2005 253 259
31. F. Pierard, and A. Kirsch-De Mesmaeker Bifunctional transition metal complexes as nucleic acid photoprobes and photoreagents Inorg. Chem. Commun. 9 2006 111 126
32. F. Zobi, B. Spingler, T. Fox, and R. Alberto Toward novel DNA binding metal complexes: structure and basic kinetic data of [M(9MeG)2(CH3OH)(CO)3]+(M=99Tc, Re) Inorg. Chem. 42 9 2006 2818 2820
33. Y. Wang, and Z. Yang Synthesis, characterization and DNA-binding properties of three 3d transition metal complexes of the Schiff base derived from diethenetriamine with PMBP Transition Met. Chem. 30 2005 902 906
34. M. Ceruti, P. Crosasso, P. Brusa, S. Arpicco, F. Dosio, and L. Cattel Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing water-soluble prodrugs of paclitaxel Control Rel. 63 2000 141 153
35. S. Chen, X. Chen, Y. Xiu, K. Sun, Z. Zong, and Y. Zhao MicroRNA 490-3P enhances the drug-resistance of human ovarian cancer cells J. Ova. Res. 7 1 2014 84
36. V. Gogvadze, S. Orrenius, and B. Zhivotovsky Multiple pathways of cytochrome c release from mitochondria in apoptosis Biochim. Biophys. Acta 757 2006 639 647
37. S.R. Maxwell Prospects for the use of antioxidant therapies Drugs 49 1995 345 361
38. A. Braca, C. Sortino, M. Politi, I. Morelli, and J. Mendez Antioxidant activity of flavonoids from Licania licaniaeflora J. Ethnopharmacol. 79 2002 379 381
39. T. Sliwinski, A. Czechowska, M. Kolodziejczak, J. Jajte, M. Wisniewska-Jarosinska, and J. Blasiak Zinc salts differentially modulate DNA damage in normal and cancer cells Cell Biol. Int. 33 2009 542 547