title: Synthesis, characterization and biological evaluation of Rutin-zinc(II) flavonoid -metal complex.
abstract: Synthesis of compounds analogous to natural products from secondary metabolites, such as flavonoids, is a promising source of novel drugs. Rutin (quercetin-3-O-rutinoside) is a natural flavone, which has, in its chemical structure, different sites for coordination with transition metals and the complexation with these metals enhances its biological properties. Rutin-zinc(II), a flavonoid-metal complex, was synthesized and characterized by UV-VIS, FT-IR, elemental analysis and (1)H NMR. The antioxidant and antitumor activities, as well as the cytotoxicity and in vivo toxicity of this complex were evaluated and compared with the free rutin. Rutin-zinc(II) has not shown any cytotoxicity against normal cells (fibroblasts and HUVECs) or toxicity in BALB/c mice, but has shown antioxidant activity in vitro and cytotoxicity against leukemia (KG1, K562 and Jurkat), multiple myeloma (RPMI8226) and melanoma (B16F10 and SK-Mel-28) cell lines in vitro. In Ehrlich ascites carcinoma model, Rutin-zinc(II) modulated the mitochondrial membrane potential and the expression of genes related to cell cycle progression, angiogenesis and apoptosis.
authors.affiliation: Faculty of Medicine, University of São Paulo, São Paulo, Brazil; Department of Biotechnology, Anhanguera University of São Paulo, São Paulo, Brazil.
authors.forename: Norma Estefania Andrades
authors.initials: NE
authors.lastname: Ikeda
authors.affiliation: Fundação Pró-Sangue Hemocentro de São Paulo, São Paulo, Brazil.
authors.forename: Estela Maria
authors.initials: EM
authors.lastname: Novak
authors.affiliation: Laboratory of Biochemistry and Biophysics, Butantan Institute, São Paulo, Brazil.
authors.forename: Durvanei Augusto
authors.initials: DA
authors.lastname: Maria
authors.affiliation: Department of Pharmacy, Anhanguera University of São Paulo, São Paulo, Brazil.
authors.forename: Adélia Segin
authors.initials: AS
authors.lastname: Velosa
authors.affiliation: Department of Pharmacy, Anhanguera University of São Paulo, São Paulo, Brazil. Electronic address: rpereira02@hotmail.com.
authors.forename: Regina Mara Silva
authors.initials: RM
authors.lastname: Pereira
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D000971:Antineoplastic Combined Chemotherapy Protocols / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects / Q000235:genetics; D002460:Cell Line / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005260:Female; D005786:Gene Expression Regulation / Q000187:drug effects; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D053078:Membrane Potential, Mitochondrial / Q000187:drug effects; D008807:Mice, Inbred BALB C; D015394:Molecular Structure; D017239:Paclitaxel / Q000008:administration & dosage / Q000494:pharmacology; D012431:Rutin / Q000737:chemistry* / Q000494:pharmacology; D059550:Toxicity Tests, Subchronic; D023041:Xenograft Model Antitumor Assays; D015032:Zinc / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D056831:Coordination Complexes; D012431:Rutin; D015032:Zinc; D017239:Paclitaxel
keywords: Antitumor; Flavonoids; Metal complex; Rutin