title: Characterization of 2,3,6,7,10,11-hexahydroxytriphenylene and its effects on cell viability in human cancer cell lines.
abstract: We synthesized 2,3,6,7,10,11-hexahydroxytriphenylene (HHTP), characterized it by electrochemistry, spectroelectrochemistry, and electron paramagnetic resonance techniques, and evaluated its cytotoxicity to human cancer cell lines. The results revealed that HHTP has accessible higher-oxidation states, especially the tris-semiquinone monoradical. This species is stable and is formed after being stored for months. HHTP exhibited cytotoxic effects on 5 human cancer cell lines, including glioma and lung cancer cells. The cytotoxic effect was evaluated based on the decrease in cell viability, increases in the percentage of cells with fragmented DNA, and elevated numbers of annexin V-PI-positive cells after HHTP treatment.
authors.affiliation: a Universidade Federal do Paraná, Dep. Química, C.P. 19081, 81531-980, Curitiba, Paraná, Brazil.
authors.forename: Karine P
authors.initials: KP
authors.lastname: Naidek
authors.affiliation: b Universidade Federal do Paraná, Dep. Bioquímica e Biologia Molecular, C.P. 19046, 81531-980, Curitiba, Paraná, Brazil.
authors.forename: Cristiane R
authors.initials: CR
authors.lastname: Zuconelli
authors.affiliation: b Universidade Federal do Paraná, Dep. Bioquímica e Biologia Molecular, C.P. 19046, 81531-980, Curitiba, Paraná, Brazil.
authors.forename: Otavio M
authors.initials: OM
authors.lastname: Cruz
authors.affiliation: a Universidade Federal do Paraná, Dep. Química, C.P. 19081, 81531-980, Curitiba, Paraná, Brazil.
authors.forename: Ronny
authors.initials: R
authors.lastname: Ribeiro
authors.affiliation: b Universidade Federal do Paraná, Dep. Bioquímica e Biologia Molecular, C.P. 19046, 81531-980, Curitiba, Paraná, Brazil.
authors.forename: Sheila M B
authors.initials: SM
authors.lastname: Winnischofer
authors.affiliation: a Universidade Federal do Paraná, Dep. Química, C.P. 19081, 81531-980, Curitiba, Paraná, Brazil.
authors.forename: Herbert
authors.initials: H
authors.lastname: Winnischofer
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D010616:Phenanthrenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: C557559:2,3,6,7,10,11-hexahydroxytriphenylene; D010616:Phenanthrenes
keywords: cell viability; cytotoxicity; cytotoxicité; hexahydroxytriphenylene; hexahydroxytriphénylène; semiquinone; viabilité cellulaire