title: New benzothieno[3,2-d]-1,2,3-triazines with antiproliferative activity: synthesis, spectroscopic studies, and biological activity.
abstract: New benzothieno[3,2-d]-1,2,3-triazines, together with precursors triazenylbenzo[b]thiophenes, were designed, synthesized and screened as anticancer agents. The structural features of these compounds prompted us to investigate their DNA binding capability through UV-vis absorption titrations, circular dichroism, and viscometry, pointing out the occurrence of groove-binding. The derivative 3-(4-methoxy-phenyl)benzothieno[3,2-d]-1,2,3-triazin-4(3H)-one showed the highest antiproliferative effect against HeLa cells and was also tested in cell cycle perturbation experiments. The obtained results assessed for the first time the anticancer activity of benzothieno[3,2-d]-1,2,3-triazine nucleus, and we related it to its DNA-binding properties.
authors.affiliation: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo-Via Archirafi, 32-90123 Palermo, Italy. Electronic address: antonino.lauria@unipa.it.
authors.forename: Antonino
authors.initials: A
authors.lastname: Lauria
authors.affiliation: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo-Via Archirafi, 32-90123 Palermo, Italy.
authors.forename: Alessia
authors.initials: A
authors.lastname: Alfio
authors.affiliation: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo-Via Archirafi, 32-90123 Palermo, Italy.
authors.forename: Riccardo
authors.initials: R
authors.lastname: Bonsignore
authors.affiliation: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo-Via Archirafi, 32-90123 Palermo, Italy.
authors.forename: Carla
authors.initials: C
authors.lastname: Gentile
authors.affiliation: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo-Via Archirafi, 32-90123 Palermo, Italy.
authors.forename: Annamaria
authors.initials: A
authors.lastname: Martorana
authors.affiliation: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo-Via Archirafi, 32-90123 Palermo, Italy.
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Gennaro
authors.affiliation: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo-Via Archirafi, 32-90123 Palermo, Italy.
authors.forename: Giampaolo
authors.initials: G
authors.lastname: Barone
authors.affiliation: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo-Via Archirafi, 32-90123 Palermo, Italy.
authors.forename: Alessio
authors.initials: A
authors.lastname: Terenzi
authors.affiliation: Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo-Via Archirafi, 32-90123 Palermo, Italy.
authors.forename: Anna Maria
authors.initials: AM
authors.lastname: Almerico
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002453:Cell Cycle / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D002942:Circular Dichroism; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014227:Triazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014783:Viscosity
chemical_list: C000595737:3-(4-methoxyphenyl)benzothieno(3,2-d)-1,2,3-triazin-4(3H)-one; D000970:Antineoplastic Agents; D013876:Thiophenes; D014227:Triazines
keywords: Antiproliferative activity; Benzothienotriazines; Cell-cycle analysis; Spectroscopic studies; VLAK