title: Squaraines bearing halogenated moieties as anticancer photosensitizers: Synthesis, characterization and biological evaluation.
abstract: We report the synthesis and characterization of a series of symmetrical indolenine-based squaraine dyes along with the evaluation of their singlet oxygen generation efficiency. The photodynamic activity of these new photosensitizers has been evaluated on a human tumor fibrosarcoma (HT-1080) cell line. The cytotoxicity increased over time and is induced by the photoactivation of bromo (Br-C4) and iodio (I-C4) long carbon chain squaraine dyes and the consequent increase in reactive oxygen species (ROS) production (p < 0.001), which leads to necrosis 6 h after treatment. Induction of cytochrome c release, DNA damage and up-regulation of GPX1, NQO1 and SOD2 mRNA gene expression after PDT were investigated.
authors.affiliation: University of Torino, Department of Drug Science and Technology, Via Pietro Giuria 13, 10125 Torino, Italy.
authors.forename: Loredana
authors.initials: L
authors.lastname: Serpe
authors.affiliation: University of Torino, Department of Chemistry and NIS Interdepartmental Centre, Via Pietro Giuria 7, 10125 Torino, Italy.
authors.forename: Silvano
authors.initials: S
authors.lastname: Ellena
authors.affiliation: University of Torino, Department of Chemistry and NIS Interdepartmental Centre, Via Pietro Giuria 7, 10125 Torino, Italy. Electronic address: nadia.barbero@unito.it.
authors.forename: Nadia
authors.initials: N
authors.lastname: Barbero
authors.affiliation: University of Torino, Department of Drug Science and Technology, Via Pietro Giuria 13, 10125 Torino, Italy.
authors.forename: Federica
authors.initials: F
authors.lastname: Foglietta
authors.affiliation: University of Torino, Department of Drug Science and Technology, Via Pietro Giuria 13, 10125 Torino, Italy.
authors.forename: Federica
authors.initials: F
authors.lastname: Prandini
authors.affiliation: University of Torino, Department of Life Sciences and Systems Biology, Via Accademia Albertina 13, 10123 Torino, Italy.
authors.forename: Maria Pia
authors.initials: MP
authors.lastname: Gallo
authors.affiliation: University of Torino, Department of Life Sciences and Systems Biology, Via Accademia Albertina 13, 10123 Torino, Italy.
authors.forename: Renzo
authors.initials: R
authors.lastname: Levi
authors.affiliation: University of Torino, Department of Chemistry and NIS Interdepartmental Centre, Via Pietro Giuria 7, 10125 Torino, Italy.
authors.forename: Claudia
authors.initials: C
authors.lastname: Barolo
authors.affiliation: University of Torino, Department of Drug Science and Technology, Via Pietro Giuria 13, 10125 Torino, Italy.
authors.forename: Roberto
authors.initials: R
authors.lastname: Canaparo
authors.affiliation: University of Torino, Department of Molecular Biotechnology and Health Science, Via Quarello15, 10135 Torino, Italy.
authors.forename: Sonja
authors.initials: S
authors.lastname: Visentin
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D016923:Cell Death / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D003503:Cyclobutanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006219:Halogens / Q000737:chemistry*; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000378:metabolism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D003503:Cyclobutanes; D006219:Halogens; D010636:Phenols; D017319:Photosensitizing Agents; D017382:Reactive Oxygen Species; C480596:squaraine
keywords: Cancer; Photodynamic therapy; Photosensitizers; Singlet oxygen; Squaraines