title: Sequestering ability to Cu2+of a new bodipy-based dye and its behavior as in vitro fluorescent sensor.
abstract: A Bodipy (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) derivative has been conceived and synthesized starting from l-aspartic acid, as a selective turn-off sensor of Cu2+ions. Its acid-base properties were determined to study the formation of metal/sensor complex species by titration of solutions each containing a different metal ion, such as Cu2+, Ca2+, Zn2+, Pb2+and Hg2+and different metal/sensor ratios. The speciation models allowed us to simulate the distribution of the metal/sensor complex species at the normal concentrations of the corresponding metals present in biological fluids. The distribution diagrams, obtained by varying the concentration of sensor 1, clearly indicate that sensor 1 responds selectively to Cu2+at micromolar concentrations, even in the presence of other more abundant metal cations Ca2+. Finally, we analyzed the cellular uptake of sensor 1 on human erythrocytes and its ability to chelate Cu2+in the cellular environment. Results indicate that it crosses the plasmatic membrane and colors the cells of a bright fluorescent red. Exposing the fluorescent cells to Cu2+results in a complete cellular photobleaching of the red fluorescence, indicating that sensor 1 is able to detect metal changes in the cytosolic environment.
authors.affiliation: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali - ChiBioFarAm, Università di Messina, 98166 Messina, Italy. Electronic address: teresa.papalia@unirc.it.
authors.forename: Teresa
authors.initials: T
authors.lastname: Papalia
authors.affiliation: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali - ChiBioFarAm, Università di Messina, 98166 Messina, Italy. Electronic address: abarattucci@unime.it.
authors.forename: Anna
authors.initials: A
authors.lastname: Barattucci
authors.affiliation: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali - ChiBioFarAm, Università di Messina, 98166 Messina, Italy. Electronic address: dbarreca@unime.it.
authors.forename: Davide
authors.initials: D
authors.lastname: Barreca
authors.affiliation: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali - ChiBioFarAm, Università di Messina, 98166 Messina, Italy. Electronic address: ebellocco@unime.it.
authors.forename: Ersilia
authors.initials: E
authors.lastname: Bellocco
authors.affiliation: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali - ChiBioFarAm, Università di Messina, 98166 Messina, Italy. Electronic address: pbonaccorsi@unime.it.
authors.forename: Paola
authors.initials: P
authors.lastname: Bonaccorsi
authors.affiliation: Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy. Electronic address: lucio.minuti@unipg.it.
authors.forename: Lucio
authors.initials: L
authors.lastname: Minuti
authors.affiliation: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali - ChiBioFarAm, Università di Messina, 98166 Messina, Italy. Electronic address: mnicolo@unime.it.
authors.forename: Marco Sebastiano
authors.initials: MS
authors.lastname: Nicolò
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo 1, 06123 Perugia, Italy. Electronic address: andrea.temperini@unipg.it.
authors.forename: Andrea
authors.initials: A
authors.lastname: Temperini
authors.affiliation: Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali - ChiBioFarAm, Università di Messina, 98166 Messina, Italy. Electronic address: cfoti@unime.it.
authors.forename: Claudia
authors.initials: C
authors.lastname: Foti
mesh_terms: D001896:Boron Compounds / Q000737:chemistry / Q000494:pharmacology; D002118:Calcium / Q000737:chemistry / Q000378:metabolism; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D003300:Copper / Q000737:chemistry / Q000494:pharmacology; D004910:Erythrocyte Membrane / Q000235:genetics / Q000378:metabolism; D005453:Fluorescence; D006801:Humans
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D056831:Coordination Complexes; D003300:Copper; D002118:Calcium
keywords: Bodipy; Cell internalization; Complexing ability; Cu(2+) sensor; Fluorescence