The zinc(ii) complex of the octa-anionic 2,3,9,10,16,17,23,24-octakis-(7-methyl-7,8-dicarba-nido-undeca-boran-8-yl)hexyl-thio-6,13,20,27-phthalocyanine (nido-[ZnMCHESPc]Cs8, ) has been obtained in the form of caesium salt through mild deboronation of the neutral precursor, the closo-[ZnMCHESPc] complex, , with CsF. has been synthesized, in turn, by heating a finely ground mixture of the appropriate phthalonitrile and zinc(ii) acetate at 180.0 °C. The complexes have been characterized by elemental analyses, FT-IR, UV-visible absorption and fluorescence emission spectroscopy, and their structures were assessed by (1)H, (13)C, (11)B, and two-dimensional homo- and hetero-correlated NMR spectroscopy experiments. showed appreciable solubility in water solution, together with a marked tendency to aggregate. Aggregation of in the hydrotropic medium resulted in significant fluorescence quenching. Instead, fluorescence quantum yields (ΦF) of 0.14 and 0.08, and singlet oxygen quantum yields (ΦΔ) of 0.63 and 0.24 were obtained for and , respectively, in a DMF solution. In vitro boron neutron capture therapy (BNCT) experiments, employing boron imaging techniques as implemented in qualitative and quantitative neutron autoradiography methods, showed that is capable of increasing the boron concentration of two selected cancerous cell lines, the DHD/K12/TRb of rat colon adenocarcinoma and UMR-106 of rat osteosarcoma, with the large-size Cs(+) counter-ions used to neutralize the negatively charged carborane polyhedra not presenting a significant obstacle to the process. Taken together, BNCT and photophysical measurement results indicated that is potentially suitable for bimodal or multimodal anticancer therapy.

Water-soluble carboranyl-phthalocyanines for BNCT. Synthesis, characterization, and in vitro tests of the Zn(ii)-nido-carboranyl-hexylthiophthalocyanine

ROSA, Angela Maria;PEPE, Antonietta;RICCIARDI, Giampaolo
2015

Abstract

The zinc(ii) complex of the octa-anionic 2,3,9,10,16,17,23,24-octakis-(7-methyl-7,8-dicarba-nido-undeca-boran-8-yl)hexyl-thio-6,13,20,27-phthalocyanine (nido-[ZnMCHESPc]Cs8, ) has been obtained in the form of caesium salt through mild deboronation of the neutral precursor, the closo-[ZnMCHESPc] complex, , with CsF. has been synthesized, in turn, by heating a finely ground mixture of the appropriate phthalonitrile and zinc(ii) acetate at 180.0 °C. The complexes have been characterized by elemental analyses, FT-IR, UV-visible absorption and fluorescence emission spectroscopy, and their structures were assessed by (1)H, (13)C, (11)B, and two-dimensional homo- and hetero-correlated NMR spectroscopy experiments. showed appreciable solubility in water solution, together with a marked tendency to aggregate. Aggregation of in the hydrotropic medium resulted in significant fluorescence quenching. Instead, fluorescence quantum yields (ΦF) of 0.14 and 0.08, and singlet oxygen quantum yields (ΦΔ) of 0.63 and 0.24 were obtained for and , respectively, in a DMF solution. In vitro boron neutron capture therapy (BNCT) experiments, employing boron imaging techniques as implemented in qualitative and quantitative neutron autoradiography methods, showed that is capable of increasing the boron concentration of two selected cancerous cell lines, the DHD/K12/TRb of rat colon adenocarcinoma and UMR-106 of rat osteosarcoma, with the large-size Cs(+) counter-ions used to neutralize the negatively charged carborane polyhedra not presenting a significant obstacle to the process. Taken together, BNCT and photophysical measurement results indicated that is potentially suitable for bimodal or multimodal anticancer therapy.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11563/111150
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