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

Daniela Pietrangeli, Angela Rosa, Antonietta Pepe, Saverio Altieri, Silva Bortolussi, Ian Postuma, Nicoletta Protti, Cinzia Ferrari, Laura Cansolino, Anna Maria Clerici, Elisa Viola, Maria Pia Donzello, Giampaolo Ricciardi

Research output: Contribution to journalArticle

15 Citations (Scopus)

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, 7) has been obtained in the form of caesium salt through mild deboronation of the neutral precursor, the closo-[ZnMCHESPc] complex, 6, with CsF. 6 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 1H, 13C, 11B, and two-dimensional homo- and hetero-correlated NMR spectroscopy experiments. 7 showed appreciable solubility in water solution, together with a marked tendency to aggregate. Aggregation of 7 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 6 and 7, 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 7 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 7 is potentially suitable for bimodal or multimodal anticancer therapy.

Original languageEnglish
Pages (from-to)11021-11028
Number of pages8
JournalDalton Transactions
Volume44
Issue number24
DOIs
Publication statusPublished - Jun 28 2015

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Boron
Neutrons
Water
Quantum yield
Zinc
Rats
Fluorescence
Singlet Oxygen
Cesium
Radiation counters
Fluorescence spectroscopy
Emission spectroscopy
Nuclear magnetic resonance spectroscopy
Quenching
Acetates
Agglomeration
Solubility
Salts
Experiments
Cells

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Water-soluble carboranyl-phthalocyanines for BNCT. Synthesis, characterization, and in vitro tests of the Zn(ii)-nido-carboranyl-hexylthiophthalocyanine. / Pietrangeli, Daniela; Rosa, Angela; Pepe, Antonietta; Altieri, Saverio; Bortolussi, Silva; Postuma, Ian; Protti, Nicoletta; Ferrari, Cinzia; Cansolino, Laura; Clerici, Anna Maria; Viola, Elisa; Donzello, Maria Pia; Ricciardi, Giampaolo.

In: Dalton Transactions, Vol. 44, No. 24, 28.06.2015, p. 11021-11028.

Research output: Contribution to journalArticle

Pietrangeli, D, Rosa, A, Pepe, A, Altieri, S, Bortolussi, S, Postuma, I, Protti, N, Ferrari, C, Cansolino, L, Clerici, AM, Viola, E, Donzello, MP & Ricciardi, G 2015, 'Water-soluble carboranyl-phthalocyanines for BNCT. Synthesis, characterization, and in vitro tests of the Zn(ii)-nido-carboranyl-hexylthiophthalocyanine', Dalton Transactions, vol. 44, no. 24, pp. 11021-11028. https://doi.org/10.1039/c5dt00394f
Pietrangeli, Daniela ; Rosa, Angela ; Pepe, Antonietta ; Altieri, Saverio ; Bortolussi, Silva ; Postuma, Ian ; Protti, Nicoletta ; Ferrari, Cinzia ; Cansolino, Laura ; Clerici, Anna Maria ; Viola, Elisa ; Donzello, Maria Pia ; Ricciardi, Giampaolo. / Water-soluble carboranyl-phthalocyanines for BNCT. Synthesis, characterization, and in vitro tests of the Zn(ii)-nido-carboranyl-hexylthiophthalocyanine. In: Dalton Transactions. 2015 ; Vol. 44, No. 24. pp. 11021-11028.
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AU - Bortolussi, Silva

AU - Postuma, Ian

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