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Issue 28, 2014
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Synthesis, characterization and biological evaluation of carboranylmethylbenzo[b]acridones as novel agents for boron neutron capture therapy

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Abstract

Herein we present the synthesis and characterization of benzo[b]acridin-12(7H)-ones bearing carboranyl moieties and test their biological effectiveness as boron neutron capture therapy (BNCT) agents in cancer treatment. The cellular uptake of these novel compounds into the U87 human glioblastoma cells was evaluated by boron analysis (ICP-MS) and by fluorescence imaging (confocal microscopy). The compounds enter the U87 cells exhibiting a similar profile, i.e., preferential accumulation in the cytoskeleton and membranes and a low cytotoxic activity (IC50 values higher than 200 μM). The cytotoxic activity and cellular morphological alterations after neutron irradiation in the Portuguese Research Reactor (6.6 × 107 neutrons cm−2 s−1, 1 MW) were evaluated by the MTT assay and by electron microscopy (TEM). Post-neutron irradiation revealed that BNCT has a higher cytotoxic effect on the cells. Accumulation of membranous whorls in the cytoplasm of cells treated with one of the compounds correlates well with the cytotoxic effect induced by radiation. Results provide a strong rationale for considering one of these compounds as a lead candidate for a new generation of BNCT agents.

Graphical abstract: Synthesis, characterization and biological evaluation of carboranylmethylbenzo[b]acridones as novel agents for boron neutron capture therapy

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Publication details

The article was received on 26 Mar 2014, accepted on 21 May 2014 and first published on 21 May 2014


Article type: Paper
DOI: 10.1039/C4OB00644E
Citation: Org. Biomol. Chem., 2014,12, 5201-5211
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    Synthesis, characterization and biological evaluation of carboranylmethylbenzo[b]acridones as novel agents for boron neutron capture therapy

    A. F. F. da Silva, R. S. G. R. Seixas, A. M. S. Silva, J. Coimbra, A. C. Fernandes, J. P. Santos, A. Matos, J. Rino, I. Santos and F. Marques, Org. Biomol. Chem., 2014, 12, 5201
    DOI: 10.1039/C4OB00644E

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