Synthesis and cellular studies of a carboranylchlorin for the PDT and BNCT of tumors

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The syntheses of closo- and nido-carboranylchlorins 4 and 5 from a known carboranylporphyrin are described. Water-soluble nido-carboranylporphyrin 5 was found to have very low dark cytotoxicity (IC50 > 500 μM using a MTT-based assay) but to be toxic in the presence of red light (IC50 = 80 μM at 0.55 J/cm2 light dose). Under the same experimental conditions, carboranylchlorin 5 was taken up by human glioma T98G cells to a significantly higher extent than chlorin e6, a chlorophyll degradation product. The preferred sites of subcellular localization of carboranylchlorin 5 were found to be the cell lysosomes. Our results suggest that carboranylchlorin 5 is a promising new dual sensitizer for the PDT and BNCT treatment of tumors. © 2006 Elsevier Ltd. All rights reserved.

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Bioorganic and Medicinal Chemistry

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