Synthesis, dark toxicity and induction of in vitro DNA photodamage by a tetra(4-nido-carboranylphenyl)porphyrin

M. G.H. Vicente, D. J. Nurco, S. J. Shetty, J. Osterloh, E. Ventre, V. Hegde, W. A. Deutsch

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49 Scopus citations


The total synthesis of tetra(4-carboranylphenyl)porphyrins 4 and 6 and their zinc(II) complexes 5 and 7 are described. These compounds were characterized by analytical and spectroscopic methods and, in the case of 5, by X-ray crystallography. The water-soluble nido-carboranylporphyrins 6 and 7 were found to have low dark toxicity towards V79 hamster lung fibroblast cells, using a clonogenic assay (50% colony survival, CS50>300 μM). Upon light activation nido-carboranylporphyrin 6 effectively induced DNA damage in vitro. Two different methods were used to assess the extent of DNA damage: the super-coiled to nicked DNA and the alkaline Comet assay using human leukemia K562 cells. Significant PDT-induced DNA damage was observed for porphyrin 6 using both assays, compared to light-only and porphyrin-only experiments. It is concluded that this type of nido-carboranylporphyrin is a promising sensitizer for both the boron neutron capture therapy and the photodynamic therapy of tumors.

Original languageEnglish
Pages (from-to)123-132
Number of pages10
JournalJournal of Photochemistry and Photobiology B: Biology
Issue number2-3
StatePublished - Nov 2002


  • BNCT
  • Carboranylporphyrin
  • DNA photodamage
  • Dark cytotoxicity
  • PDT


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