Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 5, Pages 1543-1552Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901532
Keywords
BNCT; boron; cluster compounds; photodynamic therapy; porphyrinoids
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Funding
- Ministry of Education. Science and Culture, Japan [20390379]
- Ministry of Health, Labour and Welfare [20100201]
- Japan Society for the Promotion of Science [P 08363]
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A novel series of boronated porphyrins for potential use in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) for tumor suppression is described. Protoporphyrin IX {i.e., bis(alpha-methyl-beta-pentylethylether)protoporphyrin IX, and bis(alpha-methyl-beta-dodecanylethylether)-protoporphyrin IX} bearing polyhedral borane anions (B12H11SH2-,B12H11NH3-, or B12H11OH2-) were synthesized with reasonable yields. Modification of the protoporphyrin IX structure was achieved by variation of the lengths of the alkyl chains (pentyl and dodecanyl) attached through ether linkages to the former vinyl groups. The goal of this modification was to develop boronated porphyrins with chemical and physical properties that differed from those of protoporphyrin IX. Performance of an MTT assay with each derivative revealed that the synthesized boronated porphyrins showed low cytotoxicities in a variety of cancer cells. Of these compounds, B12H11NH22--conjugated porphyrin induced a significant increase in the level of boron accumulation and PDT efficacy against HeLa cells.
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