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Boron‐Containing Protoporphyrin IX Derivatives and Their Modification for Boron Neutron Capture Therapy: Synthesis, Characterization, and Comparative In Vitro Toxicity Evaluation
Author(s) -
ElZaria Mohamed E.,
Ban Hyun Seung,
Nakamura Hiroyuki
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901532
Subject(s) - protoporphyrin ix , chemistry , porphyrin , photodynamic therapy , protoporphyrin , hela , borane , boron , nuclear chemistry , in vitro , photochemistry , organic chemistry , biochemistry , catalysis
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(α‐methyl‐β‐pentylethylether)protoporphyrin IX, and bis(α‐methyl‐β‐dodecanylethylether)protoporphyrin IX} bearing polyhedral borane anions (B 12 H 11 SH 2− , B 12 H 11 NH 3 − , or B 12 H 11 OH 2− ) 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, B 12 H 11 NH 2 2− ‐conjugated porphyrin induced a significant increase in the level of boron accumulation and PDT efficacy against HeLa cells.