Synthesis, characterization and biologic effects of polybrominated naphthalenes

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Abstract
Although polybrominated naphthalenes (PBNs) are contaminants of the commercial fire retardant fireMaster BP-6, the individual PBN isomers have not been identified. In order to study PBNs possessing an analogous level of bromination to those found in fireMaster BP-6, three synthetic PBN mixtures, averaging 5.0, 5.3, and 5.6 bromines per naphthalene were synthetized and partially characterized. The PBN mixtures were administered to immature male Wistar rats and found to be potent inducers of cytochrome P-450-dependent monooxygenases. At the lowest dose tested, 30 μmol · kg−1, each PBN mixture caused maximal induction of benzo[a]pyrene hydroxylase activity. On the basis of enzyme activities, ligand-binding spectra and sodium dodecyl sulfate-polyacrylamide gel electrophoresis, the PBN mixtures were determined to be 3-methylcholanthrene-type inducers of cytochrome P-450 (P-448), resembling qualitatively the most toxic polyhalogenated biphenyls, dibenzofurans, and dioxins in this respect. Liver weights were significantly increased and thymus weights diminished by PBN treatment. Light microscopy revealed proliferation of the smooth endoplasmic reticulum in periportal hepatocytes as a consistent change; some rats also had mild fatty changes in centrilobular hepatocytes. Thymuses displayed mild to marked depletion of cortical lymphocytes. The PBN mixtures were much more potent than fireMaster BP-6 in causing these effects; raising the possibility that PBNs are among the minor components of fireMaster BP-6 that contribute significantly to the toxicity of this environmental contaminant.

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