title: Unique behavior of 2,6-bis(bromomethyl)naphthalene as a highly active organic DNA crosslinking molecule.
abstract: Among 14 bis-halomethylated naphthalenes and quinolines, 2,6-bis(bromomethyl)naphthalene was found to have highly active crosslinking activity on DNA. The unique behavior of high microbial mutagenicity, even though it had a low propensity to form double-strands in linearized plasmid DNA, suggested that it would offer a new seed, capable of forming intrastrand crosslinks similar to cisplatin. The electron withdrawal extent of the halogen atoms, the substitution patterns of two halomethyl groups, and the introduction of a nitrogen atom into the aromatic nucleus had remarkable effects on the activity of the molecule.
authors.affiliation: Kyoritsu University of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan. higashi-ts@pha.keio.ac.jp
authors.forename: Toshinori
authors.initials: T
authors.lastname: Higashi
authors.forename: Koichi
authors.initials: K
authors.lastname: Uemura
authors.forename: Keiko
authors.initials: K
authors.lastname: Inami
authors.forename: Masataka
authors.initials: M
authors.lastname: Mochizuki
mesh_terms: D003432:Cross-Linking Reagents / Q000737:chemistry* / Q000378:metabolism; D004247:DNA / Q000032:analysis*; D009281:Naphthalenes / Q000737:chemistry* / Q000378:metabolism
chemical_list: C541659:2,6-bis(bromomethyl)naphthalene; D003432:Cross-Linking Reagents; D009281:Naphthalenes; D004247:DNA