Unique behavior of 2,6-bis(bromomethyl)naphthalene as a highly active organic DNA crosslinking molecule.
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.
Higashi
Toshinori
T
Kyoritsu University of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan. higashi-ts@pha.keio.ac.jp
Uemura
Koichi
K
Inami
Keiko
K
Mochizuki
Masataka
M
D003432:Cross-Linking Reagents / Q000737:chemistry* / Q000378:metabolism; D004247:DNA / Q000032:analysis*; D009281:Naphthalenes / Q000737:chemistry* / Q000378:metabolism
C541659:2,6-bis(bromomethyl)naphthalene; D003432:Cross-Linking Reagents; D009281:Naphthalenes; D004247:DNA