Dimeric and trimeric derivatives of the azinomycin B chromophore show enhanced DNA binding.

ABSTRACT: To explore the utility of the azinomycin B chromophore as a platform for the development of major-groove binding small molecules, we have prepared a series of 3-methoxy-5-methylnaphthalene derivatives containing diamine, triamine, and carbohydrate linker moieties. All bis- and tris-azinomycin derivatives are intercalators that display submicromolar binding affinities for calf-thymus DNA, as revealed by viscometry measurements and fluorescent intercalator displacement (FID) assays, respectively. Although the tightest binding ligand 1d (K_a = 2.42 × 10⁷ M^-1) has similar affinities for sequence diverse polynucleotides, competition binding studies with methylated phage DNA and known major and minor groove binding small molecules suggest that the tether moiety li

SUBMITTER: Balazy M 

PROVIDER: S-EPMC5513485 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature