Jump to main content
Jump to site search

Issue 21, 2017
Previous Article Next Article

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

Author affiliations

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 (Ka = 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 linking the naphthalene chromophores may occupy the major groove of DNA.

Graphical abstract: Dimeric and trimeric derivatives of the azinomycin B chromophore show enhanced DNA binding

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Apr 2017, accepted on 09 May 2017 and first published on 09 May 2017


Article type: Communication
DOI: 10.1039/C7OB00944E
Citation: Org. Biomol. Chem., 2017,15, 4522-4526
  •   Request permissions

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

    M. Balazy, A. Fausto, C. Voskanian, B. Chavez, H. Panesar and T. G. Minehan, Org. Biomol. Chem., 2017, 15, 4522
    DOI: 10.1039/C7OB00944E

Search articles by author

Spotlight

Advertisements