4-Amino-1,8-naphthalimide-based Tröger's bases as high affinity DNA targeting fluorescent supramolecular scaffolds

Org Lett. 2009 Sep 17;11(18):4040-3. doi: 10.1021/ol9013602.

Abstract

The synthesis and photophysical and biological investigation of fluorescent 1,8-naphthalimide conjugated Troger's bases 1-3 are described. These structures bind strongly to DNA in competitive media at pH 7.4, with concomitant modulation in their fluorescence emission. These structures also undergo rapid cellular uptake, being localized within the nucleus within a few hours, and are cytotoxic against HL60 and (chronic myeloid leukemia) K562 cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Naphthylamine / analogs & derivatives*
  • 1-Naphthylamine / chemistry
  • DNA / metabolism*
  • Fluorescent Dyes
  • HL-60 Cells
  • Humans
  • K562 Cells
  • Naphthalimides / chemistry*
  • Quinolones / chemistry*
  • Stereoisomerism*

Substances

  • Fluorescent Dyes
  • Naphthalimides
  • Quinolones
  • 4-amino-1,8-naphthalimide
  • DNA
  • 1-Naphthylamine