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

Emma B Veale, Daniel O Frimannsson, Mark Lawler, Thorfinnur Gunnlaugsson, Mark Lawler

Research output: Contribution to journalArticlepeer-review

108 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4040-3
Number of pages4
JournalOrganic Letters
Volume11
Issue number18
DOIs
Publication statusPublished - 17 Sep 2009

Keywords

  • 1-Naphthylamine
  • DNA
  • Fluorescent Dyes
  • HL-60 Cells
  • Humans
  • K562 Cells
  • Naphthalimides
  • Quinolones
  • Stereoisomerism

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