4-Amino-1,8-naphthalimide-based Tröger's bases as high affinity DNA targeting fluorescent supramolecular scaffolds.
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.
Veale
Emma B
EB
School of Chemistry, Center for Synthesis and Chemical Biology, Trinity College Dublin, Dublin 2, Ireland. eveale@tcd.ie
Frimannsson
Daniel O
DO
Lawler
Mark
M
Gunnlaugsson
Thorfinnur
T
D015057:1-Naphthylamine / Q000031:analogs & derivatives* / Q000737:chemistry; D004247:DNA / Q000378:metabolism*; D005456:Fluorescent Dyes; D018922:HL-60 Cells; D006801:Humans; D020014:K562 Cells; D053644:Naphthalimides / Q000737:chemistry*; D015363:Quinolones / Q000737:chemistry*; D013237:Stereoisomerism
D005456:Fluorescent Dyes; D053644:Naphthalimides; D015363:Quinolones; C086538:4-amino-1,8-naphthalimide; D004247:DNA; D015057:1-Naphthylamine