Synthesis, characterization, and cellular uptake of DNA-binding rose bengal peptidoconjugates.
Peptide conjugates of the xanthene dye rose bengal (RB) are described featuring sequences that promote DNA binding. The complexation of these conjugates with DNA causes efficient quenching of the fluorophore singlet state and suppresses singlet oxygen production. When incubated with human cells, the RB conjugates pass through the cell membrane but are not visualized in the nucleus. This behavior is in stark contrast to that exhibited by structurally analogous conjugates containing the unhalogenated xanthene dye fluorescein. These results highlight the marked sensitivity of cell permeability characteristics to subtle structural differences.
Carreon
Jay R
JR
Eugene F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Roberts
Marcel A
MA
Wittenhagen
Lisa M
LM
Kelley
Shana O
SO
D000595:Amino Acid Sequence; D004247:DNA / Q000378:metabolism*; D015696:Gene Products, tat / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D012395:Rose Bengal / Q000737:chemistry*; D013057:Spectrum Analysis
D015696:Gene Products, tat; D010455:Peptides; D012395:Rose Bengal; D004247:DNA