title: Synthesis, characterization, and cellular uptake of DNA-binding rose bengal peptidoconjugates.
abstract: 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.
authors.affiliation: Eugene F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors.forename: Jay R
authors.initials: JR
authors.lastname: Carreon
authors.forename: Marcel A
authors.initials: MA
authors.lastname: Roberts
authors.forename: Lisa M
authors.initials: LM
authors.lastname: Wittenhagen
authors.forename: Shana O
authors.initials: SO
authors.lastname: Kelley
mesh_terms: 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
chemical_list: D015696:Gene Products, tat; D010455:Peptides; D012395:Rose Bengal; D004247:DNA