Synthesis, characterization, and cellular uptake of DNA-binding rose bengal peptidoconjugates

Jay R. Carreon; Marcel A. Roberts; Lisa M. Wittenhagen; Shana O. Kelley

doi:10.1021/ol047762+

Synthesis, characterization, and cellular uptake of DNA-binding rose bengal peptidoconjugates

Jay R. Carreon, Marcel A. Roberts, Lisa M. Wittenhagen, Shana O. Kelley^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original language	English (US)
Pages (from-to)	99-102
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	1
DOIs	https://doi.org/10.1021/ol047762+
State	Published - Jan 6 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol047762+

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abstract = "(Chemical Equation Presented) 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.",

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AU - Carreon, Jay R.

AU - Roberts, Marcel A.

AU - Wittenhagen, Lisa M.

AU - Kelley, Shana O.

PY - 2005/1/6

Y1 - 2005/1/6

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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.

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Synthesis, characterization, and cellular uptake of DNA-binding rose bengal peptidoconjugates

Abstract

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