A perylenedicarboxamide linker for DNA hairpins

Frederick D. Lewis, Ligang Zhang, Richard F. Kelley, David McCamant, Michael R. Wasielewski

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The synthesis and properties of a perylenediamide diol linker and several DNA hairpins possessing this linker are described. The diol linker absorbs and fluoresces strongly in the visible. Hairpins having poly(dA)-poly(dT) stems have fluorescence quantum yields and decay times similar to those of the linker, indicating that hole injection does not occur from the singlet excited linker into the base pair domain. Fluorescence quenching by dG or dZ bases is observed when these bases are located near the linker. The strong distance dependence of fluorescence quenching is consistent with a superexchange mechanism for electron transfer. Failure to observe formation of the linker anion radical by means of femtosecond time resolved absorption spectroscopy is attributed to fast charge recombination. The properties and behavior of the perylene linker and its hairpins are compared to those of other arenedicarboxamide linkers.

Original languageEnglish
Pages (from-to)3457-3464
Number of pages8
JournalTetrahedron
Volume63
Issue number17
DOIs
Publication statusPublished - Apr 23 2007

Keywords

  • Arenedicarboxamide
  • Circular dichroism
  • Electron transfer
  • Fluorescence quenching
  • Hole injection

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Lewis, F. D., Zhang, L., Kelley, R. F., McCamant, D., & Wasielewski, M. R. (2007). A perylenedicarboxamide linker for DNA hairpins. Tetrahedron, 63(17), 3457-3464. https://doi.org/10.1016/j.tet.2006.10.089