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

Fingerprint

Fluorescence
Quenching
DNA
Perylene
Quantum yield
Absorption spectroscopy
Base Pairing
Genetic Recombination
Anions
Spectrum Analysis
Electrons
polydeoxyadenylic acid-polythymidylic acid

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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

A perylenedicarboxamide linker for DNA hairpins. / Lewis, Frederick D.; Zhang, Ligang; Kelley, Richard F.; McCamant, David; Wasielewski, Michael R.

In: Tetrahedron, Vol. 63, No. 17, 23.04.2007, p. 3457-3464.

Research output: Contribution to journalArticle

Lewis, FD, Zhang, L, Kelley, RF, McCamant, D & Wasielewski, MR 2007, 'A perylenedicarboxamide linker for DNA hairpins', Tetrahedron, vol. 63, no. 17, pp. 3457-3464. https://doi.org/10.1016/j.tet.2006.10.089
Lewis, Frederick D. ; Zhang, Ligang ; Kelley, Richard F. ; McCamant, David ; Wasielewski, Michael R. / A perylenedicarboxamide linker for DNA hairpins. In: Tetrahedron. 2007 ; Vol. 63, No. 17. pp. 3457-3464.
@article{ec7d15bcff0d49d8ac851e636ec70be5,
title = "A perylenedicarboxamide linker for DNA hairpins",
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.",
keywords = "Arenedicarboxamide, Circular dichroism, Electron transfer, Fluorescence quenching, Hole injection",
author = "Lewis, {Frederick D.} and Ligang Zhang and Kelley, {Richard F.} and David McCamant and Wasielewski, {Michael R}",
year = "2007",
month = "4",
day = "23",
doi = "10.1016/j.tet.2006.10.089",
language = "English",
volume = "63",
pages = "3457--3464",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "17",

}

TY - JOUR

T1 - A perylenedicarboxamide linker for DNA hairpins

AU - Lewis, Frederick D.

AU - Zhang, Ligang

AU - Kelley, Richard F.

AU - McCamant, David

AU - Wasielewski, Michael R

PY - 2007/4/23

Y1 - 2007/4/23

N2 - 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.

AB - 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.

KW - Arenedicarboxamide

KW - Circular dichroism

KW - Electron transfer

KW - Fluorescence quenching

KW - Hole injection

UR - http://www.scopus.com/inward/record.url?scp=33947225653&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33947225653&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2006.10.089

DO - 10.1016/j.tet.2006.10.089

M3 - Article

VL - 63

SP - 3457

EP - 3464

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 17

ER -