A perylenedicarboxamide linker for DNA hairpins

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

doi:10.1016/j.tet.2006.10.089

A perylenedicarboxamide linker for DNA hairpins

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

^*Corresponding author for this work

Chemistry

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

28 Scopus citations

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 language	English (US)
Pages (from-to)	3457-3464
Number of pages	8
Journal	Tetrahedron
Volume	63
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2006.10.089
State	Published - Apr 23 2007

Funding

The authors thank Pierre Daublain for kinetic fitting and Michael Fuller for electrochemical measurements. This research is supported by the Division of Chemical Sciences, Office of Basic Energy Sciences, U.S. Department of Energy under Contracts DE-FG02-96ER14604 (F.D.L.) and DE-FG02-99ER14999 (M.R.W.).

Keywords

Arenedicarboxamide
Circular dichroism
Electron transfer
Fluorescence quenching
Hole injection

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.10.089

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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.}",

note = "Funding Information: The authors thank Pierre Daublain for kinetic fitting and Michael Fuller for electrochemical measurements. This research is supported by the Division of Chemical Sciences, Office of Basic Energy Sciences, U.S. Department of Energy under Contracts DE-FG02-96ER14604 (F.D.L.) and DE-FG02-99ER14999 (M.R.W.). ",

year = "2007",

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doi = "10.1016/j.tet.2006.10.089",

language = "English (US)",

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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.

N1 - Funding Information: The authors thank Pierre Daublain for kinetic fitting and Michael Fuller for electrochemical measurements. This research is supported by the Division of Chemical Sciences, Office of Basic Energy Sciences, U.S. Department of Energy under Contracts DE-FG02-96ER14604 (F.D.L.) and DE-FG02-99ER14999 (M.R.W.).

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

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DO - 10.1016/j.tet.2006.10.089

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ER -

A perylenedicarboxamide linker for DNA hairpins

Abstract

Funding

Keywords

ASJC Scopus subject areas

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