Disassembly of Chromophore-Guided DNA Duplexes through Site-Selective Binding of Coralyne to Pyrene-Modified Adenine Bases

Ki Tae Kim; Tae Su Choi; Ka Young Kim; Hugh I. Kim; Byeang Hyean Kim

doi:10.1002/cplu.201600230

Disassembly of Chromophore-Guided DNA Duplexes through Site-Selective Binding of Coralyne to Pyrene-Modified Adenine Bases

Ki Tae Kim, Tae Su Choi, Ka Young Kim, Hugh I. Kim, Byeang Hyean Kim

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

2 Citations (Scopus)

Abstract

Under ambient conditions the disassembly of self-duplexes of ^PyA-modified oligodeoxyadenylates (i.e., chromophore-guided DNA assemblies) through intercalative binding of coralyne units to pyrene-modified adenine (^PyA) bases was carried out. The coralyne units, intercalated site-selectively on the 3′ sides of the ^PyA units, are stabilized through π–π stacking interactions. This competitive intercalation destabilizes the stacking interactions of pairs of ^PyA units, resulting in dissociation of the self-duplexes. This behavior, which is opposite to that of coralyne-induced self-duplex formation of natural oligodeoxyadenylates, was exploited to prepare new types of DNA modules that can be switched between two different duplex states.

Original language	English
Pages (from-to)	590-593
Number of pages	4
Journal	ChemPlusChem
Volume	81
Issue number	7
DOIs	https://doi.org/10.1002/cplu.201600230
Publication status	Published - 2016 Jul 1

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

DNA disassembly
coralyne
intercalations
molecular devices
polydeoxyadenylates

ASJC Scopus subject areas

General Chemistry

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10.1002/cplu.201600230

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title = "Disassembly of Chromophore-Guided DNA Duplexes through Site-Selective Binding of Coralyne to Pyrene-Modified Adenine Bases",

abstract = "Under ambient conditions the disassembly of self-duplexes of PyA-modified oligodeoxyadenylates (i.e., chromophore-guided DNA assemblies) through intercalative binding of coralyne units to pyrene-modified adenine (PyA) bases was carried out. The coralyne units, intercalated site-selectively on the 3′ sides of the PyA units, are stabilized through π–π stacking interactions. This competitive intercalation destabilizes the stacking interactions of pairs of PyA units, resulting in dissociation of the self-duplexes. This behavior, which is opposite to that of coralyne-induced self-duplex formation of natural oligodeoxyadenylates, was exploited to prepare new types of DNA modules that can be switched between two different duplex states.",

keywords = "DNA disassembly, coralyne, intercalations, molecular devices, polydeoxyadenylates",

author = "Kim, {Ki Tae} and Choi, {Tae Su} and Kim, {Ka Young} and Kim, {Hugh I.} and Kim, {Byeang Hyean}",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/cplu.201600230",

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AU - Kim, Ki Tae

AU - Choi, Tae Su

AU - Kim, Ka Young

AU - Kim, Hugh I.

AU - Kim, Byeang Hyean

PY - 2016/7/1

Y1 - 2016/7/1

N2 - Under ambient conditions the disassembly of self-duplexes of PyA-modified oligodeoxyadenylates (i.e., chromophore-guided DNA assemblies) through intercalative binding of coralyne units to pyrene-modified adenine (PyA) bases was carried out. The coralyne units, intercalated site-selectively on the 3′ sides of the PyA units, are stabilized through π–π stacking interactions. This competitive intercalation destabilizes the stacking interactions of pairs of PyA units, resulting in dissociation of the self-duplexes. This behavior, which is opposite to that of coralyne-induced self-duplex formation of natural oligodeoxyadenylates, was exploited to prepare new types of DNA modules that can be switched between two different duplex states.

AB - Under ambient conditions the disassembly of self-duplexes of PyA-modified oligodeoxyadenylates (i.e., chromophore-guided DNA assemblies) through intercalative binding of coralyne units to pyrene-modified adenine (PyA) bases was carried out. The coralyne units, intercalated site-selectively on the 3′ sides of the PyA units, are stabilized through π–π stacking interactions. This competitive intercalation destabilizes the stacking interactions of pairs of PyA units, resulting in dissociation of the self-duplexes. This behavior, which is opposite to that of coralyne-induced self-duplex formation of natural oligodeoxyadenylates, was exploited to prepare new types of DNA modules that can be switched between two different duplex states.

KW - DNA disassembly

KW - coralyne

KW - intercalations

KW - molecular devices

KW - polydeoxyadenylates

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Disassembly of Chromophore-Guided DNA Duplexes through Site-Selective Binding of Coralyne to Pyrene-Modified Adenine Bases

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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