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Newly characterized interaction stabilizes DNA structure: oligoethylene glycols stabilize G-quadruplexes CH–π interactions

Oligoethylene glycols are used as crowding agents in experiments that aim to understand the effects of intracellular environments on DNAs. Moreover, DNAs with covalently attached oligoethylene glycols are used as cargo carriers for drug delivery systems. To investigate how oligoethylene glycols inte...

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Autores principales: Tateishi-Karimata, Hisae, Ohyama, Tatsuya, Muraoka, Takahiro, Podbevsek, Peter, Wawro, Adam M., Tanaka, Shigenori, Nakano, Shu-ichi, Kinbara, Kazushi, Plavec, Janez, Sugimoto, Naoki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Oxford University Press 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5499538/
https://www.ncbi.nlm.nih.gov/pubmed/28453855
http://dx.doi.org/10.1093/nar/gkx299
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author Tateishi-Karimata, Hisae
Ohyama, Tatsuya
Muraoka, Takahiro
Podbevsek, Peter
Wawro, Adam M.
Tanaka, Shigenori
Nakano, Shu-ichi
Kinbara, Kazushi
Plavec, Janez
Sugimoto, Naoki
author_facet Tateishi-Karimata, Hisae
Ohyama, Tatsuya
Muraoka, Takahiro
Podbevsek, Peter
Wawro, Adam M.
Tanaka, Shigenori
Nakano, Shu-ichi
Kinbara, Kazushi
Plavec, Janez
Sugimoto, Naoki
author_sort Tateishi-Karimata, Hisae
collection PubMed
description Oligoethylene glycols are used as crowding agents in experiments that aim to understand the effects of intracellular environments on DNAs. Moreover, DNAs with covalently attached oligoethylene glycols are used as cargo carriers for drug delivery systems. To investigate how oligoethylene glycols interact with DNAs, we incorporated deoxythymidine modified with oligoethylene glycols of different lengths, such as tetraethylene glycol (TEG), into DNAs that form antiparallel G-quadruplex or hairpin structures such that the modified residues were incorporated into loop regions. Thermodynamic analysis showed that because of enthalpic differences, the modified G-quadruplexes were stable and the hairpin structures were slightly unstable relative to unmodified DNA. The stability of G-quadruplexes increased with increasing length of the ethylene oxides and the number of deoxythymidines modified with ethylene glycols in the G-quadruplex. Nuclear magnetic resonance analyses and molecular dynamics calculations suggest that TEG interacts with bases in the G-quartet and loop via CH–π and lone pair–π interactions, although it was previously assumed that oligoethylene glycols do not directly interact with DNAs. The results suggest that numerous cellular co-solutes likely affect DNA function through these CH–π and lone pair–π interactions.
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spelling pubmed-54995382017-07-10 Newly characterized interaction stabilizes DNA structure: oligoethylene glycols stabilize G-quadruplexes CH–π interactions Tateishi-Karimata, Hisae Ohyama, Tatsuya Muraoka, Takahiro Podbevsek, Peter Wawro, Adam M. Tanaka, Shigenori Nakano, Shu-ichi Kinbara, Kazushi Plavec, Janez Sugimoto, Naoki Nucleic Acids Res Chemical Biology and Nucleic Acid Chemistry Oligoethylene glycols are used as crowding agents in experiments that aim to understand the effects of intracellular environments on DNAs. Moreover, DNAs with covalently attached oligoethylene glycols are used as cargo carriers for drug delivery systems. To investigate how oligoethylene glycols interact with DNAs, we incorporated deoxythymidine modified with oligoethylene glycols of different lengths, such as tetraethylene glycol (TEG), into DNAs that form antiparallel G-quadruplex or hairpin structures such that the modified residues were incorporated into loop regions. Thermodynamic analysis showed that because of enthalpic differences, the modified G-quadruplexes were stable and the hairpin structures were slightly unstable relative to unmodified DNA. The stability of G-quadruplexes increased with increasing length of the ethylene oxides and the number of deoxythymidines modified with ethylene glycols in the G-quadruplex. Nuclear magnetic resonance analyses and molecular dynamics calculations suggest that TEG interacts with bases in the G-quartet and loop via CH–π and lone pair–π interactions, although it was previously assumed that oligoethylene glycols do not directly interact with DNAs. The results suggest that numerous cellular co-solutes likely affect DNA function through these CH–π and lone pair–π interactions. Oxford University Press 2017-07-07 2017-04-27 /pmc/articles/PMC5499538/ /pubmed/28453855 http://dx.doi.org/10.1093/nar/gkx299 Text en © The Author(s) 2017. Published by Oxford University Press on behalf of Nucleic Acids Research. http://creativecommons.org/licenses/by-nc/4.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by-nc/4.0/), which permits non-commercial re-use, distribution, and reproduction in any medium, provided the original work is properly cited. For commercial re-use, please contact journals.permissions@oup.com
spellingShingle Chemical Biology and Nucleic Acid Chemistry
Tateishi-Karimata, Hisae
Ohyama, Tatsuya
Muraoka, Takahiro
Podbevsek, Peter
Wawro, Adam M.
Tanaka, Shigenori
Nakano, Shu-ichi
Kinbara, Kazushi
Plavec, Janez
Sugimoto, Naoki
Newly characterized interaction stabilizes DNA structure: oligoethylene glycols stabilize G-quadruplexes CH–π interactions
title Newly characterized interaction stabilizes DNA structure: oligoethylene glycols stabilize G-quadruplexes CH–π interactions
title_full Newly characterized interaction stabilizes DNA structure: oligoethylene glycols stabilize G-quadruplexes CH–π interactions
title_fullStr Newly characterized interaction stabilizes DNA structure: oligoethylene glycols stabilize G-quadruplexes CH–π interactions
title_full_unstemmed Newly characterized interaction stabilizes DNA structure: oligoethylene glycols stabilize G-quadruplexes CH–π interactions
title_short Newly characterized interaction stabilizes DNA structure: oligoethylene glycols stabilize G-quadruplexes CH–π interactions
title_sort newly characterized interaction stabilizes dna structure: oligoethylene glycols stabilize g-quadruplexes ch–π interactions
topic Chemical Biology and Nucleic Acid Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5499538/
https://www.ncbi.nlm.nih.gov/pubmed/28453855
http://dx.doi.org/10.1093/nar/gkx299
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