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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Oxford University Press
2017
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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. |
format | Online Article Text |
id | pubmed-5499538 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Oxford University Press |
record_format | MEDLINE/PubMed |
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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