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Mirror-image dependence : targeting enantiomeric G-quadruplex DNA using triplex metallohelices
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Zhao, Chuanqi, Song, Hualong, Scott, Peter, Zhao, Andong, Tateishi-Karimata, Hisae, Sugimoto, Naoki, Ren, Jinsong and Qu, Xiaogang (2018) Mirror-image dependence : targeting enantiomeric G-quadruplex DNA using triplex metallohelices. Angewandte Chemie International Edition, 57 (48). pp. 15723-15727. doi:10.1002/anie.201809207 ISSN 1433-7851.
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Official URL: http://dx.doi.org/10.1002/anie.201809207
Abstract
Natural d‐DNA and l‐DNA are mirror‐image counterparts. However, because of the inherent flexibility and conformation diversity of DNA, it is still not clear how enantiomeric compounds recognize d‐DNA and l‐DNA. Herein, taking G‐quadruplex (G4) DNA as an example that has diverse conformations and distinct biofunctions, the binding of ten pairs of iron triplex metallohelices to d‐ and l‐G4 DNA were evaluated. The Δ‐enantiomer binds to d‐DNA and the Λ‐enantiomer binds to l‐DNA, exhibiting almost the same stabilization effect and binding affinity. The binding affinity of the Δ‐metallohelix with d‐G4 is nearly 70‐fold higher than that of Λ‐metallohelix binding d‐G4. Δ‐Metallohelix binding to d‐G4 follows a two‐step binding process driven by a favorable enthalpy contribution to compensate for the associated unfavorable entropy.
Item Type: | Journal Article | ||||||||||||||||||||||||
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Subjects: | R Medicine > RS Pharmacy and materia medica | ||||||||||||||||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||||||||||||||||
Library of Congress Subject Headings (LCSH): | Chiral drugs, DNA, Quadruplex nucleic acids | ||||||||||||||||||||||||
Journal or Publication Title: | Angewandte Chemie International Edition | ||||||||||||||||||||||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | ||||||||||||||||||||||||
ISSN: | 1433-7851 | ||||||||||||||||||||||||
Official Date: | 26 November 2018 | ||||||||||||||||||||||||
Dates: |
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Volume: | 57 | ||||||||||||||||||||||||
Number: | 48 | ||||||||||||||||||||||||
Page Range: | pp. 15723-15727 | ||||||||||||||||||||||||
DOI: | 10.1002/anie.201809207 | ||||||||||||||||||||||||
Status: | Peer Reviewed | ||||||||||||||||||||||||
Publication Status: | Published | ||||||||||||||||||||||||
Reuse Statement (publisher, data, author rights): | This is the peer reviewed version of the following article: Zhao, C. , Song, H. , Scott, P. , Zhao, A. , Tateishi‐Karimata, H. , Sugimoto, N. , Ren, J. and Qu, X. (2018), Mirror‐Image Dependence: Targeting Enantiomeric G‐Quadruplex DNA Using Triplex Metallohelices. Angew. Chem. Int. Ed.. . doi:10.1002/anie.201809207, which has been published in final form at https://doi.org/10.1002/anie.201809207. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. | ||||||||||||||||||||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||||||||||||||||||||
Date of first compliant deposit: | 5 November 2018 | ||||||||||||||||||||||||
Date of first compliant Open Access: | 11 October 2019 | ||||||||||||||||||||||||
RIOXX Funder/Project Grant: |
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