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Study on the recognition of G-quadruplexes by two stereoisomers of alkaloids

Analytical and Bioanalytical Chemistry volume 411, pages 5555–5561 (2019)Cite this article

Abstract

G-quadruplexes have been widely researched as new targets for cancer treatment owing to their non-canonical structure and crucial role in biological processes. Although attention has been paid to the development of selective G-quadruplex ligands, few studies have focused on the binding affinity of stereoisomers towards G-quadruplex, which will be conducive to support the optimal design of G-quadruplex ligands in future studies. Here, tetrandrine and isotetrandrine were used to study the binding affinity and difference of stereoisomers towards G-quadruplex structures. The results showed that tetrandrine had a high possibility of binding to the N-myc and Bcl-2 G-quadruplexes through hydrogen bonding, whereas the possibility of binding of isotetrandrine was low and it seemed to have no possibility of forming hydrogen bonds. Our study shows that optical isomerism of ligand molecules has an important effect on G-quadruplex recognition, which is helpful for the design of G-quadruplex ligands in future studies.

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Acknowledgements

This project was supported by Chinese Academy of Medical Sciences (CAMS) Initiative for Innovative Medicine (CAMS-I2M) 2017-I2M-1-001.

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  1. Central Research Laboratory, Peking Union Medical College Hospital, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100730, China

    Fangyuan Li, Dan Guo & Lin Kang

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  1. Fangyuan Li
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  2. Dan Guo
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Correspondence to Fangyuan Li.

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Li, F., Guo, D. & Kang, L. Study on the recognition of G-quadruplexes by two stereoisomers of alkaloids. Anal Bioanal Chem 411, 5555–5561 (2019). https://doi.org/10.1007/s00216-019-01937-5

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  • DOI: https://doi.org/10.1007/s00216-019-01937-5

Keywords

  • G-quadruplex
  • Stereoisomers
  • Recognition
  • Tetrandrine
  • Isotetrandrine