Cucurbit[7]uril-Driven Host-Guest Chemistry for Reversible Intervention of 5-Formylcytosine-Targeted Biochemical Reactions

Journal of the American Chemical Society
Shao-Ru WangXiang Zhou

Abstract

5-Formylcytosine (5fC) is identified as one of the key players in active DNA demethylation and also as an epigenetic mark in mammals, thus representing a novel attractive target to chemical intervention. The current study represents an attempt to develop a reversible 5fC-targeted intervention tool. A supramolecular aldehyde reactive probe was therefore introduced for selective conversion of the 5fC to 5fC-AD nucleotide. Using various methods, we demonstrate that cucurbit[7]uril (CB7) selectively targets the 5fC-AD nucleotide in DNA, however, the binding of CB7 to 5fC-AD does not affect the hydrogen bonding properties of natural nucleobases in duplex DNA. Importantly, CB7-driven host-guest chemistry has been applied for reversible intervention of a variety of 5fC-targeted biochemical reactions, including restriction endonuclease digestion, DNA polymerase elongation, and polymerase chain reaction. On the basis of the current study, the macrocyclic CB7 creates obstructions that, through steric hindrance, prevent the enzyme from binding to the substrate, whereas the CB7/5fC-AD host-guest interactions can be reversed by treatment with adamantanamine. Moreover, fragment- and site-specific identification of 5fC modification in DNA has...Continue Reading

References

Nov 7, 1980·Science·A Razin, A D Riggs
Jun 29, 1999·Nature·T J Matray, E T Kool
Nov 28, 2001·The Journal of Organic Chemistry·A DayB Snushall
Jul 30, 2005·Angewandte Chemie·Jason LagonaLyle Isaacs
Nov 10, 2005·Journal of the American Chemical Society·Simin LiuLyle Isaacs
Dec 22, 2005·Journal of the American Chemical Society·Lyle IsaacsKimoon Kim
Sep 14, 2007·Journal of the American Chemical Society·Chikara DohnoKazuhiko Nakatani
Dec 21, 2007·Proceedings of the National Academy of Sciences of the United States of America·Mikhail V RekharskyYoshihisa Inoue
Jan 12, 2008·Chemical Communications : Chem Comm·Douglas D YoungAlexander Deiters
Jun 18, 2009·Chembiochem : a European Journal of Chemical Biology·Douglas D YoungAlexander Deiters
Jun 4, 2011·Accounts of Chemical Research·Ziyang HaoPeng R Chen
Feb 14, 2012·Nature Chemical Biology·Liang ZhangChuan He
Jul 24, 2012·Nature Structural & Molecular Biology·Matthew W KellingerDong Wang
Nov 2, 2012·The Journal of Organic Chemistry·Liangliang ZhuYanli Zhao
Jun 28, 2013·Angewandte Chemie·Kai LiuXi Zhang
Aug 13, 2013·Trends in Biochemical Sciences·Chun-Xiao Song, Chuan He
Jan 3, 2014·Angewandte Chemie·Liping CaoLyle Isaacs
Apr 24, 2014·Nature Chemistry·Michael J BoothShankar Balasubramanian
May 21, 2014·Angewandte Chemie·Hong Hee LeeHugh I Kim
Oct 31, 2014·Journal of the American Chemical Society·Zhichang LiuJ Fraser Stoddart
Dec 10, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Guangtong WangXi Zhang
Jan 27, 2015·Chemistry of Materials : a Publication of the American Chemical Society·Qing-Lan LiYing-Wei Yang
Jan 30, 2015·Angewandte Chemie·Elke PerschFrançois Diederich
Feb 6, 2015·Nature Nanotechnology·Elio Mattia, Sijbren Otto
May 7, 2015·Journal of the American Chemical Society·Robyn E HardistyShankar Balasubramanian
May 13, 2015·Journal of the American Chemical Society·Zhan ZhangJonathan L Sessler
Jun 23, 2015·Nature Chemical Biology·Martin BachmanShankar Balasubramanian

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Citations

Sep 27, 2018·Chemical Communications : Chem Comm·X ZhouJ Jayawickramarajah
Oct 30, 2018·Angewandte Chemie·Natali DubelOliver Seitz
Mar 12, 2019·Chemical Communications : Chem Comm·Ting DuSimin Liu
Nov 19, 2019·Chemical Communications : Chem Comm·Ranjan SasmalSarit S Agasti
Sep 11, 2020·Chemistry : a European Journal·Xi ZhangJiang-Fei Xu
Aug 29, 2020·Angewandte Chemie·Yao-Hua LiuYu Liu
Jul 16, 2019·DNA Repair·Yingqian Zhang, Chuanzheng Zhou
Nov 19, 2020·Chemical Communications : Chem Comm·Ekaterina Y Chernikova, Daria V Berdnikova
Jan 23, 2019·Accounts of Chemical Research·Yafen WangXiang Zhou
Nov 18, 2018·Analytical Chemistry·Chaoxing LiuXiang Zhou
Oct 23, 2018·Analytical Chemistry·Yufeng ZhouYong Shao
Dec 12, 2018·ACS Applied Materials & Interfaces·Jia-Rui WuYing-Wei Yang
Jul 18, 2019·Journal of the American Chemical Society·Jia-Rui Wu, Ying-Wei Yang
Jun 11, 2019·Journal of the American Chemical Society·Mario GießDaniel Summerer
Feb 1, 2022·Nucleic Acids Research·Wei XiongXiang Zhou

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