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Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
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Related Experiment Video

Updated: Jul 1, 2026

Quantification of three DNA Lesions by Mass Spectrometry and Assessment of Their Levels in Tissues of Mice Exposed to Ambient Fine Particulate Matter
12:15

Quantification of three DNA Lesions by Mass Spectrometry and Assessment of Their Levels in Tissues of Mice Exposed to Ambient Fine Particulate Matter

Published on: May 29, 2019

Protein binding has a large effect on radical mediated DNA damage.

Xiaohua Peng1, Ying Z Pigli, Phoebe A Rice

  • 1Department of Chemistry, The Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.

Journal of the American Chemical Society
|September 10, 2008
PubMed
Summary

Protein binding significantly alters oxidative DNA damage by increasing radical reactivity and DNA interstrand cross-links. This research clarifies how proteins influence DNA damage in cellular environments.

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Quantification of three DNA Lesions by Mass Spectrometry and Assessment of Their Levels in Tissues of Mice Exposed to Ambient Fine Particulate Matter
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Advanced Confocal Microscopy Techniques to Study Protein-protein Interactions and Kinetics at DNA Lesions
12:43

Advanced Confocal Microscopy Techniques to Study Protein-protein Interactions and Kinetics at DNA Lesions

Published on: November 12, 2017

Area of Science:

  • Biochemistry
  • Molecular Biology
  • Genetics

Background:

  • Oxidative DNA damage is implicated in aging and diseases.
  • Previous studies on DNA radical reactivity were conducted on protein-free DNA.
  • The impact of protein binding on DNA radical reactivity in cellular contexts remains unclear.

Purpose of the Study:

  • To investigate the effect of the DNA-binding protein Hbb on the reactivity of specific DNA radicals.
  • To understand how protein-induced DNA kinking influences radical reactions.

Main Methods:

  • Generation of 5-(2'-deoxyuridinyl)methyl radical (1) and 5-(2'-deoxycytidinyl)methyl radical (2) in the presence of the Hbb protein.
  • Analysis of radical reactivity and DNA modification yields.

Main Results:

  • Hbb protein binding bends DNA and disrupts base stacking.
  • Radical reactivity at the kinking site was significantly affected by Hbb.
  • Increased conformational mobility of radicals led to higher yields of DNA interstrand cross-links.

Conclusions:

  • Protein binding, exemplified by Hbb, demonstrably alters DNA radical reactivity.
  • This study provides initial evidence of how proteins influence oxidative DNA damage mechanisms within cells.