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Cross-bridge Cycle01:26

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DNA cross-link induced by trans-4-hydroxynonenal.

Hai Huang1, Ivan D Kozekov, Albena Kozekova

  • 1Department of Chemistry, Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235, USA.

Environmental and Molecular Mutagenesis
|June 26, 2010
PubMed
Summary

Trans-4-Hydroxynonenal (HNE) can form DNA cross-links, particularly in the 5'-CpG-3' sequence. Specific stereochemistry of the HNE adduct influences its ability to form these cross-links, potentially impacting DNA replication and disease.

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Toxicology

Background:

  • Trans-4-Hydroxynonenal (HNE) is a reactive aldehyde formed from omega-6 polyunsaturated fatty acid peroxidation.
  • HNE can adduct to DNA, forming 1,N(2)-dG adducts with varying stereochemistries.
  • These adducts can undergo rearrangement and potentially form DNA cross-links.

Purpose of the Study:

  • To investigate the stereochemistry-dependent formation of DNA cross-links by HNE adducts.
  • To elucidate the mechanisms by which HNE adducts rearrange and form cyclic hemiacetals in DNA.
  • To understand the structural basis for the differential cross-linking activity of HNE diastereomers.

Main Methods:

  • Synthesis and characterization of HNE-deoxyguanosine (dG) adducts with specific stereochemistries.
  • Incorporation of HNE-dG adducts into synthetic DNA sequences.
  • Spectroscopic and computational methods (molecular mechanics) to analyze adduct conformation and reactivity.
  • Investigation of adduct rearrangement to aldehydes and cyclic hemiacetals.

Main Results:

  • Four diastereomeric 1,N(2)-dG adducts are formed by HNE.
  • The (6S,8R,11S) HNE adduct forms interstrand N(2)-dG:N(2)-dG cross-links in the 5 extbackslash'CpG-3 extbackslash' sequence.
  • Both HNE adducts rearrange to N(2)-dG aldehydes, which exist in equilibrium with cyclic hemiacetals that mask aldehyde reactivity.
  • The (6S,8R,11S) and (6R,8S,11R) cyclic hemiacetals and aldehydes orient differently within the DNA minor groove (5 extbackslash'- vs. 3 extbackslash'-direction).
  • The orientation of the (6S,8R,11S) aldehyde is proposed to be key for interchain cross-link formation.

Conclusions:

  • The stereochemistry of HNE adducts dictates their ability to form DNA cross-links.
  • Cyclic hemiacetal formation by HNE adducts contributes to slower DNA cross-linking kinetics compared to other aldehydes.
  • Differential orientation of HNE aldehyde diastereomers provides a kinetic basis for sequence-specific cross-linking.
  • In vivo DNA cross-links by HNE may disrupt DNA replication and transcription, contributing to disease etiology.