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Protein modification by adenine propenal.

Sarah C Shuck1, Orrette R Wauchope, Kristie L Rose

  • 1A. B. Hancock Jr. Memorial Laboratory for Cancer Research, Departments of Biochemistry, ‡Chemistry, and §Pharmacology, ∥Mass Spectrometry Research Center, ⊥Center in Molecular Toxicology, #Center for Structural Biology, ∇Department of Medicine, Vanderbilt Institute of Chemical Biology, and Vanderbilt-Ingram Cancer Center, Vanderbilt University School of Medicine , Nashville, Tennessee 37232-0146, United States.

Chemical Research in Toxicology
|September 12, 2014
PubMed
Summary
This summary is machine-generated.

Adenine propenal, a DNA oxidation product, forms adducts with lysine and cysteine in proteins. This modification significantly impairs the DNA repair protein XPA

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • DNA Damage and Repair

Background:

  • Base propenals are DNA oxidation products, with adenine propenal being highly reactive and mutagenic.
  • Adenine propenal forms adducts with DNA, but its interaction with proteins was previously uncharacterized.

Purpose of the Study:

  • To investigate the reaction of adenine propenal with amino acids and proteins.
  • To identify the specific protein adducts formed and their functional consequences.

Main Methods:

  • Reaction of adenine propenal with individual amino acids.
  • Proteomic analysis of adenine propenal-modified human serum albumin and the DNA repair protein XPA.
  • Assessment of XPA's DNA-binding ability after modification.

Main Results:

  • Lysine and cysteine form stable adducts with adenine propenal; histidine and arginine do not.
  • N(ε)-Oxopropenyllysine and S-oxopropenyl cysteine are major adducts.
  • Adenine propenal modification of XPA, particularly in its DNA-binding domain, significantly reduces its DNA-binding capacity.

Conclusions:

  • Adenine propenal reacts with specific amino acid residues in proteins, forming stable adducts.
  • Protein modification by adenine propenal can impair critical protein functions, such as DNA repair by XPA.