Structural characterization of adducts formed in the reaction of 2,3-epoxy-4-hydroxynonanal with deoxyguanosine.

  title={Structural characterization of adducts formed in the reaction of 2,3-epoxy-4-hydroxynonanal with deoxyguanosine.},
  author={Rama S. Sodum and Fung-Lung Chung},
  journal={Chemical research in toxicology},
  volume={2 1},
Six adducts were isolated by reverse-phase high-performance liquid chromatography from the reaction of deoxyguanosine at 50 degrees C in pH 7.0 buffer with the epoxide of trans-4-hydroxy-2-nonenal, a major alpha,beta-unsaturated aldehyde from lipid peroxidation. These adducts were designated as adducts 1-6. Structures of these adducts were fully characterized by spectroscopic methods such as UV, proton NMR, MS, and CD and by chemical reactions. Adduct 1 was previously identified as 1,N2… 
Characterization of 2'-deoxyadenosine adducts derived from 4-oxo-2-nonenal, a novel product of lipid peroxidation.
Analysis of the reaction between 2'-deoxyadenosine and 4-oxo-2-nonenal by liquid chromatography/mass spectrometry revealed the presence of three major products (adducts A(1), A(2), and B). Adducts
Stereoselective formation of in vitro nucleic acid adducts by 2,3-epoxy-4-hydroxynonanal.
RNA was extensively modified by the epoxy aldehyde, yielding both adenine and guanine nucleosides, and reactions of single-stranded DNA resulted in the formation of primarily A1 and A2, with a total adduct level of 30 nmol/mg DNA.
4-Hydroperoxy-2-nonenal-induced formation of 1,N2-etheno-2'-deoxyguanosine adducts.
HNE is concluded that HPNE, a primary product of lipid peroxidation, is a major precursor to the formation of 1,N2-etheno-dGuo, and can be considered as another lipid hydroperoxide-derived bifunctional electrophile with the potential for biological activities that are similar to HNE and ONE.
Synthesis of the four stereoisomers of 2,3-epoxy-4-hydroxynonanal and their reactivity with deoxyguanosine.
All four stereoisomers of EHN are synthesized and individually reacted them with 2'-deoxyguanosine, consistent with selective NOE spectra, vicinal coupling constants, and molecular mechanics calculations.
Formation of Bulky DNA Adducts by Non-Enzymatic Production of 1,2-Naphthoquinone-Epoxide from 1,2-Naphthoquinone under Physiological Conditions.
Results suggest that the genotoxicity of 1,2-NQ may not only be caused through oxidative DNA damage and adduct formation through Michael addition but also through non-enzymatic oxidative transformation of 2'-deoxyguanosine itself to form an intermediate PAH-epoxide which covalently binds to DNA.
2,3-epoxy-4-hydroxynonanal, a potential lipid peroxidation product for etheno adduct formation, is not a substrate of human epoxide hydrolase.
2,3-epoxy-4-hydroxynonanal is not a substrate of human epoxide hydrolase, and, thus, its possible endogenous role in the formation of promutagenic exocyclic etheno adducts in vivo is strengthened.
The Stereochemistry of trans-4-Hydroxynonenal-Derived Exocyclic 1,N2-2′-Deoxyguanosine Adducts Modulates Formation of Interstrand Cross-Links in the 5′-CpG-3′ Sequence†
Stereochemical differences in orientation suggest a kinetic basis that explains, in part, why the (6S,8R,11S) stereoisomer forms interchain cross-links in the 5′-CpG-3′ sequence whereas the ( 6R,8S,11R) stere Loisomer does not.
Conformational interconversion of the trans-4-hydroxynonenal-derived (6S,8R,11S) 1,N(2)-deoxyguanosine adduct when mismatched with deoxyadenosine in DNA.
The (6S,8R,11S) 1,N(2)-HNE-dGuo adduct of trans-4-hydroxynonenal (HNE) was incorporated into the duplex 5'-d(GCTAGCXAGTCC)-3'.5'-d(GGACTAGCTAGC)-3' [X = (6S,8R,11S) HNE-dG], in which the lesion was