DNA interstrand cross-links induced by the major oxidative adenine lesion 7,8-dihydro-8-oxoadenine.

Szczegóły
Abstrakt

Tytuł:: DNA interstrand cross-links induced by the major oxidative adenine lesion 7,8-dihydro-8-oxoadenine.
Autorzy:: Rozelle AL; Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin, Austin, TX, USA.; McKetta Department of Chemical Engineering, Cockrell School of Engineering, The University of Texas at Austin, Austin, TX, USA.
Cheun Y; Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin, Austin, TX, USA.
Vilas CK; Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin, Austin, TX, USA.; Institute for Cellular and Molecular Biology, The University of Texas at Austin, Austin, TX, USA.
Koag MC; Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin, Austin, TX, USA.
Lee S; Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin, Austin, TX, USA. .
Źródło:: Nature communications [Nat Commun] 2021 Mar 26; Vol. 12 (1), pp. 1897. Date of Electronic Publication: 2021 Mar 26.
Typ publikacji:: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't
Język:: English
Imprint Name(s):: Original Publication: [London] : Nature Pub. Group
MeSH Terms:: DNA Damage*
Oxidative Stress*
Adenine/*analogs & derivatives
DNA/*chemistry
Adenine/chemistry ; Chromatography, Liquid/methods ; Cross-Linking Reagents/chemistry ; DNA/genetics ; DNA/metabolism ; DNA Repair ; Guanine/analogs & derivatives ; Guanine/chemistry ; Mass Spectrometry/methods ; Models, Chemical ; Molecular Structure ; Oxidation-Reduction
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Substance Nomenclature:: 0 (Cross-Linking Reagents)
21149-26-8 (8-hydroxyadenine)
5614-64-2 (8-hydroxyguanine)
5Z93L87A1R (Guanine)
9007-49-2 (DNA)
JAC85A2161 (Adenine)
Entry Date(s):: Date Created: 20210327 Date Completed: 20210412 Latest Revision: 20210417
Update Code:: 20240105
PubMed Central ID:: PMC7997976
DOI:: 10.1038/s41467-021-22273-2
PMID:: 33772030
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Oxidative damage to DNA generates 7,8-dihydro-8-oxoguanine (oxoG) and 7,8-dihydro-8-oxoadenine (oxoA) as two major lesions. Despite the comparable prevalence of these lesions, the biological effects of oxoA remain poorly characterized. Here we report the discovery of a class of DNA interstrand cross-links (ICLs) involving oxidized nucleobases. Under oxidative conditions, oxoA, but not oxoG, readily reacts with an opposite base to produce ICLs, highlighting a latent alkylating nature of oxoA. Reactive halogen species, one-electron oxidants, and the myeloperoxidase/H 2 O 2 /Cl - system induce oxoA ICLs, suggesting that oxoA-mediated cross-links may arise endogenously. Nucleobase analog studies suggest C2-oxoA is covalently linked to N2-guanine and N3-adenine for the oxoA-G and oxoA-A ICLs, respectively. The oxoA ICLs presumably form via the oxidative activation of oxoA followed by the nucleophilic attack by an opposite base. Our findings provide insights into oxoA-mediated mutagenesis and contribute towards investigations of oxidative stress-induced ICLs and oxoA-based latent alkylating agents.

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