Liquid Chromatography-Tandem Mass Spectrometry Analysis of the DNA Adducts of Aristolochic Acids

Wan Chan, Yufang Zheng, Zongwei CAI*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

Electrophilic attack of aristolactam-nitrenium ion by the C7 position to the exocyclic amino group in the DNA bases led to the formation of the major adducts. In this study, liquid chromatography coupled with electrospray ionization tandem mass spectrometry was applied to the study of DNA adducts of aristolochic acid (AA). When DNA (bases and CT-DNA) was incubated with AA, dG-AAI, dG-AAII, dA-AAI, dA-AAII, dC-AAI, and dC-AAII were detected and characterized. The dC adducts of AA were identified for the first time. The soft ionization technology allowed detection of the intact DNA adducts. High-resolution MS and MS-MS capabilities of a quadrupole time-of-flight mass spectrometer were shown to be efficient for DNA adducts analysis. DNA-AA adducts showed characteristic fragmentation patterns in MS-MS analysis. The dissociative loss of 116 Da from the DNA-AA adducts, which resulted from internal hydrogen transfer and cleavage at the C{single bond}N glycosidic bond, provided a characteristic fragment for the structural elucidation.

Original languageEnglish
Pages (from-to)642-650
Number of pages9
JournalJournal of the American Society for Mass Spectrometry
Volume18
Issue number4
DOIs
Publication statusPublished - Apr 2007

Scopus Subject Areas

  • Structural Biology
  • Spectroscopy

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