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The deuteration of N 2 -ethyl-2'-deoxyguanosine (Et-dG), which is a DNA adduct generated from acetaldehyde, was studied by the addition reaction of acetaldehyde-d 4 to 2'-deoxyguanosine (dG) in deuterium oxide (D 2 O), with the aim to obtain an isotope internal standard for the liquid chromatography/tandem mass spectrometry (LC/MS/MS) quantitation of Et-dG. The replacement of the dG C-8 hydrogen atom by a deuteron atom took place at 50°C in D 2 O and afforded a mixture of Et-dG-d 4 and Et-dG-d 5 . Et-dG-d 4 , which was stable in aqueous solutions, was prepared by incubating the mixture in H 2 O at 60°C for 48 h. The calibration curve was obtained by multiple reaction monitoring (MRM) measurements using a hydrophilic interaction chromatography-electrospray ionization-tandem mass spectrometric (HILIC/ESI-MS/MS) system between the Et-dG concentration, ranging from 1.0 × 10 -10 to 4.0 × 10 -9 M in the sample solutions, and the relative peak areas of Et-dG (m/z: 296.1 → 180.1) to the value of Et-dG-d 4 (m/z: 300.2 → 184.2), with an internal standard showing good linearity (R 2 = 0.995, n = 5).

analytical sciences

Preparation of N2-Ethyl-2′-deoxyguanosine-d4 as an Internal Standard for the Electrospray Ionization–Tandem Mass Spectrometric Determination of DNA Damage by Acetaldehyde