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Preparation of Cyclic-1,N 2-propano-2'-deoxyguanosine-d 7 as an Internal Standard for ESI-MS/MS Determination of DNA Damage from Acetaldehyde

Preparation of Cyclic-1,N 2-propano-2'-deoxyguanosine-d 7 as an Internal Standard for ESI-MS/MS Determination of DNA Damage from Acetaldehyde

Yukihiro Esaka, Saki Kunishima, Hiromitsu Aruga, Takuhei Yamamoto, Hiroya Murakami, Norio Teshima, Bunji Uno

Anal Sci. 2019 Dec 10;35(12):1393-1397.

PMID: 31474658

Abstract:

Cyclic-1,N2-propano-2'-deoxyguanosine-d7 (CPr-dG-d7) was prepared as an isotopic internal standard (IS) for electrospray ionization tandem mass spectrometry (ESI-MS/MS) quantification of CPr-dG in DNA as a candidate cancer risk marker of acetaldehyde intake, mainly from drinking. The deuterated compound was reasonably synthesized from acetaldehyde-d4 and 2'-deoxyguanosine in deuterium oxide (D2O), preventing the deuterium atoms of acetaldehyde-d4 from being substituted by hydrogen atoms, which occurred seriously in aqueous synthesis media via keto-enol tautomerism. Furthermore, another deuterium atom was added from D2O to form CPr-dG-d7. After four weeks of storage in H2O at 10°C, CPr-dG-d7 was found to be sufficiently stable for practical use. The calibration curve of CPr-dG by using a hydrophilic interaction chromatography-ESI-MS/MS system with CPr-dG-d7 as the IS showed sufficient linearity from 1.0 × 10-10 to 4.0 × 10-9 M with r2 = 0.998.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1632899	Acetaldehyde-d4		1632-89-9	Price

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