title: Adduct formation identification between phenyl glycidyl ether and 2'-deoxyadenosine and thymidine by chromatography, mass spectrometry and nuclear magnetic resonance spectroscopy.
abstract: Thymidine and 2'-deoxyadenosine were reacted with phenyl glycidyl ether in order to study the formation of the corresponding 2'-deoxynucleoside adducts. Separation methods were elaborated using either reversed-phase high-performance liquid chromatography with photodiode-array detection, or centrifugal circular thin-layer chromatography. The adducts were isolated on a preparative scale and were fully characterized by UV spectroscopy, desorption chemical ionization and fast atom bombardment mass spectrometry and 270- and 360-MHz 1H NMR spectrometry. For thymidine the main adduct was characterized as N-3-(2-hydroxy-3-phenoxypropyl)thymidine. With 2'-deoxyadenosine, predominantly N-1-(2-hydroxy-3-phenoxypropyl)-2'-deoxyadenosine was formed. With longer reaction times, the formation of a minor amount of dialkylated 2'-deoxyadenosine was observed. These nucleoside adducts will be used as marker compounds for studies of DNA adduct formation.
authors.affiliation: University of Ghent, College of Pharmacy, Belgium.
authors.forename: E
authors.initials: E
authors.lastname: Van den Eeckhout
authors.forename: A
authors.initials: A
authors.lastname: De Bruyn
authors.forename: H
authors.initials: H
authors.lastname: Pepermans
authors.forename: E L
authors.initials: EL
authors.lastname: Esmans
authors.forename: I
authors.initials: I
authors.lastname: Vryens
authors.forename: J
authors.initials: J
authors.lastname: Claereboudt
authors.forename: M
authors.initials: M
authors.lastname: Claeys
authors.forename: J E
authors.initials: JE
authors.lastname: Sinsheimer
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003839:Deoxyadenosines / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010647:Phenyl Ethers / Q000378:metabolism*; D013936:Thymidine / Q000378:metabolism*
chemical_list: D003839:Deoxyadenosines; D010647:Phenyl Ethers; C016050:phenylglycidyl ether; D013936:Thymidine