Adduct formation identification between phenyl glycidyl ether and 2'-deoxyadenosine and thymidine by chromatography, mass spectrometry and nuclear magnetic resonance spectroscopy.
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.
Van den Eeckhout
E
E
University of Ghent, College of Pharmacy, Belgium.
De Bruyn
A
A
Pepermans
H
H
Esmans
E L
EL
Vryens
I
I
Claereboudt
J
J
Claeys
M
M
Sinsheimer
J E
JE
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*
D003839:Deoxyadenosines; D010647:Phenyl Ethers; C016050:phenylglycidyl ether; D013936:Thymidine