A new class of psoralen photoadducts to DNA components: isolation and characterization of 8-MOP adducts to the osidic moiety of 2'-deoxyadenosine.
The near-UV-induced photoreaction of the bifunctional 8-methoxypsoralen (8-MOP) with 2'-deoxyadenosine (dAdo) was investigated in the dry state. Four main monoadducts of 8-MOP to 2'-deoxyadenosine were separated by high performance liquid chromatography and subsequently characterized by soft ionization mass spectrometry (fast atom bombardment and plasma desorption mass spectrometries) and extensive 1H NMR analysis including nuclear Overhauser effect (NOE) measurements. These new types of furocoumarin-nucleic acid component which appear to be specific to 2'-deoxyadenosine were shown to result from recombination of the 3,4-dihydropyron-4-yl radical of 8-MOP with 2'-deoxyadenosyl radical either at the 1' or the 5' position.
Cadet
J
J
Département de Recherche Fondamentale, Centre d'Etudes Nucleáires de Grenoble, France.
Voituriez
L
L
Nardin
R
R
Viari
A
A
Vigny
P
P
D002851:Chromatography, High Pressure Liquid; D004247:DNA; D003839:Deoxyadenosines; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008730:Methoxsalen; D010777:Photochemistry
D003839:Deoxyadenosines; D004247:DNA; D008730:Methoxsalen