Major adenine products from 2-methyl-1,4-naphthoquinone-sensitized photoirradiation at 365 nm.
In this article we report the isolation and characterization of major products of adenine in dinucleoside monophosphates upon 2-methyl-1,4-naphthoquinone (menadione)-sensitized UVA irradiation. Our results show that the major products form via the coupling between the menadione moiety and the exocyclic amino group of adenine. Similar reactions were not observed for cytosine. To our knowledge, this is the first report about the direct reaction between a DNA base and a photosensitizer under 365-nm ultraviolet light irradiation. Our results are consistent with previous observation showing that N(6) radical formed on adenine upon UVA irradiation.
Wang
Yinsheng
Y
Department of Chemistry, 027, University of California at Riverside, Riverside, CA 92521-0403, USA. yinsheng.weng@ucr.edu
Liu
Zhenjiu
Z
Dixon
Cynthia
C
D000225:Adenine / Q000032:analysis* / Q000737:chemistry; D015226:Dinucleoside Phosphates / Q000737:chemistry* / Q000528:radiation effects; D009838:Oligodeoxyribonucleotides / Q000737:chemistry* / Q000528:radiation effects; D010777:Photochemistry; D017319:Photosensitizing Agents / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D014466:Ultraviolet Rays; D024483:Vitamin K 3 / Q000737:chemistry*
D015226:Dinucleoside Phosphates; D009838:Oligodeoxyribonucleotides; D017319:Photosensitizing Agents; C093708:deoxycytidylyl-3'-5'-deoxyadenosine; C020269:2'-deoxyadenylyl-(3'-5')-2'-deoxyadenosine; D024483:Vitamin K 3; D000225:Adenine