[Preliminary study on structure and chemical characteristics of deoxyguanoside-benzoquinone adducts].
OBJECTIVE
To detect the structure and chemical characteristics of the adduct from the reaction of p-benzoquinone (BQ) with deoxyguanoside (dGMP).


METHODS
dGMP and calf thymus DNA were reacted with BQ in buffered solutions with neutral pH, the reaction products were separated and purified by high performance liquid chromatograph (HPLC), and then characterized by UV spectroscopy and mass spectrometry.


RESULTS
The reaction of BQ with dGMP yielded two adduct products (Ad(1) and Ad(2) respectively). The characterized results of Ad(1) suggested that BQ reacted at the N-1 and N(2) position of dGMP by losing one H(2)O molecule, the molecular weight of Ad(1) was 437, and the molecular formula was C(16)H(16)O(8)N(5)P. Ad(1) could also be detected from calf thymus DNA reacted with BQ in vitro, which possessed the same elution profile by HPLC analysis. Meanwhile, Ad(2) was detected in the experimental condition. It was proposed that Ad(2) was formed by BQ reacted at the N-9 position of dGMP by losing one molecule of deoxyribose, the molecular weight was 241, and the molecular formula was C(11)H(7)O(2)N(5).


CONCLUSIONS
The structure of one major adduct from reaction of BQ with DNA is (3'-OH)-1, N(2)-C(6)H(5)CH-2'-deoxyguanosine-5'-monophosphate.
Dai
Yu-fei
YF
National Institute for Occupational Health and Poison Control, Chinese Center for Disease Control and Prevention, Beijing 100050, China.
Chang
Ping
P
Li
Gui-lan
GL
D016227:Benzoquinones / Q000378:metabolism*; D018736:DNA Adducts / Q000737:chemistry*; D003848:Deoxyguanine Nucleotides / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D013058:Mass Spectrometry; D008970:Molecular Weight; D013056:Spectrophotometry, Ultraviolet
D016227:Benzoquinones; D018736:DNA Adducts; D003848:Deoxyguanine Nucleotides; C004532:quinone; C007257:2'-deoxyguanosine 5'-phosphate