Synthesis, characterization and in vtro identification of N7-guanine adduct of 2-bromopropane.
Recently, we have reported that 2-bromopropane might have an immunotoxic potential in rats when exposed for 28 days. In the present studies, the possibility of 2i-deoxyguanosine adduct formation by 2-bromopropane was investigated in vitro to elucidate molecular mechanism of 2-bromopropane-induced immunosuppression. N7-Guanine adduct of 2'-bromopropane (i.e., N7-isopropyl guanine) was chemically synthesized and structurally characterized by analysis of UV, 1H-NMR, '3C-NMR, COSY and fast atom bombardment mass spectrometry to use as a reference material. Incubation of 2'-deoxyguanosine with an excess amount of 2-bromopropane in PBS buffer solution, pH 7.4, at 37 degrees C for 16 h, followed by a thermal hydrolysis, produced a detectable amount of N7-isopropyl guanine by an HPLC and UV analysis. The present results suggest that 2-bromopropane might form a DNA adduct in N7 position of 2'-deoxyguanosine at a physiological condition.
Zhao
Long-Xuan
LX
College of Pharmacy, Yeungnam University, Kyongsan, Korea.
Kim
Eun-Kyung
EK
Lim
Hyun-Tae
HT
Moon
Yoon-Soo
YS
Kim
Nam-Hee
NH
Kim
Tae-Hyung
TH
Choi
Heesung
H
Chae
Whigun
W
Jeong
Tae Cheon
TC
Lee
Eung-Seok
ES
D002851:Chromatography, High Pressure Liquid; D018736:DNA Adducts / Q000138:chemical synthesis / Q000737:chemistry*; D006147:Guanine / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet
D018736:DNA Adducts; D006842:Hydrocarbons, Brominated; D007202:Indicators and Reagents; D006147:Guanine; C103736:2-bromopropane