2--deoxyguanosine-3--phosphate and styrene-oxide

2--deoxyguanosine-3--phosphate has been researched along with styrene-oxide* in 2 studies

Other Studies

2 other study(ies) available for 2--deoxyguanosine-3--phosphate and styrene-oxide

Article	Year
Identification of N2-substituted 2'-deoxyguanosine-3'-phosphate adducts detected by 32P-postlabeling of styrene-oxide-treated DNA. Carcinogenesis, 1992, Volume: 13, Issue:3 Styrene-7,8-oxide, a metabolite of the industrial chemical styrene, was reacted with calf thymus DNA. Six adducts were detected by 32P-postlabeling. The two diastereomers of N2-(2-hydroxy-1-phenylethyl)-2'-deoxyguanosine-3'-phosphate and the corresponding N-1 substituted compounds were isolated from the aqueous reaction mixture of 2'-deoxyguanosine-3'-phosphate and styrene-7,8-oxide (pH 10.5) and characterized by liquid secondary-ion and four-sector tandem mass spectrometry, ultraviolet, circular dichroism, and fluorescence spectrophotometry, and 32P-postlabeling. Co-chromatography of the DNA-styrene-7,8-oxide reaction products with the synthetic standards showed that adduct no. 6 arose as a result of aralkylation at the N2-exocyclic site of the guanine base. The recovery of the N2-adduct was dependent on the concentration of the solvent used during octadecylsilyl chromatography. These studies revealed that the N2-guanosine derivatives are the major products of the reaction of DNA and styrene-7,8-oxide in vitro detected by 32P-postlabeling. Topics: Autoradiography; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Deoxyguanine Nucleotides; DNA; Epoxy Compounds; Spectrophotometry, Ultraviolet	1992
O6-substituted-2'-deoxyguanosine-3'-phosphate adducts detected by 32P post-labeling of styrene oxide treated DNA. Carcinogenesis, 1989, Volume: 10, Issue:6 32P post-labeling of DNA reacted with styrene oxide resulted in the detection of six adducts. In order to determine which of these corresponded to modification at the O6 position of guanine, O6-substituted styrene oxide-deoxyguanosine-3'-monophosphate derivatives were synthesized. The two synthetic isomers were purified by HPLC and the structures were confirmed by mass spectrometry and 1H NMR. 32P post-labeling and co-chromatography with the DNA-styrene-7,8-oxide reaction products resulted in the assignment of adduct number 4 as O6-(2-hydroxy-2-phenylethyl)-2'--deoxyguanosine-3',5'-bisphosphate and adduct number 5 as O6-(2-hydroxy-1-phenylethyl)-2'-deoxyguanosine-3',5'-bisphosphate. Topics: Chemical Phenomena; Chemistry; Deoxyguanine Nucleotides; DNA; Epoxy Compounds; Ethers, Cyclic; Magnetic Resonance Spectroscopy; Mass Spectrometry; Phosphorus Radioisotopes	1989

Article

Year

Identification of N2-substituted 2'-deoxyguanosine-3'-phosphate adducts detected by 32P-postlabeling of styrene-oxide-treated DNA.

Carcinogenesis, 1992, Volume: 13, Issue:3

Styrene-7,8-oxide, a metabolite of the industrial chemical styrene, was reacted with calf thymus DNA. Six adducts were detected by 32P-postlabeling. The two diastereomers of N2-(2-hydroxy-1-phenylethyl)-2'-deoxyguanosine-3'-phosphate and the corresponding N-1 substituted compounds were isolated from the aqueous reaction mixture of 2'-deoxyguanosine-3'-phosphate and styrene-7,8-oxide (pH 10.5) and characterized by liquid secondary-ion and four-sector tandem mass spectrometry, ultraviolet, circular dichroism, and fluorescence spectrophotometry, and 32P-postlabeling. Co-chromatography of the DNA-styrene-7,8-oxide reaction products with the synthetic standards showed that adduct no. 6 arose as a result of aralkylation at the N2-exocyclic site of the guanine base. The recovery of the N2-adduct was dependent on the concentration of the solvent used during octadecylsilyl chromatography. These studies revealed that the N2-guanosine derivatives are the major products of the reaction of DNA and styrene-7,8-oxide in vitro detected by 32P-postlabeling.

Topics: Autoradiography; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Deoxyguanine Nucleotides; DNA; Epoxy Compounds; Spectrophotometry, Ultraviolet

1992

O6-substituted-2'-deoxyguanosine-3'-phosphate adducts detected by 32P post-labeling of styrene oxide treated DNA.

Carcinogenesis, 1989, Volume: 10, Issue:6

32P post-labeling of DNA reacted with styrene oxide resulted in the detection of six adducts. In order to determine which of these corresponded to modification at the O6 position of guanine, O6-substituted styrene oxide-deoxyguanosine-3'-monophosphate derivatives were synthesized. The two synthetic isomers were purified by HPLC and the structures were confirmed by mass spectrometry and 1H NMR. 32P post-labeling and co-chromatography with the DNA-styrene-7,8-oxide reaction products resulted in the assignment of adduct number 4 as O6-(2-hydroxy-2-phenylethyl)-2'--deoxyguanosine-3',5'-bisphosphate and adduct number 5 as O6-(2-hydroxy-1-phenylethyl)-2'-deoxyguanosine-3',5'-bisphosphate.

Topics: Chemical Phenomena; Chemistry; Deoxyguanine Nucleotides; DNA; Epoxy Compounds; Ethers, Cyclic; Magnetic Resonance Spectroscopy; Mass Spectrometry; Phosphorus Radioisotopes

1989