³²P-HPLC analysis of N1-(2-carboxy-2-hydroxyethyl)deoxyadenosine: a DNA adduct of the acrylamide-derived epoxide glycidamide.

Acrylamide (AA) is produced in many types of food products cooked or processed at high temperature. AA is metabolized to the epoxide glycidamide (GA), which can bind to deoxyguanosine and deoxyadenosine in DNA. The GA-derived N7-guanine and N3-adenine adducts are the only products which so far have been analysed in vivo.

Identification of lignans by liquid chromatography-electrospray ionization ion-trap mass spectrometry.

The fragmentation pattern of 30 compounds belonging to different classes of the lignan family was studied by liquid chromatography-electrospray ionization ion-trap mass spectrometry. On the basis of the observed fragmentation patterns, identification of different types of lignans was achieved. For example, dibenzylbutyrolactone lignans showed a characteristic fragmentation pathway by the loss of 44 Da (CO(2)) from the lactone moiety, whereas dibenzylbutanediols showed a loss of 48 Da by a combined loss of formaldehyde and water from the 1,4-butanediol moiety.

Characterization of adducts formed in the reaction of glutaraldehyde with 2'-deoxyadenosine.

Glutaraldehyde (1,5-pentanedial) is a widely used industrial chemical that has been found to be mutagenic in bacteria and mammalian cells. In this study, we examined the reaction of glutaraldehyde with 2'-deoxyadenosine and calf thymus DNA in aqueous buffered solutions. The 2'-deoxyadenosine adducts were isolated by reversed phase HPLC and characterized by their UV absorbance and 1H and 13C NMR spectroscopic and mass spectrometric features.

Reaction of glycidamide with 2'-deoxyadenosine and 2'-deoxyguanosine--mechanism for the amide hydrolysis.

2'-Deoxyadenosine (dA) and 2'-deoxyguanosine (dG) were reacted with mutagenic epoxide glycidamide (GA, Scheme 1). The reactions yielded three GA-dA adducts (N1-GA-dA, N6-GA-dA and N1-GA-dI) and two GA-dG adducts (N1-GA-dG I and N1-GA-dG II) (Scheme 2). The structures of the adducts were characterized by spectroscopic and spectrometric methods (1H-, 13C, and 2D NMR, MS, UV).

Reaction of glyoxal with 2'-deoxyguanosine, 2'-deoxyadenosine, 2'-deoxycytidine, cytidine, thymidine, and calf thymus DNA: identification of DNA adducts.

Glyoxal (ethanedial) is an increasingly used industrial chemical that has been found to be mutagenic in bacteria and mammalian cells. In this study, the reactions of glyoxal with 2'-deoxyguanosine, 2'-deoxyadenosine, 2'-deoxycytidine, cytidine, thymidine, and calf thymus DNA have been studied in aqueous buffered solutions. The nucleoside adducts were isolated by reversed-phase liquid chromatography and characterized by their UV absorbance and 1H and 13C NMR spectroscopic and mass spectrometric features.

Identification of a novel fluorescent adduct formed in the reaction of malonaldehyde with adenosine.

Malonaldehyde was reacted with adenosine in aqueous solution at acidic conditions and the reaction mixtures were analysed by HPLC. Four major product peaks were observed in the chromatogram recorded by the UV detector at 320 nm. Two of the peaks could be deduced to the previously characterised malonaldehyde-adenosine reaction product 9-(beta-D-ribofuranosyl)-6-(5,7-diformyl-2H-3,6-dihydro-2,6-methano-1,3-oxazocin-3-yl)purine (M3A) and to the ribose analogue of the 2'-deoxy adduct 9-(2'-deoxy-beta-D-ribofuranosyl)-6-(3,5-diformyl-4-methyl-1,4-dihydro-1-pyridyl)purine (M2AA-dA).

Characterization of the adducts formed in the reactions of glycidamide with thymidine and cytidine.

Glycidamide (GA) is a mutagenic epoxide metabolite of acrylamide (AM), a high production chemical with many industrial uses. Moreover, recent findings have shown that AM is formed in starchy foods cooked at high temperatures. This has refocused the attention on this chemical and its metabolite and on their possible mutagenicity and carcinogenicity.