126875-81-8Relevant articles and documents
Synthesis of DNA strands site-specifically damaged by C8-arylamine purine adducts and effects on various DNA polymerases
Boege, Nicolas,Jacobsen, Maike I.,Szombati, Zita,Baerns, Sabrina,Di Pasquale, Francesca,Marx, Andreas,Meier, Chris
experimental part, p. 11194 - 11208 (2009/11/30)
C8-Arylamine-dG and C8-arylamine-dA adducts have been prepared using palladium cross-coupling chemistry. These adducts were subsequently converted into the corresponding 5′-O-DMTr-C8-arylamine-3′-O-phosphoramidites and then used for the automated synthesi
N-Aryl-O-(α-aminoacyl)hydroxylamines: Model Reactions with Deoxyguanosine, Guanosine and 5'-Guanosinemonophosphate for the Activation of Monocyclic Aromatic Amines (e.g. Phenacetin) into Ultimate Carcinogens
Meier, Chris,Boche, Gernot
, p. 1699 - 1705 (2007/10/02)
In in vitro model reactions of the activation of monocyclic aromatic amines by α-amino acids it is shown that α-aminohydroxamic acids 8 and 9 rearrange base-catalyzed to N-(α-aminoacyloxy)arylamines 10 and 11 which react with bionucleophiles such as deoxyguanosine (dG) (12), guanosine (G) (13) and 5'-guanosinemonophosphate (5'-GMP) (14) to form adducts.We describe the regioselective formation of the C-8 adducts of 4-chloroaniline (15), aniline (16), 4-methylaniline (17), and 4-methoxyaniline (18), respectively, , and also of N-(guanosine-8-yl)-4-methylaniline (21) and 8-(4-methylanilino)-5'-guanosinemonophosphate (22).Similar reactions of the N-(acetoxy)arylamines 20, which are very likely to be "ultimate" carcinogens of aromatic amines, lead to the same C-8 adducts 15-18, 21, and 22 in comparable yields.These in vitro reactions thus show that the N-(α-aminoacyloxy)arylamines 10 and 11 react like the N-(acetoxy)anilines 20 as "ultimate" carcinogens.Therefore, the activation of aromatic hydroxylamines by O-α-aminoacylation is of similar quality as by O-acetylation.