A new synthetic route to nucleotide adducts derived from N-acetylated and unacetylated 4-aminobiphenyl

Abstract

The carcinogen N-acetoxy-N-2-acetylaminofluorene reacts with dG and dG-containing nucleotides to give good yields of the C-8 adducts, but the analogous 4-aminobiphenyl derivative does not. Replacement of the N-acetoxy group by 2,6-dichlorobenzoyloxy circumvents this difficulty. This reaction is shown to be generally applicable, and biphenylamido adducts with dG, d(CpG), d(GpC) and d(ApG) have been prepared. A new, useful deacetylation procedure employing the heterogeneous system sodium carbonate/methanol which leads to the corresponding biphenylamino derivative without appreciable imidazole ring opening is also reported.

Synthesis, characterization and solution properties of ras sequences modified by arylamine carcinogens at the first base of codon 61

“…Hydrolysis of ABPmodified strand A gave similar results. One major peak (Figure 4), responsible for 80% of the total radioactivity, was observed by HPLC a t 280 nm and identified as dG-C8-ABP on the basis of its retention time and UV spectrum (35,49). An additional 8% of the radioactivity, which eluted at -5 min, was attributed to the nucleotide derivative of dG-C8-ABP (F. F. Kadlubar, personal communication).…”

Synthesis ofN-Acetoxy-N-benzoyl-2-aminofluorene, an Ultimate Carcinogen by LTA Oxidation of α-Phenyl-N-(2-aminofluorenyl)nitrone, andN-(2′-Deoxyguanosin-8-yl)-2-aminofluorene

“…Compound 10 was debenzoylated 23 to give product 11. The 1 H NMR peak at d = 8.76 ppm was attributed to the NH proton; and its disappearance upon addition of D 2 O, confirmed the structure 11.…”

“…Compound 11 was prepared by the method of Underwood et al 23 using the heterogeneous system (Na 2 CO 3 -MeOH) for debenzoylation of 10. Spectral data are in good agreement with those of an authentic sample.…”

Synthesis and Characterization of Model Ultimate Carcinogens/Metabolites Derived from Lead Tetraacetate Oxidation of Arylnitrones: 2′-Deoxyguanosine Adducts

“…These compounds were prepared by the method of Underwood et al 13 using heterogeneous system (Na 2 CO 3 /MeOH) for the debenzoylation of 5a-c. Spectral data are in good agreement with an authentic sample. 14,16b…”