Inhibitory effect of DNA structure on the efficiency of reaction of guanosine moieties with a nitrenium ion

Fast reactions of arylnitrenium ions with amino acids and proteins: a laser flash photolysis study

“…[4][5][6][7] Subsequent kinetic studies using both competitive trapping and laser flash photolysis (LFP) confirmed this general mechanism. 6,[8][9][10] In particular those arylnitrenium ions derived from highly carcinogenic amines were found to react very rapidly with guanine, but to be far less reactive toward water.…”

A review of emission products from bioethanol and its blends with gasoline. Background for new guidelines for emission control

“…The mechanism of toxicity by amine-containing compounds lies in the oxidation of the amine group which leads to the formation of the nitrenium form [117]. Nitrenium ions are sources of great toxicological con- cern, as they readily form adducts with DNA [118] following the reaction shown in Fig. 5.…”

Aryl Nitrenium Ions in Aqueous Solution

“…26 Novak and Kennedy showed that the self-complimentary oligomer d-ATGCAT reacts with 64h. 168 Trapping of 64h by single-stranded oligomer was about 30% as efficient as trapping by dG, whereas trapping by double-stranded oligomer was undetectable within the error limits of the method. Small amounts of trapping by the double-stranded form would be difficult to detect because of the efficient trapping by the single-stranded oligomer.…”

“…At 0 C k pUC19 /k s , the average selectivity ratio per dG moiety in pUC19, 260 M À1 , was about 2% of k dG /k s at that temperature. 168 On average, dG residues in double-stranded DNA do not efficiently trap nitrenium ions. The tertiary structure of double-helical DNA inhibits the formation of the C-8 adduct.…”