Ascorbate-Nitrite Reaction: Possible Means of Blocking the Formation of Carcinogenic N-Nitroso Compounds

@article{Mirvish1972AscorbateNitriteRP,
  title={Ascorbate-Nitrite Reaction: Possible Means of Blocking the Formation of Carcinogenic N-Nitroso Compounds},
  author={Sidney S. Mirvish and Lawrence Wallcave and Micheal C. Eagen and Philippe Shubik},
  journal={Science},
  year={1972},
  volume={177},
  pages={65 - 68}
}
The formation of carcinogenic N-nitroso compounds by the chemical reaction between nitrous acid and oxytetracycline, morpholine, piperazine, N-methylaniline, methylurea, and (in some experiments) dimethylamine was blocked by ascorbic acid. The extent of blocking depended on the compound nitrosated and on the experimental conditions. Urea and ammonium sulfamate were less effective as blocking agents. The possibility of in vivo formation of carcinogenic N-nitroso compounds from drugs could be… Expand
Accelerating effect of ascorbic acid on N-nitrosamine formation and nitrosation by oxyhyponitrite.
The reaction of nitrite ion with ascorbic acid and its effect on the rate of nitrosation of secondary amines have been investigated by differential pulse polarography in aqueous acidic solution.Expand
N-nitrosation and N-nitration of morpholine by nitrogen dioxide: inhibition by ascorbate, glutathione and alpha-tocopherol.
TLDR
Ascorbate anion and glutathione were found to inhibit the aqueous reaction between nitrogen dioxide (NO2) and morpholine (MOR) and thereby prevented the formation of N-nitrosomorpholine (NMOR), and may play an important role in the prevention of carcinogen formation in the lung due to inhaled NO2. Expand
BLOCKING THE FORMATION OF N‐NITROSO COMPOUNDS WITH ASCORBIC ACID IN VITRO AND IN VIVO *
  • S. Mirvish
  • Chemistry, Medicine
  • Annals of the New York Academy of Sciences
  • 1975
TLDR
It would be useful to be able to prevent the formation of NOcompounds in food and in vivo, since a number of readily nitrosated drugs are administered orally in largc doses, their possible nitrosation in vivo is particularly disturbing. Expand
Synergistic effect of chlorogenic acid and thiocyanate on in vitro formation of N-methyl-N-nitrosoaniline under physiological conditions.
Abstract The rate of formation of N -methyl- N -nitrosoaniline (NMNA) from nitrite and N -methylaniline in the presence of chlorogenic acid and/or thiocyanate at levels likely to be encountered inExpand
The effects of ascorbic acid and sorbic acid on N-nitrosamine formation in a heterogeneous model system
The effects of competitive nitrosation by ascorbic acid and sorbic acid on N-nitrosamine formation were studied in a heterogeneous protein-based model system containing a 20% non-aqueous phase. TheExpand
Inhibition of nitrosamine formation in vitro by sorbic acid.
TLDR
Against the formation of N -nitrosomorpholine, the inhibitory action of sorbic acid was weaker than that of ascorbic Acid, and unlike the latter acid, sorbics acid had no inhibitory effect on the nitrosation of N-methylaniline. Expand
REACTION OF NITRITE WITH VITAMINS C AND E
TLDR
Two compounds in particular, ascorbic acid and a-tocopherol, have the unique property of being both vitamins and effective blocking agents for nitrosation reactions, and it is shown how the pair can synergistically inhibitNitrosation in multiphase systems, a desirable characteristic for foods and for the lumen of the gastrointestinal tract. Expand
A study of the competitive nitrosations of pyrrolidine, ascorbic acid, cysteine and p‐cresol in a protein‐based model system
The effects of competitive C- and S-nitrosations on the formation of nitrosopyrrolidine were studied in a protein-based model system. The results obtained were compared with those of the analogousExpand
Carcinogenic and Mutagenic N-Nitroso Compounds
N-nitroso compounds have been known since about 1860 when the preparation of dimethylnitrosamine was first described. They can be formed easily by interaction of secondary or tertiary amino compoundsExpand
Inhibition of the bacterial mutagenicity of N-methyl-N'-nitro-N-nitrosoguanidine by ascorbic acid and ascorbyl palmitate.
TLDR
A comparative study of the antioxidative activity of the investigated substances in the methyl oleate (MO) system has demonstrated that AA and its derivatives have pro-oxidant properties within the limits of the concentrations studied. Expand
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