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Methylnitronitrosoguanidine

N-Methyl-N-nitroso-N′-nitroguanidine

Methylnitronitrosoguanidine (MNNG or MNG, NTG when referred to colloquially as nitrosoguanidine) is a biochemical tool used experimentally as a carcinogen and mutagen. It acts by adding alkyl groups to the O6 of guanine and O4 of thymine, which can lead to transition mutations between GC and AT. These changes do not cause a heavy distortion in the double helix of DNA and thus are hard to detect by the DNA mismatch repair system.

In organic chemistry, MNNG is used as a source of diazomethane when reacted with aqueous potassium hydroxide.

MNNG is a probable human carcinogen listed as an IARC Group 2A carcinogen.

Stability

MNNG produces diazomethane, a known methylating agent of DNA and other substrates, in basic aqueous solutions, and nitrous acid, a mutagen, in acidic solutions.

References

References

  1. ''[[Merck Index]]'', 11th Edition, '''6017'''.
  2. (1970-02-01). "Methylation of deoxyribonucleic acid in cultured mammalian cells by ''N''-methyl-''N''′-nitro-''N''-nitrosoguanidine. The influence of cellular thiol concentrations on the extent of methylation and the 6-oxygen atom of guanine as a site of methylation". Portland Press Ltd..
  3. "Forward and reverse mutagenesis in ''C. elegans''".
  4. T. Howard Black. (1983). "The Preparation and Reactions of Diazomethane". Aldrichimica Acta.
  5. [http://www.inchem.org/documents/iarc/suppl7/mnng.html ''N''-METHYL-''N''{{'-NITRO-''N''-NITROSOGUANIDINE (MNNG)], [[International Agency for Research on Cancer]]
  6. Hollaender, Alexander. (1971). "Chemical Mutagens: Principles and Methods for Their Detection". [[Springer Publishing]].
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iarc-group-2a-carcinogens mutagens nitroguanidines nitrosoguanidines
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