Methylnitronitrosoguanidine
From Wikipedia the free encyclopedia
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| Names | |
|---|---|
| Preferred IUPAC name N-Methyl-N′-nitro-N-nitrosoguanidine | |
| Other names 1-Methyl-3-nitro-1-nitrosoguanidine N-Methyl-N-nitroso-N′-nitroguanidine | |
| Identifiers | |
3D model (JSmol) | |
| Abbreviations | MNNG |
| ChemSpider | |
| ECHA InfoCard | 100.000.664 |
| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C2H5N5O3 | |
| Molar mass | 147.09 g/mol |
| Appearance | Yellow crystals |
| Melting point | 118 °C (244 °F; 391 K) (decomposes) |
| reacts violently, slowly hydrolysed | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Methylnitronitrosoguanidine (MNNG[2] or MNG, NTG when referred to colloquially as nitrosoguanidine[3]) is a biochemical tool used experimentally as a carcinogen and mutagen.[1] 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.
One of the earliest uses of methylnitronitrosoguanidine was in 1985. A group of scientists tested whether or not the chemical composition of methylnitronitrosoguanidine would directly affect the growth of tumors and cancer cells in rats.[citation needed]
In the experiment, the cancer cells from a Japanese cancer patient was injected into 8 rats. The biochemical tool and showed a decline of cancer cells in a few of the rats' bodies.
In organic chemistry, MNNG is used as a source of diazomethane when reacted with aqueous potassium hydroxide.[4]
MNNG is a probable human carcinogen listed as an IARC Group 2A carcinogen.[5]
Stability[edit]
MNNG produces diazomethane (known DNA methylating agent) in basic aqueous solutions, and nitrous acid (also mutagenic) in acidic solutions.[6]
References[edit]
- ^ a b Merck Index, 11th Edition, 6017.
- ^ Lawley, P. D.; Thatcher, Carolyn J. (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". Biochemical Journal. 116 (4). Portland Press Ltd.: 693–707. doi:10.1042/bj1160693. ISSN 0306-3283. PMC 1185415. PMID 5435496.
- ^ "Forward and reverse mutagenesis in C. elegans". WormBook. Retrieved 2021-12-01.
- ^ T. Howard Black (1983). "The Preparation and Reactions of Diazomethane" (PDF). Aldrichimica Acta. 16 (1). Archived from the original (PDF) on 2019-02-03. Retrieved 2019-02-02.
- ^ N-METHYL-N'-NITRO-N-NITROSOGUANIDINE (MNNG), International Agency for Research on Cancer
- ^ Hollaender, Alexander (1971). Chemical Mutagens : Principles and Methods for Their Detection Volume 1. Boston, MA: Springer US. p. 188. ISBN 978-1-4615-8966-2. OCLC 851813793.