Methyl methanesulfonate (MMS), also known as methyl mesylate, is an alkylating agent and a carcinogen. It is also a suspected reproductive toxicant, and may also be a skin/sense organ toxicant.[1] It is used in cancer treatment.[2]
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| Names | |||
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| Preferred IUPAC name
Methyl methanesulfonate | |||
| Other names
Methanesulfonic acid methyl ester
Methyl mesylate MMS | |||
| Identifiers | |||
3D model (JSmol)
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| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.000.568 | ||
| EC Number |
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| KEGG | |||
| MeSH | D008741 | ||
PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| C2H6O3S | |||
| Molar mass | 110.13 g/mol | ||
| Density | 1.3 g/mL at 25 °C | ||
| Boiling point | 202 to 203 °C (396 to 397 °F; 475 to 476 K) | ||
| Related compounds | |||
Related compounds
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Ethyl methanesulfonate, dimethyl sulfone, dimethyl sulfate | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical reactions with DNA
editMMS methylates DNA predominantly on N7-deoxyguanosine and N3-deoxyadenosine, and to a much lesser extent also methylates at other oxygen and nitrogen atoms in DNA bases, and also methylates one of the non-carbon bound oxygen atoms of the phosphodiester linkage. Originally, this action was believed to directly cause double-stranded DNA breaks, because homologous recombination-deficient cells are particularly vulnerable to the effects of MMS.[3] However, it is now believed that MMS stalls replication forks, and cells that are homologous recombination-deficient have difficulty repairing the damaged replication forks.[3]
See also
edit- Dimethyl sulfite, a chemical with the same molecular formula but different arrangement
References
edit- ^ Scorecard Pollution Information Site: Methyl Methanesulfonate Scorecard.org Accessed 14 Feb 08
- ^ Medical.Webends.com: Methyl Methanesulfonate Archived 2008-02-15 at the Wayback Machine Medical.webends.com Accessed 14 Feb 08
- ^ a b Lundin C, North M, Erixon K, Walters K, Jenssen D, Goldman AS, Helleday T (2005). "Methyl methanesulfonate (MMS) produces heat-labile DNA damage but no detectable in vivo DNA double-strand breaks". Nucleic Acids Research. 33 (12): 3799–3811. doi:10.1093/nar/gki681. PMC 1174933. PMID 16009812.