Methyl methanesulfonate

Methyl methanesulfonate
Names
Preferred IUPAC name
Methyl methanesulfonate
Other names
Methanesulfonic acid methyl ester
Methyl mesylate
MMS
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.568
EC Number 200-625-0
KEGG
MeSH D008741
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
 Ethyl methanesulfonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

Chemical reactions with DNA

MMS 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 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

Dimethyl sulfite, a chemical with the same molecular formula but different arrangement

References

  1. ↑ Scorecard Pollution Information Site: Methyl Methanesulfonate Scorecard.org Accessed 14 Feb 08
  2. ↑ Medical.Webends.com: Methyl Methanesulfonate Archived 2008-02-15 at the Wayback Machine. Medical.webends.com Accessed 14 Feb 08
  3. 1 2 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.
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