Methyl methanesulfonate

Methyl methanesulfonate
Names
IUPAC name
Methanesulfonic acid methyl ester
Other names
Methyl mesylate; MMS
Identifiers
66-27-3 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:25255 N
ChemSpider 4013 N
ECHA InfoCard 100.000.568
EC Number 200-625-0
KEGG C19181 YesY
MeSH D008741
PubChem 4156
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).
N verify (what is YesYN ?)
Infobox references

Methyl methanesulfonate (MMS) 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 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 1174933Freely accessible. PMID 16009812.
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