Methyl methanesulfonate

Methyl methanesulfonate
IUPAC name Methanesulfonic acid methyl ester
Other names Methyl mesylate; MMS
Identifiers
CAS number	66-27-3 Y
PubChem	4156
KEGG	C19181 Y
Jmol-3D images	Image 1
SMILES COS(=O)(=O)C
Properties
Molecular formula	C2H6O3S
Molar mass	110.13 g/mol
Y methanesulfonate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 on N⁷-deoxyguanine and N³-deoxyadenine. 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. ^ ^{a b} Lundin C, North M, Erixon K, Walters K, Jenssen D, Goldman ASH and 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1174933.