Methyl methanesulfonate

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Methyl methanesulfonate
Skeletal formula Ball-and-stick model
Identifiers
CAS number 66-27-3 YesY
PubChem 4156
ChemSpider 4013 N
EC number 200-625-0
KEGG C19181 YesY
MeSH D008741
ChEBI CHEBI:25255 N
Jmol-3D images Image 1
Properties
Molecular formula C2H6O3S
Molar mass 110.13 g/mol
Density 1.3 g/mL at 25 °C
Boiling point 202-203 °C
Related compounds
Related compounds Ethyl methanesulfonate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

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[edit]

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

References[edit]

  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.