Methyl methanesulfonate
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Methyl methanesulfonate
| Methyl methanesulfonate | |
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Methanesulfonic acid methyl ester |
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Other names
Methyl mesylate; MMS |
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| Identifiers | |
| CAS number | 66-27-3  |
| PubChem | 4156 |
| KEGG | C19181 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C2H6O3S |
| Molar mass | 110.13 g/mol |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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
- ^ Scorecard Pollution Information Site: Methyl Methanesulfonate Scorecard.org Accessed 14 Feb 08
- ^ Medical.Webends.com: Methyl Methanesulfonate Medical.webends.com Accessed 14 Feb 08
- ^ 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.
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