Chemistry:Methyl methanesulfonate
| |
| |
| Names | |
|---|---|
| Preferred IUPAC name
Methyl methanesulfonate | |
Other names
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChemSpider | |
| EC Number |
|
| KEGG | |
| MeSH | D008741 |
PubChem CID
|
|
| UNII | |
| |
| |
| Properties | |
| CH 3SO 2OCH 3 | |
| Molar mass | 110.13 g·mol−1 |
| Appearance | Colorless liquid |
| 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
|
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
| |
| 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] Its chemical formula is CH
3–SO
2–O–CH
3. It is a colorless liquid.
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 one of the non-carbon bound oxygen atoms of 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
- ↑ Scorecard Pollution Information Site: Methyl Methanesulfonate Scorecard.org Accessed 14 Feb 08
- ↑ Medical.Webends.com: Methyl Methanesulfonate Medical.webends.com Accessed 14 Feb 08
- ↑ 3.0 3.1 "Methyl methanesulfonate (MMS) produces heat-labile DNA damage but no detectable in vivo DNA double-strand breaks". Nucleic Acids Research 33 (12): 3799–3811. 2005. doi:10.1093/nar/gki681. PMID 16009812.
 |  |
