Methyl methanesulfonate
Methyl mesylate
MMS
- 66-27-3 checkY
- CHEBI:25255 ☒N
- 4013 ☒N
- 200-625-0
- AT5C31J09G checkY
- InChI=1S/C2H6O3S/c1-5-6(2,3)4/h1-2H3 ☒NKey: MBABOKRGFJTBAE-UHFFFAOYSA-N ☒N
- InChI=1/C2H6O3S/c1-5-6(2,3)4/h1-2H3Key: MBABOKRGFJTBAE-UHFFFAOYAK
- COS(=O)(=O)C
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]
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 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
[edit ]- Dimethyl sulfite, a chemical with the same molecular formula but different arrangement
References
[edit ]- ^ Scorecard Pollution Information Site: Methyl Methanesulfonate Scorecard.org Accessed 14 Feb 08
- ^ Medical.Webends.com: Methyl Methanesulfonate Archived 2008年02月15日 at the Wayback Machine Medical.webends.com Accessed 14 Feb 08
- ^ a b 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 1174933 . PMID 16009812.