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the univalent radical CH3- derived from methane (同)methyl_group, methyl radical

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/07/24 19:31:14」(JST)

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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 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]

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.

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1. コリスチン：概要 colistin an overview
2. アシネトバクター感染：治療および予防 acinetobacter infection treatment and prevention
3. グラム陰性桿菌性髄膜炎：治療 gram negative bacillary meningitis treatment
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5. 緑膿菌感染症に対する抗菌薬治療の原則 principles of antimicrobial therapy of pseudomonas aeruginosa infections

English Journal

DNA alkylation lesions and their repair in human cells: Modification of the comet assay with 3-methyladenine DNA glycosylase (AlkD).

Hašplová K, Hudecová A, Magdolénová Z, Bjøras M, Gálová E, Miadoková E, Dušinská M.SourceDepartment of Genetics, Faculty of Natural Sciences, Comenius University, Mlynska dolina, 842 15 Bratislava, Slovakia; Norwegian Institute for Air Research (NILU), PO Box 100, 2027 Kjeller, Norway.
Toxicology letters.Toxicol Lett.2012 Jan 5;208(1):76-81. Epub 2011 Oct 14.
3-Methyladenine DNA glycosylase (AlkD) belongs to a new family of DNA glycosylases; it initiates repair of cytotoxic and promutagenic alkylated bases (its main substrates being 3-methyladenine and 7-methylguanine). The modification of the comet assay (single cell gel electrophoresis) using AlkD enzy
PMID 22019460

Histone h3 lysine 56 acetylation and the response to DNA replication fork damage.

Wurtele H, Kaiser GS, Bacal J, St-Hilaire E, Lee EH, Tsao S, Dorn J, Maddox P, Lisby M, Pasero P, Verreault A.SourceAddress correspondence to Alain Verreault, alain.verreault@umontreal.ca.
Molecular and cellular biology.Mol Cell Biol.2012 Jan;32(1):154-72. Epub 2011 Oct 24.
In Saccharomyces cerevisiae, histone H3 lysine 56 acetylation (H3K56ac) occurs in newly synthesized histones that are deposited throughout the genome during DNA replication. Defects in H3K56ac sensitize cells to genotoxic agents, suggesting that this modification plays an important role in the DNA d
PMID 22025679

No Role of Homologous Recombination in Dealing with β-Lapachone Cytotoxicity in Yeast.

Quevedo O, García-Luis J, Lorenzo-Castrillejo I, Machín F.SourceUnidad de Investigación, Hospital Universitario Nuestra Señora de Candelaria , Carretera del Rosario 145, 38010 Santa Cruz de Tenerife, Spain.
Chemical research in toxicology.Chem Res Toxicol.2011 Dec 19;24(12):2106-8. Epub 2011 Nov 22.
β-Lapachone (β-lap) is a promising antitumoral agent. DNA base oxidation and alkylation are among the expected damages by β-lap. Herein, we have explored the role that the homologous recombination pathway (HR), a critical DNA repair process in Saccharomyces cerevisiae, has in the cytotoxic profil
PMID 22091990

Japanese Journal

Differences in Sensitivity to DNA-damaging Agents between XRCC4- and Artemis-deficient Human Cells

KATSUBE Takanori,MORI Masahiko,TSUJI Hideo,SHIOMI Tadahiro,SHIOMI Naoko,ONODA Makoto
Journal of radiation research 52(4), 415-424, 2011-07-16
… The XRCC4-deficient cells were highly sensitive to etoposide and 5-fluoro-2-deoxyuridine as well as IR, and moderately sensitive to camptothecin, methyl methanesulfonate, cisplatin, mitomycin C, aphidicolin and hydroxyurea, compared to the parental HCT116 cells. …
NAID 10029121959

A method for detecting genetic toxicity using the RNA synthesis response to DNA damage

Morita Yoko,Iwai Shigenori,Kuraoka Isao
The Journal of Toxicological Sciences 36(5), 515-521, 2011
… When we tested chemical agents (camptothecin, etoposide, 4-nitroquinoline-1-oxide, mitomycin C, methyl methanesulfonate, and cisplatin) in HeLa cells by the method, RSI indicative of genomic toxicity was observed in the nucleoli of the tested cells. …
NAID 130001185617

Fission yeast homologs of human XPC and CSB, rhp41 and rhp26, are involved in transcription-coupled repair of methyl methanesulfonate-induced DNA damage

Kanamitsu Kyoichiro,Ikeda Shogo
Genes & Genetic Systems 86(2), 83-91, 2011
… Methyl methanesulfonate (MMS) methylates nitrogen atoms in purines, and predominantly produces 7-methylguanine and 3-methyladenine (3-meA). …
NAID 130000758285

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★リンクテーブル★

リンク元	「MMS」「メチルメタンスルホン酸」
関連記事	「methanesulfonate」

「MMS」

Methyl methanesulfonate
	IUPAC name Methanesulfonic acid methyl ester
	Other names Methyl mesylate; MMS
Identifiers
CAS number	66-27-3
PubChem	4156
ChemSpider	4013
EC number	200-625-0
KEGG	C19181
MeSH	D008741
ChEBI	CHEBI:25255
Jmol-3D images	Image 1
	SMILES COS(=O)(=O)C ;
	InChI InChI=1S/C2H6O3S/c1-5-6(2,3)4/h1-2H3 ; Key: MBABOKRGFJTBAE-UHFFFAOYSA-N InChI=1/C2H6O3S/c1-5-6(2,3)4/h1-2H3; Key: MBABOKRGFJTBAE-UHFFFAOYAK ;
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)
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	Infobox references