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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/04/07 17:22:49」(JST)

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Structural formula of the mesylate anion

Ball-and-stick model of the mesylate anion

In chemistry, a mesylate is any salt or ester of methanesulfonic acid (CH₃SO₃H). In salts, the mesylate is present as the CH₃SO₃⁻ anion. When modifying the International Nonproprietary Name of a pharmaceutical substance containing the group or anion, the correct spelling is mesilate (as in imatinib mesilate, the mesylate salt of imatinib).^[1]

Mesylate esters are a group of organic compounds that share a common functional group with the general structure CH₃SO₂O–R, abbreviated MsO–R, where R is an organic substituent. Mesylate is considered a leaving group in nucleophilic substitution reactions.

Preparation

Mesylates are generally prepared by treating an alcohol and methanesulfonyl chloride in the presence of a base, such as triethylamine.^[2]

Mesyl

Related to mesylate, is the mesyl, an abbreviation for methanesulfonyl or CH₃SO₂ (Ms) functional group. For example, methanesulfonyl chloride is often referred to as mesyl chloride. Whereas mesylates are often hydrolytically labile, mesyl groups, when attached to nitrogen are robust with respect to hydrolysis.^[3] This functional group appears in a variety of medications, particularly cardiac (i.e. “antiarrhythmic”) but as sulfonamide moiety. Examples include Sotalol, ibutilide, sematilide, Dronedarone, Dofetilide, E-4031, and Bitopertin .

References

^ World Health Organization (February 2006). "International Nonproprietary Names Modified". INN Working Document 05.167/3. WHO. Retrieved 5 December 2008.
^ Rick L. Danheiser, Yeun-Min Tsai, and David M. Fink (1966). "A General Method for the Synthesis of Allenylsilanes: 1-Methyl-1-(trimethylsilyl)allene". Org. Synth. doi:10.15227/orgsyn.066.0001. (a procedure illustrating the use of mesylates).
^ Valerie Vaillancourt, Michele M. Cudahy, Matthew M. Kreilein and Danielle L. Jacobs "Methanesulfonyl Chloride" in E-EROS Encyclopedia for Reagents in Organic Synthesis. doi:10.1002/047084289X.rm070.pub2

UpToDate Contents

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English Journal

Simultaneous determination of alkyl mesilates and alkyl besilates in finished drug products by direct injection GC/MS.

Wollein U, Schramek N.SourceBavarian Health and Food Safety Authority, Veterinärstr. 2, 85764 Oberschleißheim, Germany.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2012 Jan 23;45(1-2):201-4. Epub 2011 Nov 17.
We report a specific, fast and feasible method for the simultaneous determination of methyl mesilate (MMS), ethyl mesilate (EMS), isopropyl mesilate (IMS), methyl besilate (MBS) and ethyl besilate (EBS) in finished drug products by GC/MS. Sample preparation was carried out by liquid extraction. The
PMID 22115865

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.
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

Parahalogenated Phenols Accelerate the Photochemical Release of Nitrogen Oxides from Frozen Solutions Containing Nitrate.

Abida O, Osthoff HD.AbstractThe photolysis of nitrate anion (NO3-) contained in surface ice and snow can be a regionally significant source of gas phase nitrogen oxides and affect the composition of the planetary boundary layer. In this study, the photochemical release of nitrogen oxides from frozen solutions containing NO3- in the presence of organic compounds was investigated. Gas phase nitrogen oxides were quantified primarily by NO-O3 chemiluminescence detection of NO and NOy (= NO + NO2 + HONO + HNO3 + ΣPAN + ΣAN ...) and cavity ring-down spectroscopy of NO2 and total alkyl nitrates (ΣAN). The photochemical production of gas phase NOy was suppressed by the presence of formate, methanesulfonate, toluene or phenol. In contrast, para-halogenated phenols (in the order of Cl>Br>F) promoted the conversion of NO3- to gas phase NOy, rationalized by acidification of the ice surface.
The journal of physical chemistry. A.J Phys Chem A.2012 Jan 3. [Epub ahead of print]
The photolysis of nitrate anion (NO3-) contained in surface ice and snow can be a regionally significant source of gas phase nitrogen oxides and affect the composition of the planetary boundary layer. In this study, the photochemical release of nitrogen
PMID 22214212

Japanese Journal

Tomato TILLING Technology: Development of a Reverse Genetics Tool for the Efficient Isolation of Mutants from Micro-Tom Mutant Libraries

Okabe Yoshihiro,Asamizu Erika,Saito Takeshi [他]
Plant and cell physiology 52(11), 1994-2005, 2011-11
… DNA pools were constructed from 3,052 ethyl methanesulfonate (EMS) mutant lines treated with 0.5 or 1.0% EMS. …
NAID 40019070970

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

MORITA Yoko,IWAI Shigenori,KURAOKA Isao
Journal of toxicological sciences 36(5), 515-521, 2011-10-01
… 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 10029481056

Related Pictures

★リンクテーブル★

リンク元	「メシル酸塩」「メタンスルホン酸塩」「mesilate」「メタンスルホン酸」「mesylate」
拡張検索	「trifluoromethanesulfonate」「colistin sodium methanesulfonate」「methyl methanesulfonate」「ethyl methanesulfonate」