Sodium 2-mercaptoethanesulfonate

Sodium 2-mercaptoethanesulfonate (MESNA) [19767-45-4] M 164.2, pKj <0 (SOj ), pK 9.53 (SH). It can be recrystd from H2O and does not melt below 250°. It can be purified further by converting to the free acid by passing a 2M soln through an ion exchange (Amberlite IR-120) column in the acid form, evaporating the eluate in a vacuum to give the acid as a viscous oil (readily dec) which can be checked by acid and SH titration. It is then dissolved in H2O, carefully neutralised with aqueous NaOH, evaporated and recrystd from H2O [7 Am Chem Soc 77 6231 1955]. 

ACE-I, angiotensin-converting enzyme inhibitor ADH, antidiuretic hormone (or vasopressin) ARB, angiotensin II receptor blocker, MESNA, sodium 2-mercaptoethanesulfonate TCA, tricyclic antidepressant Ul, urinary incontinence SUI, stress urinary incontinence UUI, urge urinary incontinence. 

SCHEME 11.6 Glycopeptide thioesterification via O-to-S acyl shift. MESNa, sodium 2-mercaptoethanesulfonate. 

The activity of sulfur towards platinum complexes has led to investigation of so-called rescue agents to ameliorate the side effects of platinum therapy, without compromising its anti-tumor activity. These nucleophilic sulfur compounds include sodium thiosulfate (STS), sodium diethyldithio-carbamate (Naddtc), (S)- 2-[(3-aminopropyl)amino]ethyl phosphorothioic acid (WR-2721, Ethyol , amifostine), glutathione (GSH), methionine, thiourea, cysteine, -acetylcysteine, penicillamine, biotin, sulfathiazole, sodium 2-mercaptoethanesulfonate (mesna), and its dimer (di)mesna (BNP-7787). The protective effect of these compounds is either due to prevention, or reversal of Pt-S adducts in proteins. Some of the more promising of the above-mentioned compounds (see Fig. 1) will be discussed below. 

Fig. 4 Chemical structure of sodium 2-mercaptoethanesulfonate (4) (MESNA) used to catalyze the native chemical ligation on the liposome surface, as described by Reulen et al. [109]...

Although the preparation of p-mercaptoethanesulfonic acid through the ammonolysis reaction is the preferred method, it is also possible to prepare the sulfonic acid by the sodium hydroxide hydrolysis of p-S-thiuronium... 

Figure 2. Upper Gradient separation of o-phthalaldehyde derivatives of 11 thiols and sodium sulfite according to Mopper and Delmas Peaks (1) sodium sulfite (100 pmol) (2) glutathione (7 pmol) (3) thloglycollate (200 pmol) (4) N-acetylcysteine (7 pmol) (5) 2-mercaptoethanesulfonate (Co-M) (10 pmol) (6) 3-mercaptoproplonate (10 pmol) (8) monothloglycerol (10 pmol) (9) 2 mercaptoethanol (10 pmol) (10) methanethiol (15 pmol) (11) ethanethlol (10 pmol) (12) 2-propanethlol (15 pmol) (13) 1 propanethlol (15 pmol). Middle Thiols In porewater in reducing sediment slurry from Biscayne Bay. Porewater water was filter-sterilized prior to derlvatlzatlon. Peak 7 sulfide (Note response factor is about 200 times lower than for thiols). Lower reagent blank in porewater matrix.

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