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Anti- and Pro-Oxidant Properties of Sodium 2-Mercaptoethane Sulphonate (Mesna)

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The OH and the NO2 radicals generated pulse radiolytically in N2O-saturated aqueous solution at pH 8-8.5 oxidize Mesna to form the corresponding thiyl radicals which on reaction with thiolate ions form an RSSR- type of transient with λmax = 420 nm. The rate constants for the formation of these transients were determined. In the absence of O2 at pH = 6, the RS radicals formed show an absorption maximum at 360 nm and an ε = 200 ± 50 dm3 mol-1 cm-1. The rate constant k ('OH + RSH) was 6 x 109 dm3 mol-1 s-1 as determined from competition kinetics. In the presence of O2 the Mesna thiyl radical was seen to rapidly add oxygen to form an RSOO' type of species with λmax = 535 nm, e = 700±50 dm3 mol-1 cm-1 and k ( RS + O2) = 1.3 x 108 dm3 mol-1 s-1. Both the RS and the RSOO radicals formed by the oxidation of Mesna were able to abstract H-atoms from ascorbate ions and k(RS' + AH-) ≅ k(RSOO + AH-) ≅ 6 - 7 x 108 dm3 mol-1 s-1. Moderately strong oxidants like CCl3OO and the (CH3 )3CO radicals, having a reduction potential of +1.4-1.6 V vs NHE were unable to oxidize Mesna. The results thus reflect on the pro- and anti-oxidant properties of Mesna.

Affiliations: 1: Chemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400 085, India


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