The Stabilization Mechanism of Acylcholinesters in Aqueous Solution by Sodium Lauryl Sulfate

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Acylcholinesters (C3 to C12) were synthesized and the stabilization effect by sodium lauryl sulfate (SLS) against hydrolysis were studied at pH 7.7. 1) The apparent distribution of cholinesters between aqueous and micellar phases of SLS solution was measured by condensation method. The correlation between the apparent distribution and the magnitude of stabilization effect was observed. 2) The hydrolytic rate of cholinesters was suppressed from 1/2 to 1/250 by the addition of 0.5% SLS. The longer the acyl chain length of cholinesters, resulted the greater the stabilization effects of SLS. There was no apparent relation between chain length and rate constant without SLS. 3) When cholinesters were mixed with SLS in aqueous solution, transient turbidity formation was observed, which was considered to be due to the metathesis. A complete dissociation of three salts concerning to the metathesis was proved by the determination of conductivity. 4) The solubility of acylcholine iodides in water was high and that of in organic solvents was limited by the polarity of the cholinesters regardless of their acylchain length. Therefore, the mechanism of stabilization from hydrolysis was considered via the solubilization of acylcholine-lauryl sulfate ion pair into micellar phase. 5) From the correlation mentioned above, it was presumed that the site of solubilization and/or the dimentional change of micelle might affect the stabilization from hydrolysis.

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