Reduced hydrolytic lability of epoprostenol in the presence of cationic micelles.
The rapid hydrolysis of epoprostenol to 6-keto-prostaglandin F1 alpha is hydronium ion-catalyzed even at pH 10 or higher. In the presence of 1.0% hexadecyltrimethylammonium chloride, the rate was reduced significantly (1580-fold at pH 2 and 283-fold at a physiological pH). This decrease in the hydrolysis rate is attributed to two causes: favorable partitioning of epoprostenol in the micellar phase and electrostatic repulsion between the hydronium ion and the cationic micellar surface.
D002384:Catalysis; D002412:Cations; D011464:Epoprostenol / Q000032:analysis*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D008823:Micelles; D011453:Prostaglandins / Q000032:analysis*; D013501:Surface-Active Agents
D002412:Cations; D008823:Micelles; D011453:Prostaglandins; D013501:Surface-Active Agents; D011464:Epoprostenol