pH-dependent interaction between acetaminophen and dioleoylphosphatidylcholine membranes

Abstract

Acetaminophen may cause acute liver failure due to overdose. Understanding the processes of adsorption and incorporation of acetaminophen into cell membranes is crucial for elucidating the mechanisms of action and toxicity of acetaminophen. We investigated the interaction between acetaminophen and a model cell membrane (dioleoylphosphatidylcholine) using surface pressure–area isotherms. Acetaminophen was incorporated into the dioleoylphosphatidylcholine membrane under basic conditions, increasing the dioleoylphosphatidylcholine molecular area. The acetaminophen uptake was explained by the adsorption of hydroxide ions onto the lipid membrane and electrostatic interaction between acetaminophen and lipid molecules under basic conditions.