Propranolol is shown to undergo lipidation reactions in three types of lipid membrane: (1) synthetic single-component glycerophospholipid liposomes; (2) liposomes formed from complex lipid mixtures extracted from E. coli or liver cells; and (3) in cellulo in Hep G2 cells. Fourteen different lipidated propranolol homologues were identified in extracts from Hep G2 cells cultured in a medium supplemented with propranolol. This isolation of lipidated drug molecules from liver cells demonstrates a new drug reactivity in living systems. Acyl transfer from lipids to the alcoholic group of propranolol was favoured over transfer to the secondary amine. Migration of acyl groups from the alcohol to the amine was diminished. Other drugs that were examined did not form detectable levels of lipidation products, but many of these drugs did affect the lysolipid levels in model membranes. The propensity for a compound to induce lysolipid formation in a model system was found to be a predictor for phospholipidosis activity in cellulo.

中文翻译：

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药物与脂膜的溶解反应†

普萘洛尔被证明在三种类型的脂膜中发生脂化反应：（1）合成单组分甘油磷脂脂质体；(2)由从大肠杆菌或肝细胞中提取的复杂脂质混合物形成的脂质体；(3) Hep G2 细胞中的纤维素。在补充普萘洛尔的培养基中培养的 Hep G2 细胞的提取物中鉴定出 14 种不同的脂化普萘洛尔同系物。从肝细胞中分离脂质化药物分子证明了生命系统中的新药物反应性。酰基从脂质转移到普萘洛尔的醇基团比转移到仲胺更有利。酰基从醇到胺的迁移减少。所检查的其他药物没有形成可检测水平的脂化产物，但其中许多药物确实影响模型膜中的溶血脂水平。人们发现，化合物在模型系统中诱导溶血脂形成的倾向是纤维素中磷脂沉积活性的预测因子。