Novel UV-Releaser of Arachidonic Acid Based on Nitrophenyl-type Photoremovable Protecting Group

Arachidonic acid (AA) is one of the most important polyunsaturated fatty acids. It is the precursor to a wide range of eicosanoids, which are involved in many signaling cascades in the body. The conversion of arachidonic acid to eicosanoids starts with its liberation from membrane phospholipids by a dedicated enzyme. Here we present photolabile “caged” analog of AA, capable of liberation of the free acid under ultraviolet (UV) light with ~340–365 nm wavelength. This can be used in cell culture studies to mimic the first step in the biosynthesis of eicosanoids. We directly confirm the production of AA using high-performance liquid chromatography (HPLC). Furthermore, we found that novel compound yields 4-times more AA in comparison with previously published alternative. Our results demonstrate that the use of the caged compounds can be used to control the release of AA with UV light. The described caged analogs of AA are likely to be anchored in the membrane and enable light-triggered liberation of the free acid to the cytoplasm. This would be superior to the usual approach using the external addition of AA to cells, which suffers from poor solubility of the acid in culture medium and uncontrolled passage through membrane.