Synthesis of an Unnatural Phospholipid for use in Pulmonary Surfactant Therapy

Best, Natasha
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University of Guelph

Neonatal respiratory distress syndrome (RDS) is a disease that affects premature infants born prior to 32 weeks gestation. The main cause is a deficiency in pulmonary surfactant due to immature type II pneumocyte cells found in the alveoli. These cells are not capable of producing the required surfactant which normally functions to reduce the surface tension at the air-liquid interface of the lungs, as well as reduce the work of breathing and prevent alveolar collapse. A current treatment method for RDS is exogenous surfactant replacement therapy involving application of an exogenous surfactant preparation directly into the lungs of premature infants. Current surfactant preparations are animal-derived and very costly. Synthetic preparations, on the other hand, are an attractive alternative. The goal of this research is to synthesize a diether phosphonolipid analogue of dipalmitoyl phosphatidylcholine (DPPC), designated DEPN-8. When incorporated into a synthetic exogenous surfactant mixture, DEPN-8 exhibits greater adsorption and surface activity compared to its natural counterpart, DPPC. The synthesis of several components related to the re-tailored synthesis of DEPN-8 will be presented and discussed below.

phospholipid, phosphonolipid, surface tension, surfactant, respiratory distress syndrome