Synthesis of phosphoester compounds using lactic acid for encapsulation of paclitaxel

Abstract

Background/Aim: In the use of paclitaxel, side-effects caused by itself or solubilizing agents have become a major obstacle. In this study we aimed to synthesize biocompatible and degradable compounds for micelles to be used as carriers for paclitaxel. Materials and Methods: Methoxypolyethylene glycol-lactate was obtained from methyl lactate and methoxypolyethylene glycol having a molecular weight of 350. Monoalkoxy phosphoryl chlorides were obtained from phosphoryl chloride and four kinds of linear alcohols. Then, four kinds of alkyl di(methoxypolyethylene glycol-lactate) phosphates were obtained from them. Results: The results of 1H NMR spectroscopy showed that alkyl di(methoxypolyethylene glycol-lactate) phosphates were successfully synthesized. When 1-dodecanol, 1-hexadecanol, 1-octadecanol, and 1-eicosanol were used as side chains, the yields were 73.5±4.2, 69.1±3.6, 72.2±2.8, and 71.8±3.7%, respectively. The spectrum of 31P NMR suggested the existence of optical isomers. Conclusion: Four kinds of phosphoester compounds for micelle preparations were synthesized using lactic acid.