Synthesis and surfactant properties of fluoroalkylated sulfonic acid oligomers as a new class of human immunodeficiency virus inhibitors

Abstract

New fluoroalkylated 2-(methacryloxy ) ethane sulfonic acid homo-oligomers were prepared in excellent to moderate yields by the reactions of fluoroalkanoyl peroxides with 2-(methacryloxy) ethane sulfonic acid (MES) under very mild conditions. These fluoroalkylated oligomers were easily soluble not only in water but also in polar solvents such as methanol, ethanol, N,N-dimethylformamide and dimethyl sulfoxide. These oligomers were able to reduce the surface tension of water to around 18 mN m −1, and had a clear breakpoint resembling a CMC (critical micelle concentration). These fluoroalkylated homo-oligomers were also shown to be potent and selective inhibitors of human immunodeficiency virus type 1 (HIV-1 ) in vitro, and were about 10-times more inhibitory to HIV-1 than dextran sulfate. Furthermore, a series of fluoroalkylated 2-( methacryloxy )ethanesulfonic acid co-oligomers containing dimethylsilicone, trimethylsilyl and alkyl segments were prepared by the reactions of fluoroalkanoyl peroxides with MES and the corresponding monomers. These co-oligomers had a similar solubility and anti-HIV-1 activity to those of the corresponding homo-oligomer.