Fluorinated functional materials possessing biological activities: gel formation of novel fluoroalkylated end-capped 2-acrylamido-2-methylpropanesulfonic acid polymers under non-crosslinked conditions

Abstract

New fluoroalkylated end-capped 2-acrylamido-2-methylpropanesulfonic acid homopolymers were prepared by reaction of fluoroalkanoyl peroxides with 2-acrylamido-2-methylpropanesulfonic acid (AMPS). Similarly, fluoroalkylated end-capped copolymers were prepared by reaction of fluoroalkanoyl peroxides with AMPS and the comonomers such as trimethylvinylsilane and methyl methacrylate. These thus-obtained fluoroalkylated end-capped AMPS polymers were found to form gels not only in water but also in organic polar solvents such as methanol, ethanol,N,N-dimethylformamide and dimethyl sulfoxide under non-crosslinked conditions. On the other hand, AMPS polymer containing fluoroalkylene units {[-R_F-(AMPS)_q]_p-} could cause no gelation under similar conditions. This suggests that fluoroalkylated end-capped AMPS polymers can cause gelation where strong aggregation of the end-capped fluoroalkyl segments is involved sterically in establishing the physical gel network in these media. Interestingly, these fluoroalkylated end-capped AMPS polymer hydrogels had a strong metal ion binding power. Moreover, it was demonstrated that these fluoroalkylated gelling polymers are potent and selective inhibitors of HIV-1 replication in cell culture. In addition, one of these gelling polymers was found to possess antibacterial activity againstStaphylococcus aureus. Therefore, these fluorinated gelling polymers are suggested to have high potential for new functional materials through their gelling ability and biological activity.