SYNTHESIS OF FLUOROALKYL END-CAPPED OLIGOMERS CONTAINING PENDANT PHOSPHINIC AND PHOSPHONIC ACID SEGMENTS—APPLICATION TO NOVEL FLUORINATED BIOACTIVE POLYMERS POSSESSING ANTIBACTERIAL AND ANTI-HIV-1 ACTIVITIES

Abstract

A variety of fluoroalkyl end-capped homo- and co-oligomers containing pendant phosphinic acid segments were prepared by the reactions of fluoroalkanoyl peroxides with 3-acryloxypropylbutylphosphinic acid (APBPA) [or 3-acryloxypropyloctylphosphinic acid (APOPA)] and comonomers such as N,N-dimethylacrylamide (DMAA) and acrylic acid (ACA). These fluorinated APBPA and APOPA homo-oligomers thus obtained were insoluble in water but were soluble in common organic solvents, and were able to reduce the surface tension of m-xylene quite effectively. Fluorinated APBPA- and APOPA cooligomers were in general soluble in water and common organic solvents, and exhibited a good surfactant property against water. In addition, PMMA [poly(methyl methacrylate)] surface modified with these fluorinated oligomers containing pendant phosphinic acid segments was found to exhibit a strong oleophobicity imparted by fluorine at the surface. Similarly, fluoroalkyl end-capped homooligomers containing pendant phosphonic acid segments were prepared by the reactions of fluoroalkanoyl peroxides with 3-acryloxypropylphosphonic acid (APPA) under mild conditions. These obtained fluorinated oligomers containing pendant phosphonic acid segments were shown to have no solubility in water and organic solvents; however, these fluorinated oligomers could cause a gelation in water. Of particular interest, fluorinated oligomers containing pendant phosphinic acid segments were found to exhibit strong antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa. Moreover, these fluorinated oligomers were also demonstrated to exhibit a potent and selective anti-HIV-1 (human immunodeficiency virus type 1) activity in vitro.