Synthesis and characterization of active ester‐functionalized fluorescent polymers: New materials for protein conjugation

Abstract

AbstractA novel fluorescent monomer, N‐acryloylamido‐ethyl‐2‐(1‐pyrene)‐butyrylamidophenylpropionyl amide, was synthesized and copolymerized with N‐vinylpyrrolidone and N‐acryloxysuccinimide to obtain a series of functional fluorescent terpolymers. Fourier transform infrared spectroscopy, 1H‐NMR spectroscopy, gel permeation chromatography, ultraviolet–visible spectroscopy, and fluorescence spectroscopy were used to characterize these polymers. The protein–polymer conjugation was examined by sodium dodecyl sulfate/polyacrylamide gel electrophoresis. The results indicate that conjugate formation between the terpolymers and protein resulted from the succinimidyl ester groups, which led to the formation of stable amido linkages with proteins. The results of the interactions with the COS‐7 cell demonstrate that these synthesized terpolymers could attach to the surfaces of cells and emit fluorescence. These terpolymers with succinimidyl ester groups and high luminescence could be used as new materials for protein conjugation. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008