Fluorescent Polyvinylphosphonate Bioconjugates for Selective Cellular Delivery

To date, many poly(ethylene glycol) (PEG) and poly(N‐isopropylacrylamide) (PNIPAAm) biomolecule conjugates have been described, but they often show long response times, are not bio‐inert, or lose function in biological fluids. Herein, we present a modular synthetic approach to generate polyvinylphos...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-02, Vol.24 (11), p.2584-2587
Main Authors: Schwarzenböck, Christina, Schaffer, Andreas, Nößner, Elfriede, Nelson, Peter J., Huss, Ralf, Rieger, Bernhard
Format: Article
Language:English
Subjects:
Chemistry
Cholesterol
Conjugates
Conjugation
delivery
Fluorescence
fluorescent polymer bioconjugate
Folic acid
Isopropylacrylamide
Phase transitions
Polyethylene glycol
Polymers
selective cellular targeting
thermoresponsive polymer
thiol-ene click chemistry
Transition temperature
Transition temperatures
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Summary:To date, many poly(ethylene glycol) (PEG) and poly(N‐isopropylacrylamide) (PNIPAAm) biomolecule conjugates have been described, but they often show long response times, are not bio‐inert, or lose function in biological fluids. Herein, we present a modular synthetic approach to generate polyvinylphosphonate biomolecule conjugates. These conjugates exhibit a sharp phase transition temperature even under physiological conditions where few other examples with this property have been described to date. Furthermore, it was feasible to add biological functions to the polymers via the conjugation step. The polyvinylphosphonate cholesterol constructs are attached to the cellular membrane and the folic acid anchored polymers are shuttled into the cells. This is an exceptional finding through a straightforward synthetic approach. Fluorescent polyvinylphosphonates were obtained by post‐polymerization transesterification. Thiol‐ene click reactions led to fluorescent cholesterol‐ and folic acid‐functionalized polyvinylphosphonates. Turbidity measurements in complex biological fluids could show the retention of the thermoresponsive properties. Concluding the confocal microscopy experiments proved to selective cellular uptake of the bioconjugates into the cells or its anchoring to the plasma membrane.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201706034