During the last century, thiol-ene reactions attracted attention due to the wide range of commercially available thiols and alkenes. The highly efficient coupling reaction, often described in literature as “click” chemistry, is performed at a defined wavelength of 365 nm under mild conditions. Our group has focused on thiol-ene photo-addition as a versatile tool for the introduction of bioactive molecules (e.g. carbohydrates, peptides) to several polymer classes. Thiol-bearing sugars (e.g. glucose, galactose, mannose) and peptide moieties (glutathione) could be successfully installed on poly(2-oxazoline)s, poly(allyl glycidyl ether) and poly(acrylamide)s. Besides the improvement of biocompatibility and solubility properties, the bioactive molecules form the basis to target particular applications. Thus, cationic polymers, which are known for their potential to transport genetic material, were modified with d-fructose allowing the targeting of human breast cancer cells besides the delivery of genetic material. Furthermore, we were able to transport plasmid DNA through the hCMEC/D3 endothelial cell layer mimicking the blood-brain barrier within microfluidically perfused biochips by the attachment of l-glutathione moieties.

Thiol-ene photo-addition as versatile tool for biomedical applications

254th National Meeting (2017)

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