| Abstract
| - For many therapeutic applications, it has become more and more important to find synthetic compounds thathave the ability to transport a variety of drugs and cargo molecules into cells and tissues. Like arginine-richcell-penetrating peptides (CPPs), it is already known that peptide mimetics such as β-peptides and peptoids canalso express a transport function. In this study, ten fluorophore-labeled chiral and achiral peptoids with differentbackbone lengths and side chains as well as three peptoids coupled to a therapeutically active porphyrin moietywere prepared using a highly modular solid-phase synthesis (SPP) approach. To compare the structural determinantswith the cellular uptake efficiency, all peptoids were analyzed by live cell imaging. All cells show an even vesiculardistribution of the internalized peptoids, also revealing that a vesicular escape into the cytosol was stronger forpeptoids with longer backbones. Moreover, the uptake efficiency correlated with both the incubation time and thegiven concentration. Toxicology tests and uptake experiments with porphyrin-coupled peptoids indicate theirsuitability for application as robust and readily available drug delivery systems or intracellular probes.
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