Size-Dependent Cellular Uptake of RGD Peptides |
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Authors: | Isabell Kemker Rebecca C. Feiner Prof. Dr. Kristian M. Müller Prof. Dr. Norbert Sewald |
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Affiliation: | 1. Organische und Bioorganische Chemie, Fakultät für Chemie, Universität Bielefeld, Universitätsstrasse 25, 33615 Bielefeld, Germany;2. Zelluläre und Molekulare Biotechnologie, Technische Fakultät, Universität Bielefeld, Universitätsstrasse 25, 33615 Bielefeld, Germany |
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Abstract: | Monomeric RGD peptides show unspecific fluid-phase uptake in cells, whereas multimeric RGD peptides are thought to be internalized by integrin-mediated endocytosis. However, a potential correlation between uptake mechanism and molecular mass has been neglected so far. A dual derivatization of peptide c(RGDw(7Br)K) was performed to investigate this. A fluorescent probe was installed by chemoselective Suzuki–Miyaura cross-coupling of the 7-bromotryptophan and a poly(ethylene glycol) (PEG) linker was attached to the lysine residue. Flow cytometry and live cell imaging confirmed unspecific uptake of the small, non-PEGylated peptide, whereas the PEG5000 peptide conjugate unveiled a selective internalization by M21 cells overexpressing αvβ3 and no uptake in αv-deficient M21L cells. |
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Keywords: | halogenated tryptophan internalization poly(ethylene glycol) RGD peptides selective uptake |
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