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Preferential Uptake of L- versus D-Amino Acid Cell-Penetrating Peptides in a Cell Type-Dependent Manner
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2011 (English)In: Chemistry and Biology, ISSN 1074-5521, E-ISSN 1879-1301, Vol. 18, no 8, 1000-1010 p.Article in journal (Refereed) Published
Abstract [en]

The use of protease-resistant D-peptides is a prominent strategy for overcoming proteolytic sensitivity in the use of cell-penetrating peptides (CPPs) as delivery vectors. So far, no major differences have been reported for the uptake of L- and D-peptides. Here we report that cationic L-CPPs are taken up more efficiently than their D-counterparts in MC57 fibrosarcoma and He La cells but not in Jurkat T leukemia cells. Reduced uptake of D-peptides co-occurred with persistent binding to heparan sulfates (HS) at the plasma membrane. In vitro binding studies of Land D-peptides with HS indicated similar binding affinities. Our results identify two key events in the uptake of CPPs: binding to HS chains and the initiation of internalization. Only the second event depends on the chirality of the CPP. This knowledge may be exploited for a stereochemistry-dependent preferential targeting of cells.

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2011. Vol. 18, no 8, 1000-1010 p.
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Biochemistry and Molecular Biology
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URN: urn:nbn:se:su:diva-68307DOI: 10.1016/j.chembiol.2011.06.006ISI: 000295203200010OAI: oai:DiVA.org:su-68307DiVA: diva2:477515
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Available from: 2012-01-13 Created: 2012-01-03 Last updated: 2017-12-08Bibliographically approved

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Hällbrink, Mattias
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