Convergent synthesis and cellular uptake of multivalent cell penetrating peptides derived from Tat, Antp, pVEC, TP10 and SAP

Eggimann, Gabriela; Buschor, Stefanie; Darbre, Tamis; Reymond, Jean-Louis (2013). Convergent synthesis and cellular uptake of multivalent cell penetrating peptides derived from Tat, Antp, pVEC, TP10 and SAP. Organic & biomolecular chemistry, 11(39), pp. 6717-6733. Royal Society of Chemistry 10.1039/c3ob41023d

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Cell penetrating peptides (CPP) are peptides of 10 to 30 residues derived from natural translocating proteins. Multivalency is known to enhance cellular uptake for the Tat peptide and closely related polycationic sequences. To test whether multivalency effects on cellular uptake might also occur with other CPP types, we prepared multivalent versions of the strongly cationic Tat, the amphipathic sequences Antp, pVEC and TP10, and the polyproline helix SAP by convergent thioether ligation of the linear CPP onto multivalent scaffolds, and evaluated their uptake in HeLa and CHO cells, intracellular localization, cytotoxicity and hemolysis. While multivalency did not increase the cellular uptake of pVEC or SAP, multivalency effects on uptake comparable to Tat were observed with TP10 and Antp, which are attributable to their polycationic nature. The efficient synthetic protocol for these divalent CPP and their localization in the cytoplasm suggest that CPP might be useful for application in cargo delivery into cells.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry
04 Faculty of Medicine > Service Sector > Institute for Infectious Diseases

UniBE Contributor:

Eggimann, Gabriela; Buschor, Stefanie; Darbre, Tamis and Reymond, Jean-Louis

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry
600 Technology > 610 Medicine & health

ISSN:

1477-0520

Publisher:

Royal Society of Chemistry

Language:

English

Submitter:

Sandra Tanja Zbinden Di Biase

Date Deposited:

26 May 2014 09:50

Last Modified:

27 Dec 2014 18:22

Publisher DOI:

10.1039/c3ob41023d

BORIS DOI:

10.7892/boris.47241

URI:

https://boris.unibe.ch/id/eprint/47241

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