Cyclization of a cell‐penetrating peptide via click‐chemistry increases proteolytic resistance and improves drug delivery. (20th May 2016)

• Record Type: Journal Article
• Authors: Reichart, Florian; Horn, Mareike; Neundorf, Ines
• Is Part Of: Journal of peptide science. Volume 22:Number 6(2016:Jun.)
• Page Start: 421
• Page End: 426
• Publication Date: 2016-05-20
• Subjects: cell‐penetrating peptides -- click‐reaction -- drug delivery -- peptide synthesis; Peptides -- Periodicals; Peptides -- Periodicals; 572.65
• DOI: 10.1002/psc.2885
• Languages: English
• ISSNs: 1075-2617

Abstract

Abstract : In this work we report synthesis and biological evaluation of a cell‐penetrating peptide (CPP), that is partly cyclized via a triazole bridge. Recently, beneficious properties have been reported for cyclized peptides concerning their metabolic stability and intracellular uptake. A CPP based on human calcitonin was used in this study, and side chain cyclization was achieved via copper catalyzed alkyne‐azide click reaction. Cell viability studies in several cell‐lines revealed no cytotoxic effects. Furthermore, efficient uptake in breast cancer MCF‐7 cells could be determined. Moreover, preliminary studies using this novel peptide as drug transporter for daunorubicin were performed. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd. Abstract : Selective side chain cyclization of a cell‐penetrating peptide results in promising cellular uptake and drug delivery properties.