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Pharmaceuticals
Volume 5
Issue 12
10.3390/ph5121265
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Article

Cell Penetrating Peptoids (CPPos): Synthesis of a Small Combinatorial Library by Using IRORI MiniKans

by
Dominik K. Kölmel
1,
Daniel Fürniss
1,
Steven Susanto
2,
Andrea Lauer
2,
Clemens Grabher
2,
Stefan Bräse
1,2 and
Ute Schepers
2,*
1
Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz Haber Weg 6, 76131 Karlsruhe, Germany
2
Institute of Toxicology and Genetics, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
*
Author to whom correspondence should be addressed.
Pharmaceuticals 2012, 5(12), 1265-1281; https://doi.org/10.3390/ph5121265
Received: 10 October 2012 / Revised: 13 November 2012 / Accepted: 14 November 2012 / Published: 23 November 2012
(This article belongs to the Special Issue Cell-penetrating Peptides 2012)
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Abstract

Cell penetrating peptoids (CPPos) are potent mimics of the corresponding cell penetrating peptides (CPPs). The synthesis of diverse oligomeric libraries that display a variety of backbone scaffolds and side-chain appendages are a very promising source of novel CPPos, which can be used to either target different cellular organelles or even different tissues and organs. In this study we established the submonomer-based solid phase synthesis of a “proof of principle” peptoid library in IRORI MiniKans to expand the amount for phenotypic high throughput screens of CPPos. The library consisting of tetrameric peptoids [oligo(N-alkylglycines)] was established on Rink amide resin in a split and mix approach with hydrophilic and hydrophobic peptoid side chains. All CPPos of the presented library were labeled with rhodamine B to allow for the monitoring of cellular uptake by fluorescent confocal microscopy. Eventually, all the purified peptoids were subjected to live cell imaging to screen for CPPos with organelle specificity. While highly charged CPPos enter the cells by endocytosis with subsequent endosomal release, critical levels of lipophilicity allow other CPPos to specifically localize to mitochondria once a certain lipophilicity threshold is reached. View Full-Text
Keywords: combinatorial chemistry; split and mix; library; peptoid; IRORI; sub-monomer; cell penetrating combinatorial chemistry; split and mix; library; peptoid; IRORI; sub-monomer; cell penetrating
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MDPI and ACS Style

Kölmel, D.K.; Fürniss, D.; Susanto, S.; Lauer, A.; Grabher, C.; Bräse, S.; Schepers, U. Cell Penetrating Peptoids (CPPos): Synthesis of a Small Combinatorial Library by Using IRORI MiniKans. Pharmaceuticals 2012, 5, 1265-1281. https://doi.org/10.3390/ph5121265

AMA Style

Kölmel DK, Fürniss D, Susanto S, Lauer A, Grabher C, Bräse S, Schepers U. Cell Penetrating Peptoids (CPPos): Synthesis of a Small Combinatorial Library by Using IRORI MiniKans. Pharmaceuticals. 2012; 5(12):1265-1281. https://doi.org/10.3390/ph5121265

Chicago/Turabian Style

Kölmel, Dominik K., Daniel Fürniss, Steven Susanto, Andrea Lauer, Clemens Grabher, Stefan Bräse, and Ute Schepers. 2012. "Cell Penetrating Peptoids (CPPos): Synthesis of a Small Combinatorial Library by Using IRORI MiniKans" Pharmaceuticals 5, no. 12: 1265-1281. https://doi.org/10.3390/ph5121265

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