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ROMP- and RAFT-Based Guanidinium-Containing Polymers as Scaffolds for Protein Mimic Synthesis.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2017 May 17; Vol. 23 (28), pp. 6858-6863. Date of Electronic Publication: 2017 May 02. - Publication Year :
- 2017
-
Abstract
- Cell-penetrating peptides are an important class of molecules with promising applications in bioactive cargo delivery. A diverse series of guanidinium-containing polymeric cell-penetrating peptide mimics (CPPMs) with varying backbone chemistries was synthesized and assessed for delivery of both GFP and fluorescently tagged siRNA. Specifically, we examined CPPMs based on norbornene, methacrylate, and styrene backbones to determine how backbone structure impacted internalization of these two cargoes. Either charge content or degree of polymerization was held constant at 20, with diguanidinium norbornene molecules being polymerized to both 10 and 20 repeat units. Generally, homopolymer CPPMs delivered low amounts of siRNA into Jurkat T cells, with no apparent backbone dependence; however, by adding a short hydrophobic methyl methacrylate block to the guanidinium-rich methacrylate polymer, siRNA delivery to nearly the entire cell population was achieved. Protein internalization yielded similar results for most of the CPPMs, though the block polymer was unable to deliver proteins. In contrast, the styrene-based CPPM yielded the highest internalization for GFP (≈40 % of cells affected), showing that indeed backbone chemistry impacts protein delivery, specifically through the incorporation of an aromatic group. These results demonstrate that an understanding of how polymer structure affects cargo-dependent internalization is critical to designing new, more effective CPPMs.<br /> (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Subjects :
- Biocompatible Materials chemistry
Cell-Penetrating Peptides chemistry
Flow Cytometry
Green Fluorescent Proteins chemistry
Green Fluorescent Proteins metabolism
Humans
Hydrophobic and Hydrophilic Interactions
Jurkat Cells
Methylmethacrylate chemistry
Norbornanes chemistry
RNA, Small Interfering chemistry
RNA, Small Interfering metabolism
Transfection methods
Biocompatible Materials chemical synthesis
Guanidine chemistry
Polymers chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 23
- Issue :
- 28
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 28370636
- Full Text :
- https://doi.org/10.1002/chem.201700423