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• W2072017110 abstract "The aim of this work is to generate polymer micelles decorated with a synthetic version of cell-penetrating peptides, which are often rich in arginine with its positively charged guanidine group. A methacrylate-based monomer with guanidinium as functional groups was prepared using arginine (M-Arg) as a building block, resulting in a zwitterionic monomer. RAFT (reversible addition–fragmentation chain transfer) polymerization was employed to generate triblock copolymers with poly(methyl methacrylate)-block-poly(polyethylene glycol methyl ether methacrylate) as the first two blocks, which were subsequently chain extended with the guanidine-based monomer to generate micelles with guanidinium functional groups on the surface. To simulate the actual oligoarginine peptide, which only carries cationic charges, the carboxylate group of P(M-Arg) was methylated to convert the zwitterionic polymer into a cationic polymer P(Me-M-Arg). For comparison, micelles based on triblock copolymers with a third block with permanently cationic charges, poly(2-methacryolyloxy ethyl) trimethyl ammonium chloride (PTMA), was prepared. The hydrodynamic diameters of the micelles were approximately 30–40 nm based on DLS and TEM. A direct correlation between surface charge (zeta potential ζ) and cytotoxicity was observed. The micelles based on the zwitterionic P(M-Arg) were nontoxic (ζ = −10 mV at pH = 7), while the methylated version P(Me-M-Arg) with a high cationic charge (ζ = +35 mV at pH = 7) were observed to be toxic. The cellular uptake of the block copolymers by OVCAR-3 ovarian cancer cell lines was found to be relatively fast (about 35% in 3 min) reaching an equilibrium after approximately 30 min. Both micelles, with either P(M-Arg) or P(Me-M-Arg) on the surface, showed an enhanced uptake compared to micelles with P(PEGMEMA) as shell only. In fact, the percentage of uptake was similar, with the difference that cells incubated with micelles with P(M-Arg) (zwitterionic) stayed alive, while P(Me-M-Arg) (cationic) led to significant cell death." @default.
• W2072017110 created "2016-06-24" @default.
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• W2072017110 date "2012-09-19" @default.
• W2072017110 modified "2023-09-30" @default.
• W2072017110 title "Zwitterionic Guanidine-Based Oligomers Mimicking Cell-Penetrating Peptides as a Nontoxic Alternative to Cationic Polymers to Enhance the Cellular Uptake of Micelles" @default.
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• W2072017110 doi "https://doi.org/10.1021/bm301351e" @default.
• W2072017110 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/22946476" @default.
• W2072017110 hasPublicationYear "2012" @default.
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