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Amphoteric, Prevailingly Cationic L ‐ A rginine Polymers of Poly(amidoamino acid) Structure: Synthesis, Acid/ B ase Properties and Preliminary Cytocompatibility and Cell‐ P ermeating Characterizations
Author(s) -
Ferruti Paolo,
Mauro Nicolò,
Falciola Luigi,
Pifferi Valentina,
Bartoli Cristina,
Gazzarri Matteo,
Chiellini Federica,
Ranucci Elisabetta
Publication year - 2014
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.201300387
Subject(s) - chemistry , cationic polymerization , polymer , arginine , piperazine , in vitro , polymer chemistry , internalization , acrylamide , biochemistry , copolymer , stereochemistry , amino acid , cell , organic chemistry
A linear amphoteric poly(amidoamino acid), L‐ARGO7, is prepared by Michael‐type polyaddition of L ‐arginine with N , N′ ‐methylenebisacrylamide. Chain‐extension of acrylamide end‐capped L‐ARGO7 oligomers with piperazine leads to high‐molecular‐weight copolymers in which L ‐arginine maintains its absolute configuration. Acid/base properties of L‐ARGO7 polymers show isolectric points of ≈10 and positive net average charges per repeating unit at pH = 7.4 from 0.25 to 0.40. These arginine‐rich synthetic polymers possibly share some of the unique biological properties of polyarginine cell‐permeating peptides. In vitro tests with mouse embryo fibroblasts balb/3T3 clone A31 show that L‐ARGO7 polymers are endowed with effective cell internalization ability combined with minimal cytotoxicity.