title: Amphoteric, prevailingly cationic L-arginine polymers of poly(amidoamino acid) structure: synthesis, acid/base properties and preliminary cytocompatibility and cell-permeating characterizations.
abstract: 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.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, Via C. Golgi 19, 20133, Milano, Italy; Consorzio Interuniversitario di Scienza e Tecnologia dei Materiali (INSTM), Via G. Giusti 9, 50121, Firenze, Italy. paolo.ferruti@unimi.it.
authors.forename: Paolo
authors.initials: P
authors.lastname: Ferruti
authors.forename: Nicolò
authors.initials: N
authors.lastname: Mauro
authors.forename: Luigi
authors.initials: L
authors.lastname: Falciola
authors.forename: Valentina
authors.initials: V
authors.lastname: Pifferi
authors.forename: Cristina
authors.initials: C
authors.lastname: Bartoli
authors.forename: Matteo
authors.initials: M
authors.lastname: Gazzarri
authors.forename: Federica
authors.initials: F
authors.lastname: Chiellini
authors.forename: Elisabetta
authors.initials: E
authors.lastname: Ranucci
mesh_terms: D000178:Acrylamides / Q000737:chemistry; D000818:Animals; D001120:Arginine / Q000737:chemistry; D002463:Cell Membrane Permeability; D002470:Cell Survival / Q000187:drug effects; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D007526:Isoelectric Point; D051379:Mice; D041681:NIH 3T3 Cells; D010455:Peptides / Q000138:chemical synthesis* / Q000494:pharmacology; D010879:Piperazines / Q000737:chemistry; D011073:Polyamines / Q000138:chemical synthesis* / Q000494:pharmacology; D055672:Static Electricity
chemical_list: D000178:Acrylamides; D010455:Peptides; D010879:Piperazines; C531249:Poly(amidoamine); D011073:Polyamines; C015462:polyarginine; D001120:Arginine; C021221:N,N'-methylenebisacrylamide
keywords: L-arginine polymers; biocompatibility; biological application of polymers; poly(amidoamine)s; poly(amidoamino acid)s