Prodendronic polyamines from stable or labile methacrylates obtained by selective Michael addition onto asymmetric diacrylic compounds

Juan Alfonso Redondo, Rodrigo Navarro, Enrique Martínez-Campos, Mõnica Pérez-Perrino, Rodrigo París, José Luis Lõpez-Lacomba, Carlos Elvira, Helmut Reinecke, Alberto Gallardo

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A new synthetic strategy for the preparation of methacrylic monomers and polymers carrying acyl β-amino groups is presented. The approach is based on the Michael addition of aliphatic amines onto asymmetric acrylic/methacrylic compounds, reacting the amine highly selectively with the acrylic unit while leaving the methacrylic moiety unreacted. The corresponding polymers are then obtained by conventional radical polymerization. The use of N,N,N,N- tetraethyldiethylenetriamine (TEDETA) as the secondary amine leads to TEDETA moieties supported on polymeric chains. The new aminopolymers are sensitive to pH and to temperature exhibiting a lower critical solution temperature of between 50 and 90 C. A further interesting feature of the new approach is that the stability toward hydrolysis of the side β-amino acyl compounds was found to be dependent on whether an acrylamide or an acrylate is employed as the acrylic group of the asymmetric starting material. The esters exhibit an enhanced sensitivity to hydrolysis, compared to standard aliphatic esters, and decompose releasing a derivative of the amine precursor, within hours or weeks, depending on the pH and temperature conditions. The use of the amides leads to stable polymers when the same experimental conditions are applied. The novel dendronic polyamines have been proven to interact with DNA and to transfect cells with efficiency close to that obtained with polyethyleneimine vectors used as positive controls.

Original languageEnglish (US)
Pages (from-to)2297-2305
Number of pages9
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume52
Issue number16
DOIs
StatePublished - Aug 15 2014
Externally publishedYes

Keywords

  • asymmetric diacrylic compounds
  • degradation
  • drug delivery systems
  • functionalization of polymers
  • gene delivery
  • hydrolysis
  • Michael addition
  • stimuli responsive polymers

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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