Chemical Modification of Acrylonitrile-Divinylbenzene Polymer Supports with Aminophosphonate Groups and Their Antibacterial Activity Testing

Molecules. 2024 Dec 23;29(24):6054. doi: 10.3390/molecules29246054.

Abstract

Bacterial contamination is a major public health concern on a global scale. Treatment resistance in bacterial infections is becoming a significant problem that requires solutions. We were interested in obtaining new polymeric functionalized compounds with antibacterial properties. Three components (polymeric amine, aldehyde, and phosphite) were used in the paper in a modified "one-pot" Kabachnik-Fields reaction, in tetrahydrofuran at 60 °C, to create the N-C-P skeleton in aminophosphonate groups. Two copolymers were thus prepared starting from an acrylonitriledivinylbenzene (AN-15%DVB) copolymer containing pendant primary amine groups modified by grafting aminophosphonate groups, i.e., aminobenzylphosphonate (Bz-DVB-AN) and aminoethylphosphonate (Et-DVB-AN). The two copolymers were characterized by FT-IR spectroscopy, SEM-EDX, TGA, and antibacterial properties. It was shown that the novel products have antibacterial qualities against S. aureus and E. coli bacteria. The sample with the strongest antibacterial activity was Et-DVB-AN. We assessed how well the Weibull model and the first-order kinetic model represent the inactivation of microbial cells in our samples. The main advantage of the new antibacterial agents developed in this work is their easy recovery, which helps to avoid environmental contamination.

Keywords: Weibull model; acrylonitrile-divinylbenzene; aminophosphonate; antimicrobial materials; multicomponent reactions.

MeSH terms

  • Acrylonitrile* / analogs & derivatives
  • Acrylonitrile* / chemistry
  • Acrylonitrile* / pharmacology
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Escherichia coli* / drug effects
  • Microbial Sensitivity Tests*
  • Organophosphonates / chemistry
  • Organophosphonates / pharmacology
  • Polymers* / chemistry
  • Polymers* / pharmacology
  • Spectroscopy, Fourier Transform Infrared
  • Staphylococcus aureus* / drug effects
  • Vinyl Compounds / chemistry
  • Vinyl Compounds / pharmacology

Substances

  • Anti-Bacterial Agents
  • Polymers
  • Acrylonitrile
  • Organophosphonates
  • divinyl benzene
  • Vinyl Compounds

Grants and funding

This work was partially supported by Program 2 of Romanian Academy, “Coriolan Dragulescu” Institute of Chemistry and by project “ICT—Interdisciplinary Center for Smart Specialization in Chemical Biology (RO-OPENSCREEN)”, MySMIS code: 127952, Contract no. 371/20.07.2020, co-financed by the European Regional Development Fund under the Competitiveness Operational Program 2014–2020.