Biodegradable Polyimidazole Particles as Contrast Agents Produced by Direct Arylation Polymerization

Biomacromolecules, vol. 22, pp. 5065–5073

Abstract

Conjugated polymer particles provide an important platform for the development of theranostic nanoagents. However, the number of biocompatible and foremost biodegradable π-conjugated polymers is limited. Imidazole is a π-conjugated motif that is abundant in biological systems. Oxidative degradation of imidazole is present in nature via enzymatic or free radical processes. In this work, we introduce polymer particles consisting purely of polyimidazole. We employ direct arylation polymerization and adapt it to a dispersion polymerization protocol to yield uniform and narrowly dispersed nanoparticles. We employ this mechanism to produce linear and cross-linked polymer particles to tune the optical properties from fluorescent to photoacoustically active. We show that the particles can be degraded by H 2 O 2 as well as by reactive oxygen species produced by cells and we detect the degradation products. Altogether, our results suggest that polyimidazole particles represent ideal candidates for theranostic applications.

Authors 5

1. Felicitas Jansen Aachen DWI - Leibniz Institute for Interactive Materials

   Universität Ulm · DWI – Leibniz Institute for Interactive Materials

   Affiliation as printed

   DWI─Leibniz Institute for Interactive Materials, Forckenbeckstraße 50, 52076 Aachen, Germany

   Institute of Organic and Macromolecular Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany

2. Philipp A. Schuster

   Universität Ulm

   Affiliation as printed

   Institute of Organic and Macromolecular Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany

3. Markus Lamla

   Universität Ulm

   Affiliation as printed

   Institute of Organic and Macromolecular Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany

4. Christian Trautwein Aachen Department of Internal Medicine III

   Universitätsklinikum Aachen · RWTH Aachen University

   Affiliation as printed

   Department of Internal Medicine III, University Hospital RWTH Aachen, Pauwelstraße 30, 52074 Aachen, Germany

5. Alexander J. C. Kuehne corresponding Aachen DWI - Leibniz Institute for Interactive Materials

   Universität Ulm · DWI – Leibniz Institute for Interactive Materials

   Affiliation as printed

   DWI─Leibniz Institute for Interactive Materials, Forckenbeckstraße 50, 52076 Aachen, Germany

   Institute of Organic and Macromolecular Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany