Synthesis, Enzymatic Degradation, and Polymer-Miscibility Evaluation of Nonionic Antimicrobial Hyperbranched Polyesters with Indole or Isatin Functionalities
| Autor: | Yang Liu, Xiaoya Li, Deepak Bushan Raina, Deniz Demircan, Baozhong Zhang, Sedef Ilk, Javier A. Linares-Pastén |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Isatin
Indoles Polymers and Plastics Polymers Polyesters Bioengineering Context (language use) 02 engineering and technology 010402 general chemistry 01 natural sciences Article Biomaterials Polyhydroxybutyrate chemistry.chemical_compound Materials Chemistry Moiety Animals Humans Burkholderiales Indole test 021001 nanoscience & nanotechnology Combinatorial chemistry 0104 chemical sciences Anti-Bacterial Agents Polyester Molecular Docking Simulation Monomer chemistry Polycaprolactone 0210 nano-technology |
| Zdroj: | Biomacromolecules |
| ISSN: | 1526-4602 1525-7797 |
| Popis: | Most macromolecular antimicrobials are ionic and thus lack miscibility/compatibility with nonionic substrate materials. In this context, nonionic hyperbranched polyesters (HBPs) with indole or isatin functionality were rationally designed, synthesized, and characterized. Antimicrobial disk diffusion assay indicated that these HBPs showed significant antibacterial activity against 8 human pathogenic bacteria compared to small molecules with indole or isatin groups. According to DSC measurements, up to 20% indole-based HBP is miscible with biodegradable polyesters (polyhydroxybutyrate or polycaprolactone), which can be attributed to the favorable hydrogen bonding between the N-H moiety of indole and the C═O of polyesters. HBPs with isatin or methylindole were completely immiscible with the same matrices. None of the HBPs leaked out from plastic matrix after being immersed in water for 5 days. The incorporation of indole into HBPs as well as small molecules facilitated their enzymatic degradation with PETase from Ideonella sakaiensis, while isatin had a complex impact. Molecular docking simulations of monomeric molecules with PETase revealed different orientations of the molecules at the active site due to the presence of indole or isatin groups, which could be related to the observed different enzymatic degradation behavior. Finally, biocompatibility analysis with a mammalian cell line showed the negligible cytotoxic effect of the fabricated HBPs. |
| Databáze: | OpenAIRE |
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