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    Nonionic nontoxic antimicrobial polymers: indole-grafted poly(vinyl alcohol) with pendant alkyl or ether groups
    (Royal Soc Chemistry, 2022) Li, Xiaoya; Ilk, Sedef; Liu, Yang; Raina, Deepak Bushan; Demircan, Deniz; Zhang, Baozhong
    A series of new nonionic antimicrobial polymers with a biodegradable polyvinyl alcohol (PVA) backbone grafted with indole units and different hydrophobic alkyl or ether groups were synthesized by facile esterification. The chemical structures and thermal properties of the obtained polymers were characterized by GPC, NMR, FTIR, WAXD, TGA and DSC analyses. All these nonionic polymers showed a significant antibacterial effect similar to gentamicin against 9 food and human pathogenic bacteria according to the disk diffusion assay. The presence of alkyl or ether groups in most cases did not significantly affect the antibacterial effect compared to the polymer with unsubstituted indole units (with N-H moieties). The impacts of the OH conversion and molecular weight of the obtained polymers on their antimicrobial and anti-quorum sensing effects were also preliminarily investigated. Finally, the obtained indole-grafted PVAs were subjected to MTT assay using a mammalian cell line and hemolysis investigations, and the results showed excellent biocompatibility, particularly for those with ether substituents.
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    Synthesis, Enzymatic Degradation, and Polymer-Miscibility Evaluation of Nonionic Antimicrobial Hyperbranched Polyesters with Indole or Isatin Functionalities
    (Amer Chemical Soc, 2021) Li, Xiaoya; Ilk, Sedef; Linares-Pasten, Javier A.; Liu, Yang; Raina, Deepak Bushan; Demircan, Deniz; Zhang, Baozhong
    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.