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Synthesis, Enzymatic Degradation, and Polymer-Miscibility Evaluation of Nonionic Antimicrobial Hyperbranched Polyesters with Indole or Isatin Functionalities

Li, Xiaoya LU ; Ilk, Sedef ; Linares-Pastén, Javier A. LU orcid ; Liu, Yang LU ; Raina, Deepak Bushan LU ; Demircan, Deniz LU and Zhang, Baozhong LU (2021) In Biomacromolecules 22(5). p.2256-2256
Abstract
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... (More)
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. (Less)
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author
; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Biomacromolecules
volume
22
issue
5
pages
2271 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:33900740
  • scopus:85106495091
ISSN
1526-4602
DOI
10.1021/acs.biomac.1c00343
project
STEPS – Sustainable Plastics and Transition Pathways, Phase 2
language
English
LU publication?
yes
id
e16253a9-cb74-402f-8c76-b7a2f443e6da
date added to LUP
2021-05-20 21:58:22
date last changed
2022-04-27 02:03:26
@article{e16253a9-cb74-402f-8c76-b7a2f443e6da,
  abstract     = {{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 <i>Ideonella sakaiensis</i>, 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.}},
  author       = {{Li, Xiaoya and Ilk, Sedef and Linares-Pastén, Javier A. and Liu, Yang and Raina, Deepak Bushan and Demircan, Deniz and Zhang, Baozhong}},
  issn         = {{1526-4602}},
  language     = {{eng}},
  month        = {{04}},
  number       = {{5}},
  pages        = {{2256--2256}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Biomacromolecules}},
  title        = {{Synthesis, Enzymatic Degradation, and Polymer-Miscibility Evaluation of Nonionic Antimicrobial Hyperbranched Polyesters with Indole or Isatin Functionalities}},
  url          = {{http://dx.doi.org/10.1021/acs.biomac.1c00343}},
  doi          = {{10.1021/acs.biomac.1c00343}},
  volume       = {{22}},
  year         = {{2021}},
}