@article{LaroqueReifarthSperlingetal.2020,
  author    = {Laroque, Sophie and Reifarth, Martin and Sperling, Marcel and Kersting, Sebastian and Kloepzig, Stefanie and Budach, Patrick and Hartlieb, Matthias and Storsberg, Joachim},
  title     = {Impact of multivalence and self-assembly in the design of polymeric antimicrobial peptide mimics},
  series = {ACS applied materials \& interfaces},
  volume    = {12},
  journal   = {ACS applied materials \& interfaces},
  number    = {27},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {1944-8244},
  doi       = {10.1021/acsami.0c05944},
  pages     = {30052 -- 30065},
  year      = {2020},
  abstract  = {Antimicrobial resistance is an increasingly serious challenge for public health and could result in dramatic negative consequences for the health care sector during the next decades. To solve this problem, antibacterial materials that are unsusceptible toward the development of bacterial resistance are a promising branch of research. In this work, a new type of polymeric antimicrobial peptide mimic featuring a bottlebrush architecture is developed, using a combination of reversible addition-fragmentation chain transfer (RAFT) polymerization and ring-opening metathesis polymerization (ROMP). This approach enables multivalent presentation of antimicrobial subunits resulting in improved bioactivity and an increased hemocompatibility, boosting the selectivity of these materials for bacterial cells. Direct probing of membrane integrity of treated bacteria revealed highly potent membrane disruption caused by bottlebrush copolymers. Multivalent bottlebrush copolymers clearly outperformed their linear equivalents regarding bioactivity and selectivity. The effect of segmentation of cationic and hydrophobic subunits within bottle brushes was probed using heterograft copolymers. These materials were found to self-assemble under physiological conditions, which reduced their antibacterial activity, highlighting the importance of precise structural control for such applications. To the best of our knowledge, this is the first example to demonstrate the positive impact of multivalence, generated by a bottlebrush topology in polymeric antimicrobial peptide mimics, making these polymers a highly promising material platform for the design of new bactericidal systems.},
  language  = {en}
}
@article{KwesigaKellingKerstingetal.2020,
  author    = {Kwesiga, George and Kelling, Alexandra and Kersting, Sebastian and Sperlich, Eric and von Nickisch-Rosenegk, Markus and Schmidt, Bernd},
  title     = {Total syntheses of prenylated isoflavones from Erythrina sacleuxii and their antibacterial activity},
  series = {Journal of natural products},
  volume    = {83},
  journal   = {Journal of natural products},
  number    = {11},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0163-3864},
  doi       = {10.1021/acs.jnatprod.0c00932},
  pages     = {3445 -- 3453},
  year      = {2020},
  abstract  = {The prenylated isoflavones 5-deoxyprenylbiochanin A (7-hydroxy-4'-methoxy-3'-prenylisoflavone) and erysubin F (7,4'-dihydroxy-8,3'-diprenylisoflavone) were synthesized for the first time, starting from mono-or di-O-allylated chalcones, and the structure of 5-deoxy-3'-prenylbiochanin A was corroborated by single-crystal X-ray diffraction analysis. Flavanones are key intermediates in the synthesis. Their reaction with hypervalent iodine reagents affords isoflavones via a 2,3-oxidative rearrangement and the corresponding flavone isomers via 2,3-dehydrogenation. This enabled a synthesis of 7,4'-dihydroxy-8,3'-diprenylflavone, a non-natural regioisomer of erysubin F. Erysubin F (8), 7,4'-dihydroxy-8,3'-diprenylflavone (27), and 5-deoxy-3'prenylbiochanin A (7) were tested against three bacterial strains and one fungal pathogen. All three compounds are inactive against Salmonella enterica subsp. enterica (NCTC 13349), Escherichia coli (ATCC 25922), and Candida albicans (ATCC 90028), with MIC values greater than 80.0 mu M. The diprenylated natural product erysubin F (8) and its flavone isomer 7,4'-dihydroxy-8,3'diprenylflavone (27) show in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA, ATCC 43300) at MIC values of 15.4 and 20.5 mu M, respectively. In contrast, the monoprenylated 5-deoxy-3'-prenylbiochanin A (7) is inactive against this MRSA strain.},
  language  = {en}
}