Halogenation as a tool to tune antimicrobial activity of peptoids
| العنوان: | Halogenation as a tool to tune antimicrobial activity of peptoids |
|---|---|
| المؤلفون: | Paul R. Hansen, Natalia Molchanova, Annelise E. Barron, Bala K. Prabhala, Håvard Jenssen, Reidar Lund, Kristian Birk Sørensen, Josefine Eilsø Nielsen |
| المصدر: | Scientific Reports Molchanova, N, Nielsen, J E, Sørensen, K B, Prabhala, B K, Hansen, P R, Lund, R, Barron, A E & Jenssen, H 2020, ' Halogenation as a tool to tune antimicrobial activity of peptoids ', Scientific Reports, vol. 10, no. 1, 14805 . https://doi.org/10.1038/s41598-020-71771-8 Molchanova, N, Nielsen, J E, Sørensen, K B, Prabhala, B K, Hansen, P R, Lund, R, Barron, A E & Jenssen, H 2020, ' Halogenation as a tool to tune antimicrobial activity of peptoids ', Scientific Reports, vol. 10, 14805 . https://doi.org/10.1038/s41598-020-71771-8 Scientific Reports, Vol 10, Iss 1, Pp 1-10 (2020) 'Scientific Reports ', vol: 10, pages: 14805-1-14805-10 (2020) |
| سنة النشر: | 2020 |
| مصطلحات موضوعية: | Staphylococcus aureus, Halogenation, Cell Survival, Antimicrobial peptides, lcsh:Medicine, chemistry.chemical_element, Microbial Sensitivity Tests, 010402 general chemistry, Microbiology, 01 natural sciences, Article, Cell Line, chemistry.chemical_compound, Peptoids, Antibiotics, Scattering, Small Angle, Chlorine, Escherichia coli, Humans, lcsh:Science, Multidisciplinary, Antimicrobials, 010405 organic chemistry, Chemistry, lcsh:R, Peptoid, Antimicrobial, Chemical biology, Combinatorial chemistry, 0104 chemical sciences, Bioavailability, Anti-Bacterial Agents, Halogen, Pseudomonas aeruginosa, lcsh:Q, Peptides, Antibacterial activity |
| الوصف: | Antimicrobial peptides have attracted considerable interest as potential new class of antibiotics against multi-drug resistant bacteria. However, their therapeutic potential is limited, in part due to susceptibility towards enzymatic degradation and low bioavailability. Peptoids (oligomers of N-substituted glycines) demonstrate proteolytic stability and better bioavailability than corresponding peptides while in many cases retaining antibacterial activity. In this study, we synthesized a library of 36 peptoids containing fluorine, chlorine, bromine and iodine atoms, which vary by length and level of halogen substitution in position 4 of the phenyl rings. As we observed a clear correlation between halogenation of an inactive model peptoid and its increased antimicrobial activity, we designed chlorinated and brominated analogues of a known peptoid and its shorter counterpart. Short brominated analogues displayed up to 32-fold increase of the activity against S. aureus and 16- to 64-fold against E. coli and P. aeruginosa alongside reduced cytotoxicity. The biological effect of halogens seems to be linked to the relative hydrophobicity and self-assembly properties of the compounds. By small angle X-ray scattering (SAXS) we have demontrated how the self-assembled structures are dependent on the size of the halogen, degree of substitution and length of the peptoid, and correlated these features to their activity. |
| وصف الملف: | application/pdf |
| تدمد: | 2045-2322 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8c85d7d68a4d5ba116ca095bc721607f https://pubmed.ncbi.nlm.nih.gov/32908179 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....8c85d7d68a4d5ba116ca095bc721607f |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 20452322 |
|---|