{"title":"Submonomer Synthesis of Inverse Polyamidoamine (i-PAMAM) Dendrimer Antibacterials","authors":"Hippolyte Personne, Xiaoling Hu, Etienne Bonvin, Jérémie Reusser, Jean-Louis Reymond","doi":"10.1002/hlca.202400041","DOIUrl":null,"url":null,"abstract":"<p>Herein we report that the submonomer method for peptoid synthesis enables access to pure i-PAMAM dendrimers up to 16 amino termini by a divergent solid-phase synthesis using the inexpensive bis(3-trifluoroacetamidopropyl)amine as branching unit. We exemplify this new and efficient approach by a structure-activity relationship study of antibacterial dendrimers obtained by appending the polycationic i-PAMAM dendrimer to a hydrophobic core consisting of either an oligoleucine peptide or an oligo-<i>N</i>-isobutylglycine peptoid. These non-hemolytic dendrimers kill Gram-negative bacteria such as <i>Pseudomonas aeruginosa, Acinetobacter baumannii</i> and <i>Escherichia coli</i> as well as the Gram-positive methicillin-resistant <i>Staphylococcus aureus</i> (MRSA) by a non-membrane disruptive mechanism involving aggregation of intracellular content as reported for antimicrobial peptoids.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400041","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Helvetica Chimica Acta","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/hlca.202400041","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Herein we report that the submonomer method for peptoid synthesis enables access to pure i-PAMAM dendrimers up to 16 amino termini by a divergent solid-phase synthesis using the inexpensive bis(3-trifluoroacetamidopropyl)amine as branching unit. We exemplify this new and efficient approach by a structure-activity relationship study of antibacterial dendrimers obtained by appending the polycationic i-PAMAM dendrimer to a hydrophobic core consisting of either an oligoleucine peptide or an oligo-N-isobutylglycine peptoid. These non-hemolytic dendrimers kill Gram-negative bacteria such as Pseudomonas aeruginosa, Acinetobacter baumannii and Escherichia coli as well as the Gram-positive methicillin-resistant Staphylococcus aureus (MRSA) by a non-membrane disruptive mechanism involving aggregation of intracellular content as reported for antimicrobial peptoids.
期刊介绍：
Helvetica Chimica Acta, founded by the Swiss Chemical Society in 1917, is a monthly multidisciplinary journal dedicated to the dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences, where molecular aspects are key to the findings. Helvetica Chimica Acta is committed to the publication of original, high quality papers at the frontier of scientific research. All contributions will be peer reviewed with the highest possible standards and published within 3 months of receipt, with no restriction on the length of the papers and in full color.
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