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Buzzacchera I , Xiao Q , Han H , Rahimi K , Li S , Kostina NY , Toebes BJ , Wilner SE , Moller M , Rodriguez-Emmenegger C , Baumgart T , Wilson DA , Wilson CJ , Klein ML , Percec V
Screening Libraries of Amphiphilic Janus Dendrimers Based on Natural Phenolic Acids to Discover Monodisperse Unilamellar Dendrimersomes
Biomacromolecules. 2019 Feb 11;20(2) :712-727
PMID: 30354069    PMCID: PMC6571140    URL: https://www.ncbi.nlm.nih.gov/pubmed/30354069
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Natural, including plant, and synthetic phenolic acids are employed as building blocks for the synthesis of constitutional isomeric libraries of self-assembling dendrons and dendrimers that are the simplest examples of programmed synthetic macromolecules. Amphiphilic Janus dendrimers are synthesized from a diversity of building blocks including natural phenolic acids. They self-assemble in water or buffer into vesicular dendrimersomes employed as biological membrane mimics, hybrid and synthetic cells. These dendrimersomes are predominantly uni- or multilamellar vesicles with size and polydispersity that is predicted by their primary structure. However, in numerous cases, unilamellar dendrimersomes completely free of multilamellar assemblies are desirable. Here, we report the synthesis and structural analysis of a library containing 13 amphiphilic Janus dendrimers containing linear and branched alkyl chains on their hydrophobic part. They were prepared by an optimized iterative modular synthesis starting from natural phenolic acids. Monodisperse dendrimersomes were prepared by injection and giant polydisperse by hydration. Both were structurally characterized to select the molecular design principles that provide unilamellar dendrimersomes in higher yields and shorter reaction times than under previously used reaction conditions. These dendrimersomes are expected to provide important tools for synthetic cell biology, encapsulation, and delivery.
1526-4602 Buzzacchera, Irene Xiao, Qi Orcid: 0000-0002-6470-0407 Han, Hong Rahimi, Khosrow Li, Shangda Kostina, Nina Yu Toebes, B Jelle Wilner, Samantha E Orcid: 0000-0002-7661-8566 Moller, Martin Orcid: 0000-0002-5955-4185 Rodriguez-Emmenegger, Cesar Orcid: 0000-0003-0745-0840 Baumgart, Tobias Orcid: 0000-0001-7385-8460 Wilson, Daniela A Orcid: 0000-0002-8796-2274 Wilson, Christopher J Orcid: 0000-0003-0760-3421 Klein, Michael L Percec, Virgil Orcid: 0000-0001-5926-0489 R01 GM097552/GM/NIGMS NIH HHS/United States Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. United States Biomacromolecules. 2019 Feb 11;20(2):712-727. doi: 10.1021/acs.biomac.8b01405. Epub 2018 Nov 7.