Screening Libraries of Amphiphilic Janus Dendrimers Based on Natural Phenolic Acids to Discover Monodisperse Unilamellar Dendrimersomes.

Autor: Buzzacchera I; Roy & Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104-6323 , United States.; DWI-Leibniz Institute for Interactive Materials , RWTH Aachen University , 52074 Aachen , Germany.; NovioSense B.V. , Transistorweg 5 , 6534 AT Nijmegen , The Netherlands., Xiao Q; Roy & Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104-6323 , United States.; Institute of Computational Molecular Science , Temple University , Philadelphia , Pennsylvania 19122 , United States., Han H; Roy & Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104-6323 , United States., Rahimi K; DWI-Leibniz Institute for Interactive Materials , RWTH Aachen University , 52074 Aachen , Germany.; Institute of Technical and Macromolecular Chemistry , RWTH Aachen University , 52074 Aachen , Germany., Li S; Roy & Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104-6323 , United States., Kostina NY; DWI-Leibniz Institute for Interactive Materials , RWTH Aachen University , 52074 Aachen , Germany.; Institute of Technical and Macromolecular Chemistry , RWTH Aachen University , 52074 Aachen , Germany., Toebes BJ; Institute of Molecules and Materials , Radboud University , Heyendaalseweg 135 , 6525 AJ Nijmegen , The Netherlands., Wilner SE; Roy & Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104-6323 , United States., Möller M; DWI-Leibniz Institute for Interactive Materials , RWTH Aachen University , 52074 Aachen , Germany.; Institute of Technical and Macromolecular Chemistry , RWTH Aachen University , 52074 Aachen , Germany., Rodriguez-Emmenegger C; DWI-Leibniz Institute for Interactive Materials , RWTH Aachen University , 52074 Aachen , Germany.; Institute of Technical and Macromolecular Chemistry , RWTH Aachen University , 52074 Aachen , Germany., Baumgart T; Roy & Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104-6323 , United States., Wilson DA; Institute of Molecules and Materials , Radboud University , Heyendaalseweg 135 , 6525 AJ Nijmegen , The Netherlands., Wilson CJ; NovioSense B.V. , Transistorweg 5 , 6534 AT Nijmegen , The Netherlands., Klein ML; Institute of Computational Molecular Science , Temple University , Philadelphia , Pennsylvania 19122 , United States., Percec V; Roy & Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , Philadelphia , Pennsylvania 19104-6323 , United States.
Jazyk: angličtina
Zdroj: Biomacromolecules [Biomacromolecules] 2019 Feb 11; Vol. 20 (2), pp. 712-727. Date of Electronic Publication: 2018 Nov 07.
DOI: 10.1021/acs.biomac.8b01405
Abstrakt: 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.
Databáze: MEDLINE
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