title: Self-Sorting and Coassembly of Fluorinated, Hydrogenated, and Hybrid Janus Dendrimers into Dendrimersomes.
abstract: The modular synthesis of a library containing seven self-assembling amphiphilic Janus dendrimers is reported. Three of these molecules contain environmentally friendly chiral-racemic fluorinated dendrons in their hydrophobic part (RF), one contains achiral hydrogenated dendrons (RH), while one denoted hybrid Janus dendrimer, contains a combination of chiral-racemic fluorinated and achiral hydrogenated dendrons (RHF) in its hydrophobic part. Two Janus dendrimers contain either chiral-racemic fluorinated dendrons and a green fluorescent dye conjugated to its hydrophilic part (RF-NBD) or achiral hydrogenated and a red fluorescent dye in its hydrophilic part (RH-RhB). These RF, RH, and RHF Janus dendrimers self-assembled into unilamellar or onion-like soft vesicular dendrimersomes (DSs), with similar thicknesses to biological membranes by simple injection from ethanol solution into water or buffer. Since RF and RH dendrons are not miscible, RF-NBD and RH-RhB were employed to investigate by fluorescence microscopy the self-sorting and coassembly of RF and RH as well as of phospholipids into hybrid DSs mediated by the hybrid hydrogenated-fluorinated RHF Janus dendrimer. The hybrid RHF Janus dendrimer coassembled with both RF and RH. Three-component hybrid DSs containing RH, RF, and RHF were formed when the proportion of RHF was higher than 40%. With low concentration of RHF and in its absence, RH and RF self-sorted into individual RH or RF DSs. Phospholipids were also coassembled with hybrid RHF Janus dendrimers. The simple synthesis and self-assembly of DSs and hybrid DSs, their similar thickness with biological membranes and their imaging by fluorescence and (19)F-MRI make them important tools for synthetic biology.
authors: Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
authors: Qi
authors: Q
authors: Xiao
authors: Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
authors: Jack D
authors: JD
authors: Rubien
authors: Department of Bioengineering, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6321, United States.
authors: Zhichun
authors: Z
authors: Wang
authors: Department of Bioengineering, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6321, United States.
authors: Ellen H
authors: EH
authors: Reed
authors: Department of Bioengineering, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6321, United States.|Department of Chemical and Biomolecular Engineering, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6391, United States.
authors: Daniel A
authors: DA
authors: Hammer
authors: Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.|Department of Physics and Astronomy, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6396, United States.
authors: Dipankar
authors: D
authors: Sahoo
authors: Department of Physics and Astronomy, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6396, United States.
authors: Paul A
authors: PA
authors: Heiney
authors: Department of Biology, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6313, United States.
authors: Srujana S
authors: SS
authors: Yadavalli
authors: Department of Biology, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6313, United States.
authors: Mark
authors: M
authors: Goulian
authors: Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
authors: Samantha E
authors: SE
authors: Wilner
authors: Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
authors: Tobias
authors: T
authors: Baumgart
authors: Department of Biochemistry and Biophysics, Perelman School of Medicine, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6059, United States.
authors: Sergei A
authors: SA
authors: Vinogradov
authors: Institute of Computational Molecular Science, Temple University , Philadelphia, Pennsylvania 19122, United States.
authors: Michael L
authors: ML
authors: Klein
authors: Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
authors: Virgil
authors: V
authors: Percec