ArticleNature chemistry2022
Bottlebrush polymers with flexible enantiomeric side chains display differential biological properties.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Antibody-mediated recognition of chiral poly(2-oxazoline) nanorods driven by enantioselectivity.Chemical science · 2026Article
- Topological Doping of Charged Bottlebrush Polymers for Efficient Artificial Ion Channels.Polymer science & technology (Washington, D.C.) · 2026Article
- Chiral Micellar Assemblies for Circularly Polarized Luminescence Amplification, Dye Encapsulation, and Multilevel Information Encryption.Angewandte Chemie (International ed. in English) · 2026Article
- Design, Scalable Synthesis, and Characterization of Poly(Oligourethane Methacrylate)s Bottlebrushes with Discrete, Sequence-Defined, and Stereocontrolled Side-Chains.Macromolecules · 2026Article
- Stereochemistry Drives the Macromolecular Conformation and Biological Activity of Glycopolymers.ACS central science · 2025Article
- Chiral covalent organic cages: Construction and chiral functions.Smart molecules : open access · 2025Review
- Water in Triple-Bond-Based Polymerizations: Roles as a Solvent or Monomer.Polymer science & technology (Washington, D.C.) · 2025Review
- Discrete Brush Polymers EnhanceJournal of the American Chemical Society · 2025Article
- Article
- Core-Shell Bottlebrush Polymers: Unmatched Delivery of Small Active Compounds Deep Into Tissues.Small (Weinheim an der Bergstrasse, Germany) · 2025Article
- Density Function Theory Study on the Energy and Circular Dichroism Spectrum for Methylene-Linked Triazole Diads Depending on the Substitution Position and Conformation.Molecules (Basel, Switzerland) · 2024Article
- Revealing the Effect of Stereocontrol on Intermolecular Interactions between Abiotic, Sequence-Defined Polyurethanes and a Ligand.ACS biomaterials science & engineering · 2024Article
- Inhibiting the Keap1/Nrf2 Protein-Protein Interaction with Protein-Like Polymers.Advanced materials (Deerfield Beach, Fla.) · 2024Article
- Chiral Materials for Optics and Electronics: Ready to Rise?Micromachines · 2024Review
- High-Throughput Synthesis, Purification, and Application of Alkyne-Functionalized Discrete Oligomers.Journal of the American Chemical Society · 2024Article
- Installing a Single Monomer within Acrylic Polymers Using Photoredox Catalysis.Journal of the American Chemical Society · 2024Article
- SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes.Beilstein journal of organic chemistry · 2024Article
- Chiral nanoparticle-remodeled gut microbiota alleviates neurodegeneration via the gut-brain axis.Nature aging · 2023Article
- Water-soluble polyphosphonate-based bottlebrush copolymersChemical science · 2023Article
- Synthesis of Bottlebrush Polymers byJournal of the American Chemical Society · 2023Article
Corrections and comments
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Authors and funding
18 authors.
Funding
Abstract
Chirality and molecular conformation are central components of life: biological systems rely on stereospecific interactions between discrete (macro)molecular conformers, and the impacts of stereochemistry and rigidity on the properties of small molecules and biomacromolecules have been intensively studied. Nevertheless, how these features affect the properties of synthetic macromolecules has received comparably little attention. Here we leverage iterative exponential growth and ring-opening metathesis polymerization to produce water-soluble, chiral bottlebrush polymers (CBPs) from two enantiomeric pairs of macromonomers of differing rigidity. Remarkably, CBPs with conformationally flexible, mirror image side chains show several-fold differences in cytotoxicity, cell uptake, blood pharmacokinetics and liver clearance; CBPs with comparably rigid, mirror image side chains show no differences. These observations are rationalized with a simple model that correlates greater conformational freedom with enhanced chiral recognition. Altogether, this work provides routes to the synthesis of chiral nanostructured polymers and suggests key roles for stereochemistry and conformational rigidity in the design of future biomaterials.
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