Self‐Assembling Multivalency – Supramolecular Polymers Assembled from Monovalent Mannose‐Labelled Discotic Molecules

Petkau-Milroy, K Katja; Brunsveld, Luc

doi:10.1002/ejoc.201300057

Cited by 17 publications

(14 citation statements)

References 45 publications

(53 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The self-assembling multivalency 25,36 of these intrinsically monovalent discotics bodes well for the display of different proteins along the same supramolecular polymer. The FRETpair proteins YFP-and CFP-SNAP were therefore simultaneously ligated to a solution of 2.…”

Section: Supramolecular Assembly Of Multiple Proteinsmentioning

confidence: 99%

Dynamic and bio-orthogonal protein assembly along a supramolecular polymer

et al. 2013

Self Cite

View full text Add to dashboard Cite

Dynamic protein assembly along supramolecular columnar polymers has been achieved through the sitespecific covalent attachment of different SNAP-tag fusion proteins to self-assembled benzylguaninedecorated discotics. The self-assembly of monovalent discotics into supramolecular polymers creates a multivalent, bio-orthogonal and self-regulating framework for protein assembly. The intrinsic reversibility of supramolecular interactions results in reorganization and exchange of building blocks allowing for dynamic intermixing of protein-functionalized discotics between different self-assembled polymers, leading to self-optimization of protein arrangement and distance as evidenced by efficient energy transfer between fluorescent proteins.

show abstract

Section: Supramolecular Assembly Of Multiple Proteinsmentioning

confidence: 99%

Dynamic and bio-orthogonal protein assembly along a supramolecular polymer

et al. 2013

Self Cite

View full text Add to dashboard Cite

show abstract

“…The natural role of saccharides as recognition units through selective binding by lectins provides a strategy for the development of responsive systems or post‐assembly functionalisation . Furthermore, saccharides are well known to form dynamic covalent bonds with boronic acids .…”

Section: Introductionmentioning

confidence: 99%

Monosaccharides as Versatile Units for Water‐Soluble Supramolecular Polymers

Leenders

Jansen

Frissen

et al. 2016

Chemistry A European J

View full text Add to dashboard Cite

Document VersionPublisher's PDF, also known as Version of Record (includes final page, issue and volume numbers)Please check the document version of this publication:• A submitted manuscript is the author's version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website.• The final author version and the galley proof are versions of the publication after peer review.• The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication General rightsCopyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research.• You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Abstract: We introduce monosaccharides as versatile watersoluble units to compatibilise supramolecular polymers based on the benzene-1,3,5-tricarboxamide (BTA) moiety with water.Alibrary of monosaccharide-based BTAs is evaluated, varying the length of the alkyl chain (hexyl, octyl, decyl and dodecyl) separating the BTAa nd saccharide units, as well as the saccharideu nits (a-glucose, b-glucose, a-mannose and a-galactose). In all cases, the monosaccharides impart excellent waterc ompatibility. The length of the alkyl chain is the determining factort oo btain either long, one-dimensional supramolecular polymers (dodecyls pacer), small aggregates (decyl spacer) or molecularly dissolved (octyl and hexyl) BTAs in water. For the BTAs comprising ad odecyl spacer, our results suggest that ac ooperative self-assembly process is operative and that the introduction of different monosaccharides does not significantly change the selfassemblyb ehaviour. Finally,w ei nvestigate the potential of post-assembly functionalisation of the formed supramolecular polymers by taking advantage of dynamic covalent bond formation between the monosaccharides and benzoxaboroles. We observe that the supramolecular polymers readily react with af luorescent benzoxaborole derivative permitting imaging of these dynamicc omplexes by confocal fluorescencemicroscopy.

show abstract

“…Subsequent alkylation of the secondary hydroxyl groups with stearic acid via a Steglich‐type esterification afforded grafted block copolymer P alkyl 5 in good yields. Click coupling between propargylated free dyes D X 3a‐b and azide‐carrying P alkyl gave dye‐conjugated polymers P X 6a‐b in a charge neutral hydroxylated (X = OH) and ionically changed sulfated (X = SO 4 − ) version, which were subjected to ultra, gel, and centrifugal filtration to remove catalyst remains and unreacted free dyes . The complete conversion of the click reaction was monitored by the disappearance of the azide band at ≈2100 cm −1 in the IR spectra (Figure S10, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Polymer—Single‐Walled Carbon Nanotube Complexes with Charged and Noncharged Dendronized Perylene Bisimides for Bioimaging Studies

Huth

Glaeske

Achazi

et al. 2018

Small

View full text Add to dashboard Cite

Fluorescent nanomaterials are expected to revolutionize medical diagnostic, imaging, and therapeutic tools due to their superior optical and structural properties. Their inefficient water solubility, cell permeability, biodistribution, and high toxicity, however, limit the full potential of their application. To overcome these obstacles, a water-soluble, fluorescent, cytocompatible polymer-single-walled carbon nanotube (SWNT) complex is introduced for bioimaging applications. The supramolecular complex consists of an alkylated polymer conjugated with neutral hydroxylated or charged sulfated dendronized perylene bisimides (PBIs) and SWNTs as a general immobilization platform. The polymer backbone solubilizes the SWNTs, decorates them with fluorescent PBIs, and strongly improves their cytocompatibility by wrapping around the SWNT scaffold. In photophysical measurements and biological in vitro studies, sulfated complexes exhibit superior optical properties, cellular uptake, and intracellular staining over their hydroxylated analogs. A toxicity assay confirms the highly improved cytocompatibility of the polymer-wrapped SWNTs toward surfactant-solubilized SWNTs. In microscopy studies the complexes allow for the direct imaging of the SWNTs' cellular uptake via the PBI and SWNT emission using the 1st and 2nd optical window for bioimaging. These findings render the polymer-SWNT complexes with nanometer size, dual fluorescence, multiple charges, and high cytocompatibility as valuable systems for a broad range of fluorescence bioimaging studies.

show abstract

Self‐Assembling Multivalency – Supramolecular Polymers Assembled from Monovalent Mannose‐Labelled Discotic Molecules

Cited by 17 publications

References 45 publications

Dynamic and bio-orthogonal protein assembly along a supramolecular polymer

Dynamic and bio-orthogonal protein assembly along a supramolecular polymer

Monosaccharides as Versatile Units for Water‐Soluble Supramolecular Polymers

Fluorescent Polymer—Single‐Walled Carbon Nanotube Complexes with Charged and Noncharged Dendronized Perylene Bisimides for Bioimaging Studies

Contact Info

Product

Resources

About