A supramolecular route for reversible protein-polymer conjugation

Biedermann, Frank; Rauwald, Urs; Zayed, Jameel M.; Scherman, Oren A.

doi:10.1039/c0sc00435a

Cited by 110 publications

(112 citation statements)

References 85 publications

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“…[50][51] Here, it was used to investigate the binding affinity of AnPy for CB [8]. The ITC experiments were performed in acetate buffer (50 mm, pH 4.75) at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Host‐Enhanced π–π Interaction for Water‐Soluble Supramolecular Polymerization

Liu

Wang

et al. 2011

Chemistry A European J

114

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Host-enhanced π-π interaction based on anthracene derivatives and cucurbit[8]uril can be used as the driving force for constructing water-soluble supramolecular polymers. For this purpose, two anthracene moieties were encapsulated into one cucurbit[8]uril cavity, forming a ternary complex. After encapsulation in the host, the distance between the two anthracene moieties was shortened, and the π-π interaction between them was enhanced significantly. To realize supramolecular polymerization, a bifunctional monomer consisting of two anthracene moieties and a short linker in between was carefully designed. Cyclization was avoided in this way. Thus, host-enhanced π-π interaction can function as a new driving force for supramolecular polymerization.

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“…[50][51] Here, it was used to investigate the binding affinity of AnPy for CB [8]. The ITC experiments were performed in acetate buffer (50 mm, pH 4.75) at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Host‐Enhanced π–π Interaction for Water‐Soluble Supramolecular Polymerization

Liu

Wang

et al. 2011

Chemistry A European J

114

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“…[31][32][33][34][35] In some cases, dye encapsulation resulted in profound changes in the emission wavelength and quantum yield, as well as increased photostability. [36,37] CB[8]-templated 1:1:1 ternary complexes have been exploited for materials assembly [38][39][40][41] with the macrocycle acting as a supramolecular "handcuff", but fluorescent first guests for CB [8] have remained scarce to date. [36,37] CB[8]-templated 1:1:1 ternary complexes have been exploited for materials assembly [38][39][40][41] with the macrocycle acting as a supramolecular "handcuff", but fluorescent first guests for CB [8] have remained scarce to date.…”

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confidence: 99%

Strongly Fluorescent, Switchable Perylene Bis(diimide) Host–Guest Complexes with Cucurbit[8]uril In Water

et al. 2012

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Supramolecular complexation of perylene bis(diimide) (PDI) dyes with the macrocyclic host cucurbit[8]uril (CB[8]) prevents self-aggregation of the dye molecules and enables their use as highly (photo)chemically stable, strongly-emitting fluorophores in water. The complexes are stimuli-responsive to binders and can be electrochemically cycled, leading to reversible on-off fluorescence switching and access to noncovalent formation of higher-order architectures in water.

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“…[16][17][18][19][20][21][22][23][24][25][26] Examples include polymer conjugation via: co-factor reconstitution, 16 the biotin-streptavidin complex, 18 supramolecular complexation with cucurbituril, 19 charge-charge 20 and metal affinity 21,24 interactions, as well as lectin-mediated complexation. 25,27,28 The advantage of noncovalent systems is that temporal control of conjugate assembly and disassembly can be asserted by the presence of competitor molecules.…”

Section: Introductionmentioning

confidence: 99%

“…25,27,28 The advantage of noncovalent systems is that temporal control of conjugate assembly and disassembly can be asserted by the presence of competitor molecules. 19 In the context of protein therapeutics it is envisaged that the biologically-active ligand-receptor complex may act as a competitor to displace the lower affinity polymer interaction. Thus, the potential interference caused by covalently attached PEG chains will be minimised.…”

Section: Introductionmentioning

confidence: 99%

Noncovalent PEGylation via Lectin–Glycopolymer Interactions

et al. 2016

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The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 2 AbstractPEGylation, the covalent modification of proteins with polyethylene glycol, is an abundantly used technique to improve the pharmacokinetics of therapeutic proteins. The drawback with this methodology is that the covalently attached PEG can impede the biological activity (e.g. reduced receptor-binding capacity). Protein therapeutics with "disposable" PEG modifiers have potential advantages over the current technology. Here, we show that a protein-polymer "Medusa complex" is formed by the combination of a hexavalent lectin with a glycopolymer. Using NMR spectroscopy, small angle X-ray scattering (SAXS), size exclusion chromatography and native gel electrophoresis it was demonstrated that the fucose-binding lectin RSL and a fucose-capped polyethylene glycol (Fuc-PEG) form a multimeric assembly. All of the experimental methods provided evidence of noncovalent PEGylation with a concomitant increase in molecular mass and hydrodynamic radius. The affinity of the protein-polymer complex was determined by ITCand competition experiments to be in the µM range, suggesting that such systems have potential biomedical applications.

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A supramolecular route for reversible protein-polymer conjugation

Cited by 110 publications

References 85 publications

Host‐Enhanced π–π Interaction for Water‐Soluble Supramolecular Polymerization

Host‐Enhanced π–π Interaction for Water‐Soluble Supramolecular Polymerization

Strongly Fluorescent, Switchable Perylene Bis(diimide) Host–Guest Complexes with Cucurbit[8]uril In Water

Noncovalent PEGylation via Lectin–Glycopolymer Interactions

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