Reversible immobilization of a protein to a gold surface through multiple host–guest interactions

Schwarz, Dennis H.; Elgaher, Walid A. M.; Hollemeyer, Klaus; Hirsch, Anna K. H.; Wenz, Gerhard

doi:10.1039/c9tb00560a

Cited by 5 publications

(4 citation statements)

References 38 publications

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“…Direct attachment of adamantyldecorated proteins should also be possible in the future, as has been demonstrated with thiolated β-CD at planar Au surfaces. 61 As a further demonstration of post-functional modification of the non-covalent click system, we synthesized a series of adamantyl derivatives featuring a PEG linker and alkyl chloride tail, suitable for reacting with HaloTagged proteins (A3Halo, A4Halo, and others). HaloTag is a recombinant modified protein fragment derived from a bacterial enzyme, that can be expressed as a linked tag to other recombinant proteins, and rapidly and specifically forms a covalent bond with small molecule alkyl halides.…”

Section: Resultsmentioning

confidence: 99%

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Supramolecular Click Chemistry for Surface Modification of Quantum Dots Mediated by Cucurbit[7]uril

McGuire,

He,

Gracie

et al. 2023

ACS Nano

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Cucurbiturils (CBs), barrel-shaped macrocyclic molecules, are capable of self-assembling at the surface of nanomaterials in their native state, via their carbonyl-ringed portals. However, the symmetrical two-portal structure typically leads to aggregated nanomaterials. We demonstrate that fluorescent quantum dot (QD) aggregates linked with CBs can be broken-up, retaining CBs adsorbed at their surface, via inclusion of guests in the CB cavity. Simultaneously, the QD surface is modified by a functional tail on the guest, thus the high affinity host–guest binding (logK a > 9) enables a non-covalent, click-like modification of the nanoparticles in aqueous solution. We achieved excellent modification efficiency in several functional QD conjugates as protein labels. Inclusion of weaker-binding guests (logK a = 4–6) enables subsequent displacement with stronger binders, realising modular switchable surface chemistries. Our general “hook-and-eye” approach to host–guest chemistry at nanomaterial interfaces will lead to divergent routes for nano-architectures with rich functionalities for theranostics and photonics in aqueous systems.

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Section: Resultsmentioning

confidence: 99%

“…In both cases, lack of the biotinylated guest at the surface stops the specific ligand-protein interaction. Direct attachment of adamantyl-decorated proteins should also be possible in the future, as has been demonstrated with thiolated β-CD at planar Au surfaces …”

Section: Resultsmentioning

confidence: 99%

Supramolecular Click Chemistry for Surface Modification of Quantum Dots Mediated by Cucurbit[7]uril

McGuire,

He,

Gracie

et al. 2023

ACS Nano

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“…The first example of a host-guest system applied to the electrochemical control of living cells attachment/detachment process was designed by Q. An et al [6] The host compound cucurbit [8]uril is able to bind two aromatic guest molecules, one of them displaying a linear RGDS peptide. L. Yang et al reported the immobilization of a divalent ferrocene-tagged protein onto -CD-modified surface and demonstrated the reversibility of the adsorption upon oxidation of the ferrocene moieties.…”

Section: Introductionmentioning

confidence: 99%

“…Schwartz et al immobilized adamantylated proteins to a -CD monolayer functionalized gold surface. [8] The addition of an excess of competitive adamantine guest molecule in solution triggered the release of bound proteins. In our group, we are particularly interested in the β-cyclodextrin/ferrocene (β-CD/Fc) inclusion complex as it is able to dissociate under mild electrochemical polarization.…”

Section: Introductionmentioning

confidence: 99%

Impact of Multimeric Ferrocene‐containing Cyclodecapeptide Scaffold on Host‐Guest Interactions at a β‐Cyclodextrin Covered Surface

et al. 2021

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Among non-covalent bonds, the host-guest interaction is an attractive way to attach biomolecules to solid surfaces since the binding strength can be tuned by the nature of host and guest partners or through the valency of the interaction. For that purpose, we synthesized cyclodecapeptide scaffolds exhibiting in a spatially controlled manner two independent domains enabling the multimeric presentation of guest molecules on one face and the other face enabling the potential grafting of a biomolecule of interest. In this work, we were interested in the β-cyclodextrin/ferrocene inclusion complex formed on β-CD monolayers functionalized surfaces. By using surface sensitive techniques such as quartz crystal microbalance and surface plasmon resonance, we quantified the influence of the guest valency on the stability of the inclusion complexes. The results show a drastic enhancement of the affinity with the gradual increase of guest valency. Considering that the sequential binding events are equal and independent, we applied the multivalent model developed by the Huskens group to extract intrinsic binding constants and an effective concentration of host.

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Dynamic Combinatorial Chemistry Unveils Nsp10 Inhibitors with Antiviral Potential Against SARS‐CoV‐2

Jumde,

Jézéquel,

Saramago

et al. 2024

Chemistry A European J

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The development of antiviral drugs against the Severe Acute Respiratory Syndrome coronavirus 2 (SARS‐CoV‐2) responsible for the recent Covid‐19 pandemic is crucial, as treatment options remain limited and vaccination does not prevent (re)infection. Two relatively underexplored targets of this virus are the 3′‐5′ exoribonuclease (ExoN) and the 2’‐O‐methyltransferase (2′‐O‐Mtase), both essential for the viral viability. The non‐structural protein Nsp14 and Nsp16 exhibit enzymatic activities for ExoN and 2′‐O‐Mtase, respectively, especially when in complex with their co‐factor protein Nsp10. The study focuses on the use of target‐directed dynamic combinatorial chemistry (tdDCC) to identify binders of Nsp10, aiming to disturb the protein‐protein interactions (PPI) involving Nsp10–Nsp14, as well as Nsp10–Nsp16. We synthesised the hits and evaluated them to assess Nsp10 affinity, ExoN and 2′‐O‐Mtase activities inhibition, and anti‐viral activity in hCoV‐229E and SARS‐CoV‐2 infected whole‐cell setting. This study reports a novel class of ExoN and/or 2′‐O‐Mtase inhibitors exhibiting anti‐viral activity against coronaviruses.

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Reversible immobilization of a protein to a gold surface through multiple host–guest interactions

Abstract: Monolayers were formed by specific interactions between adamantylated proteins (transferrin, lysozyme) and a β-cyclodextrin (β-CD) monolayer on a gold surface.

Cited by 5 publications

References 38 publications

Supramolecular Click Chemistry for Surface Modification of Quantum Dots Mediated by Cucurbit[7]uril

Supramolecular Click Chemistry for Surface Modification of Quantum Dots Mediated by Cucurbit[7]uril

Impact of Multimeric Ferrocene‐containing Cyclodecapeptide Scaffold on Host‐Guest Interactions at a β‐Cyclodextrin Covered Surface

Dynamic Combinatorial Chemistry Unveils Nsp10 Inhibitors with Antiviral Potential Against SARS‐CoV‐2

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