Redox-active host-guest supramolecular assemblies of peptides and proteins at surfaces

Brinkmann, Jenny; Wasserberg, Dorothee; Jonkheijm, Pascal

doi:10.1016/j.eurpolymj.2016.03.029

Cited by 20 publications

(17 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To date, the strongest host–guest system discovered is the inclusion complex formed between CB[7] and ferrocene (Fc) or its derivatives. − The formation constant of CB[7]@Fc inclusion complexes (10 9 –10 15 M –1 ) is even comparable with natural biotin–avidin binding pairs . The high binding affinity and other advantages of CB[7]@Fc inclusion complexes, for example, high thermostability, long-term durability, resistance to enzymatic degradation, and the reversible binding behavior, allow them to be applied as a great substitute of natural binding pairs. − To reveal the full application potential of supramolecular chemistry, efforts have been made to understand host–guest binding chemistry at molecular interfaces. − , As for CB[7], the general strategies involve either the direct assembly of CB[7] on gold, − or the immobilization of functionalized CB[7]. − The immobilization of other host molecules (β-cyclodextrin, calixarene) on gold surfaces to form self-assembled monolayers (SAMs) has been also reported. − We have recently explored the binding of CB[7] onto a binary ferrocenylundecanethiolate/octanethiolate SAM on gold (FcC11S-/C8S-Au SAM), which overcomes the limitations of weak CB[7]–gold interaction and the low efficiency of CB[ n ] functionalization . The distinct cyclic voltammetric (CV) responses of CB[7]@Fc inclusion complex allowed us to investigate the formation thermodynamics and kinetics of CB[7]@Fc inclusion complex, for the first time, at a molecular interface …”

Section: Introductionmentioning

confidence: 99%

Host–Guest Interaction at Molecular Interfaces: Cucurbit[7]uril as a Sensitive Probe of Structural Heterogeneity in Ferrocenyl Self-Assembled Monolayers on Gold

Lin

Shao

2018

J. Phys. Chem. C

View full text Add to dashboard Cite

Herein, we combine host–guest recognition chemistry and electrochemical analysis to demonstrate that the nanometer-size, supramolecular hosts can be adapted as sensitive probes for structural heterogeneity in organized molecular assemblies on a surface. In particular, we carried out thorough cyclic voltammetric (CV) studies to evaluate the binding of cucurbit[7]uril on mixed ferrocenylundecanethiolate/n-alkanethiolate self-assembled monolayers (SAMs) on gold (FcC11S-/CmS-Au) prepared with different methods (coadsorption vs postassembly exchanges) and with varied diluting n-alkanethiols. On the basis of the distinct CV responses of CB[7]@Fc complex and free Fc on the SAM surfaces, we were able to determine the conversion ratio from Fc to CB[7]@Fc, a direct indication of its overall density and uniformity. We have shown that the FcC11S-/C8S-Au prepared by coadsorption in a binary solution with low mole fraction of FcC11SH (5%) and by exchanging preassembled C8S-Au SAM with FcC11SH for a short time (1 min) has the “ideal” structure with isolated and uniformly distributed Fc groups on the surface. In contrast, with similar Fc surface coverage, the FcC11S-/C8S-Au prepared by exchanging FcC11S-Au with C8SH for a prolonged time (20 h) has clustered and nonuniformly distributed Fc groups at the surface. While consistent with previous observations based on conventional electrochemical or microscopic studies, the present finding expands the capability of host–guest chemistry as a new tool to probe the structures of organized molecular assemblies at the nanometer scale.

show abstract

Section: Introductionmentioning

confidence: 99%

Host–Guest Interaction at Molecular Interfaces: Cucurbit[7]uril as a Sensitive Probe of Structural Heterogeneity in Ferrocenyl Self-Assembled Monolayers on Gold

Lin

Shao

2018

J. Phys. Chem. C

View full text Add to dashboard Cite

show abstract

“…It should be noted that supramolecular chemistry and, particularly, hostguest interactions, are promising tools in biological as well as materials applications due to the dynamic nature of non covalent interactions and, in addition, because the incorporation of guests can be controlled using external stimuli. 47,48 In the present case, the…”

mentioning

confidence: 44%

Electrochemically driven host–guest interactions on patterned donor/acceptor self-assembled monolayers

et al. 2018

View full text Add to dashboard Cite

Here, on ITO//Au patterned substrates SAMs of ferrocene (Fc) on the Au regions and of anthraquinone (AQ) on the ITO areas are prepared, exhibiting three stable redox states. Furthermore, by selectively oxidizing or reducing the Fc or AQ units, respectively, the surface properties are locally modified. As a proof-of-concept, such a confinement of the properties is exploited to locally form host-guest complexes with β-cyclodextrin on specific surface regions depending on the applied voltage.

show abstract

“…[58][59][60][61] In general, anchoring of CB[n] to surfaces has been achieved in different ways as depicted in Figure 5. [11,57,[62][63][64][65][66] When able to covalently functionalize the CB [7] macrocycle via covalent modification of CB[n] in a strongly oxidative environment to generate reactive perallyloxy sidegroups Kim and coworkers set out to employ these functional groups to covalently anchor CB [6] and CB [7] onto surfaces. Perallyloxy-CB [6] could be anchored via the thiol-ene reaction with thiol-functionalized glass slides to form a thioether bond between surface and macrocycle ( Figure 5a).…”

Section: Cb[n]-mediated Host-guest Chemistry On Surfacesmentioning

confidence: 99%

Stimuli‐Responsive Cucurbit[n]uril‐Mediated Host‐Guest Complexes on Surfaces

Wiemann

Jonkheijm

2017

Israel Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

Supramolecular functional surfaces are at the heart of many materials and medical applications. Increasing interest can be seen for devising new supramolecular functionalization strategies of surfaces. In this review we place particular emphasis on the use of cucurbit[n]urilmediated host-guest complexation as surface functionalization strategy. The state of the art of cucurbit[n]uril-mediated host-guest complexes on surfaces is reviewed. Cucurbit [n] urils (CB[n]) are able to form strong host-guest complexes with affinities that span several orders of magnitudes up to the regime of the biotin-streptavidin pair and that can be modulated by applying remote stimuli provided suitably sensitive guests were selected. Strategies to fabricate stimuliresponsive surfaces creates versatile supramolecular systems and several applications of these types of surfaces are outlined.

show abstract

Redox-active host-guest supramolecular assemblies of peptides and proteins at surfaces

Cited by 20 publications

References 28 publications

Host–Guest Interaction at Molecular Interfaces: Cucurbit[7]uril as a Sensitive Probe of Structural Heterogeneity in Ferrocenyl Self-Assembled Monolayers on Gold

Host–Guest Interaction at Molecular Interfaces: Cucurbit[7]uril as a Sensitive Probe of Structural Heterogeneity in Ferrocenyl Self-Assembled Monolayers on Gold

Electrochemically driven host–guest interactions on patterned donor/acceptor self-assembled monolayers

Stimuli‐Responsive Cucurbit[n]uril‐Mediated Host‐Guest Complexes on Surfaces

Contact Info

Product

Resources

About