Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials

doi:10.1002/chem.201703392

Title: Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials

We report the inclusion of carboxy- and amine-substituted molecular nanodiamonds (NDs) adamantane, diamantane, and triamantane by β-cyclodextrin and γ-cyclodextrin (β-CD and γ-CD), which have particularly well-suited hydrophobicity and symmetry for an optimal fit of the host and guest molecules. We studied the host–guest interactions in detail and generally observed 1:1 association of the NDs with the larger γ-CD cavity, but observed 1:2 association for the largest ND in the series (triamantane) with β-CD. Here, we found higher binding affinities for carboxy-substituted NDs than for amine-substituted NDs. Additionally, cyclodextrin vesicles (CDVs) were decorated with d-mannose by using adamantane, diamantane, and triamantane as non-covalent anchors, and the resulting vesicles were compared with the lectin concanavalin A in agglutination experiments. Agglutination was directly correlated to the host–guest association: adamantane showed lower agglutination than di- or triamantane with β-CDV and almost no agglutination with γ-CDV, whereas high agglutination was observed for di- and triamantane with γ-CDV.

Authors:

Schibilla, Frauke ^[1] ; ; Fokina, Natalie A. ^[3] ; ; Schreiner, Peter R. ^[3] ;

Westfalische Wilhelms-Universitat Munster, Munster (Germany). Organic Chemistry Inst. and CeNTech
Westfalische Wilhelms-Universitat Munster, Munster (Germany). Organic Chemistry Inst. and CeNTech; Univ. of Duisburg-Essen, Essen (Germany)
Justus-Liebig Univ., Giessen (Germany). Inst. of Organic Chemistry
SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Institute for Materials and Energy Science (SIMES)

Publication Date:: 2017-11-06

Grant/Contract Number:: AC02-76SF00515; RA 1732/7-1

Type:: Accepted Manuscript

Journal Name:: Chemistry - A European Journal

Additional Journal Information:: Journal Volume: 23; Journal Issue: 63; Journal ID: ISSN 0947-6539

Publisher:: ChemPubSoc Europe

Research Org:: SLAC National Accelerator Lab., Menlo Park, CA (United States)

Sponsoring Org:: USDOE

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; agglutination; cyclodextrins; host–guest systems; molecular recognition; self-assembly

OSTI Identifier:: 1426597

Alternate Identifier(s):: OSTI ID: 1407823


                    Schibilla, Frauke, Voskuhl, Jens, Fokina, Natalie A., Dahl, Jeremy E.  P., Schreiner, Peter R., and Ravoo, Bart Jan. Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials.  United States: N. p.,  
        Web.  doi:10.1002/chem.201703392.

Copy to clipboard


                    Schibilla, Frauke, Voskuhl, Jens, Fokina, Natalie A., Dahl, Jeremy E.  P., Schreiner, Peter R., & Ravoo, Bart Jan. Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials.  United States.  doi:10.1002/chem.201703392.

Copy to clipboard


                    Schibilla, Frauke, Voskuhl, Jens, Fokina, Natalie A., Dahl, Jeremy E.  P., Schreiner, Peter R., and Ravoo, Bart Jan. 2017.  
        "Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials".  United States.  
        doi:10.1002/chem.201703392.  https://www.osti.gov/servlets/purl/1426597.

Copy to clipboard


                    
@article{osti_1426597,

  title        = {Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials},

  author       = {Schibilla, Frauke and Voskuhl, Jens and Fokina, Natalie A. and Dahl, Jeremy E.  P. and Schreiner, Peter R. and Ravoo, Bart Jan},

  abstractNote = {We report the inclusion of carboxy- and amine-substituted molecular nanodiamonds (NDs) adamantane, diamantane, and triamantane by β-cyclodextrin and γ-cyclodextrin (β-CD and γ-CD), which have particularly well-suited hydrophobicity and symmetry for an optimal fit of the host and guest molecules. We studied the host–guest interactions in detail and generally observed 1:1 association of the NDs with the larger γ-CD cavity, but observed 1:2 association for the largest ND in the series (triamantane) with β-CD. Here, we found higher binding affinities for carboxy-substituted NDs than for amine-substituted NDs. Additionally, cyclodextrin vesicles (CDVs) were decorated with d-mannose by using adamantane, diamantane, and triamantane as non-covalent anchors, and the resulting vesicles were compared with the lectin concanavalin A in agglutination experiments. Agglutination was directly correlated to the host–guest association: adamantane showed lower agglutination than di- or triamantane with β-CDV and almost no agglutination with γ-CDV, whereas high agglutination was observed for di- and triamantane with γ-CDV.},

  doi          = {10.1002/chem.201703392},

  journal      = {Chemistry - A European Journal},

  number       = 63,

  volume       = 23,

  place        = {United States},

  year         = {2017},

  month        = {11}

}

Copy to clipboard

Citation Metrics
Cited by: 4works
Citation information provided by
Web of Science

Save / Share this Record
Export Metadata
- Endnote
- RIS
- Excel
- CSV
- XML
Save to My Library
Send to Email

Send to Email

Email address:

Content:

Works referenced in this record:

Metal-Organic Frameworks from Edible Natural Products
journal, August 2010

Smaldone, Ronald A.; Forgan, Ross S.; Furukawa, Hiroyasu
Angewandte Chemie International Edition, Vol. 49, Issue 46, p. 8630-8634
DOI: 10.1002/anie.201002343

Similar Records

Similar records in DOE PAGES and OSTI.GOV collections:

Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials

Journal Article Schibilla, Frauke ; Voskuhl, Jens ; Fokina, Natalie A. ; ... November 2017 - Chemistry - A European Journal

Cited by 4Full Text Available
Non-equilibrium phenomena and kinetic pathways in self-assembled polyelectrolyte complexes

Journal Article Wu, Hao ; Ting, Jeffrey M. ; Werba, Olivia ; ... July 2018 - Journal of Chemical Physics

Polyelectrolyte complexation has been conventionally focused on the thermodynamic states, where assemblies have equilibrated in solutions. Far less attention has been given to complex systems that are kinetically trapped at non-equilibrium states. A combination of time-resolved dynamic light scattering, small angle X-ray scattering (SAXS), and cryogenic transmission electron microscopy (Cryo-TEM) was employed here to investigate the internal structures and morphological evolution of non-equilibrium aggregates forming from a pair of two strong block polyelectrolytes over wide time and length scales. The role of formation pathways of electrostatically driven aggregates was assessed using two processing protocols: direct dissolution and salt annealing. Themore »« less
Cited by 1
Conformational Selection as the Mechanism of Guest Binding in a Flexible Supramolecular Host

Journal Article Hong, Cynthia M. ; Kaphan, David M. ; Bergman, Robert G. ; ... June 2017 - Journal of the American Chemical Society

This work offers a detailed mechanistic investigation of host-guest encapsulation behavior in a new enzyme-mimetic metal-ligand host and provides the first observation of a conformational selection mechanism (as opposed to induced fit) in a supramolecular system. The Ga ₄L ₄ host described features a C ₃-symmetric ligand motif with meta-substituted phenyl spacers, which enables the host to initially self-assemble into an S ₄-symmetric structure and then subsequently isomerize to a T-symmetric tetrahedron for better accommodation of a sufficiently large guest. Selective inversion recovery ¹H NMR studies provide structural insights into the self-exchange behaviors of the host and the guest individuallymore »« less
Cited by 9Full Text Available
Highly stable and self-repairing membrane-mimetic 2D nanomaterials assembled from lipid-like peptoids

Journal Article Jin, Haibao ; Jiao, Fang ; Daily, Michael D. ; ... July 2016 - Nature Communications

Two-dimensional (2D) materials with molecular-scale thickness have attracted increasing interest for separation, electronic, catalytic, optical, energy and biomedical applications. Although extensive research on 2D materials, such as graphene and graphene oxide, has been performed in recent years, progress is limited on self-assembly of 2D materials from sequence-specific macromolecules, especially from synthetic sequences that could exhibit lipid-like self-assembly of bilayer sheets and mimic membrane proteins for functions. The creation of such new class of materials could enable development of highly stable biomimetic membranes that exhibit cell-membrane-like molecular transport with exceptional selectively and high transport rates. Here we demonstrate self-assembly of lipid-likemore »« less
Cited by 6Full Text Available
Highly stable and self-repairing membrane-mimetic 2D nanomaterials assembled from lipid-like peptoids

Journal Article Jin, Haibao ; Jiao, Fang ; Daily, Michael D. ; ... July 2016 - Nature Communications

An ability to develop sequence-defined synthetic polymers that both mimic lipid amphiphilicity for self-assembly of highly stable membrane-mimetic 2D nanomaterials and exhibit protein-like functionality would revolutionize the development of biomimetic membranes. Here we report the assembly of lipid-like peptoids into highly stable, crystalline, free-standing and self-repairing membrane-mimetic 2D nanomaterials through a facile crystallization process. Both experimental and molecular dynamics simulation results show that peptoids assemble into membranes through an anisotropic formation process. We further demonstrated the use of peptoid membranes as a robust platform to incorporate and pattern functional objects through large side-chain diversity and/or co-crystallization approaches. Similar to lipidmore »« less
Cited by 6Full Text Available

Access journal articles and accepted manuscripts resulting from DOE research funding

Title: Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials

Access journal articles and accepted manuscripts
resulting from DOE research funding