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

Abstract

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];

^[2]; Fokina, Natalie A. ^[3];

^[4]; Schreiner, Peter R. ^[3];

^[1]

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

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

Sponsoring Org.:: USDOE

OSTI Identifier:: 1426597

Alternate Identifier(s):: OSTI ID: 1407823

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

Resource 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

Country of Publication:: United States

Language:: English

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

Citation Formats


                    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., 2017. 
        Web.  doi:10.1002/chem.201703392.

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                    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.

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                    Schibilla, Frauke, Voskuhl, Jens, Fokina, Natalie A., Dahl, Jeremy E.  P., Schreiner, Peter R., and Ravoo, Bart Jan. Mon .  
        "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.

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@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}

}

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DOI: 10.1002/chem.201703392

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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

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

Abstract

Citation Formats

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

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