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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:
 [1] ; ORCiD logo [2] ;  [3] ; ORCiD logo [4] ;  [3] ; ORCiD logo [1]
  1. Westfalische Wilhelms-Universitat Munster, Munster (Germany). Organic Chemistry Inst. and CeNTech
  2. Westfalische Wilhelms-Universitat Munster, Munster (Germany). Organic Chemistry Inst. and CeNTech; Univ. of Duisburg-Essen, Essen (Germany)
  3. Justus-Liebig Univ., Giessen (Germany). Inst. of Organic Chemistry
  4. SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Institute for Materials and Energy Science (SIMES)
Publication Date:
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.
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.
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.
@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}
}

Works referenced in this record:

Metal-Organic Frameworks from Edible Natural Products
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  • Smaldone, Ronald A.; Forgan, Ross S.; Furukawa, Hiroyasu
  • Angewandte Chemie International Edition, Vol. 49, Issue 46, p. 8630-8634
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