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:
-
[2];
[4];
[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:
- 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.
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. 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.
@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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