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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:
 [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:
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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Works referenced in this record:

Cyclodextrins and their uses: a review
journal, May 2004


Supramolecular Materials Cross-Linked by Host–Guest Inclusion Complexes: The Effect of Side Chain Molecules on Mechanical Properties
journal, April 2017


Cucurbit[7]uril⋅Guest Pair with an Attomolar Dissociation Constant
journal, January 2014

  • Cao, Liping; Šekutor, Marina; Zavalij, Peter Y.
  • Angewandte Chemie International Edition, Vol. 53, Issue 4
  • DOI: 10.1002/anie.201309635

Unraveling the Structure–Affinity Relationship between Cucurbit[ n ]urils ( n = 7, 8) and Cationic Diamondoids
journal, February 2017

  • Sigwalt, David; Šekutor, Marina; Cao, Liping
  • Journal of the American Chemical Society, Vol. 139, Issue 8
  • DOI: 10.1021/jacs.7b00056

Supramolecular Guest–Host Interactions for the Preparation of Biomedical Materials
journal, October 2015


Water Structure Recovery in Chaotropic Anion Recognition: High-Affinity Binding of Dodecaborate Clusters to γ-Cyclodextrin
journal, May 2015

  • Assaf, Khaleel I.; Ural, Merve S.; Pan, Fangfang
  • Angewandte Chemie, Vol. 127, Issue 23
  • DOI: 10.1002/ange.201412485

High-affinity host–guest chemistry of large-ring cyclodextrins
journal, January 2016

  • Assaf, Khaleel I.; Gabel, Detlef; Zimmermann, Wolfgang
  • Organic & Biomolecular Chemistry, Vol. 14, Issue 32
  • DOI: 10.1039/C6OB01161F

Diamantane. II. Preparation of derivatives of diamantane
journal, October 1974

  • Gund, Tamara M.; Nomura, M.; Schleyer, P. v. R.
  • The Journal of Organic Chemistry, Vol. 39, Issue 20
  • DOI: 10.1021/jo00934a010

Supramolecular Chemistry at Interfaces: Host–Guest Interactions for Fabricating Multifunctional Biointerfaces
journal, April 2014

  • Yang, Hui; Yuan, Bin; Zhang, Xi
  • Accounts of Chemical Research, Vol. 47, Issue 7
  • DOI: 10.1021/ar500105t

Social Self-Sorting of Colloidal Families in Co-Assembling Microgel Systems
journal, January 2017

  • Han, Kang; Go, Dennis; Tigges, Thomas
  • Angewandte Chemie International Edition, Vol. 56, Issue 8
  • DOI: 10.1002/anie.201612196

Dynamic Macromolecular Material Design-The Versatility of Cyclodextrin-Based Host-Guest Chemistry
journal, June 2017

  • Schmidt, Bernhard V. K. J.; Barner-Kowollik, Christopher
  • Angewandte Chemie International Edition, Vol. 56, Issue 29
  • DOI: 10.1002/anie.201612150

Diamondoids: functionalization and subsequent applications of perfectly defined molecular cage hydrocarbons
journal, January 2014

  • Gunawan, Maria A.; Hierso, Jean-Cyrille; Poinsot, Didier
  • New J. Chem., Vol. 38, Issue 1
  • DOI: 10.1039/C3NJ00535F

“Diamonds are a chemist's best friend”: die großen Geschwister des Adamantans
journal, January 2008

  • Schwertfeger, Hartmut; Fokin, Andrey A.; Schreiner, Peter R.
  • Angewandte Chemie, Vol. 120, Issue 6
  • DOI: 10.1002/ange.200701684

Molecular Printboards:  Monolayers of β-Cyclodextrins on Silicon Oxide Surfaces
journal, June 2004

  • Onclin, Steffen; Mulder, Alart; Huskens, Jurriaan
  • Langmuir, Vol. 20, Issue 13
  • DOI: 10.1021/la049561k

Complexation Thermodynamics of Cyclodextrins
journal, July 1998

  • Rekharsky, Mikhail V.; Inoue, Yoshihisa
  • Chemical Reviews, Vol. 98, Issue 5
  • DOI: 10.1021/cr970015o

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

  • Smaldone, Ronald A.; Forgan, Ross S.; Furukawa, Hiroyasu
  • Angewandte Chemie, Vol. 122, Issue 46
  • DOI: 10.1002/ange.201002343

Synthetic Routes to Aminotriamantanes, Topological Analogues of the Neuroprotector Memantine®
journal, March 2009


Water Structure Recovery in Chaotropic Anion Recognition: High-Affinity Binding of Dodecaborate Clusters to γ-Cyclodextrin
journal, May 2015

  • Assaf, Khaleel I.; Ural, Merve S.; Pan, Fangfang
  • Angewandte Chemie International Edition, Vol. 54, Issue 23
  • DOI: 10.1002/anie.201412485

Sugar-Decorated Sugar Vesicles: Lectin-Carbohydrate Recognition at the Surface of Cyclodextrin Vesicles
journal, January 2010

  • Voskuhl, Jens; Stuart, Marc C. A.; Ravoo, Bart Jan
  • Chemistry - A European Journal, Vol. 16, Issue 9
  • DOI: 10.1002/chem.200902423

Nanodiamonds in sugar rings: an experimental and theoretical investigation of cyclodextrin–nanodiamond inclusion complexes
journal, January 2012

  • Voskuhl, Jens; Waller, Mark; Bandaru, Sateesh
  • Organic & Biomolecular Chemistry, Vol. 10, Issue 23
  • DOI: 10.1039/c2ob06915f

Molecular recognition of bilayer vesicles
journal, January 2009

  • Voskuhl, Jens; Ravoo, Bart Jan
  • Chem. Soc. Rev., Vol. 38, Issue 2
  • DOI: 10.1039/B803782P

Cyclodextrin-adamantanecarboxylate inclusion complexes: studies of the variation in cavity size
journal, January 1985

  • Cromwell, William C.; Bystrom, Katarina; Eftink, Maurice R.
  • The Journal of Physical Chemistry, Vol. 89, Issue 2
  • DOI: 10.1021/j100248a029

Cucurbit[7]uril⋅Guest Pair with an Attomolar Dissociation Constant
journal, January 2014

  • Cao, Liping; Šekutor, Marina; Zavalij, Peter Y.
  • Angewandte Chemie, Vol. 126, Issue 4
  • DOI: 10.1002/ange.201309635

Synthesis of Diamondoid Carboxylic Acids
journal, November 2011

  • Fokina, Natalie; Tkachenko, Boryslav; Dahl, Jeremy
  • Synthesis, Vol. 2012, Issue 02
  • DOI: 10.1055/s-0031-1289617

A carbohydrate-based hydrogel containing vesicles as responsive non-covalent cross-linkers
journal, January 2014

  • Himmelein, Sabine; Lewe, Vanessa; Stuart, Marc C. A.
  • Chemical Science, Vol. 5, Issue 3
  • DOI: 10.1039/c3sc52964a

Dynamisches makromolekulares Materialdesign - die Vielseitigkeit von Cyclodextrin-basierter Wirt-Gast-Chemie
journal, June 2017

  • Schmidt, Bernhard V. K. J.; Barner-Kowollik, Christopher
  • Angewandte Chemie, Vol. 129, Issue 29
  • DOI: 10.1002/ange.201612150

Cyclodextrin-Based Host–Guest Supramolecular Nanoparticles for Delivery: From Design to Applications
journal, April 2014

  • Hu, Qi-Da; Tang, Gu-Ping; Chu, Paul K.
  • Accounts of Chemical Research, Vol. 47, Issue 7
  • DOI: 10.1021/ar500055s

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

Bilayer Vesicles of Amphiphilic Cyclodextrins: Host Membranes That Recognize Guest Molecules
journal, February 2005

  • Falvey, Patrick; Lim, Choon Woo; Darcy, Raphael
  • Chemistry - A European Journal, Vol. 11, Issue 4
  • DOI: 10.1002/chem.200400905

Cyclodextrin-based supramolecular nanoparticles for biomedical applications
journal, January 2017

  • Mejia-Ariza, Raquel; Graña-Suárez, Laura; Verboom, Willem
  • Journal of Materials Chemistry B, Vol. 5, Issue 1
  • DOI: 10.1039/C6TB02776H

Diamonds are a Chemist's Best Friend: Diamondoid Chemistry Beyond Adamantane
journal, January 2008

  • Schwertfeger, Hartmut; Fokin, Andrey A.; Schreiner, Peter R.
  • Angewandte Chemie International Edition, Vol. 47, Issue 6
  • DOI: 10.1002/anie.200701684