Cyclodextrin-based supramolecular nanoparticles stabilized by balancing attractive host–guest and repulsive electrostatic interactions

Suárez, Laura Graña; Verboom, Willem; Huskens, Jurriaan

doi:10.1039/c4cc03136a

Cited by 37 publications

(26 citation statements)

References 22 publications

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“…Furthermore, hydrolyzing the non-reacted anhydrides to carboxylates, provides good solubility in aqueous solutions (pKa 1 = 4)4445. This approach resulted in the synthesis of two fluorescent β-CD-PIBMA-polymers and one solely fluorescent PIBMA 39 -polymer without β-CD for control experiments.…”

Section: Resultsmentioning

confidence: 99%

Obtaining control of cell surface functionalizations via Pre-targeting and Supramolecular host guest interactions

Rood

Spa

Welling

et al. 2017

Sci Rep

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The use of mammalian cells for therapeutic applications is finding its way into modern medicine. However, modification or “training” of cells to make them suitable for a specific application remains complex. By envisioning a chemical toolbox that enables specific, but straight-forward and generic cellular functionalization, we investigated how membrane-receptor (pre)targeting could be combined with supramolecular host-guest interactions based on β-cyclodextrin (CD) and adamantane (Ad). The feasibility of this approach was studied in cells with membranous overexpression of the chemokine receptor 4 (CXCR4). By combining specific targeting of CXCR4, using an adamantane (Ad)-functionalized Ac-TZ14011 peptide (guest; KD = 56 nM), with multivalent host molecules that entailed fluorescent β-CD-Poly(isobutylene-alt-maleic-anhydride)-polymers with different fluorescent colors and number of functionalities, host-guest cell-surface modifications could be studied in detail. A second set of Ad-functionalized entities enabled introduction of additional surface functionalities. In addition, the attraction between CD and Ad could be used to drive cell-cell interactions. Combined we have shown that supramolecular interactions, that are based on specific targeting of an overexpressed membrane-receptor, allow specific and stable, yet reversible, surface functionalization of viable cells and how this approach can be used to influence the interaction between cells and their surroundings.

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Section: Resultsmentioning

confidence: 99%

Obtaining control of cell surface functionalizations via Pre-targeting and Supramolecular host guest interactions

Rood

Spa

Welling

et al. 2017

Sci Rep

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“…Our group recently reported an SNP study in which the function of the monovalently host–guest interacting Ad‐PEG was evaluated in more detail . SNPs were stabilized by multivalent host–guest interactions of p‐tert ‐butylphenyl (TBP) and β‐CD using β‐CD and TBP‐modified poly(isobutyl‐ alt ‐maleic acid) (PiBMA) ( Figure ).…”

Section: Supramolecular Nanoparticles Mediated By Host–guest Interactmentioning

confidence: 99%

“…a) Schematic representation of SNP formation from poly(isobutyl‐ alt ‐maleic acid) (PiBMA) grafted with β‐CD as the host polymer, PiBMA functionalized with p‐tert‐butylphenyl (TBP) as the guest polymer and Ad‐PEG. b) Structures of TBP‐PiBMA (left) and CD‐PiBMA (right) …”

Section: Supramolecular Nanoparticles Mediated By Host–guest Interactmentioning

confidence: 99%

Soft Supramolecular Nanoparticles by Noncovalent and Host–Guest Interactions

Stoffelen

Huskens

2015

Small

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Supramolecular chemistry provides a tool for the formation of highly ordered structures by means of noncovalent interactions. Soft supramolecular nanoparticles are self-assembled nanoassemblies based on small building blocks and stabilized by basic noncovalent interactions, selective host-guest interactions, or a combination of different interaction types. This review provides an overview of the existing approaches for the formation of supramolecular nanoparticles by various types of noncovalent interactions, with a strong focus on host-guest-mediated assemblies. The approaches are ordered based on the nature of the stabilizing supramolecular interaction, while focusing on the aspects that determine the particle structure. Where applicable, the use of these self-assembled nanostructures as vectors in molecular diagnostics and therapeutics is described as well. The stable yet reversible nature of supramolecular interactions and their chemical flexibility offer great prospects for the development of highly engineered nanoparticles which are compatible with the complexity of living systems.

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“…The contribution of the repulsive factors to the stability of the assembly could already be observed from the stability of the modified hosts themselves and will also inhibit further aggregation between the separate nanoparticle assemblies, as evidenced from the absence of change in the DLS size distribution plots over the course of 2 weeks. Therefore, the stability and assembly of this system relies on the subtle balance of attractive host–guest and hydrophobic interactions and repulsive Coulombic or steric factors, as was achieved before in other dynamic supramolecular cyclodextrin assemblies …”

Section: Resultsmentioning

confidence: 84%

Mechanochemical Preparation of Stable Sub‐100 nm γ‐Cyclodextrin:Buckminsterfullerene (C60) Nanoparticles by Electrostatic or Steric Stabilization

Guyse

Rosa

Hoogenboom

2018

Chemistry A European J

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Buckminster fullerene (C )'s main hurdle to enter the field of biomedicine is its low bioavailability, which results from its extremely low water solubility. A well-known approach to increase the water solubility of C is by complexation with γ-cyclodextrins. However, the formed complexes are not stable in time as they rapidly aggregate and eventually precipitate due to attractive intermolecular forces, a common problem in inclusion complexes of cyclodextrins. In this study we attempt to overcome the attractive intermolecular forces between the complexes by designing custom γ-cyclodextrin (γCD)-based supramolecular hosts for C that inhibit the aggregation found in native γCD-C complexes. The approach entails the introduction of either repulsive electrostatic forces or increased steric hindrance to prevent aggregation, thus enhancing the biomedical application potential of C . These modifications have led to new sub-100 nm nanostructures that show long-term stability in solution.

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Cyclodextrin-based supramolecular nanoparticles stabilized by balancing attractive host–guest and repulsive electrostatic interactions

Cited by 37 publications

References 22 publications

Obtaining control of cell surface functionalizations via Pre-targeting and Supramolecular host guest interactions

Obtaining control of cell surface functionalizations via Pre-targeting and Supramolecular host guest interactions

Soft Supramolecular Nanoparticles by Noncovalent and Host–Guest Interactions

Mechanochemical Preparation of Stable Sub‐100 nm γ‐Cyclodextrin:Buckminsterfullerene (C60) Nanoparticles by Electrostatic or Steric Stabilization

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