Oxidant-responsive ferrocene-based cyclodextrin complex coacervate core micelles

Camilla Facciotti, Vittorio Saggiomo, Simon van Hurne, Anton Bunschoten, Rebecca Kaup, Aldrik H. Velders*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Coacervate-core micelles are considered promising materials for several applications, from catalysis to drug delivery. However, oxidant-responsive coacervate-core micelles, able to undergo structural changes upon specific oxidation stimuli, are not well reported. Here, we present a novel ferrocene–dipicolinic acid derivative as redox-responsive subcomponent to be incorporated in cyclodextrin-based coacervate core micelles, C4Ms, with tuneable core structure and responsiveness towards H2O2 treatment. The Fc-C4Ms are formed combining three orthogonal supramolecular interactions, namely (i) metal-to-ligand coordination between europium(III) ions and dipicolinic acid molecules, (ii) host-guest interaction between beta cyclodextrins and ferrocenes and (iii) electrostatic coacervation interaction. The micelle stability against oxidation can be controlled by varying three main parameters: (a) the core-unit structure, from monomeric metal complexes to supramolecular oligomers, (b) the H2O2 equivalents and c) the ratio between redox-responsive and non-redox-responsive bislinker. The H2O2-responsive ferrocene-based systems might have an interesting application, e.g. reactive oxygen species-mediated drug delivery.

Original languageEnglish
JournalSupramolecular Chemistry
DOIs
Publication statusE-pub ahead of print - 5 Nov 2019

Fingerprint

Cyclodextrins
Micelles
Oxidants
Drug delivery
beta-Cyclodextrins
Europium
Oxidation
Coordination Complexes
Coulomb interactions
Oligomers
Catalysis
Reactive Oxygen Species
Metals
Ions
Ligands
Derivatives
Molecules
Acids
ferrocene
Oxidation-Reduction

Keywords

  • complex coacervate core micelles
  • cyclodextrin
  • ferrocene
  • Host-guest
  • stimuli-responsive

Cite this

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title = "Oxidant-responsive ferrocene-based cyclodextrin complex coacervate core micelles",
abstract = "Coacervate-core micelles are considered promising materials for several applications, from catalysis to drug delivery. However, oxidant-responsive coacervate-core micelles, able to undergo structural changes upon specific oxidation stimuli, are not well reported. Here, we present a novel ferrocene–dipicolinic acid derivative as redox-responsive subcomponent to be incorporated in cyclodextrin-based coacervate core micelles, C4Ms, with tuneable core structure and responsiveness towards H2O2 treatment. The Fc-C4Ms are formed combining three orthogonal supramolecular interactions, namely (i) metal-to-ligand coordination between europium(III) ions and dipicolinic acid molecules, (ii) host-guest interaction between beta cyclodextrins and ferrocenes and (iii) electrostatic coacervation interaction. The micelle stability against oxidation can be controlled by varying three main parameters: (a) the core-unit structure, from monomeric metal complexes to supramolecular oligomers, (b) the H2O2 equivalents and c) the ratio between redox-responsive and non-redox-responsive bislinker. The H2O2-responsive ferrocene-based systems might have an interesting application, e.g. reactive oxygen species-mediated drug delivery.",
keywords = "complex coacervate core micelles, cyclodextrin, ferrocene, Host-guest, stimuli-responsive",
author = "Camilla Facciotti and Vittorio Saggiomo and {van Hurne}, Simon and Anton Bunschoten and Rebecca Kaup and Velders, {Aldrik H.}",
year = "2019",
month = "11",
day = "5",
doi = "10.1080/10610278.2019.1685094",
language = "English",
journal = "Supramolecular Chemistry",
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T1 - Oxidant-responsive ferrocene-based cyclodextrin complex coacervate core micelles

AU - Facciotti, Camilla

AU - Saggiomo, Vittorio

AU - van Hurne, Simon

AU - Bunschoten, Anton

AU - Kaup, Rebecca

AU - Velders, Aldrik H.

PY - 2019/11/5

Y1 - 2019/11/5

N2 - Coacervate-core micelles are considered promising materials for several applications, from catalysis to drug delivery. However, oxidant-responsive coacervate-core micelles, able to undergo structural changes upon specific oxidation stimuli, are not well reported. Here, we present a novel ferrocene–dipicolinic acid derivative as redox-responsive subcomponent to be incorporated in cyclodextrin-based coacervate core micelles, C4Ms, with tuneable core structure and responsiveness towards H2O2 treatment. The Fc-C4Ms are formed combining three orthogonal supramolecular interactions, namely (i) metal-to-ligand coordination between europium(III) ions and dipicolinic acid molecules, (ii) host-guest interaction between beta cyclodextrins and ferrocenes and (iii) electrostatic coacervation interaction. The micelle stability against oxidation can be controlled by varying three main parameters: (a) the core-unit structure, from monomeric metal complexes to supramolecular oligomers, (b) the H2O2 equivalents and c) the ratio between redox-responsive and non-redox-responsive bislinker. The H2O2-responsive ferrocene-based systems might have an interesting application, e.g. reactive oxygen species-mediated drug delivery.

AB - Coacervate-core micelles are considered promising materials for several applications, from catalysis to drug delivery. However, oxidant-responsive coacervate-core micelles, able to undergo structural changes upon specific oxidation stimuli, are not well reported. Here, we present a novel ferrocene–dipicolinic acid derivative as redox-responsive subcomponent to be incorporated in cyclodextrin-based coacervate core micelles, C4Ms, with tuneable core structure and responsiveness towards H2O2 treatment. The Fc-C4Ms are formed combining three orthogonal supramolecular interactions, namely (i) metal-to-ligand coordination between europium(III) ions and dipicolinic acid molecules, (ii) host-guest interaction between beta cyclodextrins and ferrocenes and (iii) electrostatic coacervation interaction. The micelle stability against oxidation can be controlled by varying three main parameters: (a) the core-unit structure, from monomeric metal complexes to supramolecular oligomers, (b) the H2O2 equivalents and c) the ratio between redox-responsive and non-redox-responsive bislinker. The H2O2-responsive ferrocene-based systems might have an interesting application, e.g. reactive oxygen species-mediated drug delivery.

KW - complex coacervate core micelles

KW - cyclodextrin

KW - ferrocene

KW - Host-guest

KW - stimuli-responsive

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M3 - Article

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