Preparation of Vesicles and Nanoparticles of Amphiphilic Cyclodextrins Containing Labile Disulfide Bonds

Darren Nolan, Raphael Darcy, B.J. Ravoo

    Research output: Contribution to journalArticleAcademic

    49 Citations (Scopus)

    Abstract

    Amphiphilic cyclodextrin derivatives were prepared in which a disulfide bond connects the hydrophobic substituents to the macrocycle. These compounds were obtained by 1,3-dicyclohexylcarbodiimide-mediated coupling reactions of heptakis(6-amino-6-deoxy)-B-cyclodextrins and disulfide-containing carboxylic acids of increasing hydrophobicity. To improve the water solubility of the cyclodextrins, oligo(ethylene glycol) substituents were grafted to the secondary side of the cyclodextrin molecules. The amphiphilic cyclodextrins form vesicles or nanoparticles in water, which disintegrate in the presence of the disulfide reducing agent dithiothreitol. Hydrophobic guest molecules are released from the nanoparticles upon cleavage of the disulfides.
    Original languageUndefined
    Pages (from-to)4469-4472
    JournalLangmuir
    Volume19
    Issue number10
    DOIs
    Publication statusPublished - 2003

    Keywords

    • IR-59318

    Cite this

    Nolan, Darren ; Darcy, Raphael ; Ravoo, B.J. / Preparation of Vesicles and Nanoparticles of Amphiphilic Cyclodextrins Containing Labile Disulfide Bonds. In: Langmuir. 2003 ; Vol. 19, No. 10. pp. 4469-4472.
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    abstract = "Amphiphilic cyclodextrin derivatives were prepared in which a disulfide bond connects the hydrophobic substituents to the macrocycle. These compounds were obtained by 1,3-dicyclohexylcarbodiimide-mediated coupling reactions of heptakis(6-amino-6-deoxy)-B-cyclodextrins and disulfide-containing carboxylic acids of increasing hydrophobicity. To improve the water solubility of the cyclodextrins, oligo(ethylene glycol) substituents were grafted to the secondary side of the cyclodextrin molecules. The amphiphilic cyclodextrins form vesicles or nanoparticles in water, which disintegrate in the presence of the disulfide reducing agent dithiothreitol. Hydrophobic guest molecules are released from the nanoparticles upon cleavage of the disulfides.",
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    author = "Darren Nolan and Raphael Darcy and B.J. Ravoo",
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    Preparation of Vesicles and Nanoparticles of Amphiphilic Cyclodextrins Containing Labile Disulfide Bonds. / Nolan, Darren; Darcy, Raphael; Ravoo, B.J.

    In: Langmuir, Vol. 19, No. 10, 2003, p. 4469-4472.

    Research output: Contribution to journalArticleAcademic

    TY - JOUR

    T1 - Preparation of Vesicles and Nanoparticles of Amphiphilic Cyclodextrins Containing Labile Disulfide Bonds

    AU - Nolan, Darren

    AU - Darcy, Raphael

    AU - Ravoo, B.J.

    PY - 2003

    Y1 - 2003

    N2 - Amphiphilic cyclodextrin derivatives were prepared in which a disulfide bond connects the hydrophobic substituents to the macrocycle. These compounds were obtained by 1,3-dicyclohexylcarbodiimide-mediated coupling reactions of heptakis(6-amino-6-deoxy)-B-cyclodextrins and disulfide-containing carboxylic acids of increasing hydrophobicity. To improve the water solubility of the cyclodextrins, oligo(ethylene glycol) substituents were grafted to the secondary side of the cyclodextrin molecules. The amphiphilic cyclodextrins form vesicles or nanoparticles in water, which disintegrate in the presence of the disulfide reducing agent dithiothreitol. Hydrophobic guest molecules are released from the nanoparticles upon cleavage of the disulfides.

    AB - Amphiphilic cyclodextrin derivatives were prepared in which a disulfide bond connects the hydrophobic substituents to the macrocycle. These compounds were obtained by 1,3-dicyclohexylcarbodiimide-mediated coupling reactions of heptakis(6-amino-6-deoxy)-B-cyclodextrins and disulfide-containing carboxylic acids of increasing hydrophobicity. To improve the water solubility of the cyclodextrins, oligo(ethylene glycol) substituents were grafted to the secondary side of the cyclodextrin molecules. The amphiphilic cyclodextrins form vesicles or nanoparticles in water, which disintegrate in the presence of the disulfide reducing agent dithiothreitol. Hydrophobic guest molecules are released from the nanoparticles upon cleavage of the disulfides.

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    U2 - 10.1021/la034330j

    DO - 10.1021/la034330j

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    JO - Langmuir

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