A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

• significant potential for photodynamic therapy. Herein we report that squaraines can be immobilized on a self-assembled nanocarrier composed of amphiphilic cyclodextrins to enhance their photochemical activity. To this end, a squaraine was equipped with two adamantane moieties that act as anchors for the

• -assembled from amphiphilic cyclodextrin [27]. Given their negligible toxicity cyclodextrins have been utilized as carriers in a number of studies [28][29]. Amphiphilic cyclodextrins substituted with hydrophobic alkyl groups on the primary side and hydrophilic oligo(ethylene glycol) units on the secondary

• 30 µM (since approximately 50% of the amphiphilic cyclodextrins reside at the interior surface of the CDV and AdSq is too large and too polar to pass the membrane), saturation is reached at a six-fold excess of host to guest, even though both are present in micromolar concentrations only. The binding

Aggregation behavior of amphiphilic cyclodextrins in a nonpolar solvent: evidence of large-scale structures by atomistic molecular dynamics simulations and solution studies

• Giuseppina Raffaini,
• Fabio Ganazzoli and
• Antonino Mazzaglia

Beilstein J. Org. Chem. 2016, 12, 73–80, doi:10.3762/bjoc.12.8

• nanoaggregates even in apolar solvents. Keywords: aggregation; amphiphilic cyclodextrins; molecular dynamics; nanoparticles; self-assembly; simulations; Introduction Amphiphilic cyclodextrins (aCD) are a class of molecules highly investigated for their self-assembly properties and inherent potential

• . Furthermore, as the technique is highly sensitive to the aggregates presence, it was not possible to exclude the presence of even nanometric-sized clusters apart from the bigger aggregates [13]. Conclusion Amphiphilic cyclodextrins (aCD) are almost invariably investigated in a water environment for their

• scattering investigations show that, indeed also in a nonpolar solvent such as dichloromethane, these amphiphilic cyclodextrins give rise to quite well defined aggregates, or nanostructures, having a hydrodynamic radius of about 80 nm and a relatively modest polydispersity. This result obtained with a

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

• Giuseppina Raffaini,
• Antonino Mazzaglia and
• Fabio Ganazzoli

Beilstein J. Org. Chem. 2015, 11, 2459–2473, doi:10.3762/bjoc.11.267

• report a theoretical study of the aggregation of a few amphiphilic cyclodextrins carrying hydrophobic thioalkyl groups and hydrophilic ethylene glycol moieties at opposite rims, focusing on the initial nucleation stage in an apolar solvent and in water. The study is based on atomistic molecular dynamics

• correlating their structures with the pharmaceutical properties. Keywords: aggregation; amphiphilic cyclodextrins; micelles; molecular dynamics simulations; nanoparticles; self-assembly; Introduction Inclusion complexes with supramolecular structures formed by native or modified cyclodextrins (CDs) are

• attracting an increasing attention [1][2][3][4][5][6][7][8], including also the new polymeric CD nanogels [9] and nanosponges [10][11][12][13]. Over the past twenty years, amphiphilic cyclodextrins (aCD) formed with α-, β-, or γ-CD have given rise to a wide interest in the scientific community because of

Removal of volatile organic compounds using amphiphilic cyclodextrin-coated polypropylene

• Ludmilla Lumholdt,
• Sophie Fourmentin,
• Thorbjørn T. Nielsen and
• Kim L. Larsen

Beilstein J. Org. Chem. 2014, 10, 2743–2750, doi:10.3762/bjoc.10.290

• for quantification of the uptake exploiting the volatile nature of benzene and its derivatives. The capacity was shown to increase beyond the expected stoichiometries of guest–host complexes with ratios of up to 16:1. Keywords: amphiphilic cyclodextrins; polypropylene; static headspace chromatography

A green approach to the synthesis of novel phytosphingolipidyl β-cyclodextrin designed to interact with membranes

• Yong Miao,
• Florence Djedaïni-Pilard and
• Véronique Bonnet

Beilstein J. Org. Chem. 2014, 10, 2654–2657, doi:10.3762/bjoc.10.278

• Yong Miao Florence Djedaini-Pilard Veronique Bonnet LG2A FRE-CNRS 3517 Institut de Chimie de Picardie FR CNRS 3085, SFR Condorcet, UPJV, 33 rue St Leu, 80039 Amiens, France 10.3762/bjoc.10.278 Abstract This work reports the synthesis of a new family of mono-substituted amphiphilic cyclodextrins

• with a promising yield. Keywords: fatty ester; green chemistry; lipase; mono-substituted amphiphilic cyclodextrins; peptide Coupling; solvent-free medium; transesterification; Introduction Cyclodextrins (CDs) are sustainable compounds which are particularly interesting in the frame of pharmaceutical

Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2012, 8, 1543–1551, doi:10.3762/bjoc.8.175

• guest interaction with the surface of the vesicles has become a useful system to investigate recognition, adhesion and fusion of biological cell membranes [24][25][26]. In this context, amphiphilic cyclodextrins are a promising platform due to their ability to form stable bilayer vesicles that can be