Abstract
Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions, use of enzymes). The ring opening reaction of methyl oleate epoxide needs ball-milling and is highly specific of cyclodextrins in solventless conditions. L-CDs are thus composed of complex mixtures that were deciphered by an extensive structural analysis using mainly mass spectrometry and NMR spectroscopy. In addition, as part of their potential use as vectors of active drugs, these products were submitted to an integrity study on in vitro model of the blood-brain-barrier (BBB) and the intestinal epithelium. No toxicity has been observed, suggesting that applications for the vectorization of active ingredients can be expected.
Highlights
Because of their cyclic structure, cyclodextrins (CDs) are able to accommodate hydrophobic molecules in their cavity, resulting in inclusion complexes
We have synthesized monosubstituted cyclodextrins-bearing hydrophobic anchors such as cholesterol [4], phospholipidyl [5], or glycerolipidyl [6] that are inserted into lipid membranes [7]
We have developed an easy pathway for lipidyl-cyclodextrins (L-CDs) synthesis with controlled DS
Summary
Because of their cyclic structure, cyclodextrins (CDs) are able to accommodate hydrophobic molecules in their cavity, resulting in inclusion complexes This property is at the origin of their many applications in various fields such as the pharmaceutical industry, cosmetics, hygiene, food processing, and chemistry, through catalysis and chromatographic techniques [1,2]. The different strategies envisaged to carry out the opening reaction of the epoxide obtained by CDs is described Activation modes such as ultrasound [8,9], microwaves [10,11], or mechanochemistry [12] are considered as useful green tools for the chemical modification of cyclodextrins. This is why the implementation of an accurate characterization is fundamental and a real challenge in our work It is well-known that complex CDs derivatives mixtures lead to broad and unresolved 1H-NMR signals [16] preventing the attribution of their inextricable spectra.
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