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Biomolecules. 2020 Feb 20;10(2). pii: E339. doi: 10.3390/biom10020339.

New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling.

Author information

1
LG2A UMR CNRS 7378, Université de Picardie Jules Verne, 80039 Amiens CEDEX, France.
2
Plateforme Analytique, Université de Picardie Jules Verne, 80039 Amiens CEDEX, France.
3
Univ. Artois, CNRS, Centrale Lille, Univ. Lille, UMR 8181-UCCS-Unité de Catalyse et Chimie du Solide, F-62300 Lens, France.
4
LBHE EA 2465, Université d'Artois, 62307 Lens CEDEX, France.

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.

KEYWORDS:

ball milling; cyclodextrin; host-guest chemistry; mass spectrometry; sustainability

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