Maleimide-acetylcholine headed bolaamphiphilic vesicles made from ricinoleic acid: Prospective active targeted drug delivery systems.

Autor: Ewonkem MB; Department of Chemistry, Ben-Gurion University, Be'er Sheva 84105, Israel; Department of Chemistry, University of Douala, PO Box 2701, Douala, Cameroon. Electronic address: myewon@gmail.com., Grinberg S; Department of Chemistry, Ben-Gurion University, Be'er Sheva 84105, Israel.
Jazyk: angličtina
Zdroj: Chemistry and physics of lipids [Chem Phys Lipids] 2018 May; Vol. 212, pp. 96-110. Date of Electronic Publication: 2018 Feb 02.
DOI: 10.1016/j.chemphyslip.2018.01.009
Abstrakt: Based on ricinoleic acid, two asymmetric bolaamphiphiles with unsymmetrical hydrophobic skeletons and two different hydrophilic head groups were designed and synthesized. The first bola compound had acetylcholine (ACh) and maleimide (MAL) head groups while the second was derived from the first bolaamphiphile by thiol-ene conjugation of its maleimide moiety with l-glutathione and possessed ACh and l-glutathione-MAL head groups. Both synthetic bolaamphiphiles were characterized by common spectroscopic methods. The asymmetric bola compound with ACh and MAL head groups was investigated for its ability to self-aggregate into nanoparticles and showed to form in aqueous media nano-sized vesicles that were stable, positively charged and had symmetrical monolayer membrane with antiparallel packing. These vesicles prepared with or without membrane stabilizers such as cholesterol (CHOL) and cholesteryl hemisuccinate (CHEMS) were able to encapsulate carboxyfluorescein (CF), a water soluble and self-quenching marker and particularly those without additives were more CF encapsulating. The synthesis of bolaamphiphile with ACh-l-glutathione-MAL head groups gives evidence that the bola with ACh and MAL head groups can be utilized as a precursor of a plethora of asymmetric bolas.
(Copyright © 2018 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
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