Enzymatic hydrolysis of monoacylglycerols and their cyclopropanated derivatives: Molecular structure and nanostructure determine the rate of digestion

Livia Salvati Manni; Michael Duss; Salvatore Assenza; Ben J Boyd; Ehud M Landau; Wye-Khay Fong

doi:10.1016/j.jcis.2020.11.110

Enzymatic hydrolysis of monoacylglycerols and their cyclopropanated derivatives: Molecular structure and nanostructure determine the rate of digestion

J Colloid Interface Sci. 2021 Apr 15:588:767-775. doi: 10.1016/j.jcis.2020.11.110. Epub 2020 Nov 28.

Authors

Livia Salvati Manni¹, Michael Duss², Salvatore Assenza³, Ben J Boyd⁴, Ehud M Landau⁵, Wye-Khay Fong⁶

Affiliations

¹ Department of Chemistry, University of Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland; School of Chemistry and University of Sydney Nano Institute, The University of Sydney, NSW 2006, Australia. Electronic address: livia.salvatimanni@sydney.edu.au.
² Department of Chemistry, University of Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland; Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, Canada.
³ Departamento de Física Teórica de la Materia Condensada, Universidad Autónoma de Madrid, E-28049 Madrid, Spain; Condensed Matter Physics Center (IFIMAC), Universidad Autónoma de Madrid, E-28049 Madrid, Spain.
⁴ Drug Delivery, Disposition and Dynamics and ARC Centre of Excellence in Convergent Bio-Nano Science and Technology, Monash Institute of Pharmaceutical Sciences, Monash University (Parkville Campus), 381 Royal Parade, Parkville, VIC 3052, Australia.
⁵ Department of Chemistry, University of Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland. Electronic address: ehud.landau@chem.uzh.ch.
⁶ Discipline of Chemistry, School of Environmental and Life Sciences, University of Newcastle, Callaghan 2308, NSW, Australia. Electronic address: khay.fong@newcastle.edu.au.

PMID: 33309146
DOI: 10.1016/j.jcis.2020.11.110

Abstract

Colloidal lipidic particles with different space groups and geometries (mesosomes) are employed in the development of new nanosystems for the oral delivery of drugs and nutrients. Understanding of the enzymatic digestion rate of these particles is key to the development of novel formulations. In this work, the molecular structure of the lipids has been systematically tuned to examine the effect on their self-assembly and digestion rate. The kinetic and phase changes during the lipase-catalysed hydrolysis of mesosomes formed by four synthetic cyclopropanated lipids and their cis-unsaturated analogues were monitored by dynamic small angle X-ray scattering and acid/base titration. It was established that both the phase behaviour and kinetics of the hydrolysis are greatly affected by small changes in the molecular structure of the lipid as well as by the internal nanostructure of the colloidal particles.

Keywords: Cubic phases; Cyclopropanated lipids; Enzymatic hydrolysis; Hexagonal phases; Lipid nanoparticles; Lipids; Mesophases; Nanostructured lipids; Phase behaviour; SAXS.