Preparation and Membrane Properties of Oxidized Ceramide Derivatives.

A1 Journal article (refereed)

Internal Authors/Editors

Publication Details

List of Authors: Matsufuji, Kinoshita, Möuts, Slotte, Matsumori
Publication year: 2018
Journal: Langmuir
Journal acronym: Langmuir
Volume number: 34
Issue number: 1
Start page: 465
End page: 471
ISSN: 1520-5827


Ceramide is a bioactive lipid with important roles in several biological
processes including cell proliferation and apoptosis. Although
3-ketoceramides that contain a keto group in place of the 3-OH group of
ceramide occur naturally, ceramide derivatives oxidized at the primary
1-OH group have not been identified to date. To evaluate how the
oxidative state of the 1-OH group affects the physical properties of
membranes, we prepared novel ceramide derivatives in which the 1-OH
group was oxidized to a carboxylic acid (PCerCOOH) or methylester
(PCerCOOMe) and examined the rigidity of their monolayers and the
formation of gel domains in palmitoyloleoylphosphatidylcholine (POPC) or
sphingomyelin (SM) bilayers. As a result, PCerCOOH and PCerCOOMe
exhibited membrane properties similar to those of native ceramide,
although the deprotonated form of PCerCOOH, PCerCOO, exhibited markedly lower rigidity and higher miscibility with POPC and SM. This was attributed to the electrostatic repulsion of the negative charge, which hampered the formation of the ceramide-enriched gel domain. The similarities in the properties of PCerCOOMe and ceramide revealed the potential to introduce various functional groups onto PCerCOOH via ester or amide linkages; therefore, these derivatives will also provide a new strategy for developing molecular probes, such as fluorescent ceramides, and inhibitors of ceramide-related enzymes.

Last updated on 2020-06-07 at 04:51