Preparation and Membrane Properties of Oxidized Ceramide Derivatives

Takaaki Matsufuji, Masanao Kinoshita, Anna Möuts, J. Peter Slotte, Nobuaki Matsumori

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)465-471
Number of pages7
JournalLangmuir
Volume34
Issue number1
DOIs
Publication statusPublished - Jan 9 2018

Fingerprint

Ceramides
membranes
Derivatives
Membranes
preparation
rigidity
Sphingomyelins
gels
Rigidity
apoptosis
Gels
activity (biology)
carboxylic acids
linkages
inhibitors
amides
lipids
enzymes
esters
Molecular Probes

All Science Journal Classification (ASJC) codes

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

Cite this

Preparation and Membrane Properties of Oxidized Ceramide Derivatives. / Matsufuji, Takaaki; Kinoshita, Masanao; Möuts, Anna; Slotte, J. Peter; Matsumori, Nobuaki.

In: Langmuir, Vol. 34, No. 1, 09.01.2018, p. 465-471.

Research output: Contribution to journalArticle

Matsufuji, Takaaki ; Kinoshita, Masanao ; Möuts, Anna ; Slotte, J. Peter ; Matsumori, Nobuaki. / Preparation and Membrane Properties of Oxidized Ceramide Derivatives. In: Langmuir. 2018 ; Vol. 34, No. 1. pp. 465-471.
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