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Preparation and Membrane Properties of Oxidized Ceramide Derivatives.
- Source :
-
Langmuir . 1/9/2018, Vol. 34 Issue 1, p465-471. 7p. - Publication Year :
- 2018
-
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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 07437463
- Volume :
- 34
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Langmuir
- Publication Type :
- Academic Journal
- Accession number :
- 127244928
- Full Text :
- https://doi.org/10.1021/acs.langmuir.7b02654