Biophysical Properties of Novel 1-Deoxy-(Dihydro)ceramides Occurring in Mammalian Cells

Biophysical Journal

Volumn 107, Issue 12, 2014, Pages 2850-2859

  Jiménez Rojo, Noemi ^a   Sot, Jesús ^a   Busto, Jon V ^a   Shaw, Walt A ^b   Duan, Jingjing ^c   Merrill, Alfred H ^c   Alonso, Alicia ^a   Goñi, Félix M ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b Avanti Polar Lipids   (United States)

^c GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MAMMALIA; SPHINGOIDEA;

CERAMIDE; DIHYDROCERAMIDE; LIPOSOME;

ANIMAL; CELL LINE; CHEMISTRY; METABOLISM; MOUSE;

ANIMALS; CELL LINE; CERAMIDES; MICE; UNILAMELLAR LIPOSOMES;

EID: 84920131449     PISSN: 00063495     EISSN: 15420086     Source Type: Journal    
DOI: 10.1016/j.bpj.2014.10.010     Document Type: Article

References (29)

1. N.C. Zitomer, and T. Mitchell R.T. Riley Ceramide synthase inhibition by fumonisin B1 causes accumulation of 1-deoxysphinganine: a novel category of bioactive 1-deoxysphingoid bases and 1-deoxydihydroceramides biosynthesized by mammalian cell lines and animals J. Biol. Chem. 284 2009 4786 4795
2. A.H. Merrill Jr. Sphingolipid and glycosphingolipid metabolic pathways in the era of sphingolipidomics Chem. Rev. 111 2011 6387 6422
3. M. Salcedo, and C. Cuevas F. Wandosell The marine sphingolipid-derived compound ES 285 triggers an atypical cell death pathway Apoptosis 12 2007 395 409
4. A.M. Sánchez, and S. Malagarie-Cazenave I. Díaz-Laviada Spisulosine (ES-285) induces prostate tumor PC-3 and LNCaP cell death by de novo synthesis of ceramide and PKCζ activation Eur. J. Pharmacol. 584 2008 237 245
5. C. Massard, and R. Salazar J.C. Soria Phase I dose-escalating study of ES-285 given as a three-hour intravenous infusion every three weeks in patients with advanced malignant solid tumors Invest. New Drugs 30 2012 2318 2326
6. P. Schöffski, and H. Dumez G. Giaccone Spisulosine (ES-285) given as a weekly three-hour intravenous infusion: results of a phase I dose-escalating study in patients with advanced solid malignancies Cancer Chemother. Pharmacol. 68 2011 1397 1403
7. R.D. Baird, and J. Kitzen J. Verweij Phase I safety, pharmacokinetic, and pharmacogenomic trial of ES-285, a novel marine cytotoxic agent, administered to adult patients with advanced solid tumors Mol. Cancer Ther. 8 2009 1430 1437
8. A. Rotthier, and A. Penno K. Janssens Characterization of two mutations in the SPTLC1 subunit of serine palmitoyltransferase associated with hereditary sensory and autonomic neuropathy type I Hum. Mutat. 32 2011 E2211 E2225
9. A. Rotthier, and M. Auer-Grumbach V. Timmerman Mutations in the SPTLC2 subunit of serine palmitoyltransferase cause hereditary sensory and autonomic neuropathy type I Am. J. Hum. Genet. 87 2010 513 522
10. R.A. Zuellig, and T. Hornemann J.-H. Jang Deoxysphingolipids, a novel biomarker for type 2 diabetes, are cytotoxic for insulin-producing cells Diabetes 63 2013 1326 1339
11. A. Othman, and M.F. Rütti T. Hornemann Plasma deoxysphingolipids: a novel class of biomarkers for the metabolic syndrome? Diabetologia 55 2012 421 431
12. F.M. Goñi, and A. Alonso Biophysics of sphingolipids I. Membrane properties of sphingosine, ceramides and other simple sphingolipids Biochim. Biophys. Acta 1758 2006 1902 1921
13. F.M. Goñi, and A. Alonso Effects of ceramide and other simple sphingolipids on membrane lateral structure Biochim. Biophys. Acta 1788 2009 169 177
14. E.A. Dennis, and R.A. Deems S. Subramaniam A mouse macrophage lipidome J. Biol. Chem. 285 2010 39976 39985
15. H. Sakagami, and K. Kishino T. Oizumi Cell death induced by nutritional starvation in mouse macrophage-like RAW264.7 cells Anticancer Res. 29 2009 343 347
16. N. Jiménez-Rojo, and A.B. García-Arribas F.M. Goñi Lipid bilayers containing sphingomyelins and ceramides of varying N-acyl lengths: a glimpse into sphingolipid complexity Biochim. Biophys. Acta 1838 1 Pt B 2014 456 464
17. K. Sims, and C.A. Haynes A.H. Merrill Jr. Kdo2-lipid A, a TLR4-specific agonist, induces de novo sphingolipid biosynthesis in RAW264.7 macrophages, which is essential for induction of autophagy J. Biol. Chem. 285 2010 38568 38579
18. J.V. Busto, and M.L. Fanani A. Alonso Coexistence of immiscible mixtures of palmitoylsphingomyelin and palmitoylceramide in monolayers and bilayers Biophys. J. 97 2009 2717 2726
19. M.L. Fanani, and B. Maggio Phase state and surface topography of palmitoyl-ceramide monolayers Chem. Phys. Lipids 163 2010 594 600
20. J.M. Smaby, and V.S. Kulkarni R.E. Brown The interfacial elastic packing interactions of galactosylceramides, sphingomyelins, and phosphatidylcholines Biophys. J. 70 1996 868 877
21. J. Shah, and J.M. Atienza G.G. Shipley Structural and thermotropic properties of synthetic C16:0 (palmitoyl) ceramide: effect of hydration J. Lipid Res. 36 1995 1936 1944
22. L. Silva, and R.F. de Almeida M. Prieto Ceramide-platform formation and -induced biophysical changes in a fluid phospholipid membrane Mol. Membr. Biol. 23 2006 137 148
23. Y.J. Björkqvist, and J. Brewer B. Westerlund Thermotropic behavior and lateral distribution of very long chain sphingolipids Biochim. Biophys. Acta 1788 2009 1310 1320
24. S.N. Pinto, and L.C. Silva M. Prieto Effect of ceramide structure on membrane biophysical properties: the role of acyl chain length and unsaturation Biochim. Biophys. Acta 1808 2011 2753 2760
25. Y.A. Hannun, and L.M. Obeid Many ceramides J. Biol. Chem. 286 2011 27855 27862
26. F. Dupuy, M.L. Fanani, and B. Maggio Ceramide N-acyl chain length: a determinant of bidimensional transitions, condensed domain morphology, and interfacial thickness Langmuir 27 2011 3783 3791
27. S. Grösch, S. Schiffmann, and G. Geisslinger Chain length-specific properties of ceramides Prog. Lipid Res. 51 2012 50 62
28. B. Westerlund, and P.M. Grandell J.P. Slotte Ceramide acyl chain length markedly influences miscibility with palmitoyl sphingomyelin in bilayer membranes Eur. Biophys. J. 39 2010 1117 1128
29. R.A. Zuellig, and T. Hornemann S. Sonda Deoxysphingolipids, novel biomarkers for type 2 diabetes, are cytotoxic for insulin-producing cells Diabetes 63 2014 1326 1339