Exogenous ether lipids predominantly target mitochondria

PLoS ONE

Volumn 7, Issue 2, 2012, Pages

  Kuerschner, Lars ^a   Richter, Doris ^c   Hannibal Bach, Hans Kristian ^b   Gaebler, Anne ^a   Shevchenko, Andrej ^c   Ejsing, Christer S ^b   Thiele, Christoph ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^c MAX PLANCK INSTITUTE OF MOLECULAR CELL BIOLOGY AND GENETICS   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EDELFOSINE; ETHER DERIVATIVE; ETHER PHOSPHATIDYLCHOLINE; ETHER PHOSPHATIDYLETHANOLAMINE; POLYENE ETHER LIPID DERIVATIVE; POLYFOSINE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; ETHER PHOSPHOLIPID; GLYCEROL ETHER;

APOPTOSIS; ARTICLE; CELL MEMBRANE; CELL MIGRATION; CELL STRAIN COS7; CELL STRUCTURE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; ENDOPLASMIC RETICULUM; FLUORESCENCE; HUMAN; HUMAN CELL; LIPID ANALYSIS; LIPID METABOLISM; MASS SPECTROMETRY; MITOCHONDRION; ANIMAL; CHEMISTRY; DRUG EFFECT; METABOLISM; TRANSPORT AT THE CELLULAR LEVEL;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BIOLOGICAL TRANSPORT; ENDOPLASMIC RETICULUM; GLYCERYL ETHERS; HUMANS; MITOCHONDRIA; PHOSPHOLIPID ETHERS;

EID: 84856866905     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0031342     Document Type: Article

References (49)

1. Nagan N, Zoeller RA, (2001) Plasmalogens: biosynthesis and functions. Prog Lipid Res 40: 199-229.
2. Gorgas K, Teigler A, Komljenovic D, Just WW, (2006) The ether lipid-deficient mouse: tracking down plasmalogen functions. Biochim Biophys Acta 1763: 1511-1526.
3. Thai TP, Rodemer C, Jauch A, Hunziker A, Moser A, et al. (2001) Impaired membrane traffic in defective ether lipid biosynthesis. Hum Mol Genet 10: 127-136.
4. Pike LJ, Han X, Chung KN, Gross RW, (2002) Lipid rafts are enriched in arachidonic acid and plasmenylethanolamine and their composition is independent of caveolin-1 expression: a quantitative electrospray ionization/mass spectrometric analysis. Biochemistry 41: 2075-2088.
5. Brites P, Waterham HR, Wanders RJ, (2004) Functions and biosynthesis of plasmalogens in health and disease. Biochim Biophys Acta 1636: 219-231.
6. Post JA, Verkleij AJ, Roelofsen B, Op de Kamp JA, (1988) Plasmalogen content and distribution in the sarcolemma of cultured neonatal rat myocytes. FEBS Lett 240: 78-82.
7. Bartz R, Li WH, Venables B, Zehmer JK, Roth MR, et al. (2007) Lipidomics reveals that adiposomes store ether lipids and mediate phospholipid traffic. J Lipid Res 48: 837-847.
8. Munder PG, Westphal O, (1990) Antitumoral and other biomedical activities of synthetic ether lysophospholipids. Chem Immunol 49: 206-235.
9. Houlihan WJ, Lohmeyer M, Workman P, Cheon SH, (1995) Phospholipid antitumor agents. Med Res Rev 15: 157-223.
10. Danker K, Reutter W, Semini G, (2010) Glycosidated phospholipids: uncoupling of signalling pathways at the plasma membrane. Br J Pharmacol 160: 36-47.
11. Diomede L, Colotta F, Piovani B, Re F, Modest EJ, et al. (1993) Induction of apoptosis in human leukemic cells by the ether lipid 1-octadecyl-2-methyl-rac-glycero-3-phosphocholine. A possible basis for its selective action. Int J Cancer 53: 124-130.
12. Mollinedo F, Martinez-Dalmau R, Modolell M, (1993) Early and selective induction of apoptosis in human leukemic cells by the alkyl-lysophospholipid ET-18-OCH3. Biochem Biophys Res Commun 192: 603-609.
13. Zerp SF, Vink SR, Ruiter GA, Koolwijk P, Peters E, et al. (2008) Alkylphospholipids inhibit capillary-like endothelial tube formation in vitro: antiangiogenic properties of a new class of antitumor agents. Anticancer Drugs 19: 65-75.
14. Zoeller RA, Layne MD, Modest EJ, (1995) Animal cell mutants unable to take up biologically active glycerophospholipids. J Lipid Res 36: 1866-1875.
15. Gajate C, Fonteriz RI, Cabaner C, Alvarez-Noves G, Alvarez-Rodriguez Y, et al. (2000) Intracellular triggering of Fas, independently of FasL, as a new mechanism of antitumor ether lipid-induced apoptosis. Int J Cancer 85: 674-682.
16. van Blitterswijk WJ, Verheij M, (2008) Anticancer alkylphospholipids: mechanisms of action, cellular sensitivity and resistance, and clinical prospects. Curr Pharm Des 14: 2061-2074.
17. van Blitterswijk WJ, Hilkmann H, Storme GA, (1987) Accumulation of an alkyl lysophospholipid in tumor cell membranes affects membrane fluidity and tumor cell invasion. Lipids 22: 820-823.
18. Tokumura A, Tsutsumi T, Nishioka Y, Tsukatani H, (1997) Exogenously added alkylmethylglycerophosphocholine and alkylmethylcarbamylglycerophosphocholine accumulate in plasma membranes more than in intracellular membranes of rabbit platelets. Chem Phys Lipids 86: 75-83.
19. Cuvillier O, Mayhew E, Janoff AS, Spiegel S, (1999) Liposomal ET-18-OCH(3) induces cytochrome c-mediated apoptosis independently of CD95 (APO-1/Fas) signaling. Blood 94: 3583-3592.
20. Gajate C, Santos-Beneit AM, Macho A, Lazaro M, Hernandez-De Rojas A, et al. (2000) Involvement of mitochondria and caspase-3 in ET-18-OCH(3)-induced apoptosis of human leukemic cells. Int J Cancer 86: 208-218.
21. Vogler WR, Whigham E, Bennett WD, Olson AC, (1985) Effect of alkyl-lysophospholipids on phosphatidylcholine biosynthesis in leukemic cell lines. Exp Hematol 13: 629-633.
22. Wieder T, Haase A, Geilen CC, Orfanos CE, (1995) The effect of two synthetic phospholipids on cell proliferation and phosphatidylcholine biosynthesis in Madin-Darby canine kidney cells. Lipids 30: 389-393.
23. Boggs KP, Rock CO, Jackowski S, (1995) Lysophosphatidylcholine and 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine inhibit the CDP-choline pathway of phosphatidylcholine synthesis at the CTP:phosphocholine cytidylyltransferase step. J Biol Chem 270: 7757-7764.
24. Mollinedo F, Gajate C, Martin-Santamaria S, Gago F, (2004) ET-18-OCH3 (edelfosine): a selective antitumour lipid targeting apoptosis through intracellular activation of Fas/CD95 death receptor. Curr Med Chem 11: 3163-3184.
25. Besson P, Gore J, Vincent E, Hoinard C, Bougnoux P, (1996) Inhibition of Na+/H+ exchanger activity by an alkyl-lysophospholipid analogue in a human breast cancer cell line. Biochem Pharmacol 51: 1153-1158.
26. Hoffman DR, Thomas VL, Snyder F, (1992) Inhibition of cellular transport systems by alkyl phospholipid analogs in HL-60 human leukemia cells. Biochim Biophys Acta 1127: 74-80.
27. Kuerschner L, Ejsing CS, Ekroos K, Shevchenko A, Anderson KI, et al. (2005) Polyene-lipids: a new tool to image lipids. Nat Methods 2: 39-45.
28. Spandl J, White DJ, Peychl J, Thiele C, (2009) Live cell multicolor imaging of lipid droplets with a new dye, LD540. Traffic 10: 1579-1584.
29. Ejsing CS, Sampaio JL, Surendranath V, Duchoslav E, Ekroos K, et al. (2009) Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry. Proc Natl Acad Sci U S A 106: 2136-2141.
30. Ekroos K, Chernushevich IV, Simons K, Shevchenko A, (2002) Quantitative profiling of phospholipids by multiple precursor ion scanning on a hybrid quadrupole time-of-flight mass spectrometer. Anal Chem 74: 941-949.
31. Ejsing CS, Duchoslav E, Sampaio J, Simons K, Bonner R, et al. (2006) Automated identification and quantification of glycerophospholipid molecular species by multiple precursor ion scanning. Anal Chem 78: 6202-6214.
32. Ekroos K, Ejsing CS, Bahr U, Karas M, Simons K, et al. (2003) Charting molecular composition of phosphatidylcholines by fatty acid scanning and ion trap MS3 fragmentation. J Lipid Res 44: 2181-2192.
33. Hsu FF, Turk J, (2000) Characterization of phosphatidylethanolamine as a lithiated adduct by triple quadrupole tandem mass spectrometry with electrospray ionization. J Mass Spectrom 35: 595-606.
34. Vink SR, van Blitterswijk WJ, Schellens JH, Verheij M, (2007) Rationale and clinical application of alkylphospholipid analogues in combination with radiotherapy. Cancer Treat Rev 33: 191-202.
35. Cereghetti GM, Scorrano L, (2006) The many shapes of mitochondrial death. Oncogene 25: 4717-4724.
36. Takamori S, Holt M, Stenius K, Lemke EA, Gronborg M, et al. (2006) Molecular anatomy of a trafficking organelle. Cell 127: 831-846.
37. Massey JB, Bick DH, Pownall HJ, (1997) Spontaneous transfer of monoacyl amphiphiles between lipid and protein surfaces. Biophys J 72: 1732-1743.
38. Thumser AE, Voysey JE, Wilton DC, (1994) The binding of lysophospholipids to rat liver fatty acid-binding protein and albumin. Biochem J 301: 801-806.
39. Xu Y, Malhotra A, Ren M, Schlame M, (2006) The enzymatic function of tafazzin. J Biol Chem 281: 39217-39224.
40. Ausili A, Torrecillas A, Aranda FJ, Mollinedo F, Gajate C, et al. (2008) Edelfosine is incorporated into rafts and alters their organization. J Phys Chem B 112: 11643-11654.
41. Osman C, Voelker DR, Langer T, (2011) Making heads or tails of phospholipids in mitochondria. J Cell Biol 192: 7-16.
42. Thiele C, Spandl J, (2008) Cell biology of lipid droplets. Curr Opin Cell Biol 20: 378-385.
43. Quesada E, Delgado J, Gajate C, Mollinedo F, Acuna AU, et al. (2004) Fluorescent phenylpolyene analogues of the ether phospholipid edelfosine for the selective labeling of cancer cells. J Med Chem 47: 5333-5335.
44. Nieto-Miguel T, Gajate C, Mollinedo F, (2006) Differential targets and subcellular localization of antitumor alkyl-lysophospholipid in leukemic versus solid tumor cells. J Biol Chem 281: 14833-14840.
45. Mollinedo F, Fernandez M, Hornillos V, Delgado J, Amat-Guerri F, et al. (2011) Involvement of lipid rafts in the localization and dysfunction effect of the antitumor ether phospholipid edelfosine in mitochondria. Cell Death Dis 2: e158.
46. Sprong H, van der Sluijs P, van Meer G, (2001) How proteins move lipids and lipids move proteins. Nat Rev Mol Cell Biol 2: 504-513.
47. Torrecillas A, Aroca-Aguilar JD, Aranda FJ, Gajate C, Mollinedo F, et al. (2006) Effects of the anti-neoplastic agent ET-18-OCH3 and some analogs on the biophysical properties of model membranes. Int J Pharm 318: 28-40.
48. Busto JV, Sot J, Goni FM, Mollinedo F, Alonso A, (2007) Surface-active properties of the antitumour ether lipid 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine (edelfosine). Biochim Biophys Acta 1768: 1855-1860.
49. Goonesinghe A, Mundy ES, Smith M, Khosravi-Far R, Martinou JC, et al. (2005) Pro-apoptotic Bid induces membrane perturbation by inserting selected lysolipids into the bilayer. Biochem J 387: 109-118.