Involvement of lipid rafts in the localization and dysfunction effect of the antitumor ether phospholipid edelfosine in mitochondria

Cell Death and Disease

Volumn 2, Issue 5, 2011, Pages

  Mollinedo, F ^a   Fernandez M ^b   Hornillos, V ^c   Delgado, J ^c   Amat Guerri, F ^c   Acuna A U ^d   Nieto Miguel, T ^a   Villa Pulgarin J A ^a,e   Gonzalez Garcia C ^f   Cen A V ^f,g   Gajate, C ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b Universidad Castilla La Mancha   (Spain)

^c INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^d INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^e Centro Hispano Luso de Investigaciones Agrarias (CIALE)   (Spain)

^f UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

^g CENTRO DE INVESTIGACIÓN BIOMÉDICA EN RED SOBRE ENFERMEDADES NEURODEGENERATIVAS CIBERNED   (Spain)

Author keywords

Apoptosis; Cancer therapy; Edelfosine; Ether phospholipid; Lipid rafts; Mitochondria

Indexed keywords

[1 0 [11' (6'' ETHYL 1'',3'',5'',7'' TETRAMETHYL 4'',4'' DIFLUORO 4'' BORA 3A'',4A'' DIAZA INDACEN 2'' YL)UNDECYL] 2 O METHYL RAC GLYCERO 3 PHOSPHOCHOLINE]; [1 O (15' PHENYLPENTADECA 10',12',14' TRIEN 8' YNYL) 2 O METHYL RAC GLYCERO 3 PHOSPHOCHOLINE]; [1 O [13' (1'',3'',5'',7'' TETRAMETHYL 4'',4'' DIFLUORO 4'' BORA 3A'',4A'' DIAZA INDACEN 2'' YL)TRIDEC 12' YNYL] 2 O METHYL RAC GLYCERO 3 PHOSPHOCHOLINE]; ANTINEOPLASTIC AGENT; CYCLOSPORIN A; EDELFOSINE; PROTEIN BCL XL; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; ETHER PHOSPHOLIPID; PROTEIN BCL X;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CHEMOTHERAPY; CELL MEMBRANE; COMPETITIVE INHIBITION; CONJUGATION; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; FLOW CYTOMETRY; FLUORESCENCE ANALYSIS; GENE OVEREXPRESSION; HELA CELL; HUMAN; HUMAN CELL; LIPID RAFT; MEMBRANE PERMEABILITY; MITOCHONDRIAL MEMBRANE POTENTIAL; MITOCHONDRION; MITOCHONDRION SWELLING; PRIORITY JOURNAL; STRUCTURE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FLUORESCENCE; GENE EXPRESSION; GENETIC TRANSFECTION; GENETICS; METABOLISM; MITOCHONDRIAL MEMBRANE; MOLECULARLY TARGETED THERAPY; NEOPLASM; PATHOLOGY; STRUCTURE ACTIVITY RELATION; TRANSPORT AT THE CELLULAR LEVEL;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BCL-X PROTEIN; BIOLOGICAL TRANSPORT; FEMALE; FLUORESCENCE; GENE EXPRESSION; HELA CELLS; HUMANS; MEMBRANE MICRODOMAINS; MEMBRANE POTENTIAL, MITOCHONDRIAL; MITOCHONDRIA; MITOCHONDRIAL MEMBRANES; MOLECULAR STRUCTURE; MOLECULAR TARGETED THERAPY; NEOPLASMS; PHOSPHOLIPID ETHERS; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION;

EID: 79959971349     PISSN: None     EISSN: 20414889     Source Type: Journal    
DOI: 10.1038/cddis.2011.41     Document Type: Article

References (40)

1. Galluzzi L, Larochette N, Zamzami N, Kroemer G. Mitochondria as therapeutic targets for cancer chemotherapy. Oncogene 2006; 25: 4812-4830. (Pubitemid 44192089)
2. Neuzil J, Dyason JC, Freeman R, Dong LF, Prochazka L, Wang XF et al. Mitocans as anticancer agents targeting mitochondria: lessons from studies with vitamin E analogues, inhibitors of complex II. J Bioenerg Biomembr 2007; 39: 65-72. (Pubitemid 46877173)
3. L. Cancer Res 1997; 57: 1320-1328. (Pubitemid 27152558)
4. 3 (Edelfosine), a proapoptotic agent in tumor cells. Curr Drug Metab 2002; 3: 491-525. (Pubitemid 34987482)
5. 3 (edelfosine): a selective antitumour lipid targeting apoptosis through intracellular activation of Fas/CD95 death receptor. Curr Med Chem 2004; 11: 3163-3184. (Pubitemid 39539180)
6. Mollinedo F. Antitumor ether lipids: proapoptotic agents with multiple therapeutic indications. Expert Opin Ther Patents 2007; 17: 385-405. (Pubitemid 46567158)
7. Ausili A, Torrecillas A, Aranda FJ, Mollinedo F, Gajate C, Corbalan-Garcia S et al. Edelfosine is incorporated into rafts and alters their organization. J Phys Chem B 2008; 112: 11643-11654.
8. Busto JV, del Canto-Jañez E, Goñ i FM, Mollinedo F, Alonso A. Combination of the antitumour cell ether lipid edelfosine with sterols abolishes haemolytic side effects of the drug. J Chem Biol 2008; 1: 89-94.
9. van der Luit AH, Budde M, Ruurs P, Verheij M, van Blitterswijk WJ. Alkyl-lysophospholipid accumulates in lipid rafts and induces apoptosis via raft-dependent endocytosis and inhibition of phosphatidylcholine synthesis. J Biol Chem 2002; 277: 39541-39547. (Pubitemid 35190932)
10. Gajate C, Del Canto-Janez E, Acuna AU, Amat-Guerri F, Geijo E, Santos-Beneit AM et al. Intracellular triggering of Fas aggregation and recruitment of apoptotic molecules into Fas-enriched rafts in selective tumor cell apoptosis. J Exp Med 2004; 200: 353-365. (Pubitemid 39031254)
11. Gajate C, Gonzalez-Camacho F, Mollinedo F. Involvement of raft aggregates enriched in Fas/CD95 death-inducing signaling complex in the antileukemic action of edelfosine in Jurkat cells. PLoS ONE 2009; 4: e5044.
12. Mollinedo F, de la Iglesia-Vicent J, Gajate C, Estella-Hermoso de Mendoza A, Villa-Pulgarin JA, Campanero MA et al. Lipid raft-targeted therapy in multiple myeloma. Oncogene 2010; 29: 3748-3757.
13. Zaremberg V, Gajate C, Cacharro LM, Mollinedo F, McMaster CR. Cytotoxicity of an anticancer lysophospholipid through selective modification of lipid raft composition. J Biol Chem 2005; 280: 38047-38058. (Pubitemid 41642419)
14. 3 induces apoptosis through translocation and capping of Fas/CD95 into membrane rafts in human leukemic cells. lood 2001; 98: 3860-3863.
15. Nieto-Miguel T, Gajate C, Mollinedo F. Differential targets and subcellular localization of antitumor alkyl-lysophospholipid in leukemic versus solid tumor cells. J Biol Chem 2006; 281: 14833-14840. (Pubitemid 43855188)
16. Nieto-Miguel T, Fonteriz RI, Vay L, Gajate C, Lopez-Hernandez S, Mollinedo F. Endoplasmic reticulum stress in the proapoptotic action of edelfosine in solid tumor cells. Cancer Res 2007; 67: 10368-10378. (Pubitemid 350070812)
17. Gajate C, Mollinedo F. Edelfosine and perifosine induce selective apoptosis in multiple myeloma by recruitment of death receptors and downstream signaling molecules into lipid rafts. Blood 2007; 109: 711-719. (Pubitemid 46105973)
18. 3-induced apoptosis of human leukemic cells. Int J Cancer 2000; 86: 208-218. (Pubitemid 30180816)
19. Gajate C, Gonzalez-Camacho F, Mollinedo F. Lipid raft connection between extrinsic and intrinsic apoptotic pathways. Biochem Biophys Res Commun 2009; 380: 780-784.
20. Bernardi P, Vassanelli S, Veronese P, Colonna R, Szabo I, Zoratti M. Modulation of the mitochondrial permeability transition pore. Effect of protons and divalent cations. J Biol Chem 1992; 267: 2934-2939.
21. Di Lisa F, Bernardi P. Mitochondrial function as a determinant of recovery or death in cell response to injury. Mol Cell Biochem 1998; 184: 379-391. (Pubitemid 28398620)
22. Zamzami N, Marchetti P, Castedo M, Hirsch T, Susin SA, Masse B et al. Inhibitors of permeability transition interfere with the disruption of the mitochondrial transmembrane potential during apoptosis. FEBS Lett 1996; 384: 53-57. (Pubitemid 26114720)
23. Bakht O, Delgado J, Amat-Guerri F, Acuna AU, London E. The phenyltetraene lysophospholipid analog PTE-ET-18-OMe as a fluorescent anisotropy probe of liquid ordered membrane domains (lipid rafts) and ceramide-rich membrane domains. Biochim Biophys Acta 2007; 1768: 2213-2221. (Pubitemid 47379610)
24. Soccio RE, Breslow JL. Intracellular cholesterol transport. Arterioscler Thromb Vasc Biol 2004; 24: 1150-1160. (Pubitemid 38880002)
25. Sorice M, Manganelli V, Matarrese P, Tinari A, Misasi R, Malorni W et al. Cardiolipinenriched raft-like microdomains are essential activating platforms for apoptotic signals on mitochondria. FEBS Lett 2009; 583: 2447-2450.
26. Ciarlo L, Manganelli V, Garofalo T, Matarrese P, Tinari A, Misasi R et al. Association of fission proteins with mitochondrial raft-like domains. Cell Death Differ 2010; 17: 1047-1058.
27. Garofalo T, Giammarioli AM, Misasi R, Tinari A, Manganelli V, Gambardella L et al. Lipid microdomains contribute to apoptosis-associated modifications of mitochondria in T cells. Cell Death Differ 2005; 12: 1378-1389. (Pubitemid 41521928)
28. De Pinto V, Benz R, Palmieri F. Interaction of non-classical detergents with the mitochondrial porin. A new purification procedure and characterization of the pore-forming unit. Eur J Biochem 1989; 183: 179-187. (Pubitemid 19185266)
29. Ziolkowski W, Szkatula M, Nurczyk A, Wakabayashi T, Kaczor JJ, Olek RA et al. Methylbeta-cyclodextrin induces mitochondrial cholesterol depletion and alters the mitochondrial structure and bioenergetics. FEBS Lett 2010; 584: 4606-4610.
30. Ardail D, Privat JP, Egret-Charlier M, Levrat C, Lerme F, Louisot P. Mitochondrial contact sites. Lipid composition and dynamics. J Biol Chem 1990; 265: 18797-18802.
31. Grimm S, Brdiczka D. The permeability transition pore in cell death. Apoptosis 2007; 12: 841-855. (Pubitemid 46653295)
32. Maxfield FR, Wustner D. Intracellular cholesterol transport. J Clin Invest 2002; 110: 891-898.
33. Crain RC, Clark RW, Harvey BE. Role of lipid transfer proteins in the abnormal lipid content of Morris hepatoma mitochondria and microsomes. Cancer Res 1983; 43: 3197-3202. (Pubitemid 13061572)
34. Montero J, Morales A, Llacuna L, Lluis JM, Terrones O, Basanez G et al. Mitochondrial cholesterol contributes to chemotherapy resistance in hepatocellular carcinoma. Cancer Res 2008; 68: 5246-5256.
35. Mollinedo F, de la Iglesia-Vicente J, Gajate C, Estella-Hermoso de Mendoza A, Villa-Pulgarin JA, de Frias M et al. In vitro and in vivo selective antitumor activity of Edelfosine against mantle cell lymphoma and chronic lymphocytic leukemia involving lipid rafts. Clin Cancer Res 2010; 16: 2046-2054.
36. Gajate C, Fonteriz RI, Cabaner C, Alvarez-Noves G, Alvarez-Rodriguez Y, Modolell M et al. Intracellular triggering of Fas, independently of FasL, as a new mechanism of antitumor ether lipid-induced apoptosis. Int J Cancer 2000; 85: 674-682. (Pubitemid 30080481)
37. Li Y, Prinz WA. ATP-binding cassette (ABC) transporters mediate nonvesicular, raftmodulated sterol movement fom the plasma membrane to the endoplasmic reticulum. J Biol Chem 2004; 279: 45226-45234. (Pubitemid 39430938)
38. 2+-dependent mitochondrial apoptosis. Mol Cell 2009; 36: 500-511.
39. de Brito OM, Scorrano L. Mitofusin 2 tethers endoplasmic reticulum to mitochondria. Nature 2008; 456: 605-610.
40. Jordan J, Galindo MF, Tornero D, Benavides A, Gonzalez C, Agapito MT et al. Superoxide anions mediate veratridine-induced cytochrome c release and caspase activity in bovine chromaffin cells. Br J Pharmacol 2002; 137: 993-1000. (Pubitemid 35440739)