Antitumor alkylphospholipid analogs: A promising and growing family of synthetic cell membrane-targeting molecules for cancer treatment

Anti-Cancer Agents in Medicinal Chemistry

Volumn 14, Issue 4, 2014, Pages 495-498

  Mollinedo, Faustino ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 O HEXADECYL 2 O METHYL 3 O (2 AMINO-2 DEOXY BETA D GLUCOPYRANOSYL) SN GLYCEROL; 1 O OCTADECYL 2 O (2 (MYO INOSITOLYLETHYL) SN GLYCERO 3 (R/S) PHOSPHATIDYLCHOLINE; ANTINEOPLASTIC AGENT; ANTITUMOR ALKYLPHOSPHOLIPID ANALOG; DNA; EDELFOSINE; ERUCYLPHOSPHOCHOLINE; ERUFOSINE; ETHER LIPID; LYSOPHOSPHOLIPID; MILTEFOSINE; PERIFOSINE; THROMBOCYTE ACTIVATING FACTOR; UNCLASSIFIED DRUG; PLASMALOGEN;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; CANCER THERAPY; CELL ADHESION; CELL FUNCTION; CELL MEMBRANE; CELL MIGRATION; CELL SURVIVAL; CLINICAL TRIAL (TOPIC); EDITORIAL; HUMAN; INFLAMMATION; NEOPLASM; SIGNAL TRANSDUCTION; ANIMAL; CHEMISTRY; METABOLISM; MOLECULARLY TARGETED THERAPY; ULTRASTRUCTURE;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL MEMBRANE; HUMANS; MOLECULAR TARGETED THERAPY; NEOPLASMS; PLASMALOGENS;

EID: 84908122155     PISSN: 18715206     EISSN: 18755992     Source Type: Journal    
DOI: 10.2174/1871520614999140313160011     Document Type: Editorial

References (28)

1. Gajate, C.; Mollinedo F. Biological activities, mechanisms of action and biomedical prospect of the antitumor ether phospholipid ET-18-OCH3 (edelfosine), a proapoptotic agent in tumor cells. Curr. Drug Metab., 2002, 3, 491-525.
2. Munder, P.G.; Westphal, O. Antitumoral and other biomedical activities of synthetic ether lysophospholipids. Chem. Immunol., 1990, 49, 206-235.
3. Mollinedo, F.; Martinez-Dalmau, R.; Modolell, M. Early and selective induction of apoptosis in human leukemic cells by the alkyl-lysophospholipid ET-18-OCH3. Biochem. Biophys. Res. Commun., 1993, 192, 603-609.
4. Diomede, L.; Colotta, F.; Piovani, B.; Re, F.; Modest, E.J.; Salmona, M. 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, 1993, 53, 124-130.
5. Mollinedo, F.; Fernandez-Luna, J.L.; Gajate, C.; Martin-Martin, B.; Benito, A.; Martinez-Dalmau, R.; Modolell, M. Selective induction of apoptosis in cancer cells by the ether lipid ET-18-OCH3 (Edelfosine): Molecular structure requirements, cellular uptake, and protection by Bcl-2 and Bcl-XL. Cancer Res., 1997, 57, 1320-1328.
6. Gajate, C.; Del Canto-Janez, E.; Acuna, A.U.; Amat-Guerri, F.; Geijo, E.; Santos-Beneit, A.M.; Veldman, R.J.; Mollinedo, F. 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.
7. Gajate, C.; Fonteriz, R.I.; Cabaner, C.; Alvarez-Noves, G.; Alvarez-Rodriguez, Y.; Modolell, M.; Mollinedo, F. Intracellular triggering of Fas, independently of FasL, as a new mechanism of antitumor ether lipid-induced apoptosis. Int. J. Cancer, 2000, 85, 674-682.
8. 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.
9. Mollinedo, F.; De la Iglesia-Vicente, J.; Gajate, C.; De Mendoza, E-H.A.; Villa-Pulgarin, J.A.; Campanero, M.A.; Blanco-Prieto, M.J. Lipid raft-targeted therapy in multiple myeloma. Oncogene, 2010, 29, 3748-3757.
10. Mollinedo, F.; DelaIglesia-Vicente, J.; Gajate, C.; De Mendoza, E-H.A.; Villa-Pulgarin, J.A.; De Frias, M.; Roue, G.; Gil, J.; Colomer, D.; Campanero, M.A.; Blanco-Prieto, M.J. 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.
11. Eibl, H.; Unger, C. Hexadecylphosphocholine: A new and selective antitumor drug. Cancer Treat. Rev., 1990, 17, 233-242.
12. Terwogt, J.M.; Mandjes, I.A.; Sindermann, H.; Beijnen, J.H.; Ten Bokkel Huinink, W.W. Phase II trial of topically applied miltefosine solution in patients with skin-metastasized breast cancer. Br. J. Cancer, 1999, 79, 1158-1161.
13. Mollinedo, F.; Gajate, C.; Martin-Santamaria, S.; Gago, F. ET-18-OCH3 (edelfosine): a selective antitumour lipid targeting apoptosis through intracellular activation of Fas/CD95 death receptor. Curr. Med. Chem., 2004, 11, 3163-3184.
14. Samadder, P.; Bittman, R.; Byun, HS.; Arthur, G. A glycosylated antitumor ether lipid kills cells via paraptosis-like cell death. Biochem. Cell Biol., 2009, 87, 401-414.
15. Jahreiss, L.; Renna, M.; Bittman, R.; Arthur, G.; Rubinsztein, D.C. 1-O-Hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl)-sn-glycerol (Gln) induces cell death with more autophagosomes which is autophagy-independent. Autophagy, 2009, 5, 835-846.
16. Van der Luit, A.H.; Budde, M.; Ruurs, P.; Verheij, M.; Van Blitterswijk, W.J. 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.
17. Van der Luit, A.H.; Vink, S.R.; Klarenbeek, J.B.; Perrissoud, D.; Solary, E.; Verheij, M.; Van Blitterswijk, W.J. A new class of anticancer alkylphospholipids uses lipid rafts as membrane gateways to induce apoptosis in lymphoma cells. Mol. Cancer Ther., 2007, 6, 2337-2345.
18. Gajate, C.; Mollinedo, F. The antitumor ether lipid ET-18-OCH3 induces apoptosis through translocation and capping of Fas/CD95 into membrane rafts in human leukemic cells. Blood, 2001, 98, 3860-3863.
19. Mollinedo, F.; Gajate, C. Fas/CD95 death receptor and lipid rafts: New targets for apoptosis-directed cancer therapy. Drug Resist. Updat., 2006, 9, 51-73.
20. Mollinedo, F.; Gajate, C. Lipid rafts and clusters of apoptotic signaling molecule-enriched rafts in cancer therapy. Future Oncol., 2010, 6, 811-821.
21. Mollinedo, F.; Gajate, C. Lipid rafts, death receptors and CASMERs: new insights for cancer therapy. Future Oncol., 2010, 6, 491-494.
22. Reis-Sobreiro, M.; Roue, G.; Moros, A.; Gajate, C.; De la Iglesia-Vicente, J.; Colomer, D.; Mollinedo, F. Lipid raft-mediated Akt signaling as a therapeutic target in mantle cell lymphoma. Blood Cancer J., 2013, 3, e118.
23. Gajate, C.; Matos-da-Silva, M.; Dakir, EL.; Fonteriz, RI.; Alvarez, J.; Mollinedo, F. Antitumor alkyl-lysophospholipid analog edelfosine induces apoptosis in pancreatic cancer by targeting endoplasmic reticulum. Oncogene, 2012, 31, 2627-2639.
24. Nieto-Miguel, T.; Fonteriz, R.I.; 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.
25. 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.
26. Mollinedo, F.; Fernandez, M.; Hornillos, V.; Delgado, J.; Amat-Guerri, F.; Acuna, A.U.; Nieto-Miguel, T.; Villa-Pulgarin, J.A.; Gonzalez-Garcia, C.; Cena, V.; Gajate, C. Involvement of lipid rafts in the localization and dysfunction effect of the antitumor ether phospholipid edelfosine in mitochondria. Cell Death Dis., 2011, 2, e158.
27. Kuerschner, L.; Richter, D.; Hannibal-Bach, H.K.; Gaebler, A.; Shevchenko, A.; Ejsing, C.S.; Thiele, C. Exogenous ether lipids predominantly target mitochondria. PLoS ONE, 2012, 7, e31342.
28. Cuesta-Marban, A.; Botet, J.; Czyz, O.; Cacharro, L.M.; Gajate, C.; Hornillos, V.; Delgado, J.; Zhang, H.; Amat-Guerri, F.; Acuna, A.U.; McMaster, C.R.; Revuelta, J.L.; Zaremberg, V.; Mollinedo, F. Drug uptake, lipid rafts, and vesicle trafficking modulate resistance to an anticancer lysophosphatidylcholine analogue in yeast. J. Biol. Chem., 2013, 288, 8405-8418.