Mechanisms of action of lysophospholipid analogues against trypanosomatid parasites

Transactions of the Royal Society of Tropical Medicine and Hygiene

Volumn 100, Issue SUPPL. 1, 2006, Pages

  Urbina, Julio A ^a  

^a INSTITUTO VENEZOLANO DE INVESTIGACIONES CIENTÍFICAS   (Venezuela)

Author keywords

Antiparasitic activity; Apoptosis; Leishmaniasis; Lysophospholipid analogues; Phosphatidylcholine; Trypanosomatid

Indexed keywords

ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; ANYLGERANOL; CERAMIDE; CHELERYTHRINE; CHOLINE PHOSPHATE CYTIDYLYLTRANSFERASE; CHOLINEPHOSPHOTRANSFERASE; EDELFOSINE; EDIFENPHOS; ENZYME INHIBITOR; ERGOSTEROL; FARNESOL; FAS ANTIGEN; FUMONISIN B1; ILMOFOSINE; IPROBENFOS; KETOCONAZOLE; LYSOPHOSPHOLIPID; MEMBRANE LIPID; MILTEFOSINE; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE METHYLTRANSFERASE; PHOSPHOLIPASE C; PROTEIN KINASE C; SPHINGOMYELIN; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROTOZOAL ACTIVITY; APOPTOSIS; ARTICLE; CELL STRUCTURE; DRUG CLASSIFICATION; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; GASTROINTESTINAL SYMPTOM; GROWTH INHIBITION; HUMAN; IMMUNE SYSTEM; IMMUNOMODULATION; IN VITRO STUDY; IN VIVO STUDY; LEISHMANIA; LIPID METABOLISM; MAMMAL CELL; NONHUMAN; PARASITOSIS; PROTEIN SYNTHESIS INHIBITION; SIGNAL TRANSDUCTION; SKIN METASTASIS; STRUCTURE ANALYSIS; TARGET CELL; TRYPANOSOMA CRUZI; VISCERAL LEISHMANIASIS;

ANIMALS; APOPTOSIS; CELL COMMUNICATION; HUMANS; IMMUNOLOGIC FACTORS; LIPID METABOLISM; LYSOPHOSPHOLIPIDS; MEMBRANE LIPIDS; SURFACE-ACTIVE AGENTS; TRYPANOCIDAL AGENTS; TRYPANOSOMA; TRYPANOSOMIASIS;

MAMMALIA; TRYPANOSOMA CRUZI; TRYPANOSOMATIDAE;

EID: 33749341812     PISSN: 00359203     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.trstmh.2006.03.010     Document Type: Article

References (71)

1. Achterberg V., and Gercken G. Cytotoxicity of ester and ether lysophospholipids on Leishmania donovani promastigotes. Mol. Biochem. Parasitol. 23 (1987) 117-122
2. Achterberg V., and Gercken G. Metabolism of ether lysophospholipids in Leishmania donovani promastigotes. Mol. Biochem. Parasitol. 26 (1987) 277-287
3. Ameisen J.C., Idziorek T., Billaut-Multo O., Loyens M., Yissier J.P., Potentier A., and Ouaissi A. Apoptosis in a unicellular eukaryote (Trypanosoma cruzi): implications for the evolutionary origin and role of programmed cell death in the control of cell proliferation, differentiation and survival. Parasitol. Today 12 (1996) 49
4. Arthur G., and Bittman R. The inhibition of cell signaling pathways by antitumor ether lipids. Biochim. Biophys. Acta 1390 (1998) 85-102
5. Bhattacharya S.K., Jha T.K., Sundar S., Thakur C.P., Engel J., Sindermann H., Junge K., Karbwang J., Bryceson A.D., and Berman J.D. Efficacy and tolerability of miltefosine for childhood visceral leishmaniasis in India. Clin. Infect. Dis. 38 (2004) 217-221
6. Boggs K.P., Rock C.O., and Jackowski S. Lysophosphatidylcholine attenuates the cytotoxic effects of the antineoplastic phospholipid 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine. J. Biol. Chem. 270 (1995) 11612-11618
7. Contreras L.M., Vivas J., and Urbina J.A. Altered lipid composition and enzyme activities of plasma membranes from Trypanosoma (Schizotrypanum) cruzi epimastigotes grown in the presence of sterol biosynthesis inhibitors. Biochem. Pharmacol. 53 (1997) 697-704
8. Croft S.L., Seifert K., and Duchene M. Antiprotozoal activities of phospholipid analogues. Mol. Biochem. Parasitol. 126 (2003) 165-172
9. Cui Z., and Houweling M. Phosphatidylcholine and cell death. Biochim. Biophys. Acta 1585 (2002) 87-96
10. Cui Z., Houweling M., Chen M.H., Record M., Chap H., Vance D.E., and Terce F. A genetic defect in phosphatidylcholine biosynthesis triggers apoptosis in Chinese hamster ovary cells. J. Biol. Chem. 271 (1996) 14668-14671
11. Das M., Mukherjee S.B., and Shaha C. Hydrogen peroxide induces apoptosis-like death in Leishmania donovani promastigotes. J. Cell Sci. 114 (2001) 2461-2469
12. de Castro S.L., Santa-Rita R., Urbina J.A., and Croft S.L. Antiprotozoal lysophospholipid analogues: a comparison of their activity against trypanosomatid parasites and tumor cells. Mini Revs. Med. Chem. 4 (2004) 139-148
13. Debrabant A., Lee N., Bertholet S., Duncan R., and Nakhasi H.L. Programmed cell death in trypanosomatids and other unicellular organisms. Int. J. Parasitol. 33 (2003) 257-267
14. Engelmann J., Henke J., Willker W., Kutscher B., Nossner G., Engel J., and Leibfritz D. Early stage monitoring of miltefosine induced apoptosis in KB cells by multinuclear NMR spectroscopym. Anticancer Res. 16 (1996) 1429-1439
15. Escobar P., Yardley V., and Croft S.L. Activities of hexadecylphosphocholine (miltefosine), Ambisome and sodium stibogluconate (pentostam) against Leishmania donovani in immunodeficient scid mice. Antimicrob. Agents Chemother. 45 (2001) 1872-1875
16. Gajate C., and Mollinedo F. The antitumor ether lipid ET-18-OCH(3) induces apoptosis through translocation and capping of Fas/CD95 into membrane rafts in human leukemic cells. Blood 98 (2001) 3860-3863
17. Geilen C.C., Haase A., Wieder T., Arndt D., Zeisig R., and Reutter W. Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis. J. Lipid Res. 35 (1994) 625-632
18. Giantonio B.J., Derry C., McAleer C., McPhillips J.J., and O'Dwyer P.J. Phase I and pharmacokinetic study of the cytotoxic ether lipid ilmofosine administered by weekly two-hour infusion in patients with advanced solid tumors. Clin. Cancer Res. 10 (2004) 1282-1288
19. Guan J.L. Cell biology: Integrins, rafts, Rac, and Rho. Science 303 (2004) 773-774
20. Haase R., Wieder T., Geilen C.C., and Reutter W. The phospholipid analogue hexadexylphosphocholine inhibits phosphatidylcholine biosynthesis in Madin-Darby canine kidney cells. FEBS Lett. 288 (1991) 129-132
21. Hampton R.Y., and Morand O.H. Sphingomyelin synthase and PKC activation. Science 246 (1989) 1050
22. Hannun Y.A., and Obeid L.M. Ceramide: an intracellular signal for apoptosis. Trends Biochem. Sci. 20 (1995) 73-77
23. Howe A.G., Zaremberg V., and McMaster C.R. Cessation of growth to prevent cell death due to inhibition of phosphatidylcholine synthesis is impaired at 37 degrees C in Saccharomyces cerevisiae. J. Biol. Chem. 277 (2002) 44100-44107
24. Jha T.K., Sundar S., Thakur C.P., Bachmann P., Karbwang J., Fischer C., Voss A., and Berman J. Miltefosine, an oral agent, for the treatment of Indian visceral leishmaniasis. N. Engl. J. Med. 341 (1999) 1795-1800
25. Jha T.K., Sundar S., Thakur C.P., Bachmann P., Karbwang J., Fisher C., Voss A., and Berman J. Miltefosine, an oral agent, for the treatment of Indian visceral leishmaniasis. N. Engl. J. Med. 341 (1999) 1795-1800
26. Kuhlencord A., Maniera T., Eibl H., and Unger C. Hexadecylphosphocholine: oral treatment of visceral leishmaniasis in mice. Antimicrob. Agents Chemother. 36 (1992) 1630-1634
27. Lee N., Bertholet S., Debrabant A., Muller J., Duncan R., and Nakhasi H.L. Programmed cell death in the unicellular protozoan parasite Leishmania. Cell Death Differ. 9 (2002) 53-64
28. Lira R., Contreras L.M., Santa-Rita R., and Urbina J.A. Mechanism of action of antiproliferative alkyl-lysophospholipids against the protozoan parasite Trypanosoma cruzi. Potentiation of in vitro activity by the sterol biosynthesis inhibitor ketoconazole. J. Antimicrob. Chemother. 47 (2001) 537-546
29. Lux H., Heise N., Klenner T., Hart D.T., and Opperdoes F.R. Ether-lipid (alkyl-phospholipid analog) metabolism and the mechanism of action of ether-lipid analogs in Leishmania. Mol. Biochem. Parasitol. 111 (2000) 1-14
30. Malaquias A.T., and Oliveira M.M. Phospholipid signalling pathways in Trypanosoma cruzi growth control. Acta Trop. 73 2 (1999) 93-108
31. Mollinedo F., Gajate C., Martin-Santamaria S., and Gago F. ET-18-OCH3 (edelfosine): a selective antitumour lipid targeting apoptosis through intracellular activation of Fas/CD95 death receptor. Curr. Med. Chem. 11 (2004) 3163-3184
32. Murray H.W. Clinical and experimental advances in treatment of visceral leishmaniasis. Antimicrob. Agents Chemother. 45 (2001) 2185-2197
33. Murray H.W. Progress in the treatment of a neglected infectious disease: visceral leishmaniasis. Expert Rev. Anti. Infect. Ther. 2 (2004) 279-292
34. Murray H.W. Treatment of visceral leishmaniasis in 2004. Am. J. Trop. Med. Hyg. 71 (2004) 787-794
35. Murray H.W., and Delph-Etienne S. Visceral leishmanicidal activity of hexadecylphosphocholine (miltefosine) in mice deficient in T cells and activated macrophage microbicidal mechanisms. J. Infect. Dis. 181 (2000) 795-799
36. Ngwenya B.Z., Fiavey N.P., and Mogashoa M.M. Anti-neoplastic action of peritoneal macrophages following oral administration of ether analogues of lysophospholipids. Eur. J. Cancer 28A (1992) 1637-1642
37. Nishizuka Y. Intracellular signaling by hydrolysis of phospholipids and activation of protein kinase C. Science 258 (1992) 607-614
38. Paris C., Loiseau P.M., Bories C., and Breard J. Miltefosine induces apoptosis-like death in Leishmania donovani promastigotes. Antimicrob. Agents Chemother. 48 (2004) 852-859
39. Piacenza L., Peluffo G., and Radi R. L-arginine-dependent suppression of apoptosis in Trypanosoma cruzi: contribution of the nitric oxide and polyamine pathways. Proc. Natl. Acad. Sci. USA 98 (2001) 7301-7306
40. Planting A.S., Stoter G., and Verweij J. Phase II study of daily oral miltefosine (hexadecylphosphocholine) in advanced colorectal cancer. Eur. J. Cancer 29A (1993) 518-519
41. Ramos B., Salido G.M., Campo M.L., and Claro E. Inhibition of phosphatidylcholine synthesis precedes apoptosis induced by C2-ceramide: protection by exogenous phosphatidylcholine. Neuroreport 11 (2000) 3103-3108
42. Robson G.D., Wiebe M., Kuhn P.J., and Trinci A.P.J. Inhibitors of phospholipid biosynthesis. In: Kuhn P.J., Trinci A.P.J., Jung M.J., Goosey M.W., and Copping L.G. (Eds). Biochemistry of Cell Walls and Membranes in Fungi (1990), Springer-Verlag, Berlin 245-281
43. Ruiter G.A., Verheij M., Zerp S.F., and van Blitterswijk W.J. Alkyl-lysophospholipids as anticancer agents and enhancers of radiation-induced apoptosis. Int. J. Radiat. Oncol. Biol. Phys. 49 (2001) 415-419
44. Santa-Rita R., Barbosa H.S., Meirelles M.N.L., and de Castro S.L. Effect of alkyl-lysophospholipids on the proliferation and differentiation of Trypanosoma cruzi. Acta Trop. 75 (2000) 219-228
45. Santa-Rita R., Lira R., Barbosa H.S., Urbina J.A., and de Castro S.L. Antiproliferative synergism of lysophospholipid analogues and ketoconazole against Trypanosoma cruzi (Kinetoplastida: Trypanosomatidae): cellular and ultrastructural analysis. J. Antimicrob. Chemother. 55 (2005) 780-784
46. Simons K., and Ikonen E. Functional lipid rafts in cell membranes. Nature 387 (1997) 569-571
47. Smorenburg C.H., Seynaeve C., Bontenbal M., Planting A.S., Sindermann H., and Verweij J. Phase II study of miltefosine 6% solution as topical treatment of skin metastases in breast cancer patients. Anticancer Drugs 11 (2000) 825-828
48. Stafford R.E., Fanni T., and Dennis E.A. Interfacial properties and critical micelle concentration of lysophospholipids. Biochemistry 28 (1989) 5113-5120
49. Sundar S., Rosenkaimer F., Makharia M.K., Goyal A.K., Mandal A.K., Voss A., Hilgard P., and Murray H.W. Trial of oral miltefosine for visceral leishmaniasis. Lancet 352 (1998) 1821-1823
50. Sundar S., Gupta L.B., Makharia M.K., Singh M.K., Voss A., Rosenkaimer F., Engel J., and Murray H.W. Oral treatment of visceral leishmaniasis with miltefosine. Ann. Trop. Med. Parasitol. 93 (1999) 589-597
51. Sundar S., Gupta L.B., Makharia M.K., Singh M.K., Voss A., Rosenkaimer F., Engel J., and Murray H.W. Oral treatment of visceral leishmaniasis with miltefosine. Ann. Trop. Med. Parasitol. 93 (1999) 589-597
52. Sundar S., Jha T.K., Thakur C.P., Engel J., Sindermann H., Fischer C., Junge K., Bryceson A., and Berman J. Oral miltefosine for Indian visceral leishmaniasis. N. Engl. J. Med. 347 (2002) 1739-1746
53. Sundar S., Jha T.K., Sindermann H., Junge K., Bachmann P., and Berman J. Oral miltefosine treatment in children with mild to moderate Indian visceral leishmaniasis. Pediatr. Infect. Dis. J. 22 (2003) 434-438
54. Thakur C.P., Sinha P.K., Singh R.K., Hassan S.M., and Narain S. Miltefosine in a case of visceral leishmaniasis with HIV co-infection; and rising incidence of this disease in India. Trans. R. Soc. Trop. Med. Hyg. 94 (2000) 696-697
55. Unger C., Fleer E.A., Kotting J., Neumuller W., and Eibl H. Antitumoral activity of alkylphosphocholines and analogues in human leukemia cell lines. Prog. Exp. Tumor Res. 34 (1992) 25-32
56. Urbina J.A., and Docampo R. Specific chemotherapy of Chagas disease: controversies and advances. Trends Parasitol. 19 (2003) 495-501
57. van der Luit A.H., Budde M., Ruurs P., Verheij M., and 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. 277 (2002) 39541-39547
58. van der Luit A.H., Budde M., Verheij M., and Van Blitterswijk W.J. Different modes of internalization of apoptotic alkyl-lysophospholipid and cell-rescuing lysophosphatidylcholine. Biochem. J. 374 (2003) 747-753
59. van der Sanden M.H., Houweling M., Duijsings D., Vaandrager A.B., and van Golde L.M. Inhibition of phosphatidylcholine synthesis is not the primary pathway in hexadecylphosphocholine-induced apoptosis. Biochim. Biophys. Acta 1636 (2004) 99-107
60. Verma N.K., and Dey C.S. Possible mechanism of miltefosine-mediated death of Leishmania donovani. Antimicrob. Agents Chemother. 48 (2004) 3010-3015
61. Verweij J., Planting A., van der Burg M., and Stoter G. A dose-finding study of miltefosine (hexadecylphosphocholine) in patients with metastatic solid tumours. J. Cancer Res. Clin. Oncol. 118 (1992) 606-608
62. Vogler W.R., Shoji M., Hayzer D.J., Xie Y.P., and Renshaw M. The effect of edelphosine on CTP:cholinephosphate activity in leukemic cell lines. Leuk. Res. 20 (1996) 947-951
63. Walkey C.J., Donohue L.R., Bronson R., Agellon L.B., and Vance D.E. Disruption of the murine gene encoding phosphatidylethanolamine N-methyltransferase. Proc. Natl. Acad. Sci. USA 94 (1997) 12880-12885
64. Walkey C.J., Yu L., Agellon L.B., and Vance D.E. Biochemical and evolutionary significance of phospholipid methylation. J. Biol. Chem. 273 (1998) 27043-27046
65. Wieder T., Haase A., Geilen C.C., and Orfanos C.E. The effect of two synthetic phospholipids on cell proliferation and phosphatidylcholine biosynthesis in Madin-Darby canine kidney cells. Lipids 30 (1995) 389-393
66. Wieder T., Perlitz C., Wieprecht M., Huang R.T., Geilen C.C., and Orfanos C.E. Two new sphingomyelin analogues inhibit phosphatidylcholine biosynthesis by decreasing membrane-bound CTP: phosphocholine cytidylyltransferase levels in HaCaT cells. Biochem. J. 311 (1995) 873-879
67. Wieder T., Orfanos C.E., and Geilen C.C. Induction of ceramide-mediated apoptosis by the anticancer phospholipid analog, hexadecylphosphocholine. J. Biol. Chem. 273 (1998) 11025-11031
68. Wieder T., Reutter W., Orfanos C.E., and Geilen C.C. Mechanisms of action of phospholipid analogs as anticancer compounds. Prog. Lipid. Res. 38 (1999) 249-259
69. Wright M.M., Howe A.G., and Zaremberg V. Cell membranes and apoptosis: role of cardiolipin, phosphatidylcholine, and anticancer lipid analogues. Biochem. Cell Biol. 82 (2004) 18-26
70. Yamamoto N., Ngwenya B.Z., Sery T.W., and Pieringer R.A. Activation of macrophages by ether analogues of lysophospholipids. Cancer Immunol. Immunother. 25 (1987) 185-192
71. Zaremberg V., and McMaster C.R. Differential partitioning of lipids metabolized by separate yeast glycerol-3-phosphate acyltransferases reveals that phospholipase D generation of phosphatidic acid mediates sensitivity to choline-containing lysolipids and drugs. J. Biol. Chem. 277 (2002) 39035-39044