Синтез бесфосфорных алкильных глицеролипидов — потенциальных противоопухолевых соединений
Диссертация
Среди многочисленных производных фактора активации тромбоцитов отдельного внимания заслуживают вещества немутагенной природы, обладающие биологической полиактивностью. Так, например, в литературе описаны: перифозин, милтефозин, илмофозин, эдельфозин и другие. Вышеназванные липиды проявляют анти-ВИЧ-1 и ФАТ-антагонистическую активности, обладают антинеопластическими свойствами. Кроме того, эти… Читать ещё >
Список литературы
- Snyder F., Lee T.Ch., Blank M.L. Platelet-activating factor and related ether lipid mediators. Biological activities, metabolism and regulation. // Annals of New York Academy of Sciences. 1989. -V. 568. — P. 35.
- Braguest P., Godfroid J.J. Conformational properties of PAF acether receptor on platelets based on structure activity studies. // Platelet Activating Factor and Related Lipid Mediators. — 1987. — P. 191.
- Tence, M., E. Coeffier, E Heymans, J. Polonsky, J. J. Godfroid, and J. Benveniste. Structural analogs of platelet-activating factor (PAF-acether). // Biochimie. 1981. — V.63 — P. 3−20.
- Edward A. S. Phase I Trial of Perifosine (NSC 639 966) on a Loading Dose/Maintenance Dose Schedule in Patients with Advanced Cancer. // Clinical Cancer Research. 2004. -V. 10.-7450−7456.
- Lynn V. U., Kim В., Jennifer V., Rebecca M., Kendra Т., Jill K., Rhoda A., Dona A., George W. Miltefosine: great expectations against visceral leishmaniasis. // Drug review. -2003. -V. 49. P. 101−103.
- Murray H. W., Etienne S. Visceral leishmanicidal activity of hexadecylphosphocholine (miltefosine) in mice deficient in Tcells and activated macrophage microcidal mechanisms. // J. Inf Dis. 2000. — V. 181. — P. 795−799.
- Ricardo M. S., Andrea H. P., Helene S. В., Solange L. de Castro. Effect of the lysophospholipid analogues edelfosine, ilmofosine and miltefosine against Leishmania amazonensis. // J. of Antimicrobial Chemotherapy. 2004. -V. 54. — P. 704−710.
- Hanauske A. R., Degen D., Marshall M. H., Hilsenbeck S. G., McPhillips J. J., Von Hoff D. D. Preclinical activity of ilmofosine against human tumor colony forming units in vitro. // Anticancer Drugs. 1992. — V. 3. — P. 43−46.
- H.Gajate C., Mollinedo F. Biological activities, mechanisms of action and biomedical prospects of the antitumor ether phospholipid ET-18-OCH3 (Edelfosine), a proapoptotic agent in tumor cells. // Curr. Drug Metab. 2002. — V. 3. — P. 491- 525.
- Helmut K., Mangold H.K. Synthesis of biologically active ether lipids. // Prog. Biochem. Pharmacol. 1988. -V. 22. — P. 100−108.
- Jan C.R., Wu S.N., Tseng C.J. The ether lipid ET-18-OCH3 increases cytosolic Ca2+ concentrations in Madin Darby canine kidney cells. // Br. J. Pharmacol. 1999. -V. 127.- № 6. P. 1502.
- Civoli F., Pauig S.B., Daniel L.W. Differentiation of HL-60 cells distinguishes between cytostatic and cytotoxic effects of the alkylphospholipid ET-18-OCH3. // Cancer Chemother. Pharmacol. 1996. -V. 38. — P. 269.
- Ruiter G. A., Verheij M., Zerp S. F., and van W. Blitterswijk. Alkyl-lysophospholipids as anticancer agents and enhancers of radiation-induced apoptosis. // J. Rad. Oncol. Biol. Phys. 2001. — V. 49. — P. 415−419.
- Samadder P., Richards C., Bittman R. The antitumor ether lipid 1-Q-octadecyI-2−0-methyl-rac-glycerophosphocholine (ET-18-OCH3) inhibits the association between Ras and Raf-1. //Anticancer Res. 2003. — V. 23. — P. 2291−225.
- Zhou X., Arthur G. The relationship between cellular ether glycerophospholipid content and sensitivity of cancer cells to l-O-octadecyl-2-O-methyl-glycerophosphocholine. // Anticancer Res. 1992. — V. 12. — № 5. — P. 1559−1562.
- 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. -V. 192. — P. 603−609.
- Botzler C., Ellwart J., Gunther W., Eissner G., Multhoff G. Synergistic effects of heat and ET-18-OCH3 on membrane expression of hsp70 and lysis of leukemic K562 cells. // Exp. Hematol. 1999. — V.27. — № 3. — P. 470−478.
- Girgert R., Schweizer P., Bock I., Narr R., Bruchelt G. Cytotoxicity of ether phospholipid BM 41.440 on neuroblastoma cells. // J. Cancer Res. Clin. Oncol. 1995. -V. 121. — P. 262−266.
- Hanahan, D. J. Platelet activating factor: a biologically active phosphoglyceride. // Rev. Biochem. 1986. -V. 53. — P. 483−509.
- Scheel-Toellner D., Wang K., Singh R., Majeed S., Raza K., Curnow S.J., Salmon M., Lord J.M. The death-inducing signalling complex is recruited to lipid rafts in Fas-induced apoptosis. // Biochem. Biophys. Res. Commun. -2002. -V. 297. P. 876−879.
- Zaremberg V., Gajate C., Cacharro L.M., Mollinedo F., McMaster C.R. Cytotoxicity of an anti-cancer lysophospholipid through selective modification of lipid raft composition. // J. Biol. Chem. 2005. -V. 280. — P. 38 047−38 058.
- Hoffman J., Utz I., Spitaler M., Hofer S., Rybczynska M., Beck W.T., Herrmann D.B.J., Grunicke H. Resistance to the new anti-cancer phospholipid ilmofosine (BM 41.440). // Br. J. Cancer. 1997. — V. 76. — P. 862.
- Hanauske A. R., Degen D., Marshall M. H., Hilsenbeck S. G., McPhillips J. J., Von Hoff D. D. Preclinical activity of ilmofosine against human tumor colony forming units in vitro. // Anticancer Drugs. 1992. — V. 3. — P. 43−46.
- Herrmann D. В., Pahlke W., Opitz H. G., Bicker U. In vivo antitumor activity of ilmofosine. // Cancer Treat. Rev. 1990. -V. 17. — P. 247−252.
- Duclos R.I., Chia H.H., Abdelmageed O.H., Esber H., Fournier D.J., Makriyannis A. Synthesis of racemic and nearly optically pure ether lipids and evaluation of in vitro antineoplastic activities. // J. Med. Chem. 1994. — V. 37. — P. 41−47.
- Principe P., Braquet P. Advances in ether phospholipids treatment of cancer. // Crit. Rev. Oncol. Hematol. 1995. -V. 18. — P. 155.
- Berdel W.E., Okamoto S. Ether lipids in cancer chemotherapy. // J. Med. Clin. 1990. -V. 39. — № 2. — P. 75−78.
- Berdel W.E., Andereesen R., Murder P.G. Synthetic alkyl-phospholipid analogs: a new class of antitumor agents. // Phospholipids and Cellular Regulation.- 1989. P. 42−73.
- Vogler W.R., Olson A.C., Hajdu J., Shoji M., Raynor R., Kuo J.F. Structure-function relationships of alkyl-lysophospholipid analogs in selective antitumor activity. // Lipids. -1993. V. 28. — № 6. — P. 511.
- Andereesen R. Ether-phospholipids in the therapy of cancer. II Progress in Biochemical Pharmacology. 1998. — V.22. — P. 118−131.
- Ivan Blitterswijk W.J., Hilkmann H., Storme G.A. Accumulation of an alkyl lysophospholipid in tumor cell membranes affects membrane fluidity and tumor cell invasion. И Lipids. 1987. — V. 22. — P. 820−823.
- Seewold M.J., Olsen R.A., Sehgal I., Melder D.C., Modest E.J., Powis G. Inhibition of grouwn factor dependent inositol phosphate Ca2+ signaling by antitumor ether lipid analogues. // Cancer Res. 1990. — V. 50. — P. 4458.
- Shen N.Y., Hwang S.B., Doebber T.W., Robbins J.C. The chemical and biological properties of PAF agonist, antagonist and biosynthetic inhibitors. // Platelet Activating Factor and Related Lipid Mediators. 1987. — P. 153−158.
- Civoli F., Daniel L.W. Quaternary ammonium analogs of ether lipids inhibit the activation of protein kinase С and the growth of human leukemia cell lines. // Cancer Chemother Pharmacol. 1998. — V. 42. — P. 319.
- Van Blitterswijk W.J., Van der bend R., Kramer I.M., Verhoeven A.J., Hilkmann H., De Widt J. A. Metabolite of an antineoplastic ether phospholipid may inhibit transmembrane signaling via protein kinase C. // Lipids.- 1987.-V. 22. P. 842.
- Hoffman D. R., Hajdu J., Snyder F. Cytotoxicity of platelet activating factor and related alkyl-phospholipid analogs in human leukemia cells, polymorphonuclear neutrophils, and skin fibroblasts. // Blood. 1984, — V. 63 — P. 545−552.
- Winkler J.D., Eris Т., Sung C.M., Chabot-Fletcher M., Mayer R.J., Surette M.E., Chilton F.H. Inhibitors of coenzyme A-independent transacylase induce apoptosis in human HL-60 cells. // J. Pharmacol. Exp. Ther. 1996. — V. 279. — P. 956.
- Van der Luit A. H., Budde M., Ruurs P. Alkyl-lysophospholipid accumulates in lipid rafts and induces apoptosis via raftdependent endocytosis and inhibition of phosphatidylcholine synthesis. И J Biol Chem. 2002. -V. 277. — P.39 541−39 547.
- Diomede L., Principe P., Domingo M.T., Broquet C., Chabrier P.E., Braquet P., Salmona M. Effect of PAF antagonists on the cytotoxic activity of anti-neoplastic ether phospholipids. // J. Oncol. 1993. -V. 2. — P. 777−782.
- Pat. 0.302.744 A2 Ера. С 07 D 239/36. Preparation of glycerol derivatives and antitumor agents and pharmaceutical compositions containing them. / Keizo I., Hiroaki N., Eiko I.
- Berdel W.E., Greiner E., Fink U., Zenker K.S., Stavrov D., Trappe A., Fahlbusch R., Reichert A., Rasstetter. Cytotoxic effects of alkyl-lysophospholipids in human brain tumor cells.//Oncology. -1989. V.41. — P. 140−145.
- Berdel E.W. Membrane interactive lipids as experimental anticancer drugs. II Br. J. Cancer. 1991. -V. 64. — P. 208.
- Crumpton S.C., Goz В., Ishaq K.S. Novel lipid analogs with cytostatic and cytocidal activity. //Anticancer Res. 1988. -V. 8. — P. 1316.
- Евр. пат. 336 142, МКИ C07F9/12 Novel antagonists of platelet activating factor / Wissner A., Schaub R.E., Sum P.E. Опубл. 11.10.1989. Бюлл. 89/41.
- Godfroid J.J., Heymans F. Chemistry of PAF antagonists. // Prog. Biochem. Pharmacol. — 1988. — V. 22.-P. 25.
- Маслов M.A., Морозова Н. Г., Серебренникова Г. А. Удобный метод получения катионных глицеролипидов с потенциальной биологической активностью. II Изв. АН, Сер. хим. 2002. — № 10. — С. 1778.
- Kudo I., Nojima S., Chang H.-W., Yanoshita R., Hayashi H., Kondo E., Nomura H., Inoue K. Antitumor activity of synthetic alkyllysophospholipids with or without PAF activity. II Lipids. 1987. — V. 22. — P. 862.
- Ricardo M. Santa-Rita, Andrea Henriques-Pons, Helene S. Barbosa, Solange L. Castro. Effect of the lysophospholipid analogues edelfosine, ilmofosine and miltefosine against. // Leishmania amazonensis. 2002. — V.4. — P. 704−710.
- Shen N.Y., Hwang S.B., Doebber T.W. and Robbins J.C. The chemical and biological properties of PAF agonist, antagonist and biosynthetic inhibitors. // Platelet Activating Factor and Related Lipid Mediators. 1987. — P. 153−158.
- Peters A.C., Ahmad I., Janoff A.S., Pushkareva M.Y., Mayhew E. Growth inhibitory effects of liposome-associated 1−0-octadecyl-2−0-methyl-sn-glycero-3-phosphocholine. //Lipids. 1997. — V. 32. — P. 1045.
- Berdel W.E., Munder P.G. Antineoplastic actions of ether lipids related to platelet-activating factor. Platelet-activating factor and related lipid mediators // Plenum Publishing Corporation. 1987. — P. 449−467.
- Константинова И.Д., Серебренникова Г. А. Положительно заряженные липиды: структура, методы синтеза, применение // Успехи химии. 1996. — Т. 65. — № 6. — С. 581.
- Маслов М.А., Сычева Е. В., Морозова Н. Г., Серебренникова Г. А. Синтез алкильных глицеролипидов с различными катионными головками, присоединенными непосредственно к глицериновому скелету. // Изв. АН, Серия хим. 1999. — № 7. -С. 1381.
- Schreiber B.M., Layne M.D. and Modest E.J. Superoxide production by macrophages stimulated in vivo with synthetic ether lipids. // Lipids. 1994. — V. 29. — № 4. — P. 237.
- Heymans F., Borrel M.C., Broquet C., Lefort J., Godfroid J.J. Structure activity relationship in PAF -acether. 2. rac-1-Octadecyl-2-acetyl-3-y-(dimethylamino) propyl.glycerol. // J. Med. Chem. — 1985. -V. 28. — P. 1094.
- Godfroid J.J. and Heymans F. Chemistry of PAF antagonists. // Progress in Biochemical Pharmacology. 1998. -V. 22. — P. 25.
- Pat. 0.321.296 Ai EPA. С 07 D 249/14. Preparation of lipid analogs as Platelet Activation Factor (PAF) antagonists and Antitumor Agents. / Susumu K., Takeaki M., Tatsuo Т., Morio K.
- Desquand S. Effects of PAF antagonists in experimental models possible therapeutical implication. // Therapie. -1993. — V. 48. -№ 6. — P. 585−589.
- Blank, M. L., T-c. Lee, V. Fitzgerald, and F. Snyder. A specific acetylhydrolase for 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine (a hypotensive and platelet-activating lipid). //J. Biol. Chem. 1981. — P. 175−178.
- Noseda A., White J.G., Godwin P.I., Jerome W.G. Membrane damage in leukemic cells induced by ether and ester lipids: an electron microscopic study.// Experimental and Molecular Pathology. 1989. — V.50. — P. 69−83.
- Arthur G., Bitmann R. The inhibition of cell signaling pathways by antitumor ether lipids. // Biochim. Biophys. Acta. 1998. — P. 85−102.
- Vallari D. S, Record M, Smith Z. L, Snyder F. O-alkyl-O-methylglycerophosphocholine, an antineoplastic lipid, undergoes spontaneous redistribution between biological membranes prepared from HL-60 cells. // Biochim Biophys Acta. 1989 — P. 250−254.
- Jon V. Busto a, Jesus Sot a, Felix M. Surface-active properties of the antitumour ether lipid 1−0-octadecyl-2−0-methyl-rac-glycero-3-phosphocholine (edelfosine) // Biochimica et Biophysica Acta. 2007. — P. 1855−1860.
- Torrecillas A., Aroca-Aguilar J.D., Aranda F.J., Gajate C., Mollinedo F., Corbalan-Garcia S. Effects of the antineoplastic agent ET-18-OCH3 and some analogs on the biophysical properties of model membranes. // J. Pharm. 2006. — P. 28−40.
- Berdel W.E. and Munder P.G. Antineoplastic actions of ether lipids related to platelet-activating factor. Platelet-activating factor and related lipid mediators // Plenum Publishing Corporation. 1987. — P. 449−467.
- Barbara L. Herwaldt. Miltefosine — The Long-Awaited Therapy for Visceral Leishmaniasis. // Biochemistry. 1999. — V. 341. — P. 1840−1842.
- Croft, S. L., Neal, R. A., Thornton, E. A. Antileishmanial activity of the ether phospholipid ilmofosine. // Transactions of the Royal Society of Tropical Medicine and Hygiene. -1993. -V. 87. P. 217−219.
- Maslov M.A., Morozova N.G. and Serebrennikova G.A. Convenient synthesis of cationic glycerolipids via methylthiomethyl ethers. // Mendeleev Commun.-2000. № 2. — P. 65.
- Константинова И.Д., Зайцева H.M., Ушакова И. П., Серебренникова Г. А. Синтез катионных липидов алкильного типа с коротко цепными заместителями при атоме С(2) глицеринового скелета. // Изв. АН, Сер. хим. 1994. — №. 10. — С. 1826.
- Gajate С., 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, — V. 3. — P. 491−525.
- Jendrossek V., Handrick. R. Membrane targeted anticancer drugs: potent inducers of apoptosis and putative radiosensitisers. // Curr. Med. Chem. Anti-Canc. Agents. 2003. — V. 3. — P. 343−353.
- Wang K.S., Monden M., Kanai Т., Gotoh M., Umeshita K., Ukei T. and Mori T. Protective effect of platelet-activating factor antagonist on ischemia-induced liver injury in rats. // Surgery. 1993. — V. 113. — №. 1. — P. 76.
- Arthur G., Bitmann R. The inhibition of cell signaling pathways by antitumor ether lipids. // Biochim. Biophys. Acta. 1998. -V. 390. — P. 85−102.
- Godfroid J.J., Heymans F. Chemistry of PAF antagonists. // Biochem. Pharmacol. -1988.-V. 22.-P. 25
- Berdel W.E. and Munder P.G. Antineoplastic actions of ether lipids related to platelet-activating factor. // Platelet-activating factor and related lipid mediators. 1987. — P. 449−467.
- Nieto-Miguel Т., Gajate C., Mollinedo F. Differential targets and subcellular localization of antitumor alkyl-lysophospholipid in leukemic versus solid tumor cells. // J. Biol. Chem. -2006.-V. 281.-P. 14 833−14 840.
- Gajate C., 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. 2001. -V. 98. — P. 3860−3863.
- 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. — V. 109. — P. 711−719.
- Anatoly N. Pinchuk, Mark A. Rampy, Marc A. Longino, Scott Skinner. Synthesis and Structure-Activity Relationship Effects on the Tumor Avidity of Radioiodinated Phospholipid Ether Analogues. // Med. Chem. -2006. -V. 49. P. 2155−2165.
- Meyer K. L., Schwendner S. W. Counsell R.E. Potential tumor or organ imaging agents. Radioiodinated phospholipid ethers. //J. Med. Chem. 1989. V. 32. — P. 2142−2147.
- Counsell R.E., Schwendner S.W., Meyer K. L., Haradahira T. Tumor visualization with a radioiodinated phospholipids ether. // J. Nucl. Med. 1990. -V. 31. — P. 332−336.
- Plotzke K. P., Fisher, S. J., Wahl, R. L" Olken, N. M" Skinner, R.W., Gross, M. D" Counsell R. E. Selective localization of a radioiodinated phospholipid ether analog in human tumor xenografts. // J. Nucl. Med. 1993. — V.34. — P. 787−792.
- Plotzke К. P., Haradahira Т., Stancato L, Olken N. M., Skinner R. W. Gross, M. D" Wahl, R.L.- Counsell, R.E. Selective localization of radioiodinated alkylphosphocholine derivatives in tumors. // Nucl. Med. Biol. -1992. V. 19. — P. 765−773.
- Rampy M. A., Chou T. S., Pinchuk A. N., Skinner R. W. S., Gross M. D., Fisher S., Wahl R. L., Counsell R. E. Synthesis and biological evaluation of radioiodinated phospholipid ether analogs. // Nucl. Med. Biol. 1995. — V. 22. — P. 505−512.
- Eibl H., Hilgard P., Unger C. A comparison of hemolytic activity, serum binding and tissue distribution. // In Progress in Experimental Tumor Research. 1992. — V. 34. — P. 131−142.
- Kotting J., Berger M. R., Unger C., Eibl H. Alkylphosphocholines: lnfluence of structural variation and biodistribution at antineoplasticallyactive concentrations. // Cancer Chemother. Pharmacol. 1992. -V. 30. — P. 105−112.
- Романова С.Г., Штиль А. А., Серебренникова Г. А. Синтез новых бесфосфорных аналогов эдельфозина и их цитотоксичность. // Биоорган. Химия. 2008. — Т. 34. -№ 6. — С. 827−830.
- Романова С.Г. Заявка на патент:получение бесфосфорного алкильного глицеролипида, содержащего флуоресцентную метку в полярном домене. От 24.10.08. № 54 578. — регистрационный номер 2 008 142 023.
- Wagner, В. A.- Buettner, G. R.- Oberley, L. W.- Burns, С. P. Sensitivity of K-562 and HL60 cells to edelfosin, an ether lipid drug, correlates with production of active oxygen species. // Cancer Res. 1998. — V. 58. — P. 2809−2816.
- Mossman T. Rapid colorimetric assay for cellular growth and survival: application to proliferation. // J. Immunol. Methods. 1983. -V. 89. — P. 271−277.
- Справочник (под ред. А.Д.Третьякова). Оценка мутагенного действия препаратов. В кн.: Ветеринарные препараты. Москва, ВО Агропромиздат. — 1988. — С. 258 271.
- Белицкий Г. А., Фонштейн Л. М., Худолей В. В. Совол как индуктор микросомальных ферментов, активирующих проканцерогены. // Экспериментальная онкология. -1987.-Т. 9. № 3. — С.20−22.
- Фонштейн Л.М., Абелев С. К., Бобринев Е. В. Методы первичного выявления генетической активности с помощью бактериальных тест-систем m (методичекие указания) 1983.
- Pinchuk, A. N.- Mitsner, В. I.- Shvets, V. I. l-O-Benzyl-2-O-methylrac-glycerol: a key intermediate for synthesis of ether glycerolipids. // Chem. Phys. Lipids. 1991. — V. 59. — P. 263−265.
- Rampy M. A., Pinchuk A. N" Weichert J. P., Skinner R. W. S" Fisher S. J., Wahl R. L., Gross M. D., Counsell R. E. Synthesis and biological evaluation of radioiodinated phospholipid ether stereoisomers. // J. Med. Chem. 1995. -V. 38. — P. 3156−3162.