Synthesis and antiproliferative activity of cytidine-5'-alkylphosphonophosphates and structurally related compounds

Chemistry and Physics of Lipids

Volumn 83, Issue 1, 1996, Pages 77-85

  Brachwitz, H ^a,b   Lachmann, U ^b   Thomas, Y ^a   Bergmann, J ^a   Berdel, W E ^a   Langen, P ^b  

^a CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

^b MAX DELBRÜCK CENTER FOR MOLECULAR MEDICINE   (Germany)

Author keywords

Antiproliferative activity; Cytidine 5' alkyl(acyl)deoxyglycerophosphonophosphates; Cytidine 5' alkylphosphonophosphate; Fast atom bombardment mass spectrometry; Phospholipid nucleoside conjugates

Indexed keywords

CYTIDINE 5' ALKYLACYLDEOXYGLYCEROPHOSPHONOPHOSPHATE; CYTIDINE 5' ALKYLDEOXYGLYCEROPHOSPHONOPHOSPHATE; CYTIDINE 5' HEXADECYLPHOSPHONOPHOSPHATE; CYTIDINE DERIVATIVE; CYTOSTATIC AGENT; GLYCEROPHOSPHATE; PHOSPHOLIPASE C; PHOSPHOLIPID; UNCLASSIFIED DRUG;

ARTICLE; CANCER INHIBITION; CELL PROLIFERATION; CHEMICAL BOND; CONTROLLED STUDY; DRUG EFFECT; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; HUMAN; HUMAN CELL; PRIORITY JOURNAL; TUMOR CELL LINE;

EID: 0030590463     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/0009-3084(96)02599-6     Document Type: Article

References (26)

1. [1] C.I. Hong, S.H. An, D.J. Buchheit, A. Nechaev, A.J. Kirisits, C.R. West and W.E. Berdel (1986) Nucleoside Conjugates. 7. Synthesis and antitumor activity of 1-β-D-Arabinosylcytosine conjugates of ether lipids. J. Med. Chem. 29, 2038-2044.
2. [2] W.E. Berdel, S. Danhauser, C.I. Hong, H.D. Schick, A. Reichert, R. Busch, J. Rastetter (1988) Influence of 1-β-d-arabinofuranosylcytosine conjugates of lipids on the growth and metastasis of Lewis lung carcinoma. Cancer Res. 48, 826-829.
3. [3] C.I. Hong, A. Nechaev, A.J. Kirisits, R. Vig, S.W. Hui and C.R. West (1995) Nucleoside Conjugate. 14. Synthesis and antitumor activity of 1-β-D-Arabinosylcytosine conjugates of ether lipids with improved water solubility. J. Med. Chem. 38, 1629-1634.
4. [4] Brachwitz and M.v. Janta-Lipinski (1990) Verfahren zur Herstellung von 2′,3′-Didesoxythymidin-5′-diphosphat-1,2-di-O-alkylglycerolen und von deren Salzen. Deutsches Patent DD 279-249.
5. [5] G.M.T. van Wijk, K.Y. Hostetler, M. Schlame and H. van den Bosch (1991) Cytidine diphosphate diglyceride analogs of antiretroviral dideoxynucleosides: evidence for release of dideoxynucleoside-monophosphates by phospholipid biosynthetic enzymes in rat liver subcellular fractions. Biochim. Biophys. Acta 1086, 99-105.
6. [6] G.M. van Wijk, K.Y. Hostetler and H. van den Bosch (1991) Lipid conjugates of antiretroviral agents: release of antiretroviral nucleoside monophosphates by a nuclesoside diphosphate diglyceride hydrolase activity from rat liver mitochondria. Biochim. Biophys. Acta 1084, 307-310.
7. [7] H. Brachwitz, P. Langen and F. Paltauf (1990) Cytidine-5′-diphosphate-alkylglycerol analogs (CDP-AG) - a new class of cytostatically active phospholipids. Cancer Res. Clin. Oncol. (Supplement) 116, 993.
8. [8] P. Langen, H.R. Maurer, H. Brachwitz, K. Eckert, A. Veit and C. Vollgraf (1992) Cytostatic effects of various alkyl phospholipid analogues on different cells in vitro. Anticancer Res. 12, 2109-2112.
9. [9] H. Brachwitz, R. Schönfeld, P. Langen, F. Paltauf and A. Hermetter (1990) New cytidine-5′-diphosphate alkanols and glycerols, a process for preparing them and their use. Patent PCT WO 90/02134.
10. [10] J.D. Schmitt, A.B. Nixon, A. Emilsson, L.W. Daniel and R.L. Wykle (1992) A facile synthesis of 1-O-alkyl-2-(R)-hydroxypropane-3-phosphonocholine (lyso-phosphono-platelet activating factor). Chem. Phys. Lipids 62, 263-268.
11. [11] B.P. Lugovkin (1957) Synthesis of esters of 8-caffeinyl-methylphosphonic acid. Zhur. Obshch. Khim. 27, 1524-1526; C. A. (1958) 52, 3829.
12. [11] B.P. Lugovkin (1957) Synthesis of esters of 8-caffeinyl-methylphosphonic acid. Zhur. Obshch. Khim. 27, 1524-1526; C. A. (1958) 52, 3829.
13. [12] T. Morita, Y. Okammoto and H. Sakurai (1978) A convenient dealkylation of dialkyl phosphonates by chlorotrimethylsilane in the presence of sodium iodide. Tetrahedron Lett. 28, 2523-2526.
14. [13] P.W. Deroo, A.F. Rosenthal, Y.A. Isaacson, L.A. Vargas and R. Bittman (1976) Synthesis of DL-2,3-diacylpropyl-phosphonylcholines from DL-2,3-diacyloxyiodopropanes. Chem. Phys. Lipids 16, 60-70.
15. [14] B.A. Arbuzov and B.P. Lugovkin (1952) Synthesis of esters of phosphonic acids containing heterocyclic radicals. II. Ethylesters of phosphonic acids with oxygen-bearing heterocyclic radicals. Zhur. Obshch. Khim. 22, 1193-1198; C. A. (1953) 47, 4871.
16. [14] B.A. Arbuzov and B.P. Lugovkin (1952) Synthesis of esters of phosphonic acids containing heterocyclic radicals. II. Ethylesters of phosphonic acids with oxygen-bearing heterocyclic radicals. Zhur. Obshch. Khim. 22, 1193-1198; C. A. (1953) 47, 4871.
17. [15] H. Disselnkötter, F. Lieb, H. Oedinger and D. Wendisch (1985) Synthese von Phosphonoanalogen des 2-O-Acetyl-1-O-hexadecyl(octadecyl)-sn-3-glycerophosphorylcholins (Platelet-Activating Factor). Arch. Pharm. 318, 659-700.
18. [16] M. Kates (1972) Techniques of lipidology: isolation, analysis and identification of lipids. In: T.S. Work and E. Work (Eds.), Laboratory Techniques in Biochemistry and Molecular Biology, American Elsevier Publishing Co., Inc., New York, p. 421.
19. [17] S.L. Morris-Natschke, K.L. Meyer, C.J. Arasco, Jr., C. Piantadosi, F. Rossi, P.L. Godwin and E.J. Modest (1990) Synthesis of quaternary amine ether lipids and evaluation of neoplastic cell growth inhibitory properties. J. Med Chem. 33, 1812-1818.
20. [18] P. Comfurius and R.F.A. Zwaal (1977) The enzymatic synthesis of phosphatidylserine and purification by CM-cellulose column chromatography. Biochim. Biophys. Acta 488, 36-42.
21. [19] J.G. Moffatt and H.G. Khorana (1961) Nucleoside Polyphosphates. 10. The synthesis and some reactions of nucleoside-5′ phosphoromorpholidates and related compounds. Improved methods for the preparation of nucleoside-5′ polyphosphates. J. Am. Chem. Soc. 83, 649-658.
22. [20] H. Brachwitz, P. Langen and J. Schildt (1984) Halo Lipids. 7. Synthesis of rac-1-chloro-1-deoxy-2-O-hexadecylglycero-3-phosphocholine. Chem. Phys. Lipids 34, 355-362.
23. [21] A. Klemer, B. Brandt, U. Hofmeister and E.R. Rüter (1983) Synthese einiger chlordesoxyglycoside und ihr einsatz zur darstellung von desoxy-und aminodesoxy-zuckern. Liebigs Ann. Chem., 1920-1929.
24. [22] J.T. Mason, A.V. Broccoli and C.-H. Huang (1981) A method for the synthesis of isomerically pure saturated mixed-chain phosphatidylcholines. Anal. Biochem. 113, 96-101.
25. [23] R. Bittman, A.F. Rosenthal, L.A. Vargas (1984) Synthesis of phospholipids via dimethylphosphoryl chloride. Chem. Phys. Lipids 34, 201-205.
26. [24] H. Eibl, P. Hilgard and C. Unger (Eds.), (1992) Alkylphosphocholines: New Drugs in Cancer Therapie, Prog. Exp. Tumor Res., Karger, Basel, Bd. 34.