Synthesis of dehydroepiandrosterone analogues modified with phosphatidic acid moiety

Steroids

Volumn 75, Issue 13-14, 2010, Pages 1146-1152

  Smuga, Damian A ^a   Smuga, Małgorzata ^a   Świzdor, Alina ^a   Panek, Anna ^a   Wawrzeńczyk, Czesław ^a  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

Author keywords

7 OH DHEA; DHEA; DHEA modification; Phosphatides; Phosphatidic acid; Phospholipids

Indexed keywords

1,2 DIACYL SN GLYCERO 3 PHOSPHO PRASTERONE; PHOSPHATIDIC ACID; PRASTERONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ANIMALS; BIOTRANSFORMATION; DEHYDROEPIANDROSTERONE; FUSARIUM; LECITHINS; PHOSPHATIDIC ACIDS; PHOSPHOLIPASE D; PRODRUGS; STREPTOMYCES;

EID: 77957269887     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2010.08.001     Document Type: Article

References (36)

1. N.A. Compagnone, and S.H. Mellon Neurosteroids: biosynthesis and function of these novel neuromodulators Front Neuroendocrinol 21 1 2000 1 56 (Pubitemid 30105920)
2. I.H. Zwain, and S.S.C. Yen Neurosteroidogenesis in astrocytes, oligodendrocytes, and neurons of cerebral cortex of rat brain Endocrinology 140 8 1999 3843 3852 (Pubitemid 30645442)
3. I.H. Zwain, and S.S.C. Yen Dehydroepiandrosterone: biosynthesis and metabolism in the brain Endocrinology 140 2 1999 880 887
4. D.L. Auci, C. Ahlem, M. Li, R. Trauger, C. Dowding, and F. Paillard The immunobiology and therapeutic potential of androstene hormones and their synthetic derivatives: novel anti-inammatory and immune regulating steroid hormones Mod Aspects Immunobiol 3 2 2003 64 70
5. F. Labrie, V. Luu-The, A. Belanger, S.-X. Lin, J. Simard, and G. Pelletier Is dehydroepiandrosterone a hormone? J Endocrinol 187 2 2005 169 196 (Pubitemid 41685178)
6. J. Williams The effects of dehydroepiandrosterone on carcinogenesis, obesity, the immune system, and aging Lipids 35 3 2000 325 331 (Pubitemid 30198778)
7. M. Araghiniknam, S. Chung, T. Nelson-White, C. Eskelson, and R.R. Watson Antioxidant activity of dioscorea and dehydroepiandrosterone (DHEA) in older humans Life Sci 59 11 1996 147 157 (Pubitemid 26264466)
8. A. Marwah, P. Marwah, and H. Lardy Ergosteroids. VI. Metabolism of dehydroepiandrosterone by rat liver in vitro: a liquid chromatographic-mass spectrometric study J Chromatogr B, Analyt Technol Biomed Life Sci 767 2 2002 285 299 (Pubitemid 34142320)
9. Y. Matsuzaki, and A. Honda Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents Curr Pharm Des 12 26 2006 3411 3421 (Pubitemid 44375466)
10. R.F. van Vollenhoven Dehydroepiandrosterone for the treatment of systemic lupus erythematosus Expert Opin Pharmacother 3 1 2002 23 31 (Pubitemid 34763959)
11. D.L. Auci, C.L. Reading, and J.M. Frincke 7-Hydroxy androstene steroids and a novel synthetic analogue with reduced side effects as a potential agent to treat autoimmune diseases Autoimmun Rev 8 5 2009 369 372
12. J. Dulos, and A.H. Boots DHEA metabolism in arthritis Ann N Y Acad Sci 1069 2006 401 413
13. R. Morfin Involvement of steroids and cytochromes P450 species in the triggering of immune defenses J Steroid Biochem Mol Biol 80 3 2002 273 290 (Pubitemid 34308467)
14. V. Chmielewski, F. Drupt, and R. Morfin Dexamethasone-induced apoptosis of mouse thymocytes: prevention by native 7alpha-hydroxysteroids Immunol Cell Biol 78 3 2000 238 246 (Pubitemid 30415459)
15. D.M. Lambert Rationale and applications of lipids as prodrug carriers Eur J Pharm Sci 11 Suppl. 2 2000 S15 S27
16. N. Hidaka, M. Takami, and Y. Suzuki Enzymatic phosphatidylation of thiamin, pantothenic acid, and their derivatives J Nutr Sci Vitaminol 54 3 2008 255 261 (Pubitemid 352008311)
17. M. Takami, N. Hidaka, S. Miki, and Y. Suzuki Enzymatic synthesis of novel phosphatidylkojic acid and phosphatidylarbutin, and their inhibitory effects on tyrosinase activity Biosci Biotechnol Biochem 58 1994 1716 1717
18. S. Shuto, H. Itoh, S. Ueda, S. Imamura, K. Fukukawa, and M. Tsujino A facile enzymatic synthesis of 5′-(3-sn-phosphatidyl)nucleosides and their antileukemic activities Chem Pharm Bull 36 1 1988 209 217 (Pubitemid 18073385)
19. R.L. Alexander, and G.L. Kucera Lipid nucleoside conjugates for the treatment of cancer Curr Pharm Des 11 9 2005 1079 1089 (Pubitemid 40403369)
20. Y. Yamamoto, M. Hosokawa, and K. Miyashita Application of phospholipases for highly functional phospholipid preparation C.T. Hou, J.-F. Shaw, Biocatalysis and agricultural biotechnology 2009 CRC Press, Taylor and Francis Group Boca Raton 317 337
21. G.W. Oertel, and P. Benes Inhibition of glucose-6-phosphate dehydrogenase by steroids. VI. Effects of new synthetic dehydroepiandroster-one conjugates upon the activity of human placental glucose-6-phosphate dehydrogenase J Steroid Biochem 3 6 1972 903 905
22. J.R. Williams, and J.C. Boehm Studies on the synthesis of dehydroepiandrosterone (DHEA) phosphatide Steroids 60 4 1995 333 336
23. L. Palacios, and T. Wang Egg-yolk lipid fractionation and lecithin characterization J Am Oil Chem Soc 82 8 2005 571 578 (Pubitemid 43066380)
24. E.K. Ryu, R.J. Ross, T. Matsushita, M. MacCoss, C.I. Hong, and C.R. West Phospholipid-nucleoside conjugates, 3. Syntheses and preliminary biological evaluation of 1-β-d-arabino-furanosylcytosine 5′-monophosphate-l-1,2- dipalmitin and selected 1-β-d-arabinofurano-sylcytosine 5′-diphosphate-l-1,2-diacylglycerols J Med Chem 25 11 1982 1322 1329 (Pubitemid 13222042)
25. G.V. Marinetti Hydrolysis of lecithin with sodium methoxide Biochemistry 1 1962 350 353
26. T. Kolek Biotransformation. XLVII. Transformations of 5-ene steroids in Fusarium culmorum culture J Steroid Biochem Mol Biol 71 1-2 1999 83 90 (Pubitemid 28545119)
27. K. Patel, J. Morrisett, and J. Sparrow A convenient synthesis of phosphatidylcholines: acylation of sn-glycero-3-phosphocholine with fatty acid anhydride and 4-pyrrolidinopyridine J Lipid Res 20 5 1979 674 677 (Pubitemid 10246723)
28. D.M. Lambert, G.K.E. Scriba, B. Gallez, J.H. Poupaert, and P. Dumont Glyceride conjugates as drug carriers Curr Med Chem 1 5 1995 376 391
29. H. Tapiero, G.N. Ba, P. Couvreur, and K.D. Tew Polyunsaturated fatty acids (PUFA) and eicosanoids in human health and pathologies Biomed Pharmacother 56 5 2002 215 222 (Pubitemid 35245217)
30. P.C. Calder Polyunsaturated fatty acids, inflammation, and immunity Lipids 36 9 2001 1007 1024 (Pubitemid 33065203)
31. A.P. Simopoulos Omega-3 fatty acids in health and disease and in growth and development Am J Clin Nutr 54 3 1991 438 463
32. K. Ichihara, H. Iwasaki, K. Ueda, R. Takizawa, H. Naito, and M. Tomosugi Synthesis of phosphatidylcholine: an improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine Chem Phys Lipids 137 1-2 2005 94 99 (Pubitemid 41405834)
33. A. Singh An efficient synthesis of phosphatidylcholines J Lipid Res 31 August (8) 1990 1522 1525 (Pubitemid 20261917)
34. A. Todd Some current problems in polynucleotide chemistry Proc Chem Soc Lond 1961 187 228
35. G. Weimann, and H.G. Khorana Studies on polynucleotides. XVII. On the mechanism of internucleotide bond synthesis by the carbodiimide method J Am Chem Soc 84 22 1962 4329 4341
36. T.M. Jacob, and H.G. Khorana Studies on polynucleotides. XXX. A comparative study of reagents for the synthesis of the C3′-C5′ internucleotidic linkage J Am Chem Soc 86 8 1964 1630 1635