An efficient and novel method for the synthesis of cardiolipin and its analogs

Lipids

Volumn 39, Issue 3, 2004, Pages 285-290

  Lin, Zhen ^a   Ahmad, Moghis U ^a   Ali, Shoukath M ^a   Ahmad, Imran ^a  

^a NeoPharm Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONTROLLED DRUG DELIVERY; GLYCEROL; OXIDATION; SYNTHESIS (CHEMICAL);

CARDIOLILIPIN; COUPLING REACTIONS; LIPOSOMAL DRUG DELIVERY;

LIPIDS;

1,2 O DIMYRISTOYLGLYCEROL; CARDIOLIPIN; GLYCEROL; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; DRUG DELIVERY SYSTEM; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

CARDIOLIPINS; CHEMISTRY, ORGANIC; MOLECULAR STRUCTURE;

EID: 2942566540     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-004-1231-5     Document Type: Article

References (26)

1. Ioannou, P., and Golding, B.T. (1979) Cardiolipins: Their Chemistry and Biochemistry, Prog. Lipid Res. 17, 279-318.
2. Semin, B.K., Saraste, M., and Wikstrom, M. (1984) Calorimetric Studies of Cytochrome Oxidase-Phospholipid Interactions, Biochim. Biophys. Acta 769, 15-22.
3. Thompson, D.A., and Ferguson-Miller, S. (1983) Lipid and Subunit III Depleted Cytochrome c Oxidase Purified by Horse Cytochrome c Affinity Chromatography in Lauryl Maltoside, Biochemistry 22, 3178-3187.
4. Chen, Q.P., and Li, Q.T. (2001) Effect of Cardiolipin on Proton Permeability of Phospholipid Liposomes: The Role of Hydration at the Lipid-Water Interface, Arch. Biochem. Biophys. 389, 201-206.
5. Chauhan, A., Ray, I., and Chauhan, V.P. (2000) Interaction of Amyloid β-Protein with Anionic Phospholipids: Possible Involvement of Lys28 and C-Terminus Aliphatic Amino Acids, Neurochem. Res. 25, 423-429.
6. Weissig, V., and Torchilin, V. P. (2000) Mitochondriotropic Cationic Vesicles: A Strategy Towards Mitochondrial Gene Therapy, Curr. Pharm. Biotechnol. 1, 325-346.
7. Fernandez, J.A., Kojima, K., Petäjäa, J., Hackeng, T.M., and Griffin, J.H. (2000) Cardiolipin Enhances Protein C Pathway Anticoagulant Activity, Blood Cells, Mol. Dis. 26, 115-123.
8. Guilmin, T., Goormaghtigh, E., Brasseur, R., Caspers, J., and Ruysschaert, J.M. (1982) Evaluation of the Anesthetic-Lipid Association Constant. A Monolayer Approach, Biochim. Biophys. Acta 685, 169-176.
9. Mestres, C., Ortiz, A., Haro, I., Reig, F., and Alsina, M.A. (1997) Influence of Phospholipidic Charge on the Interaction of a Multiple Antigenic Peptide from Hepatitis A Virus with Monolayers and Bilayers, Langmuir 13, 5669-5673.
10. Tavitian, B., Marzabal, S., Boutet, V., Kuhnast, B., Terrazzino, S., Moynier, M., Dolle, F., Deverre, J.R., and Thierry, A.R. (2002) Characterization of a Synthetic Anionic Vector for Oligonucleotide Delivery Using in vivo Whole Body Dynamic Imaging, Pharm. Res. 19, 367-376.
11. Deborah, J. (2002) Encapsulating the Science of Liposomes, Drug Discov. Devel. 5(5), 28-32 (www.dddmag.com).
12. Gokhale, P.C., Radhakrishnan, B., Husain, S.R., Abernethy, D. R., Sacher, R., Dritschilo, A., and Rahman, A. (1996) An Improved Method of Encapsulation of Doxorubicin in Liposomes: Pharmacological, Toxicological and Therapeutic Evaluation, Br. J. Cancer 74, 43-48.
13. Thierry, A.R., Rahman, A., and Dritschilo, A. (1994) A New Procedure for the Preparation of Liposomal Doxorubicin: Biological Activity in Multidrug-Resistant Tumor Cells, Cancer Chemother. Pharmacol. 35, 84-88.
14. Saunders, R.M., and Schwarz, H.P. (1966) Synthesis of Phosphatidylglycerol and Diphosphatidylglycerol, J. Am. Chem Soc. 88, 3844-3847.
15. Ramirez, F., Ioannou, P.V., Marecek, J.F., Dodd, G.H., and Golding, B.T. (1977) Synthesis of Phospholipids by Means of Cyclic Enediol Pyrophosphates Optically Active Monovalent and Divalent Cation Salts of Diphosphatidylglycerol (cardiolipin), Tetrahedron 33, 599-608.
16. Duralski, A.A., Spooner, P.J.R., Rankin, S.E., and Watts, A. (1998) Synthesis of Isotopically Labelled Cardiolipins, Tetrahedron Lett. 39, 1607-1610.
17. Mishina, I.M., Vasilenko, I.A., Stepanov, A.E., and Shvets, V.I. (1987) Studies on Complex Lipids. Synthesis of Diphosphatidyl-glycerol (cardiolipin) with Unsaturated Fatty Acids, Bioorg. Khim. 13, 1110-1115.
18. Mishina, I.M., Vasilenko, I.A., Stepanov, A.E., and Shvets, V.I. (1984) Study of Lipids. Synthesis of Phosphatidylglycerol and Diphosphatidylglycerol, Zh. Org. Khim. 20, 985-988.
19. Inoue, K., and Nojima, S. (1968) Immunochemical Studies of Phospholipids. II. Syntheses of Cardiolipin and Analogues, Chem. Pharm. Bull. 16, 76-81.
20. De Haas, G.H., Bonsen, P.P.M., and Van Deenen, L.L.M. (1966) Studies on Cardiolipin III. Structural Identity of Ox-Heart Cardiolipin and Synthetic Diphosphatidyl Glycerol, Biochim. Biophys. Acta 116, 114-124.
21. Atkinson, T., and Smith, M. (1984) Oligonucletide Synthesis-A Practical Approach (Gait, M.J., ed.), IRL, Oxford.
22. Beaucage, S.L., and Radhakrishnan, P.I. (1993) The Synthesis of Specific Ribonucleotides and Unrelated Phosphorylated Biomolecules by the Phosphoramidite Method, Tetrahedron 49, 10441-10488.
23. Bruzik, K.S., and Kubiak, R.J. (1995) General Synthesis of Phosphatidylinositol 3-Phosphates, Tetrahedron Lett. 36, 2415-2418.
24. Martin, S.F., Josey, J.A., Wong, Y.-L., and Dean, D.W. (1994) General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-glycerols, J. Org. Chem. 59, 4805-4820.
25. March, J. (1992) Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th edn., pp. 826-828, John Wiley & Sons, New York.
26. Xia, J., and Hui, Y.Z. (1999) Synthesis of a Small Library of Mixed-Acid Phospholipids from D-Mannitol as a Homochiral Starting Material, Chem. Pharm. Bull. 47, 1659-1663.