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Research Article

Anticancer double lipid prodrugs: liposomal preparation and characterization

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Pages 296-305 | Received 06 Dec 2010, Accepted 12 Feb 2011, Published online: 26 Mar 2011

References

  • Andresen, T. L., Davidsen, J., Begtrup, M., Mouritsen, O. G., Jorgensen, K. (2004). Enzymatic release of antitumor ether lipids by specific phospholipase A2 activation of liposome-forming prodrugs. J Med Chem 47:1694–1703.
  • Andresen, T. L., Jensen, S. S., Jorgensen, K. (2005a). Advanced strategies in liposomal cancer therapy: problems and prospects of active and tumor specific drug release. Progr Lipid Res 44:68–97.
  • Andresen, T. L., Jensen, S. S., Kaasgaard, T., Jorgensen, K. (2005b). Triggered activation and release of liposomal prodrugs and drugs in cancer tissue by secretory phospholipase A2. Curr Drug Deliv 2:353–362.
  • Andresen, T. L., Jensen, S. S., Madsen, R., Jorgensen, K. (2005c). Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue. J Med Chem 48:7305–7314.
  • Arouri, A., Dathe, M., Blume, A. (2009). Peptide induced demixing in PG/PE lipid mixtures: a mechanism for the specificity of antimicrobial peptides towards bacterial membranes? Biochim Biophys Acta 1788:650–659.
  • Barenholz, Y. (2003). Relevancy of drug loading to liposomal formulation therapeutic efficacy. J Liposome Res 13:1–8.
  • Chen, Y., Hu, L. (2009). Design of anticancer prodrugs for reductive activation. Med Res Rev 29:29–64.
  • Chowdhry, B. Z., Lipka, G., Sturtevant, J. M. (1984). Thermodynamics of phospholipid-sucrose interactions. Biophys J 46:419–421.
  • Christensen, M. S., Pedersen, P. J., Andresen, T. L., Madsen, R., Clausen, M. H. (2010). Isomerization of all-(E)-retinoic acid mediated by carbodiimide activation—synthesis of ATRA ether lipid conjugates. Eur J Org Chem 719–724.
  • Das, M., Mohanty, C., Sahoo, S. K. (2009). Ligand-based targeted therapy for cancer tissue. Exp Opin Drug Deliv 6:285–304.
  • Davidsen, J., Jorgensen, K., Andresen, T. L., Mouritsen, O. G. (2003). Secreted phospholipase A2 as a new enzymatic trigger mechanism for localised liposomal drug release and absorption in diseased tissue. Biochim Biophys Acta 1609:95–101.
  • Davidsen, J., Mouritsen, O. G., Jorgensen, K. (2002). Synergistic permeability enhancing effect of lysophospholipids and fatty acids on lipid membranes. Biochim Biophys Acta 1564:256–262.
  • de Carvalho, L. M., Schwedt, G. (2001). Polarographic determination of dithionite and its decomposition products: kinetic aspects, stabilizers, and analytical application. Anal Chim Acta 436:293–300.
  • Gordeliy, V. I., Kiselev, M. A., Lesieur, P., Pole, A. V., Teixeira, J. (1998). Lipid membrane structure and interactions in dimethyl sulfoxide/water mixtures. Biophys J 75:2343–2351.
  • Graff, J. R., Konicek, B. W., Deddens, J. A., Chedid, M., Hurst, B. M., Colligan, B., et al. (2001). Expression of group IIa secretory phospholipase A2 increases with prostate tumor grade. Clin Cancer Res 7:3857–3861.
  • Grit, M., Crommelin, D. J. A. (1992). The effect of aging on the physical stability of liposome dispersions. Chem Phys Lipids 62:113–122.
  • Guler, S. D., Ghosh, D. D., Pan, J., Mathai, J. C., Zeidel, M. L., Nagle, J. F., et al. (2009). Effects of ether vs. ester linkage on lipid bilayer structure and water permeability. Chem Phys Lipids 160:33–44.
  • Hanahan, D., Weinberg, R. A. (2000). The hallmarks of cancer. Cell 100:57–70.
  • Hashizaki, K., Taguchi, H., Itoh, C., Sakai, H., Abe, M., Saito, Y., et al. (2005). Effects of poly(ethylene glycol) (PEG) concentration on the permeability of PEG-grafted liposomes. Chem Pharm Bull 53:27–31.
  • Hata, T., Matsuki, H., Kaneshina, S. (2000). Effect of local anesthetics on the phase transition temperatures of ether- and ester-linked phospholipid bilayer membranes. Coll Surf B 18:41–50.
  • Honger, T., Jorgensen, K., Biltonen, R. L., Mouritsen, O. G. (1996). Systematic relationship between phospholipase A2 activity and dynamic lipid bilayer microheterogeneity. Biochemistry 35:9003–9006.
  • Hoyrup, P., Mouritsen, O. G., Jorgensen, K. (2001). Phospholipase A(2) activity towards vesicles of DPPC and DMPC-DSPC containing small amounts of SMPC. Biochim Biophys Acta 1515:133–143.
  • Huang, C., Li, S. (1999). Calorimetric and molecular mechanics studies of the thermotropic phase behavior of membrane phospholipids. Biochim Biophys Acta 1422:273–307.
  • Huster, D., Muller, P., Arnold, K., Herrmann, A. (2001). Dynamics of membrane penetration of the fluorescent 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD) group attached to an acyl chain of phosphatidylcholine. Biophys J 80:822–831.
  • Jemal, A., Siegel, R., Ward, E., Hao, Y., Xu, J., Thun, M. J. (2009). Cancer statistics, 2009. CA Cancer J Clin 59:225–249.
  • Jensen, S. S., Andresen, T. L., Davidsen, J., Høyrup, P., Shnyder, S. D., Bibby, M. C., et al. (2004). Secretory phospholipase A2 as a tumor-specific trigger for targeted delivery of a novel class of liposomal prodrug anticancer etherlipids. Mol Cancer Ther 3:1451–1458.
  • Jiang, J., Neubauer, B. L., Graff, J. R., Chedid, M., Thomas, J. E., Roehm, N. W., et al. (2002). Expression of group IIA secretory phospholipase A2 is elevated in prostatic intraepithelial neoplasia and adenocarcinoma. Am J Pathol 160:667–671.
  • Kaasgaard, T., Andresen, T. L. (2010). Liposomal cancer therapy: exploiting tumor characteristics. Exp Opin Drug Deliv 7:225–243.
  • Kashiwagi, M., Friess, H., Uhl, W., Berberat, P., Abou-Shady, M., Martignoni, M., et al. (1999). Group II and IV phospholipase A2 are produced in human pancreatic cancer cells and influence prognosis. Gut 45:605–612.
  • Kennedy, B. P., Soravia, C., Moffat, J., Xia, L., Hiruki, T., Collins, S., et al. (1998). Overexpression of the nonpancreatic secretory group II PLA2 messenger RNA and protein in colorectal adenomas from familial adenomatous polyposis patients. Cancer Res 58:500–503.
  • Kisak, E. T., Coldren, B., Evans, C. A., Boyer, C., Zasadzinski, J. A. (2004). The vesosome—a multicompartment drug delivery vehicle. Curr Med Chem 11:199–219.
  • Kisak, E. T., Coldren, B., Zasadzinski, J. A. (2002). Nanocompartments enclosing vesicles, colloids, and macromolecules via interdigitated lipid bilayers. Langmuir 18:284–288.
  • Kiyohara, H., Egami, H., Kako, H., Shibata, Y., Murata, K., Ohshima, S., et al. (1993). Immunohistochemical localization of group II phospholipase A2 in human pancreatic carcinomas. Int J Pancreatol 13:49–57.
  • Klein, C. A. (2009). Parallel progression of primary tumours and metastases. Nat Rev Cancer 9:302–312.
  • Kraske, W. V., Mountcastle, D. B.. (2001). Effects of cholesterol and temperature on the permeability of dimyristoylphosphatidylcholine bilayers near the chain melting phase transition. Biochim Biophys Acta 1514:159–164.
  • Kudo, I. (2004). Diversity of phospholipase A2 enzymes. Biol Pharm Bull 27:1157.
  • Lambeau, G., Gelb, M. H. (2008). Biochemistry and physiology of mammalian secreted phospholipases A2. Annu Rev Biochem 77:495–520.
  • Langner, M., Hui, S. (2000). Effect of free fatty acids on the permeability of 1,2-dimyristoyl-sn-glycero-3-phosphocholine bilayer at the main phase transition. Biochim Biophys Acta 1463:439–447.
  • Langner, M., Hui, S. W. (1993). Dithionite penetration through phospholipid bilayers as a measure of defects in lipid molecular packing. Chem Phys Lipids 65:23–30.
  • Laye, J. P., Gill, J. H. (2003). Phospholipase A2 expression in tumours: a target for therapeutic intervention? Drug Discov Today 8:710–716.
  • Leidy, C., Linderoth, L., Andresen, T. L., Mouritsen, O. G., Jorgensen, K., Peters, G. H. (2006). Domain-induced activation of human phospholipase A2 type IIA: local versus global lipid composition. Biophys J 90:3165–3175.
  • Lund, B. W., Knapp, A. E., Piu, F., Gauthier, N. K., Begtrup, M., Hacksell, U., et al. (2009). Design, synthesis, and structure-activity analysis of isoform-selective retinoic acid receptor beta ligands. J Med Chem 52:1540–1545.
  • Lund, B. W., Piu, F., Gauthier, N. K., Eeg, A., Currier, E., Sherbukhin, V., et al. (2005). Discovery of a potent, orally available, and isoform-selective retinoic acid beta2 receptor agonist. J Med Chem 48:7517–7519.
  • Malam, Y., Loizidou, M., Seifalian, A. M. (2009). Liposomes and nanoparticles: nanosized vehicles for drug delivery in cancer. Trends Pharmacol Sci 30:592–599.
  • Matsuki, H., Miyazaki, E., Sakano, F., Tamai, N., Kaneshina, S. (2007). Thermotropic and barotropic phase transitions in bilayer membranes of ether-linked phospholipids with varying alkyl chain lengths. Biochim Biophys Acta 1768:479–489.
  • Matsuki, H., Okuno, H., Sakano, F., Kusube, M., Kaneshina, S. (2005). Effect of deuterium oxide on the thermodynamic quantities associated with phase transitions of phosphatidylcholine bilayer membranes. Biochim Biophys Acta 1712:92–100.
  • Matsumura, Y., Maeda, H. (1986). A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer Res 46:6387–6392.
  • Mayer, L. D., Krishna, R., Webb, M., Bally, M. (2000). Designing liposomal anticancer drug formulations for specific therapeutic applications. J Liposome Res 10:99–115.
  • McIntyre, J. C., Sleight, R. G. (1991). Fluorescence assay for phospholipid membrane asymmetry. Biochemistry 30:11819–11827.
  • Mills, J. K., Needham, D. (2005). Lysolipid incorporation in dipalmitoylphosphatidylcholine bilayer membranes enhances the ion permeability and drug release rates at the membrane phase transition. Biochim Biophys Acta 1716:77–96.
  • Minko, T., Dharap, S. S., Pakunlu, R. I., Wang, Y. (2004). Molecular targeting of drug delivery systems to cancer. Curr Drug Targ 5:389–406.
  • Mouritsen, O. G., Andresen, T. L., Halperin, A., Hansen, P. L., Jakobsen, A. F., Jensen, U. B., et al. (2006). Activation of interfacial enzymes at membrane surfaces. J Phys Condens Mat 18:1293–1304.
  • Murata, K., Egami, H., Kiyohara, H., Oshima, S., Kurizaki, T., Ogawa, M. (1993). Expression of group-II phospholipase A2 in malignant and non-malignant human gastric mucosa. Br J Cancer 68:103–111.
  • Papahadjopoulos, D., Moscarello, M., Eylar, E. H., Isac, T. (1975). Effects of proteins on thermotropic phase transitions of phospholipid membranes. Biochim Biophys Acta 401:317–335.
  • Pedersen, P. J., Adolph, S. K., Andresen, T. L., Madsen, M. W., Madsen, R., Clausen, M. H. (2010a). Prostaglandin phospholipid conjugates with unusual biophysical and cytotoxic properties. Bioorg Med Chem Lett 20:4456–4458.
  • Pedersen, P. J., Adolph, S. K., Subramanian, A. K., Arouri, A., Andresen, T. L., Mouritsen, O. G., et al. (2010b). Liposomal formulation of retinoids designed for enzyme triggered release. J Med Chem 53:3782–3792.
  • Pedersen, P. J., Christensen, M. S., Ruysschaert, T., Linderoth, L., Andresen, T. L., Melander, F., et al. (2009). Synthesis and biophysical characterization of chlorambucil anticancer ether lipid prodrugs. J Med Chem 52:3408–3415.
  • Provencher, S. W. (1982). CONTIN: a general purpose constrained regularization program for inverting noisy linear algebraic and integral equations. Comput Phys Commun 27:229–242.
  • Risbo, J., Jorgensen, K., Sperotto, M. M., Mouritsen, O. G. (1997). Phase behavior and permeability properties of phospholipid bilayers containing a short-chain phospholipid permeability enhancer. Biochim Biophys Acta 1329:85–96.
  • Ruocco, M. J., Siminovitch, D. J., Griffin, R. G. (1985). Comparative study of the gel phases of ether- and ester-linked phosphatidylcholines. Biochemistry 24:2406–2411.
  • Sandstrom, M. C., Ickenstein, L. M., Mayer, L. D., Edwards, K. (2005). Effects of lipid segregation and lysolipid dissociation on drug release from thermosensitive liposomes. J Contr Rel 107:131–142.
  • Silvander, M., Johnsson, M., Edwards, K. (1998). Effects of PEG-lipids on permeability of phosphatidylcholine/cholesterol liposomes in buffer and in human serum. Chem Phys Lipids 97:15–26.
  • Six, D. A., Dennis, E. A. (2000). The expanding superfamily of phospholipase A2 enzymes: classification and characterization. Biochim Biophys Acta 1488:1–19.
  • Stutts, K. J. (1987). Liquid chromatographic assay of dithionite and thiosulfate. Anal Chem 59:543–544.
  • Tribler, L., Jensen, L. T., Jorgensen, K., Brunner, N., Gelb, M. H., Nielsen, H. J., et al. (2007). Increased expression and activity of group IIA and X secretory phospholipase A2 in peritumoral versus central colon carcinoma tissue. Anticancer Res 27:3179–3185.
  • Yu, Z. W., Quinn, P. J. (1995). Phase stability of phosphatidylcholines in dimethylsulfoxide solutions. Biophys J 69:1456–1463.
  • Zucker, D., Marcus, D., Barenholz, Y., Goldblum, A. (2009). Liposome drugs’ loading efficiency: a working model based on loading conditions and drug’s physicochemical properties. J Contr Rel 139:73–80.

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