Lipases, liposomes and lipid-prodrugs

Current Opinion in Colloid and Interface Science

Volumn 18, Issue 5, 2013, Pages 419-431

  Arouri, Ahmad ^a   Hansen, Anders Højgaard ^a   Rasmussen, Thomas Elmelund ^a   Mouritsen, Ole G ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

Drug delivery; Interface; Liposome; Phospholipase; Prodrug

Indexed keywords

ACTIVATED ENZYMES; DRUG FORMULATIONS; DRUG-DELIVERY SYSTEMS; FUNCTIONAL PROPERTIES; INTERFACIAL PHENOMENA; LIPID MOLECULES; PHOSPHOLIPASES; PRODRUGS;

BINDING SITES; DRUG DELIVERY; INTERFACES (MATERIALS); LIPOSOMES;

CONTROLLED DRUG DELIVERY;

ARGINYLGLYCYLASPARTIC ACID; BIOLOGICAL MARKER; CALCEIN; CAPSAICIN; CHLORAMBUCIL; CHOLESTEROL; CISPLATIN; DOXORUBICIN; FATTY ACID; FUMAGILLIN; GAMMA UROGASTRONE; GLYCEROL; IBUPROFEN; INDOMETACIN; LIPID; LIPOSOME; NUCLEOSIDE ANALOG; OLEIC ACID; OPSONIN; PHOSPHOLIPASE A2; POLYMER; PRODRUG; PROSTAGLANDIN; RECEPTOR; RETINOIC ACID; SUCCINIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE; VALPROIC ACID; VITRONECTIN RECEPTOR;

APOPTOSIS; BIOCOMPATIBILITY; BLOOD TOXICITY; CANCER THERAPY; CELL MEMBRANE; CYTOTOXICITY; DRUG ACTIVITY; DRUG DELIVERY SYSTEM; DRUG POTENCY; DRUG RELEASE; DRUG UPTAKE; ENDOSOME; ENTROPY; ENZYME ACTIVATION; GENE SILENCING; HUMAN; HYDROLYSIS; LIPID BILAYER; LIPID COMPOSITION; LIPID MEMBRANE; LYMPHATIC DRAINAGE; MACROMOLECULE; MEMBRANE MODEL; MEMBRANE PERMEABILITY; MOLECULE; NONHUMAN; PHASE TRANSITION; PHYSICAL CHEMISTRY; REVIEW; SOLID; SYNTHESIS; TEMPERATURE; TUMOR GROWTH; TUMOR VASCULARIZATION;

EID: 84882264988     PISSN: 13590294     EISSN: 18790399     Source Type: Journal    
DOI: 10.1016/j.cocis.2013.06.001     Document Type: Review

References (183)

1. Arouri A., Mouritsen O.G. Membrane-perturbing effect of fatty acids and lysolipids. Prog Lipid Res 2013, 52:130-140.
2. Mouritsen O.G. Lipids, curvature, and nano-medicine. Eur J Lipid Sci Technol 2011, 113:1174-1187.
3. Bangham A.D., Standish M.M., Watkins J.C. Diffusion of univalent ions across the lamellae of swollen phospholipids. J Mol Biol 1965, 13:238-252.
4. Barenholz Y. Liposome application: problems and prospects. Curr Opin Colloid Interface Sci 2001, 6:66-77.
5. Gabizon A.A., Shmeeda H., Zalipsky S. Pros and cons of the liposome platform in cancer drug targeting. J Liposome Res 2006, 16:175-183.
6. Torchilin V.P. Recent advances with liposomes as pharmaceutical carriers. Nat Rev Drug Discov 2005, 4:145-160.
7. Storm G., Crommelin D.J.A. Liposomes: quo vadis?. Pharm Sci Technol Today 1998, 1:19-31.
8. Immordino M.L., Dosio F., Cattel L. Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential. Int J Nanomedicine 2006, 1:297-315.
9. Chang H.I., Yeh M.K. Clinical development of liposome-based drugs: formulation, characterization, and therapeutic efficacy. Int J Nanomedicine 2012, 7:49-60.
10. Andresen T.L., Jensen S.S., Jorgensen K. Advanced strategies in liposomal cancer therapy: problems and prospects of active and tumor specific drug release. Prog Lipid Res 2005, 44:68-97.
11. Gregoriadis G., Ryman B.E. Liposomes as carriers of enzymes or drugs - new approach to treatment of storage diseases. Biochem J 1971, 124:P58.
12. Scherphof G.L., Dijkstra J., Spanjer H.H., Derksen J.T., Roerdink F.H. Uptake and intracellular processing of targeted and nontargeted liposomes by rat Kupffer cells in vivo and in vitro. Ann N Y Acad Sci 1985, 446:368-384.
13. Patel H.M. Serum opsonins and liposomes: their interaction and opsonophagocytosis. Crit Rev Ther Drug Carrier Syst 1992, 9:39-90.
14. Devine D.V., Wong K., Serrano K., Chonn A., Cullis P.R. Liposome-complement interactions in rat serum: implications for liposome survival studies. Biochim Biophys Acta 1994, 1191:43-51.
15. Harshima H., Sakata K., Funato K., Kiwada H. Enhanced hepatic uptake of liposomes through complement activation depending on the size of liposomes. Pharm Res 1994, 11:402-406.
16. Damen J., Regts J., Scherphof G. Transfer and exchange of phospholipid between small unilamellar liposomes and rat plasma high density lipoproteins Dependence on cholesterol content and phospholipid composition. Biochim Biophys Acta 1981, 665:538-545.
17. Kubitschke J., Javor S., Rebek J. Deep cavitand vesicles-multicompartmental hosts. Chem Commun 2012, 48:9251-9253.
18. Safinya C.R., Ewert K.K. Materials chemistry: Liposomes derived from molecular vases. Nature 2012, 489:372-374.
19. Senior J., Gregoriadis G. Is half-life of circulating liposomes determined by changes in their permeability. FEBS Lett 1982, 145:109-114.
20. Allen T.M., Hansen C., Rutledge J. Liposomes with prolonged circulation times: factors affecting uptake by reticuloendothelial and other tissues. Biochim Biophys Acta 1989, 981:27-35.
21. Klibanov A.L., Maruyama K., Torchilin V.P., Huang J. Amphipathic polyethyleneglycols effectively prolong the circulation time of liposomes. FEBS Lett 1990, 268:235-237.
22. Marsh D., Bartucci R., Sportelli L. Lipid membranes with grafted polymers: physicochemical aspects. Biochim Biophys Acta 2003, 1615:33-59.
23. Davidson R.L. Handbook of water-soluble gums and resins 1980, McGraw-Hill Companies.
24. Dreborg S., Akerblom E.B. Immunotherapy with monomethoxypolyethylene glycol modified allergens. Crit Rev Ther Drug Carrier Syst 1990, 6:315-365.
25. Yamaoka T., Tabata Y., Ikada Y. Distribution and tissue uptake of poly(ethylene glycol) with different molecular weights after intravenous administration to mice. J Pharm Sci 1994, 83:601-606.
26. Needham D., McIntosh T.J., Lasic D.D. Repulsive interactions and mechanical stability of polymer-grafted lipid membranes. Biochim Biophys Acta 1992, 1108:40-48.
27. Matsumura Y., Maeda H. A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumor agent smancs. Cancer Res 1986, 46:6387-6392.
28. Zalipsky S., Qazen M., Walker J.A., Mullah N., Quinn Y.P., Huang S.K. New detachable poly(ethylene glycol) conjugates: cysteine-cleavable lipopolymers regenerating natural phospholipid, diacyl phosphatidylethanolamine. Bioconjug Chem 1999, 10:703-707.
29. Kale A.A., Torchilin V.P. Design, synthesis, and characterization of pH-sensitive PEG-PE conjugates for stimuli-sensitive pharmaceutical nanocarriers: the effect of substitutes at the hydrazone linkage on the ph stability of PEG-PE conjugates. Bioconjug Chem 2007, 18:363-370.
30. Kim H.-K., Van den Bossche J., Hyun S.-H., Thompson D.H. Acid-triggered release via dePEGylation of fusogenic liposomes mediated by heterobifunctional phenyl-substituted vinyl ethers with tunable pH-sensitivity. Bioconjug Chem 2012, 23:2071-2077.
31. Park J.W., Benz C.C., Martin F.J. Future directions of liposome-and immunoliposome-based cancer therapeutics. Semin Oncol 2004, 31:196-205.
32. Park J.W., Kirpotin D.B., Hong K., Shalaby R., Shao Y., Nielsen U.B., et al. Tumor targeting using anti-her2 immunoliposomes. J Control Release 2001, 74:95-113.
33. Buttel I., Voller K., Schneider C. Immunogenicity and its impact on benefit/risk considerations in the authorisation of biopharmaceuticals. Curr Drug Saf 2010, 5:287-292.
34. Rosenberg A.S. Immunogenicity of biological therapeutics: a hierarchy of concerns. Dev Biol (Basel) 2003, 112:15-21.
35. Mastrobattista E., Koning G., Storm G. Immunoliposomes for the targeted delivery of antitumor drugs. Adv Drug Deliv Rev 1999, 40:103-127.
36. Daniels T.R., Bernabeu E., Rodríguez J.A., Patel S., Kozman M., Chiappetta D.A., et al. The transferrin receptor and the targeted delivery of therapeutic agents against cancer. Biochim Biophys Acta 1820, 2012:291-317.
37. Kakudo T., Chaki S., Futaki S., Nakase I., Akaji K., Kawakami T., et al. Transferrin-modified liposomes equipped with a pH-sensitive fusogenic peptide: an artificial viral-like delivery system. Biochemistry 2004, 43:5618-5628.
38. Maruyama K. Intracellular targeting delivery of liposomal drugs to solid tumors based on EPR effects. Adv Drug Deliv Rev 2011, 63:161-169.
39. Peer D., Margalit R. Tumor-targeted hyaluronan nanoliposomes increase the antitumor activity of liposomal Doxorubicin in syngeneic and human xenograft mouse tumor models. Neoplasia 2004, 6:343-353.
40. Leamon C.P., Low P.S. Delivery of macromolecules into living cells: a method that exploits folate receptor endocytosis. Proc Natl Acad Sci U S A 1991, 88:5572-5576.
41. Moret F., Scheglmann D., Reddi E. Folate-targeted PEGylated liposomes improve the selectivity of PDT with meta-tetra(hydroxyphenyl)chlorin (m-THPC). Photochem Photobiol Sci 2013, 12:823-834.
42. Ishii Y., Aramaki Y., Hara T., Tsuchiya S., Fuwa T. Preparation of EGF labeled liposomes and their uptake by hepatocytes. Biochem Biophys Res Commun 1989, 160:732-736.
43. Chen C.-W., Lu D.-W., Yeh M.-K., Shiau C.-Y., Chiang C.-H. Novel RGD-lipid conjugate-modified liposomes for enhancing siRNA delivery in human retinal pigment epithelial cells. Int J Nanomedicine 2011, 6:2567-2580.
44. Nimjee S.M., Rusconi C.P., Sullenger B.A. Aptamers: an emerging class of therapeutics. Annu Rev Med 2005, 56:555-583.
45. Ellington A.D., Szostak J.W. In vitro selection of RNA molecules that bind specific ligands. Nature 1990, 346:818-822.
46. Tuerk C., Gold L. Systematic evolution of ligands by exponential enrichment: RNA ligands to bacteriophage T4 DNA polymerase. Science 1990, 249:505-510.
47. C-hB Chen, Dellamaggiore K.R., Ouellette C.P., Sedano C.D., Lizadjohry M., Chernis G.A., et al. Aptamer-based endocytosis of a lysosomal enzyme. Proc Natl Acad Sci U S A 2008, 105:15908-15913.
48. Wilner S.E., Wengerter B., Maier K., de Lourdes Borba Magalhães M., Del Amo D.S., Pai S., et al. An RNA alternative to human transferrin: a new tool for targeting human cells. Mol Ther Nucleic Acids 2012, 1:e21.
49. Chen C-hB, Chernis G.A., Hoang V.Q., Landgraf R. Inhibition of heregulin signaling by an aptamer that preferentially binds to the oligomeric form of human epidermal growth factor receptor-3. Proc Natl Acad Sci U S A 2003, 100:9226-9231.
50. Mi J., Zhang X., Giangrande P.H., McNamara J.O., Nimjee S.M., Sarraf-Yazdi S., et al. Targeted inhibition of alphavbeta3 integrin with an RNA aptamer impairs endothelial cell growth and survival. Biochem Biophys Res Commun 2005, 338:956-963.
51. Chen Y., Hu L. Design of anticancer prodrugs for reductive activation. Med Res Rev 2009, 29:29-64.
52. Das M., Mohanty C., Sahoo S.K. Ligand-based targeted therapy for cancer tissue. Expert Opin Drug Deliv 2009, 6:285-304.
53. Kaasgaard T., Andresen T.L. Liposomal cancer therapy: exploiting tumor characteristics. Expert Opin Drug Deliv 2010, 7:225-243.
54. Malam Y., Loizidou M., Seifalian A.M. Liposomes and nanoparticles: nanosized vehicles for drug delivery in cancer. Trends Pharmacol Sci 2009, 30:592-599.
55. Minko T., Dharap S.S., Pakunlu R.I., Wang Y. Molecular targeting of drug delivery systems to cancer. Curr Drug Targets 2004, 5:389-406.
56. You J.O., Almeda D., Ye G.J., Auguste D.T. Bioresponsive matrices in drug delivery. J Biol Eng 2010, 4:15.
57. Bisby R.H., Mead C., Morgan C.G. Wavelength-programmed solute release from photosensitive liposomes. Biochem Biophys Res Commun 2000, 276:169-173.
58. Landon C.D., Park J.-Y., Needham D., Dewhirst M.W. Nanoscale drug delivery and hyperthermia: the materials design and preclinical and clinical testing of low temperature-sensitive liposomes used in combination with mild hyperthermia in the treatment of local cancer. Open Nanomed J 2011, 3:38-64.
59. Schroeder A., Honen R., Turjeman K., Gabizon A., Kost J., Barenholz Y. Ultrasound triggered release of cisplatin from liposomes in murine tumors. J Control Release 2009, 137:63-68.
60. Andresen T.L., Thompson D.H., Kaasgaard T. Enzyme-triggered nanomedicine: drug release strategies in cancer therapy. Mol Membr Biol 2010, 27:353-363.
61. de Fougerolles A., Vornlocher H.-P., Maraganore J., Lieberman J. Interfering with disease: a progress report on siRNA-based therapeutics. Nat Rev Drug Discov 2007, 6:443-453.
62. Simões S., Slepushkin V., Düzgünes N., Pedroso de Lima M.C. On the mechanisms of internalization and intracellular delivery mediated by pH-sensitive liposomes. Biochim Biophys Acta 2001, 1515:23-37.
63. Simões S., Moreira J.N., Fonseca C., Düzgüneş N., de Lima M.C.P. On the formulation of pH-sensitive liposomes with long circulation times. Adv Drug Deliv Rev 2004, 56:947-965.
64. Yatvin M.B., Weinstein J.N., Dennis W.H., Blumenthal R. Design of liposomes for enhanced local release of drugs by hyperthermia. Science 1978, 202:1290-1293.
65. Needham D., Anyarambhatla G., Kong G., Dewhirst M.W. A new temperature-sensitive liposome for use with mild hyperthermia: characterization and testing in a human tumor xenograft model. Cancer Res 2000, 60:1197-1201.
66. Gelb M.H., Jain M.K., Berg O.G. Inhibition of phospholipase A2. FASEB J 1994, 8:916-924.
67. Kupferberg J.P., Yokoyama S., Kezdy F.J. The kinetics of the phospholipase A2-catalyzed hydrolysis of egg phosphatidylcholine in unilamellar vesicles. Product inhibition and its relief by serum albumin. J Biol Chem 1981, 256:6274-6281.
68. Stephens W.W., Walker J.L., Myers W. The action of cobra poison on the blood: a contribution to the study of passive immunity. J Pathol Bacteriol 1898, 5:279-301.
69. Kudo I. Diversity of phospholipase A2 enzymes. Biol Pharm Bull 2004, 27:1158-1164.
70. Lambeau G., Gelb M.H. Biochemistry and physiology of mammalian secreted phospholipases A2. Annu Rev Biochem 2008, 77:495-520.
71. Six D.A., Dennis E.A. The expanding superfamily of phospholipase A2 enzymes: classification and characterization. Biochim Biophys Acta 2000, 1488:1-19.
72. Murakami M., Kudo I. Phospholipase A2. J Biochem (Tokyo) 2002, 131:285-292.
73. Pedersen P.J., Adolph S.K., Subramanian A.K., Arouri A., Andresen T.L., Mouritsen O.G., et al. Liposomal formulation of retinoids designed for enzyme triggered release. J Med Chem 2010, 53:3782-3792.
74. Yu B., Rogers J., Nicol G., Theopold K., Seshadri K., Vishweshwara S., et al. Catalytic significance of the specificity of divalent cations as KS* and k cat* cofactors for secreted phospholipase A2. Biochemistry 1998, 37:12576-12587.
75. Ramirez F., Jain M.K. Phospholipase A2 at the bilayer interface. Proteins 1991, 4:229-239.
76. Berg O.G., Gelb M.H., Tsai M., Jain M.K. Interfacial enzymology: the secreted phospholipase a2 paradigm. Chem Rev 2001, 101:2613-2654.
77. Mouritsen O.G., Andresen T.L., Halperin A., Hansen P.L., Jakobsen A.F., Jensen U.B., et al. Activation of interfacial enzymes at membrane surfaces. J Phys Condens Matter 2006, 18:1293-1304.
78. Honger T., Jorgensen K., Biltonen R.L., Mouritsen O.G. Systematic relationship between phospholipase A2 activity and dynamic lipid bilayer microheterogeneity. Biochemistry 1996, 35:9003-9006.
79. Hoyrup P., Callisen T.H., Jensen M.O., Halperin A., Mouritsen O.G. Lipid protrusions, membrane softness, and enzymatic activity. Phys Chem Chem Phys 2004, 6:1608-1615.
80. Halperin A., Mouritsen O. Role of lipid protrusions in the function of interfacial enzymes. Eur Biophys J 2005, 34:967-971.
81. Bayburt T., Yu B., Lin H., Browning J., Jain M., Gelb M. Human nonpancreatic secreted phospholipase A2: interfacial parameters, substrate specificities, and competitive inhibitors. Biochemistry 1993, 32:573-582.
82. Leidy C., Linderoth L., Andresen T.L., Mouritsen O.G., Jorgensen K., Peters G.H. Domain-induced activation of human phospholipase A2 type IIA: local versus global lipid composition. Biophys J 2006, 90:3165-3175.
83. Bezzine S. On the binding preference of human groups IIA and X phospholipases A2 for membranes with anionic phospholipids. J Biol Chem 2002, 277:48523-48534.
84. Canaan S. Unusual mode of binding of human group IIA secreted phospholipase A2 to anionic interfaces as studied by continuous wave and time domain electron paramagnetic resonance spectroscopy. J Biol Chem 2002, 277:30984-30990.
85. Diraviyam K., Murray D. Computational analysis of the membrane association of group IIA secreted phospholipases A2: a differential role for electrostatics. Biochemistry 2006, 45:2584-2598.
86. Simonsen A.C. Activation of phospholipase A2 by ternary model membranes. Biophys J 2008, 94:3966-3975.
87. Vermehren C., Kiebler T., Hylander I., Callisen T., Jørgensen K. Increase in phospholipase A2 activity towards lipopolymer-containing liposomes. Biochim Biophys Acta 1998, 1373:27-36.
88. Andresen T.L., Davidsen J., Begtrup M., Mouritsen O.G., Jorgensen K. Enzymatic release of antitumor ether lipids by specific phospholipase A2 activation of liposome-forming prodrugs. J Med Chem 2004, 47:1694-1703.
89. Zhu G., Mock J.N., Aljuffali I., Cummings B.S., Arnold R.D. Secretory phospholipase A(2) responsive liposomes. J Pharm Sci 2011, 100:3146-3159.
90. Apitz-Castro R., Jain M.K., De Haas G.H. Origin of the latency phase during the action of phospholipase A2 on unmodified phosphatidylcholine vesicles. Biochim Biophys Acta 1982, 688:349-356.
91. Burack W.R., Biltonen R.L. Lipid bilayer heterogeneities and modulation of phospholipase A2 activity. Chem Phys Lipids 1994, 73:209-222.
92. Arouri A., Mouritsen O.G. Phospholipase A2-susceptible liposomes of anticancer double lipid-prodrugs. Eur J Pharm Sci 2012, 45:408-420.
93. Hoyrup P., Davidsen J., Jorgensen K. Lipid membrane partitioning of lysolipids and fatty acids: effects of membrane phase structure and detergent chain lengths. J Phys Chem B 2001, 105:2649-2657.
94. Hui D. Phospholipase A(2) enzymes in metabolic and cardiovascular diseases. Curr Opin Lipidol 2012, 23:235-240.
95. Murakami M., Kudo I. New phospholipase A(2) isozymes with a potential role in atherosclerosis. Curr Opin Lipidol 2003, 14:431-436.
96. Tselepis A.D., John Chapman M. Inflammation, bioactive lipids and atherosclerosis: potential roles of a lipoprotein-associated phospholipase A2, platelet activating factor-acetylhydrolase. Atheroscler Suppl 2002, 3:57-68.
97. Belinsky G.S., Rajan T.V., Saria E.A., Giardina C., Rosenberg D.W. Expression of secretory phospholipase A2 in colon tumor cells potentiates tumor growth. Mol Carcinog 2007, 46:106-116.
98. Cai Q., Zhao Z., Antalis C., Yan L., Del Priore G., Hamed A.H., et al. Elevated and secreted phospholipase A2 activities as new potential therapeutic targets in human epithelial ovarian cancer. FASEB J 2012, 26:3306-3320.
99. Hu J.-j., Tian G., Zhang N. Cytosolic phospholipase A(2) and its role in cancer. Clin Oncol Cancer Res 2011, 8:71-76.
100. Tosato G., Segarra M., Salvucci O. Cytosolic phospholipase A2(alpha) and cancer: a role in tumor angiogenesis. J Natl Cancer Inst 2010, 102:1377-1379.
101. Murata K., Egami H., Kiyohara H., Oshima S., Kurizaki T., Ogawa M. Expression of group-II phospholipase A2 in malignant and non-malignant human gastric mucosa. Br J Cancer 1993, 68:103-111.
102. Scott K.F., Sajinovic M., Hein J., Nixdorf S., Galettis P., Liauw W., et al. Emerging roles for phospholipase A2 enzymes in cancer. Biochimie 2010, 92:601-610.
103. Tribler L., Jensen L.T., Jorgensen K., Brunner N., Gelb M.H., Nielsen H.J., et al. Increased expression and activity of group IIA and X secretory phospholipase A2 in peritumoral versus central colon carcinoma tissue. Anticancer Res 2007, 27:3179-3185.
104. Abe T., Sakamoto K., Kamohara H., Hirano Y., Kuwahara N., Ogawa M. Group II phospholipase A2 is increased in peritoneal and pleural effusions in patients with various types of cancer. Int J Cancer 1997, 74:245-250.
105. Yamashita S., Yamashita J., Ogawa M. Overexpression of group II phospholipase A2 in human breast cancer tissues is closely associated with their malignant potency. Br J Cancer 1994, 69:1166-1170.
106. Matsuda Y., Ogawa M., Sakamoto K., Yamashita S., Kanda A., Kohno M., et al. Development of a radioimmunoassay for human group-II phospholipase A2 and demonstration of postoperative elevation. Enzyme 1991, 45:200-208.
107. Jensen S.S., Andresen T.L., Davidsen J., Høyrup P., Shnyder S.D., Bibby M.C., et al. Secretory phospholipase A2 as a tumor-specific trigger for targeted delivery of a novel class of liposomal prodrug anticancer etherlipids. Mol Cancer Ther 2004, 3:1451-1458.
108. de Jonge M.J.A., Slingerland M., Loos W.J., Wiemer E.A.C., Burger H., Mathijssen R.H.J., et al. Early cessation of the clinical development of LiPlaCis, a liposomal cisplatin formulation. Eur J Cancer 2010, 46:3016-3021.
109. Cheong I., Huang X., Bettegowda C., Diaz L.A., Kinzler K.W., Zhou S., et al. A bacterial protein enhances the release and efficacy of liposomal cancer drugs. Science 2006, 314:1308-1311.
110. Cheong I., Huang X., Thornton K., Diaz L.A., Zhou S. Targeting cancer with bugs and liposomes: ready, aim, fire. Cancer Res 2007, 67:9605-9608.
111. Joshi N., Kaviratna A., Banerjee R. Multi trigger responsive, surface active lipid nanovesicle aerosols for improved efficacy of paclitaxel in lung cancer. Integr Biol 2013, 5:239-248.
112. Arpicco S., Dosio F., Stella B., Cattel L. Anticancer prodrugs: an overview of major strategies and recent developments. Curr Top Med Chem 2011, 11:2346-2381.
113. Singh Y., Palombo M., Sinko P.J. Recent trends in targeted anticancer prodrug and conjugate design. Curr Med Chem 2008, 15:1802-1826.
114. Silva A.T., Chung M.C., Castro L.F., Guido R.V., Ferreira E.I. Advances in prodrug design. Mini Rev Med Chem 2005, 5:893-914.
115. Charman W.N., Porter C.J.H. Lipophilic prodrugs designed for intestinal lymphatic transport. Adv Drug Deliv Rev 1996, 19:149-169.
116. Serova M., Galmarini C.M., Ghoul A., Benhadji K., Green S.R., Chiao J., et al. Antiproliferative effects of sapacitabine (CYC682), a novel 2'-deoxycytidine-derivative, in human cancer cells. Br J Cancer 2007, 97:628-636.
117. Caron J., Lepeltier E., Reddy L.H., Lepêtre-Mouelhi S., Wack S., Bourgaux C., et al. Squalenoyl gemcitabine monophosphate: synthesis, characterisation of nanoassemblies and biological evaluation. Eur J Org Chem 2011, 2615-2628.
118. Sagnella S.M., Gong X., Moghaddam M.J., Conn C.E., Kimpton K., Waddington L.J., et al. Nanostructured nanoparticles of self-assembled lipid pro-drugs as a route to improved chemotherapeutic agents. Nanoscale 2011, 3:919-924.
119. Barenholz Y. Relevancy of drug loading to liposomal formulation therapeutic efficacy. J Liposome Res 2003, 13:1-8.
120. Zucker D., Marcus D., Barenholz Y., Goldblum A. Liposome drugs' loading efficiency: A working model based on loading conditions and drug's physicochemical properties. J Control Release 2009, 139:73-80.
121. Peters A.C., Ahmad I., Janoff A.S., Pushkareva M.Y., Mayhew E. Growth inhibitory effects of liposome-associated 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine. Lipids 1997, 32:1045-1054.
122. Andresen T.L., Jensen S.S., Madsen R., Jorgensen K. Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue. J Med Chem 2005, 48:7305-7314.
123. Berkovic D. Cytotoxic etherphospholipid analogues. Gen Pharmacol 1998, 31:511-517.
124. Linderoth L., Fristrup P., Hansen M., Melander F., Madsen R., Andresen T.L., et al. Mechanistic study of the sPLA2-mediated hydrolysis of a thio-ester pro anticancer ether lipid. J Am Chem Soc 2009, 131:12193-12200.
125. Pedersen P.J., Christensen M.S., Ruysschaert T., Linderoth L., Andresen T.L., Melander F., et al. Synthesis and biophysical characterization of chlorambucil anticancer ether lipid prodrugs. J Med Chem 2009, 52:3408-3415.
126. Pedersen P.J., Adolph S.K., Andresen T.L., Madsen M.W., Madsen R., Clausen M.H. Prostaglandin phospholipid conjugates with unusual biophysical and cytotoxic properties. Bioorg Med Chem Lett 2010, 20:4456-4458.
127. Pedersen P.J., Viart H.M.F., Melander F., Andresen T.L., Madsen R., Clausen M.H. Synthesis of tocopheryl succinate phospholipid conjugates and monitoring of phospholipase A(2) activity. Bioorg Med Chem 2012, 20:3972-3978.
128. Christensen M.S., Pedersen P.J., Andresen T.L., Madsen R., Clausen M.H. Isomerization of all-(E)-retinoic acid mediated by carbodiimide activation - synthesis of ATRA ether lipid conjugates. Eur J Org Chem 2010, 2010:719-724.
129. Linderoth L., Peters G.H., Madsen R., Andresen T.L. Drug delivery by an enzyme-mediated cyclization of a lipid prodrug with unique bilayer-ormation properties. Angew Chem Int Ed 2009, 48:1823-1826.
130. Arouri A., Mouritsen O.G. Anticancer double lipid prodrugs: liposomal preparation and characterization. J Liposome Res 2011, 21:296-305.
131. Lund B.W., Knapp A.E., Piu F., Gauthier N.K., Begtrup M., Hacksell U., et al. Design, synthesis, and structure-activity analysis of isoform-selective retinoic acid receptor beta ligands. J Med Chem 2009, 52:1540-1545.
132. Lund B.W., Piu F., Gauthier N.K., Eeg A., Currier E., Sherbukhin V., et al. Discovery of a potent, orally available, and isoform-selective retinoic acid beta2 receptor agonist. J Med Chem 2005, 48:7517-7519.
133. Madsen J.J., Linderoth L., Subramanian A.K., Andresen T.L., Peters G.H. Secretory phospholipase A(2) activity toward diverse substrates. J Phys Chem B 2011, 115:6853-6861.
134. Fricker G., Kromp T., Wendel A., Blume A., Zirkel J., Rebmann H., et al. Phospholipids and lipid-based formulations in oral drug delivery. Pharm Res 2010, 27:1469-1486.
135. Carriere F., Barrowman J.A., Verger R., Laugier R. Secretion and contribution to lipolysis of gastric and pancreatic lipases during a test meal in humans. Gastroenterology 1993, 105:876-888.
136. Brockman H.L. Kinetic behavior of the pancreatic lipase-colipase-lipid system. Biochimie 2000, 82:987-995.
137. Whitcomb D.C., Lowe M.E. Human pancreatic digestive enzymes. Dig Dis Sci 2007, 52:1-17.
138. Brownlee I.A., Forster D.J., Wilcox M.D., Dettmar P.W., Seal C.J., Pearson J.P. Physiological parameters governing the action of pancreatic lipase. Nutr Res Rev 2010, 23:146-154.
139. Dahan A., Duvdevani R., Dvir E., Elmann A., Hoffman A. A novel mechanism for oral controlled release of drugs by continuous degradation of a phospholipid prodrug along the intestine: in-vivo and in-vitro evaluation of an indomethacin-lecithin conjugate. J Control Release 2007, 119:86-93.
140. Dahan A., Duvdevani R., Shapiro I., Elmann A., Finkelstein E., Hoffman A. The oral absorption of phospholipid prodrugs: in vivo and in vitro mechanistic investigation of trafficking of a lecithin-valproic acid conjugate following oral administration. J Control Release 2008, 126:1-9.
141. Kurz M., Scriba G.K.E. Drug-phospholipid conjugates as potential prodrugs: synthesis, characterization, and degradation by pancreatic phospholipase A2. Chem Phys Lipids 2000, 107:143-157.
142. Lalanne M., Khoury H., Deroussent A., Bosquet N., Benech H., Clayette P., et al. Metabolism evaluation of biomimetic prodrugs by in vitro models and mass spectrometry. Int J Pharm 2009, 379:235-243.
143. Skanji R., Andrieux K., Lalanne M., Caron J., Bourgaux C., Degrouard J., et al. A new nanomedicine based on didanosine glycerolipidic prodrug enhances the long term accumulation of drug in a HIV sanctuary. Int J Pharm 2011, 414:285-297.
144. Dhaneshwar S., Tewari K., Joshi S., Godbole D., Ghosh P. Diglyceride prodrug strategy for enhancing the bioavailability of norfloxacin. Chem Phys Lipids 2011, 164:307-313.
145. Sugihara J., Furuuchi S., Ando H., Takashima K., Harigaya S. Studies on intestinal lymphatic absorption of drugs. II. Glyceride prodrugs for improving lymphatic absorption of naproxen and nicotinic acid. J Pharmacobio-Dyn 1988, 11:555-562.
146. Sugihara J., Furuuchi S., Nakano K., Harigaya S. Studies on intestinal lymphatic absorption of drugs. I. Lymphatic absorption of alkyl ester derivatives and alpha-monoglyceride derivatives of drugs. J Pharmacobio-Dyn 1988, 11:369-376.
147. Pan D., Sanyal N., Schmieder A.H., Senpan A., Kim B., Yang X., et al. Antiangiogenic nanotherapy with lipase-labile Sn-2 fumagillin prodrug. Nanomed 2012, 7:1507-1519.
148. Zhou H.-f., Yan H., Senpan A., Wickline S.A., Pan D., Lanza G.M., et al. Suppression of inflammation in a mouse model of rheumatoid arthritis using targeted lipase-labile fumagillin prodrug nanoparticles. Biomaterials 2012, 33:8632-8640.
149. Heerklotz H. Interactions of surfactants with lipid membranes. Q Rev Biophys 2008, 41:205-264.
150. Israelachvili J.N. Intermolecular and surface forces. Amsterdam 2010, Academic Press, Waltham, MA.
151. Israelachvili J.N., Mitchell D.J., Ninham B.W. Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers. J Chem Soc, Faraday Trans 2 1976, 72:1525-1568.
152. Kumar V.V. Complementary molecular shapes and additivity of the packing parameter of lipids. Proc Natl Acad Sci U S A 1991, 88:444-448.
153. Mouritsen O.G. Physical chemistry of curvature and curvature stress in membranes. Current Physical Chemistry 2013, 3:17-26.
154. Seddon J.M., Templer R.H. Polymorphism of lipid-water systems. Handbook of Biological Physics Structure and Dynamics of Membranes 1995, 97-160. Elsevier, Amsterdam. R. Lipowsky, E. Sackmann (Eds.).
155. Jain M.K., van Echteld C.J., Ramirez F., de Gier J., de Haas G.H., van Deenen L.L. Association of lysophosphatidylcholine with fatty acids in aqueous phase to form bilayers. Nature 1980, 284:486-487.
156. Jain M.K., De Haas G.H. Structure of 1-acyl lysophosphatidylcholine and fatty acid complex in bilayers. Biochim Biophys Acta 1981, 642:203-211.
157. Lictenberg D., Barenholz Y. Liposomes: preparation, characterization, and preservation. Methods Biochem Anal 1988, 337-462. Wiley, New York. D. Glick (Ed.).
158. Davidsen J., Mouritsen O.G., Jorgensen K. Synergistic permeability enhancing effect of lysophospholipids and fatty acids on lipid membranes. Biochim Biophys Acta 2002, 1564:256-262.
159. Jespersen H., Andersen J.H., Ditzel H.J., Mouritsen O.G. Lipids, curvature stress, and the action of lipid prodrugs: free fatty acids and lysolipid enhancement of drug transport across liposomal membranes. Biochimie 2012, 94:2-10.
160. Mouritsen O.G., Zuckermann M.J. What's so special about cholesterol?. Lipids 2004, 39:1101-1113.
161. Blume A. Dynamic properties. Phospholipids Handbook 1993, 455-509. Marcel Dekker, New York. G. Cevc (Ed.).
162. Hac A.E., Seeger H.M., Fidorra M., Heimburg T. Diffusion in two-component lipid membranes-a fluorescence correlation spectroscopy and Monte Carlo simulation study. Biophys J 2005, 88:317-333.
163. Rosholm K.R., Arouri A., Hansen P.L., Gonzalez-Perez A., Mouritsen O.G. Characterization of fluorinated catansomes: A promising vector in drug-delivery. Langmuir 2012, 28:2773-2781.
164. Matsuki H., Miyazaki E., Sakano F., Tamai N., Kaneshina S. Thermotropic and barotropic phase transitions in bilayer membranes of ether-linked phospholipids with varying alkyl chain lengths. Biochim Biophys Acta 2007, 1768:479-489.
165. Davidsen J., Jorgensen K., Andresen T.L., Mouritsen O.G. Secreted phospholipase A2 as a new enzymatic trigger mechanism for localised liposomal drug release and absorption in diseased tissue. Biochim Biophys Acta 2003, 1609:95-101.
166. Hsieh C.C., Yen M.H., Liu H.W., Lau Y.T. Lysophosphatidylcholine induces apoptotic and non-apoptotic death in vascular smooth muscle cells: in comparison with oxidized LDL. Atherosclerosis 2000, 151:481-491.
167. Kong J.Y., Rabkin S.W. Palmitate-induced apoptosis in cardiomyocytes is mediated through alterations in mitochondria: prevention by cyclosporin A. Biochim Biophys Acta 2000, 1485:45-55.
168. Sparagna G.C., Hickson-Bick D.L., Buja L.M., McMillin J.B. A metabolic role for mitochondria in palmitate-induced cardiac myocyte apoptosis. Am J Physiol Heart Circ Physiol 2000, 279:H2124-H2132.
169. van der Luit A.H., Budde M., Ruurs P., Verheij M., van Blitterswijk W.J. Alkyl-lysophospholipid accumulates in lipid rafts and induces apoptosis via raft-dependent endocytosis and inhibition of phosphatidylcholine synthesis. J Biol Chem 2002, 277:39541-39547.
170. Lapre J.A., Termont D.S., Groen A.K., Van der Meer R. Lytic effects of mixed micelles of fatty acids and bile acids. Am J Physiol 1992, 263:G333-G337.
171. Reman F.C., Demel R.A., Degier J., Vandeene Ll, Eibl H., Westphal O. Studies on lysis of red cells and bimolecular lipid leaflets by synthetic lysolecithins, lecithins and structural analogs. Chem Phys Lipids 1969, 3:221-233.
172. Weltzien H.U. Cytolytic and membrane-perturbing properties of lysophosphatidylcholine. Biochim Biophys Acta 1979, 559:259-287.
173. Bagatolli L.A., Ipsen J.H., Simonsen A.C., Mouritsen O.G. An outlook on organization of lipids in membranes: searching for a realistic connection with the organization of biological membranes. Prog Lipid Res 2010, 49:378-389.
174. Foged C., Nielsen H.M., Frokjaer S. Phospholipase A2 sensitive liposomes for delivery of small interfering RNA (siRNA). J Liposome Res 2007, 17:191-196.
175. Foged C., Nielsen H.M., Frokjaer S. Liposomes for phospholipase A(2) triggered siRNA release: preparation and in vitro test. Int J Pharm 2007, 331:160-166.
176. Rasmussen N., Andersen J.H., Jespersen H., Mouritsen O.G., Ditzel H.J. Effect of free fatty acids and lysolipids on cellular uptake of doxorubicin in human breast cancer cell lines. Anticancer Drugs 2010, 21:674-677.
177. Garzon-Aburbeh A., Poupaert J.H., Claesen M., Dumont P. A lymphotropic prodrug of L-dopa: synthesis, pharmacological properties, and pharmacokinetic behavior of 1,3-dihexadecanoyl-2-[(S)-2-amino-3-(3,4-dihydroxyphenyl)prop anoyl] propane-1,2,3-triol. J Med Chem 1986, 29:687-691.
178. Scott D.L., Otwinowski Z., Gelb M.H., Sigler P.B. Crystal structure of bee-venom phospholipase A2 in a complex with a transition-state analogue. Science 1990, 250:1563-1566.
179. Harris L.J., Larson S.B., Hasel K.W., McPherson A. Refined structure of an intact IgG2a monoclonal antibody. Biochemistry 1997, 36:1581-1597.
180. Hall D.R., Hadden J.M., Leonard G.A., Bailey S., Neu M., Winn M., et al. The crystal and molecular structures of diferric porcine and rabbit serum transferrins at resolutions of 2.15 and 2.60 A, respectively. Acta Crystallogr D Biol Crystallogr 2002, 58:70-80.
181. Baouendi M., Cognet J.A., Ferreira C.S., Missailidis S., Coutant J., Piotto M., et al. Solution structure of a truncated anti-MUC1 DNA aptamer determined by mesoscale modeling and NMR. FEBS J 2012, 279:479-490.
182. Montelione G.T., Wuthrich K., Burgess A.W., Nice E.C., Wagner G., Gibson K.D., et al. Solution structure of murine epidermal growth factor determined by NMR spectroscopy and refined by energy minimization with restraints. Biochemistry 1992, 31:236-249.
183. Heller H., Schaefer M., Schulten K. Molecular dynamics simulation of a bilayer of 200 lipids in the gel and in the liquid crystal phase. J Phys Chem 1993, 97:8343-8360.