Controlling liposome blood clearance by surface-grafted polymers

Advanced Drug Delivery Reviews

Volumn 32, Issue 1-2, 1998, Pages 139-152

  Woodle, Martin C ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Biodistribution; Liposome; Pharmacokinetics; Polyethylene glycol (PEG); Polymer brush; Targeting

Indexed keywords

BLOOD; DRUG INTERACTIONS; LIPIDS; PHARMACOKINETICS; PLASTIC COATINGS; POLYETHYLENE GLYCOLS;

BIODISTRIBUTION; LIGANDS; LIPOSOMES;

CONTROLLED DRUG DELIVERY;

LIPOSOME; POLYMER;

CONJUGATION; DRUG CLEARANCE; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG TARGETING; LIGAND BINDING; PHAGOCYTOSIS; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN BLOOD LEVEL; PROTEIN STABILITY; REVIEW; TISSUE DISTRIBUTION;

EID: 0032496678     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(97)00136-1     Document Type: Review

References (129)

1. Senior J.H. Fate and behavior of liposomes in vivo: A review of controlling factors. Crit. Rev. Ther. Drug Carrier Syst. 3:1987;123-193.
2. D.D. Lasic, Liposomes: From Physics to Applications, Elsevier, Amsterdam, 1993.
3. G. Storm, C. Oussoren, P.A.M. Peeters, Y. Barenholz, Tolerability of liposomes in vivo, in: G. Gregoriadis (Ed.), Liposome Technology, Vol. 3, CRC Press, Boca Raton, FL, 1993, pp. 345-383.
4. C.J. Porter, M.C. Davies, S.S. Davis, L. Illum, Microparticulate systems for site-specific therapy - bone marrow targeting, in: A.J. Domb (Ed.), Polymeric Site-specific Pharmacotherapy, Wiley, New York, 1994, pp. 157-204.
5. Daemen T., Regts J., Meesters M., TenKate M.T., Bakker-Woudenberg I.A.J.M., Scherphof G.L. Toxicity of doxorubicin entrapped within long-circulating liposomes. J. Control. Release. 44:1997;65-76.
6. K.J. Hwang, in: M. Ostro (Ed.), Liposomes from Biophysics to Therapeutics, Marcel Dekker, New York, 1987, pp. 109-156.
7. Forssen E.A., Male-Brune R., Adler-Moore J.P., Lee M.J., Schmidt P.G., Krasieva T.B., Shimizu S., Tromberg B.J. Fluorescence imaging studies for the disposition of daunorubicin liposomes (DaunoXome) within tumor tissue. Cancer Res. 56:1996;2066-2075.
8. Forssen E.A., Coulter D.M., Proffitt R.T. Selective in vivo localization of daunorubicin small unilamellar vesicles in solid tumors. Cancer Res. 52(12):1992;3255-3261.
9. Forssen E.A., Ross M.E. Daunoxome treatment of solid tumors: Preclinical and clinical investigations. J. Liposome Res. 4:1994;481-512.
10. Fielding R.M., Feistner B., Moon-McDermott L.et al. Reduced clearance and volume of distribution in rats. Pharm. Res. 13:1996;S-479.
11. J.G. Riess, Fluorinated vesicles from self-aggregated perfluoroalkylated amphipliles, J. Drug Targeting (1994).
12. + permeability, active doxorubicin encapsulation and stability, in human serum. Biochim. Biophys. Acta. 1194:1994;61-68.
13. Ravily V., Santaella C., Vierling P. Phase behavior of fluorocarbon di-O-alkyl-glycerophosphocholines and glycerophosphoethanolamines and long-term shelf stability of fluorinated liposomes. Biochim. Biophys. Acta. 1324:1997;1-17.
14. Allen T. The use of glycolipids and hydrophilic polymers in avoiding rapid uptake of liposomes by the mononuclear phagocyte system. Adv. Drug Deliv. Rev. 13:1994;285-309.
15. Gabizon A.A. Liposome circulation time and tumor targeting: Implications for cancer chemotherapy. Adv. Drug Deliv. Rev. 16:1995;285-294.
16. Chonn A., Cullis P.R. Recent advances in liposomal drug-delivery systems. Curr. Opin. Biotechnol. 6:1995;698-708.
17. Liu D. Biological factors involved in blood clearance of liposomes by liver. Adv. Drug Deliv. Rev. 24:1997;201-213.
18. Woodle M.C., Lasic D.D. Sterically stabilized liposomes. Biochim. Biophys. Acta. 1113:1992;171-199.
19. D.D. Lasic, F.J. Martin, Stealth Liposomes, CRC Press, Boca Raton, FL, 1995.
20. M.C. Woodle, G. Storm, Long Circulating Liposomes: Old Drugs, New Therapeutics, R.G. Landes, Austin, Texas, 1997.
21. Thorpe P.E., Burrows F.J. Antibody-directed targeting of the vasculature of solid tumors. Breast Cancer Res. Treat. 36:1995;237-251.
22. Jain R.K. Delivery of molecular medicine to solid tumors. Science. 271:1996;1079-1080.
23. 111In: Tumour accumlation less than that of labelled serum proteins. J. Cancer Res. Clin. Oncol. 122:1996;45-54.
24. Storm G., Nassander U.K., Vingerhoeds M.H., Steerenberg P.A., Crommelin D.J.A. Antibody-targeted liposomes to deliver doxorubicin to ovarian cancer cells. J. Liposome Res. 4:1994;641-666.
25. Papahadjopoulos D., Allen T.M., Gabizon A., Mayhew E., Matthay K., Huang S.K., Lee K-D., Woodle M.C., Lasic D.D., Redemann C., Martin F.J. Sterically stabilized liposomes: Improvements in pharmacokinetics and antitumor therapeutic efficacy. Proc. Natl. Acad. Sci. USA. 88:1991;11460-11464.
26. Lasic D.D. Sterically stabilized liposomes. Angew. Chem. Int. Ed. Engl. 33:1994;1685-1698.
27. Torchilin V.P., Omelyanenko V.G., Papisov M.I., Bogdanov A.A., Trubetskoy V.S., Herron J.N., Gentry C.A. Poly(ethylene glycol) on the liposome surface: On the mechanism of polymer-coated liposome longevity. Biochim. Biophys. Acta. 1195:1994;11-20.
28. Senior J., Delgado C., Fisher D., Tilcock C., Gregoriadis G. Biochim. Biophys. Acta. 1062:1991;77-82.
29. T.M. Allen, D. Papahadjopoulos, Sterically stabilized ('Stealth') liposomes: Pharmacokinetics and therapeutic advantages, in: G. Gregoriadis (Ed.), Liposome Technology, Vol. 3. CRC Press, Boca Raton, FL, 1993, pp. 59-72.
30. Torchillin V., Papisov M.I. Hypothesis: Why do polyethylene glycol-coated liposomes circulate so long? J. Liposome Res. 4:1994;725-739.
31. Torchillin V.P., Shtilman M.I., Trubetskoy V.S., Whiteman K., Milstein A.M. Amphiphilic vinyl polymers effectively prolong liposome circulation time in vivo. Biochim. Biophys. Acta. 1195:1994;181-184.
32. Maruyama K., Okuizumi S., Ishida O., Yamauchi H., Kikuchi H., Iwatsuru M. Phosphatidyl polyglycerols prolong liposome circulation in vivo. Int. J. Pharm. 111:1994;103-107.
33. Woodle M.C., Engbers C.M., Zalipsky S. New amphipathic polymer-lipid conjugates froming long-circulating reticuloendothelial system-evading liposomes. Bioconj. Chem. 5(6):1994;493-496.
34. Zalipsky S., Hansen C.B., Oaks J.M., Allen T.M. Evaluation of blood clearance rates and biodistribution of poly(2-oxazoline)-grafted liposomes. J. Pharm. Sci. 85:1996;1133-1137.
35. Zalipsky S. Functionalized poly(ethylene glycol)s for preparation of biologically relevant conjugates. Bioconj. Chem. 6:1995;150-165.
36. S. Zalipsky, Polyethylene glycol-lipid conjugates, in: D. Lasic, F. Martin (Eds.), Stealth Liposomes, CRC Press, Boca Raton, FL, 1995, pp. 93-102.
37. Zalipsky S. Synthesis of an end-group functionalized polyethylene glycol-lipid conjugate for preparation of polymer-grafted liposomes. Bioconj. Chem. 4:1993;296-299.
38. Zalipsky S., Brandeis E., Newman M.S., Woodle M.C. Long circulating, cationic liposomes containing amino-PEG-phosphatidylethanolamine. FEBS Lett. 353:1994;71-74.
39. Haselgrubler T., Amerstorfer A., Schindler H., Gruber H.J. Synthesis and applications of a new poly(ethylene glycol) derivative for the crosslinking of amines with thiols. Bioconj. Chem. 6:1995;242-248.
40. Shahinian S., Silvius J.R. Doubly-lipid-modified protein sequence motifs exhibit long-lived anchorage to lipid bilayer membranes. Biochim. Biophys. Acta. 1239:1995;157-167.
41. Lasic D.D., Woodle M.C., Martin F.J., Valentincic T. The structure of Stealth lipid-lecthin mixture. Period. Biol. 93:1991;287-290.
42. Parr M.J., Ansell S.M., Choi L.S., Cullis P.R. Factors influenceing the retention and chemical stability of poly(ethylene glycol)-lipid conjugates incorporated into large unilamellar vesicles. Biochim. Biophys. Acta. 1195:1994;21-30.
43. Hristova K., Kenworthy A.K., McIntosh T.J. Effect of bilayer composition on the phase behavior of liposomal suspensions containing poly(ethylene glycol)-lipids. Macromolecules. 28:1995;7693-7699.
44. Kenworthy A.K., Simon S.A., McIntosh T.J. Structure and phase behavior of lipid suspensions containing phospholipids with covalently attached poly(ethylene glycol). Biophys. J. 68:1995;1903-1920.
45. Holland J.W., Cullis P.R., Madden T.D. Poly(ethylene glycol)-lipid conjugates promote bilayer formation in mixtures of non-bilayer-forming lipids. Biochemistry. 35:1996;2610-2617.
46. Uster P.S., Allen T.M., Daniel B.E., Mendez C.J., Newman M.S., Zhu G.Z. Insertion of poly(ethylene glycol) derivatized phospholipid into pre-formed liposomes results in prolonged in vivo circulation time. FEBS Lett. 386:1996;243-246.
47. Kirpotin D., Hong K., Mullah N., Papahadjopoulos D., Zalipsky S. Liposomes with detachable polymer coating: Destabilization and fusion of dioleoylphophatidylethanolamine vesicles triggered by cleavage of surface-grafted poly(ethylene glycol). FEBS Lett. 388:1996;115-118.
48. Ho R.J.Y., Rouse B.T., Huang L. Target-sensitive immunoliposomes: Preparation and characterization. Biochemistry. 25:1986;5500-5506.
49. Wang C.Y., Huang L. Highly efficient DNA delivery mediated by pH-sensitive immunoliposomes. Biochemistry. 28:1989;9508-9514.
50. Babbitt B., Burtis L., Dentinger P., Constantinides P., Hillis L., McGirl B., Huang L. Contact-dependent, immunecomplex-mediated lysis of hapten-sensitized liposomes. Bioconj. Chem. 4:1993;199-205.
51. Tari A.M., Fuller N., Boni L.T., Collins D., Rand P., Huang L. Interactions of liposome bilayers composed of 1,2-diacyl-3-succinylglycerol with protons and divalent cations. Biochim. Biophys. Acta. 1192:1994;253-262.
52. Zhou F., Huang L. Liposome-mediated cytoplasmic delivery of proteins: An effective means of accessing the MHC class I-restricted antigen presentation pathway. Immunomethods. 4:1994;229-235.
53. D. Collins, pH-sensitive liposomes as tools for cytoplasmic delivery, in: J.R. Philippot, F. Schuber (Eds.), Liposomes as Tools in Basic Research and Industry, CRC Press, Boca Raton, FL, 1994, pp. 201-214.
54. Yoshioka H. Surface modification of haemoglobin-containing liposomes with polyethylene glycol prevents liposome aggregation in blood plasma. Biomaterials. 12:1991;861-864.
55. Needham D., Hristova K., McIntosh T.J., Dewhirst M., Wu N., Lasic D.D. Polymer-grafted liposomes: Physical basis for the 'Stealth' property. J. Liposome Res. 2(3):1992;411-430.
56. Woodle M.C. Surface modified liposomes: Assessment and characterization for increased stability and prolonged blood circulation. Chem. Phys. Lipids. 64:1993;249-262.
57. Blume G., Cevc G. Molecular mechansim of the lipid vesicle longevity in vivo. Biochim. Biophys. Acta. 1146:1993;157-168.
58. Khul T.L., Leckband D.E., Lasic D.D., Israelachvili J.N. Modulation of interaction forces between bilayers exposing short-chained ethylene oxide headgroups. Biophys. J. 66:1994;1479-1488.
59. Kenworthy A.K., Hristova K., Needham D., McIntosh T.J. Range and magnitude of the steric pressure between bilayers containing phospholipids with covalently attached poly(ethylene glycol). Biophys. J. 68:1995;1921-1936.
60. Jansen J., Song X., Brook D.E. Interfacial thickness of liposomes containing poly(ethylene glycol)-cholesterol from electrophoresis. Biophys. J. 70:1996;313-320.
61. Cohen J., Khorosheva V., Woodle M. Brush-like behavior of the polymeric coat of sterically stabilized liposomes. Biophys. J. 70:1996;A223.
62. Oku N., Tokudome Y., Namba Y., Saito N., Endo M., Hasegawa Y., Kawai M., Tsukada H., Okada S. Effect of serum protein binding on real-time trafficking of liposomes with different charges analyzed by positron emission tomography. Biochim. Biophys. Acta. 1280:1996;149-154.
63. S. Zalipsky, M.C. Woodle, D.D. Lasic, F.J. Martin, Lipid-polymer conjugates and liposomes, US Patent 5,631,018, Sequus Pharmaceuticals, Inc., USA, 1997.
64. M.C. Woodle, M.S. Newman, P.K. Working, Biological properties of sterically stabilized liposomes, in: D. Lasic, F. Martin (Eds.), Stealth Liposomes, CRC Press, Boca Raton, FL, 1995, pp. 103-118.
65. D. Papahadjopoulos, A.A. Gabizon, Sterically stabilized (Stealth) liposomes: Pharmacological properties and drug carrying potential in cancer, in: J.R. Philippot, F. Schuber (Eds.), Liposomes as Tools in Basic Research and Industry, CRC Press, Boca Raton, FL, 1994, pp. 177-188.
66. Harasym T.O., Tardi P., Longman S.A., Ansell S.M., Bally M.B., Cullis P.R., Lewis S.L.C. Poly(ethylene glycol)-modified phospholipids prevent aggregation during covalent conjugation of proteins to lipsomes. Bioconj. Chem. 6:1995;187-194.
67. Mori A., Klibanov A.L., Torchilin V.P., Huang L. Influence of the steric barrier of amphipathic poly(ethyleneglycol) and ganglioside GM1 on the circulation time of liposomes and on the target binding of immunoliposomes in vivo. FEBS Lett. 284:1991;263-266.
68. Park J.W., Hong K., Carter P., Asgar H., Guo L.Y., Keller G.A., Wirth C., Shalaby R., Knotts C., Wood W.I., Papahadjopoulos D., Benz C.C. Development of anti-p185HER2 immunoliposomes for cancer therapy. Proc. Natl. Acad. Sci. USA. 92:1995;1327-1331.
69. Amselem S., Cohen R., Barenholz Y. In vitro tests to predict in vivo performance of liposomal dosage forms. Chem. Phys. Lipids. 64:1993;219-237.
70. Moghimi S.M., Davis S.S. Innovations in avoiding particle clearance from blood by Kupffer cells: Cause for reflection. Crit. Rev. Ther. Drug Carrier Syst. 11:1994;31-59.
71. Huang S.K., Mayhew E.M., Gilani S., Lasic D.D., Martin F.J., Papahadjopoulos D. Pharmacokinetics and therapeutics of sterically stabilized liposomes in mice bearing C-26 colon carcinoma. Cancer Res. 52:1992;6774-6781.
72. Trubetskoy V.S., Torchilin V.P. New approaches in the chemical design of Gd-containing liposome for use in magnetic resonance imaging of lymph nodes. J. Liposome Res. 4:1994;961-980.
73. Moghimi S.M., Hawley A.E., Christy N.M., Gray T., Illum L., Davis S.S. Surface engineered nanoparticles with enhanced drainage into lymphatics and uptake by macrophage of the regional lymph nodes. FEBS Lett. 344:1994;25-30.
74. Allen T.M., Newman M.S., Woodle M.C., Mayhew E., Uster P.S. Pharmacokinetics and antitumor activity of vincristine encapsulated in sterically stabilized liposomes. Int. J. Cancer. 62:1995;199-204.
75. Gabizon A., Isacson R., Libson E., Kaufman B., Uziely B., Catane R., Ben-Dor C.G., Rabello E., Cass Y., Peretz T. Clinical studies of liposome-encapsulated doxorubicin. Acta Oncol. 33(7):1994;779-786.
76. Amantea M.A., Forrest A., Northfelt D.W. Population pharmacokinetics and pharmacodynamics of pegylated-liposomal doxorubicin in patients with AIDS-related Kaposi's sarcoma. Clin. Pharmacol. Ther. 61:1997;301-311.
77. Litzinger D.C., Huang L. Amphipathic poly(ethylene glycol) 5000-stabilized dioleoylphosphatidylethanolamine liposomes accumulate in spleen. Biochim. Biophys. Acta. 1127:1992;249-254.
78. Scherphof G.L., Morselt H., Allen T.M. Intrahepatic distribution of long-circulating liposomes containing poly(ethylene glycol) distearoyl phosphatidylethanolamine. J. Liposome Res. 4:1994;213-228.
79. Woodle M.C., Storm G., Newman M.S., Jekot J.J., Collins L.R., Martin F.J., Szoka F.C. Prolonged systemic delivery of peptide drugs by long-circulating liposomes: Illustration with vasopressin in the Brattleboro rat. Pharm. Res. 9:1992;260-265.
80. Goren D., Horowitz A.T., Zalipsky S., Woodle M.C., Yarden Y., Gabizon A. Targeting of Stealth liposomes to erbB2 (Her/2) Receptor: In vitro and in vivo studies. Br. J. Cancer. 74:1996;1749-1756.
81. A. Gabizon, F.M. Muggia, Initial clinical evaluation of pegylated-liposomal doxorubicin in solid tumors, in: M.C. Woodle, G. Storm (Eds.), Long Circulating Liposomes: Old Drugs, New Therapeutics, R.G. Landes, Austin, Texas, in press.
82. Oku N., Tokudome Y., Tsukada H., Kosugi T., Namba Y., Okada S. In vivo trafficking of long-circulating liposomes in tumour-bearing mice determined by positron emission tomography. Biopharm. Drug Dispos. 17:1996;435-441.
83. Unezaki S., Maruyama K., Hosoda J-I., Nagae I., Koyanagi Y., Nakata M., Ishida O., Iwatsuru M., Tsuchiya S. Direct measurement of the extravasation of polyethyleneglycol-coated liposomes into solid tumor by in vivo fluorescence microscopy. Int. J. Pharm. 144:1996;11-17.
84. Storm G., Crommelin D.J.A. Colloidal systems for tumor targeting. Hybridoma. 16:1997;119-125.
85. Vaage J., Donovan D., Uster P., Working P. Tumour uptake of doxorubicin in polyethylene glycol-coated liposomes and therapeutic effect against a xenografted human pancreatic carcinoma. Br. J. Cancer. 75:1997;482-486.
86. S.K. Huang, F.J. Martin, D.S. Friend, D. Papahadjopoulos, Mechanism of stealth liposomes accumulation in some pathological tissues, in: D. Lasic, F. Martin (Eds.), Stealth Liposomes, CRC Press, Boca Raton, FL, 1995, pp. 119-126.
87. M. Dewhirst, D. Needham, Extravasation of stealth liposomes into tumors: Direct measurement of accumulation and vascular permeability using a skin-flap window chamber, in: D. Lasic, F. Martin (Eds.), Stealth Liposomes, CRC Press, Boca Raton, FL, 1995, pp. 127-138.
88. Woodle M.C. Sterically stabilized liposome therapeutics. Adv. Drug Deliv. Rev. 16:1995;249-265.
89. Gaber M.H., Wu N.Z., Hong K., Huang S.K., Dewhirst M.W., Papahadjopoulos D. Thermosensitive liposomes: Extravasation and release of contents in tumor microvascular networks. Int. J. Radiat. Oncol. Biol. Phys. 36:1996;1177-1187.
90. N.L. Bowman, P.R. Cullis, L.D. Mayer, M.B. Bally, M.S. Webb, Liposomal vincristine: The central role of drug retention in defining therapeutically optimized anti-cancer formulations, in: M.C.Woodle, G. Storm (Eds.), Long Circulating Liposomes: Old Drugs, New Therapeutics, R.G. Landes, Austin, Texas, in press.
91. S. Zalipsky, P. Boulikas, N. Mullah, J.H. Harding, C.M. Engbers, M.C. Woodle, Increased systemic exposure of peptides by covalent fixation to extremities of PEG-grafted liposomes, in: Western Biotech Conference, San Diego, 1995, American Chemical Society.
92. Oku N., Tokudome Y., Koike C., Nishikawa N., Mori H., Saiki I., Okada S. Liposomal Arg-Gly-Asp analogs effectively inhibit metastatic B16 melanoma colonization in murine lungs. Life Sci. 58:1996;2263-2270.
93. Vingerhoeds M.H., Haisma H.J., van Muigen M., van de Rijt R.B.J., Crommelin D.J.A., Storm G. A new application for liposomes in cancer therapy: Immunoliposomes bearing enzymes (immuno-enzymosomes) for site-specific activation of prodrugs. FEBS Lett. 336:1993;485-490.
94. Blume G., Cevc G., Crommelin M.D.J.A., Bakker-Woudenberg I.A.J.M., Kluft C., Storm G. Specific targeting with poly(ethylene glycol)-modified liposomes: Coupling of homing devices to the ends of the polymeric chains combines effective target binding with long circulation times. Biochim. Biophys. Acta. 1149:1993;180-184.
95. Holland J.W., Hui C., Cullis P.R., Madden T.D. Poly(ethylene glycol)-lipid conjugates regulate the calcium-induced fusion of liposomes composed of phosphatidylethanolamine and phosphatidylserine. Biochemistry. 35:1996;2618-2624.
96. Maruyama K., Kennel S.J., Huang L. Lipid composition is important for highly efficient target binding and retention of immunoliposomes. Proc. Natl. Acad. Sci. USA. 87:1990;5744-5748.
97. Klibanov A.L., Maruyama K., Beckerleg A.M., Torchilin V.P., Huang L. Activity of amphipathic poly(ethylene glycol) 5000 to prolong the circulation time of liposomes depends on the liposome size and is unfavorable for immunliposome binding to target. Biochim. Biophys. Acta. 1062:1991;142-148.
98. A. Mori, L. Huang, Immunoliposome targeting in a mouse model: Optimization and therapeutic application, in: G. Gregoriadis (Ed.), Liposome Technology, Vol. 3, CRC Press, Boca Raton, FL, 1993, pp. 153-162.
99. Torchilin V.P., Klibanov A.L., Huang L., O'Donnell S., Nossiff N.D., Khaw B.A. Targeted accumulation of polyethylene glycol-coated immunoliposomes in infarcted rabbit myocardium. FASEB J. 6:1992;2716-2719.
100. Mori A., Kennel S.J., Huang L. Immunotargeting of liposomes containing lipophilic antitumor prodrugs. Pharm. Res. 10:1993;507-514.
101. Ahmad I., Longenecker M., Samuel J., Allen T.M. Antibody-targeted delivery of doxorubicin entrapped in sterically stabilized liposomes can eradicate lung cancer in mice. Cancer Res. 53:1993;1484-1488.
102. Zalipsky S., Newman M.S., Puntambekar B., Woodle M.C. Model ligands linked to polymer chains on liposomal surfaces: Application of a new functionalized polyethylene glycol lipid conjugate. Polym. Mater. Sci. Eng. 67:1993;519-520.
103. N. Emanuel, E. Bolotin, E. Kedar, Y. Barenholz, Tumor targeting of anti-cancer drug by sterically stabilized immunoliposomes, in: G. Gregoriadis, A. Florence (Eds.), Liposomes in Drug Delivery: The Nineties and Beyond, Centre for Drug Delivery Research, University of London, London, 1993, 72 pp.
104. Allen T.M., Agrawal A.K., Ahmad I., Hansen C.B., Zalipsky S. Antibody-mediated targeting of long-circulating (Stealth™) liposomes. J. Liposome Res. 4:1994;1-25.
105. Trubetskoy V.S., Narula J., Khaw B.A., Torchilin V.P. Chemically optimized antimyosin Fab conjuates with chelating polymers: Importance of the nature of the protein-polymer single site covalent bond for biodistribution and infarction localization. Bioconj. Chem. 4:1993;251-255.
106. Zara J., Pomato N., McCabe R.P., Bredehorst R., Vogel C-W. Cobra venom factor immunoconjugates: Effects of carbohydrate-directed versus amino group-directed conjugation. Bioconj. Chem. 6:1995;367-372.
107. Huwyler J., Wu D., Pardridge W.M. Brain drug delivery of small molecules using immunoliposomes. Proc. Natl. Acad. Sci. USA. 93:1996;14164-14169.
108. Kirpotin D., Park J.W., Hong K., Zalipsky S., Li W-L., Carter P., Benz C.C., Mullah N., Papahadjopoulos D. Sterically stabilized anti-HER2 immunoliposomes: Design and targeting to human breast cancer cells in vitro. Biochemistry. 36:1997;66-75.
109. Lee R.J., Low P.S. Delivery of liposomes into cultured KB cells via folate receptor-mediated endocytosis. J. Biol. Chem. 269(5):1994;3198-3204.
110. S. Zalipsky, P. Boulikas, B. Puntambekar, C.M. Engbers, M.C. Woodle, Polyethylene glycol-grafted liposome as a long-circulating platform presenting covalently bound laminine pentapeptide, YIGSR, in: Seventh International Symposium on Recent Advances in Drug Delivery Systems, Salt Lake City, Utah, 1995.
111. 3, a synthetic glycopeptide for the asialogylcoprotein receptor. Bioconj. Chem. 5:1994;612-620.
112. DeFrees S.A., Phillips L., Guo L., Zalipsky S. Sialyl lewis x liposomes as a multivalent ligand and inhibitor of e-selectin mediated cellular adhesion. J. Am. Chem. Soc. 118:1996;6101-6104.
113. Deol P., Khuller G.K. Lung specific stealth liposomes: Stability, biodistribution and toxicity of liposomal antitubercular drugs in mice. Biochim. Biophys. Acta. 1334:1997;161-172.
114. J-S. Remy, C. Sirlin, J-P. Behr, Gene transfer with cationic amphiphiles, in: J.R. Philippot, F. Schuber (Eds.), Liposomes as Tools in Basic Research and Industry, CRC Press, Boca Raton, FL, 1994, pp. 159-170.
115. Bally M.B., Zhang Y-P., Wong F.M.P., Kong S., Wasan E., Reimer E.L. Lipid/DNA complexes as an intermediate in the preparation of particles for gene transfer: An alternative to cationic liposome/DNA aggregates. Adv. Drug Deliv. Rev. 24:1997;275-290.
116. Liu F., Yang J., Huang L., Liu D. Effect of non-ionic surfactants on the formation of DNA/emulsion complexes and emulsion-mediated gene transfer. Pharm. Res. 13:1996;1642-1646.
117. Liu F., Yang J., Huang L., Liu D. New cationic lipid formulations for gene transfer. Pharm. Res. 13:1996;1856-1860.
118. Hara T., Liu F., Liu D., Huang L. Emulsion formulations as a vector for gene delivery in vitro and in vivo. Adv. Drug Deliv. Rev. 24:1997;265-271.
119. J. Wilschut, D. Hoekstra, Membrane Fusion, Marcel Dekker, New York, 1991.
120. M.C.P. de Lima, D. Hoekstra, Liposomes, viruses, and membrane fusion, in: J.R. Philippot, F. Schuber (Eds.), Liposomes as Tools in Basic Research and Industry, CRC Press, Boca Raton, FL, 1994, pp. 137-156.
121. N. Duzgunes, S. Nir, Liposomes as tools for elucidating the mechanism of membrane fusion, in: J.R. Philippot, F. Schuber (Eds.), Liposomes as Tools in Basic Research and Industry, CRC Press, Boca Raton, FL, 1994, pp. 103-136.
122. R.E. Sobol, K.J. Scanlon, The Internet Book of Gene Therapy, Appleton & Lange, Stamford, Connecticut, 1995.
123. Vlassov V.V., Balakireva L.A., Yakubov L.A. Transport of oligonucleotides across natural and model membranes. Biochim. Biophys. Acta. 1197:1994;95-108.
124. Nestle F.O., Mitra R.S., Bennett C.F., Chan H., Nickoloff B.J. Cationic lipid is not required for uptake and selective inhibitory activity of ICAM-1 phosphorothioate antisense oligonucleotides in keratinocytes. J. Invest. Dermatol. 103:1994;569-575.
125. L. Leserman, Liposomes as transporters of oligonucleotides, in: J.R. Philippot, F. Schuber (Eds.), Liposomes as Tools in Basic Research and Industry, CRC Press, Boca Raton, FL, 1994, pp. 215-223.
126. Gold L. Oligonucleotides as research, diagnostic, and therapeutic agents. J. Biol. Chem. 270:1995;13581-13584.
127. Slepushkin V.A., Simoes S., Dazin P., Newman M.S., Guo L.S., deLima M.C.P., Duzgunes N. Sterically stabilized pH-sensitive liposomes - intracellular delivery of aqueous contents and prolonged circulation in vivo. J. Biol. Chem. 272:1997;2382-2388.
128. N.C. Phillips, Influence of amphiphilic poly(ethylene glycol) (PEG) on cationic liposome-DNA interactions, in: T.W.J. Dubensky, R.W. Malone, R.K. Scheule, J.A. Wolff (Eds.), Delivery and Design of Genetic Medicines: Developing Self-Assembling Systems, Annapolis, June 23-24, 1997, IBC.
129. J. Vaage, E. Barbera, Tissue uptake and therapeutic effects of Stealth doxorubicin, in: D. Lasic, F. Martin (Eds.), Stealth Liposomes, CRC Press, Boca Raton, FL, 1995, pp. 149-171.