Antibody derivatization and conjugation strategies: Application in preparation of stealth immunoliposome to target chemotherapeutics to tumor

Journal of Controlled Release

Volumn 150, Issue 1, 2011, Pages 2-22

  Manjappa, Arehalli S ^a   Chaudhari, Kiran R ^a   Venkataraju, Makam P ^a   Dantuluri, Prudhviraju ^a   Nanda, Biswarup ^a   Sidda, Chennakesavulu ^a   Sawant, Krutika K ^a   Ramachandra Murthy, Rayasa S ^b  

^a M S UNIVERSITY OF BARODA   (India)

^b ISF COLLEGE OF PHARMACY   (India)

Author keywords

Affisomes; Conjugation strategies; Fab fragments; Monoclonal antibody; scFv; Thiolation techniques

Indexed keywords

AFFISOMES; ANTIBODY CONJUGATE; BILAYER SURFACE; CONJUGATED LIPOSOMES; CONJUGATION STRATEGIES; DERIVATIZATION TECHNIQUES; DERIVATIZATIONS; DIAGNOSTIC APPLICATIONS; IMMUNOLIPOSOMES; NUMBER OF METHODS; SCFV; SINGLE CHAIN VARIABLE FRAGMENTS; STEALTH LIPOSOMES; TARGETED DRUG DELIVERY; THIOLATION;

ALLERGIES; DRUG DELIVERY; MERGERS AND ACQUISITIONS; MONOCLONAL ANTIBODIES; PHOSPHOLIPIDS; PROTEINS; SURFACE PLASMON RESONANCE;

LIPOSOMES;

2 IMINOTHIOLANE; 3 (2 PYRIDYLDITHIO)PROPIONIC ACID N HYDROXYSUCCINIMIDE ESTER; AMINE; AMINO ACID; ANTIBODY CONJUGATE; CARBOHYDRATE; CARBOXYL GROUP; DISULFIDE; IMMUNOLIPOSOME; LIPOSOME; OXALIPLATIN; PEGINTERFERON; PHOSPHOLIPID; PROPIONIC ACID; S ACETYLMERCAPTOSUCCINIC ANHYDRIDE; SINGLE CHAIN FRAGMENT VARIABLE ANTIBODY; SUCCINIC ANHYDRIDE; SUCCINIMIDYL ACETYLTHIOPROPIONATE; SUCCINIMIDYLOXYCARBONY ALPHA METHYL ALPHA(2 PYRIDYLDITHIO)TOLUENE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

CANCER CHEMOTHERAPY; CHEMICAL STRUCTURE; DERIVATIZATION; PRIORITY JOURNAL; PROTEIN MODIFICATION; REVIEW;

ANIMALS; ANTIBODIES; ANTINEOPLASTIC AGENTS; HUMANS; IMMUNOCONJUGATES; LIPOSOMES; NEOPLASMS;

EID: 79951944060     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2010.11.002     Document Type: Review

References (153)

1. N. Oku, Anticancer therapy using glucuronate modified long-circulating liposomes, Adv. Drug Delivery Rev. 40 (1999) 63-73.
2. T.M. Allen, C.B. Hansen, Pharmacokinetics of stealth versus conventional liposomes: effect of dose, Biochim. Biophys. Acta 1068 (1991) 133-141.
3. J.H. Senior, Fate and behaviour of liposomes in vivo: a review of controlling factors, Crit. Rev. Ther. Drug Carrier Syst. 3 (1987) 123-193. (Pubitemid 17219201)
4. H.M. Patel, Serum opsonins and liposomes: their interaction and opsonophagocytosis, Crit. Rev. Ther. Drug Carrier Syst. 9 (1992) 39-90.
5. M. Woodle, D. Lasic, Sterically stabilized liposomes, Biochim. Biophys. Acta 1113 (1992) 171-199.
6. F.J. Martin, Clinical Pharmacology and Antitumor Efficacy of DOXIL (PEGylated Liposomal Doxorubicin). Medical Applications of Liposomes, Elsevier, Amsterdam, 1998, pp. 635-688.
7. K. Maruyama, O. Ishida, T. Takizawa, K. Moribe, Possibility of active targeting to tumor tissues with liposomes, Adv. Drug Delivery Rev. 40 (1999) 89-102.
8. E. Mastrobattista, G.A. Koning, G. Storm, Immunoliposomes for the targeted delivery of antitumor drugs, Adv. Drug Delivery Rev. 40 (1999) 103-127.
9. G. Kohler, C. Milstein, Continuous cultures of fused cells secreting antibody of predefined specificity, Nature 256 (1975) 495-497.
10. P.A.M. Peeters, G. Storm, D.J.A. Crommelin, Immunoliposomes in vivo: state of the art, Adv. Drug Deliv. Rev. 1 (1987) 249-266.
11. P. Carter, L. Smith, M. Ryan, Identification and validation of cell surface antigens for antibody targeting in oncology, Endocr.-Relat. Cancer 11 (2004) 11659-11687.
12. P.A. McCarron, S.A. Olwill, W.M.Y. Marouf, R.J. Buick, B. Walker, C.J. Scott, Antibody conjugates and therapeutic strategies, Mol. Interv. 5 (6) (2005) 368-380.
13. J.W. Goding, Monoclonal Antibodies: Principles and Practice, Academic Press, Orlando, 1986, pp. 6-58.
14. E. Harlow, D. Lane, Antibodies: A Laboratory Manual, Cold Spring, New York, 1988, pp. 23-135.
15. E.A. Padlan, Anatomy of the antibody molecule, Mol. Immunol. 31 (3) (1994) 169-217.
16. A. Coulter, R. Harris, Simplified preparation of rabbit Fab′ fragments, J. Immunol. Meth. 59 (1983) 199-203.
17. 2 fragments from monoclonal IgG of different rat JgC subclasses, J. Immunol. Meth. 64 (1983) 141-146.
18. G.T. Hermanson, Bioconjugate Techniques, second ed, Academic press, USA, 2008, pp. 783-823.
19. J.L. Palmer, A. Nissonoff, Reduction and reoxidation of a critical disulfide bond in the rabbit antibody molecule, J. Biol. Chem. 238 (1963) 2393-2398.
20. M.M.C. Sun, K.S. Beam, C.G. Cerveny, K.J. Hamblett, R.S. Blackmore, M.Y. Torgov, F.G.M. Handley, P.D. Senter, S.C. Alley, Reduction-alkylation strategies for the modification of specific monoclonal antibody disulfides, Bioconjugate Chem. 16 (2005) 1282-1290. (Pubitemid 41368132)
21. A. Béduneau, P. Saulnier, F. Hindré, A. Clavreul, J.C. Leroux, J.P. Benoit, Design of targeted lipid nanocapsules by conjugation of whole antibodies and antibody Fab′ fragments, Biomater. 28 (33) (2007) 4978-4990. (Pubitemid 47371148)
22. P. Simard, J.-C. Leroux, pH-sensitive immunoliposomes specific to the CD33 cell surface antigen of leukemic cells, Int. J. Pharm. 381 (2) (2009) 86-96.
23. G.T. Hermanson, Bioconjugate Techniques, Second ed, Academic press, USA, 2008, p. 67.
24. R.N. Perham, J.O. Thomas, Reaction of tobacco mosaic virus with a thiol-containing imidoester and a possible application to X-ray diffraction analysis, J. Mol. Biol. 62 (1971) 415-418.
25. R.R. Traut, A. Bollen, R.R. Sun, J.W.B. Hershey, J. Sundberg, L.R. Pierce, Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30s ribosome, Biochem. 12 (1973) 3266-3273.
26. R. Jue, J.M. Lambert, L.R. Pierce, R.R. Traut, Addition of sulfhydryl groups to Escherichia coli ribosomes by protein modification with 2-iminothiolane (methyl 4-mercap-tobutyrimidate), Biochem. 17 (1978) 5399-5405.
27. A.C. Alagon, T.P. King, Activation of polysaccharides with 2-iminothiolane and its uses, Biochem. 19 (1980) 4341-4345.
28. T.T. Sun, A. Bollen, L. Kahan, R.R. Traut, Topography of ribosomal proteins of the Escherichia coli 30S subunit as studied with the reversible cross-linking reagent methyl 4-mercaptobutyrimidate, Biochem. 13 (1974) 2334-2340.
29. Z. Hillel, C.W. Wu, Subunit topography of RNA polymerase from Escherichia coli. A crosslinking study with bifunctional reagents, Biochem. 16 (1977) 3334-3342.
30. M.E. Birnbaumer, W.T. Schrader, B.W.O. Malley, Chemical cross-linking of chick oviduct progesterone-receptor subunits using a reversible bifunctional cross-linking agent, Biochem. J. 181 (1979) 201-213. (Pubitemid 9236529)
31. S.S. Ghosh, P.M. Kao, A.W. McCue, H.L. Chappelle, Use of maleimide-thiol coupling chemistry for efficient syntheses of oligonucleotide-enzyme conjugate hybridization robes, Bioconjugate Chem. 1 (1990) 71-76.
32. A.L. Tarentino, A.W. Phelan, T.H. Plummer, 2-Iminothiolane: a reagent for the introduction of sulfhydryl groups into oligosaccharides derived from asparagine-linked glycans, Glycobiology 3 (1993) 279-285. (Pubitemid 23232162)
33. R. Singh, L. Kats, W.A. Blättler, J.M. Lambert, Formation of N-substituted 2-iminothiolanes when amino groups in proteins and peptides are modified by 2-iminothiolane, Anal. Biochem. 236 (1) (1996) 114-125.
34. J. Carlsson, H. Drevin, R. Axen, Protein thiolation and reversible protein-protein conjugation. N-Succinimidyl 3(2-pyridyldithio) propionate, a new heterobifunctional reagent, Biochem. J. 173 (1978) 723-737.
35. V.P. Chekhonin, O.I. Gurina, A.V. Lokhonina, A.E. Ryabinina, M.A. Maksimova, A.V. Semenova, PEG-treated immunoliposomes specific for the Schwann cells of neural tissue, Biochem. Biophys. Molecul. Biol. 417 (2007) 560-562.
36. K. Hashimoto, J.E. Loader, S.C. Kinsky, Iodoacetylated and biotinylated liposomes: effect of spacer length on sulfhydryl ligand binding and avidin precipitability, Biochim. Biophys. Acta 856 (1986) 556-565.
37. M. Mercadal, J.C. Domingo, J. Petriz, J. Garcia, M.A. de Madariaga, Preparation of immunoliposomes bearing poly(ethylene glycol)-coupled monoclonal antibody linked via a cleavable disulfide bond for ex vivo applications, Biochim. Biophys. Acta 1509 (1-2) (2000) 299-310.
38. P.E. Thorpe, P.M. Wallace, P.P. Knowles, M.G. Relf, A.N. Brown, G.J. Watson, R.E. Knyba, E.J. Wawrzynczak, D.C. Blakey, New coupling agents for the synthesis of immunotoxins containing a hindered disulfide bond with improved stability in vivo, Cancer Res. 47 (1987) 5924-5931. (Pubitemid 18018731)
39. G.A. Koning, J.A.A.M. Kamps, G.L. Scherphof, Efficient intracellular delivery of 5-fluorodeoxyuridine into colon cancer cells by targeted immunoliposomes, Cancer Detect. Prev. 26 (2002) 299-307.
40. R.J.S. Duncan, P.D. Weston, R. Wrigglesworth, A new reagent which may be used to introduce sulfhydryl groups into proteins, and its use in the preparation of conjugates for immunoassay, Anal. Biochem. 132 (1983) 68-73.
41. F.J. Martin, T.D. Heath, New RRC, Liposomes A Practical Approach, 1990, pp. 163-182, UK.
42. V. Ghetie, M.A. Till, M.A. Ghetie, T. Tucker, J. Porter, E.J. Patzer, E.J. Patzer, J.A. Richardson, J.W. Uhr, E.S. Vitetta, Preparation and characterization of conjugates of recombinant CD4 and deglycosylated ricin A chain using different cross-linkers, Bioconjugate Chem. 1 (1990) 24-31.
43. M. Amessou, A. Fradagrada, T. Falguières, J.M. Lord, D.C. Smith, L.M. Roberts, C. Lamaze, L. Johannes, Syntaxin 16 and syntaxin 5 are required for efficient retrograde transport of several exogenous and endogenous cargo proteins, J. Cell Sci. 120 (2007) 1457-1468. (Pubitemid 46780038)
44. D.V. Sakharov, A.F.H. Jie, M.E.A. Bekkers, J.J. Emeis, D.C. Rijken, Polylysine as a vehicle for extracellular matrix-targeted local drug delivery, providing high accumulation and long-term retention within the vascular wall, Arterioscler. Thromb. Vasc. Biol. 21 (2001) 943-948.
45. I.M. Klotz, R.E. Heiney, Introduction of sulfhydryl groups into proteins using acetylmercaptosuccinic anhydride, Arch. Biochem. Biophys. 96 (1962) 605.
46. E. Rector, S.R.J. Schwenck, T.S. Tse, A.H. Sehon, A method for the preparation of protein-protein conjugates of predetermined composition, J. Immunol. Meth. 24 (1978) 321-336.
47. N. Fuji, K. Akaji, Y. Hayashi, H. Yajima, Studies on peptides. CXXV. 3-(3- p -methoxybenzylthiopropionyl)-thiazolidine-2-thione and its analogs as reagents for the introduction of the mercapto group into peptides and proteins, Chem. Pharm. Bull. 33 (1985) 362-367.
48. F.J. Martin, T.D. Heath, New RRC, Liposomes A Practical Approach, 1990, pp. 173-174, UK.
49. T.D. Heath, B.A. Macher, D. Paphadjopoulos, Covalent attachment of immunoglobulins to liposomes via glycosphingolipids, Biochim. Biophys. Acta 640 (1981) 66-81.
50. S. Dreborg, E.B. Akerblom, Immunotherapy with monomethoxypoly(ethylene glycol) modified allergens, Crit. Rev. Ther. Drug Carrier Syst. 6 (1990) 315-365. (Pubitemid 20216395)
51. S.N.J. Pang, Final report on the safety of poly(ethylene glycols) (PEGs) 6, 8, 32, 75, 150, 14 M, J. Am. Coll. Toxicol. 12 (1993) 429-456.
52. D. Needham, T.J. McIntosh, D.D. Lasic, Repulsive interactions andmechanical stability of polymer-grafted lipid membranes, Biochim. Biophys. Acta 1108 (1992) 40-48.
53. J.W. Park, K. Hong, D.B. Kirpotin, O. Meyer, D. Papahadjopoulos, C.C. Benz, Anti-HER2 immunoliposomes for targeted therapy of human tumors, Caner Lett. 118 (2) (1997) 153-160. (Pubitemid 27450276)
54. T. Skjørringe, T. Gjetting, T.G. Jensen, A modified protocol for efficient DNA encapsulation into pegylated 2 immunoliposomes (PILs), J. Control. Release 139 (2009) 140-145.
55. C.B. Pattillo, B. Venegas, F.J. Donelson, L.D. Valle, L.C. Knight, P.L.-G. Chong, M.F. Kiani, Radiation-guided targeting of combretastatin encapsulated immunoliposomes to mammary tumors, Pharm. Res. 26 (5) (2009) 1093-1100.
56. T. Yang, M.K. Choi, F.D. Cui, J.S. Kim, S.J. Chung, C.K. Shim, D.D. Kim, Preparation and evaluation of paclitaxel-loaded PEGylated immunoliposomes, J. Control. Release 120 (2007) 169-177. (Pubitemid 47061489)
57. K. Laginha, D. Mumbengegwi, T. Allen, Liposomes targeted via two different antibodies: assay, B-cell binding and cytotoxicity, Biochim. Biophys. Acta 1711 (2005) 25-32. (Pubitemid 40726397)
58. U.B. Nielsen, D.B. Kirpotin, E.M. Pickering, K. Hong, J.W. Park, M.R. Shalaby, Y. Shao, C.C. Benz, J.D. Marks, Therapeutic efficacy of anti-ErbB2 immunoliposomes targeted by a phage antibody selected for cellular endocytosis, Biochim. Biophys. Acta 1591 (1-3) (2002) 109-118.
59. J.W. Park, D.B. Kirpotin, K. Hong, R. Shalaby, Y. Shao, U.B. Nielsen, J.D. Marks, D. Papahadjopoulos, C.C. Benz, Tumor targeting using anti-her2 immunoliposomes, J. Control. Release 74 (2001) 95-113. (Pubitemid 32727613)
60. J.W. Park, K. Hong, P. Carter, H. Asgari, L.Y. Guo, G.A. Keller, C. Wirth, R. Shalaby, C. Kotts, W.I. Wood, Development of anti-p185HER2 immunoliposomes for cancer therapy, Proc. Natl Acad. Sci. USA 92 (1995) 1327-1331.
61. D. Kirpotin, J.W. Park, K. Hong, S. Zalipsky, W.L. Li, P. Carter, C.C. Benz, D. Papahadjopoulos, Sterically stabilized anti-HER2 immunoliposomes: design and targeting to human breast cancer cell in vitro, Biochem. 36 (1) (1997) 66-75. (Pubitemid 27024679)
62. R. Schier, J.D. Marks, E.J. Wolf, G. Apell, C. Wong, J.E. McCartney, M.A. Bookman, J.S. Huston, L.L. Houston, L.M. Weiner, In vitro and in vivo characterization of a human anti-c-erbB-2 single-chain Fv isolated from a filamentous phage antibody library, Immunotech. 1 (1) (1995) 73-81.
63. C. Brignole, D. Marimpietri, C. Gambini, T.M. Allen, M. Ponzoni, F. Pastorino, Development of Fab′ fragments of anti-GD2 immunoliposomes entrapping doxorubicin for experimental therapy of human neuroblastoma, Cancer Lett. 197 (1-2) (2003) 199-204. (Pubitemid 36860011)
64. E.H. Moase, W. Qi, T. Ishida, Z. Gabos, B.M. Longenecker, G.L. Zimmermann, L. Ding, M. Krantz, T.M. Allen, Anti-MUC-1 immunoliposomal doxorubicin in the treatment of murine models of metastatic breast cancer, Biochim. Biophys. Acta 1510 (1-2) (2001) 43-55.
65. T.M. Allen, E. Brandeis, C.B. Hansen, G.Y. Kao, S. Zalipsky, A new strategy for attachment of antibodies to sterically stabilized liposomes resulting in efficient targeting to cancer cells, Biochim. Biophys. Acta 1237 (1995) 99-108.
66. S.M. Ansell, P.G. Tardi, S.S. Buchkowsky, 3-(2-pyridyldithio)propionic acid hydrazide as a cross-linker in the formation of liposome-antibody conjugates, Bioconj. Chem. 7 (4) (1996) 490-496.
67. S.M. Moghimi, The effect of methoxy-PEG chain length and molecular architecture on lymph node targeting of immuno-PEG liposomes, Biomater. 27 (1) (2006) 136-144. (Pubitemid 41225377)
68. M. Mercadal, J.C. Domingo, J. Petriz, J. Garcia, M.A. de Madariaga, A novel strategy affords high-yield coupling of antibody to extremities of liposomal surface grafted PEG chains, Biochim. Biophys. Acta 1418 (1999) 232-238.
69. I.-Y. Kim, Y.S. Kang, D.S. Lee, H.J. Park, E.K. Choi, Y.K. Oh, H.-J. Son, J.-S. Kim, Antitumor activity of EGFR targeted pH-sensitive immunoliposomes encapsulating gemcitabine in A549 xenograft nude mice, J. Control. Rel. 140 (1) (2009) 55-60.
70. T.M. Allen, C.B. Hansen, S. Zalipsky, Stealth Liposome, CRC press, US, 1995, pp. 233-242.
71. V.P. Chekhonin, Y.A. Zhirkov, O.I. Gurina, I.A. Ryabukhin, S.V. Lebedev, I.A. Kashparov, T.B. Dmtriyeva, PEGylated immunoliposomes directed against brain astrocytes, Drug Deliv. 12 (2004) 1-6. (Pubitemid 40066254)
72. D.G. Giard, S.A. Aaronson, G.J. Todaro, P. Arnstein, J.H. Kersey, H. Dosik, W.P. Parks, In vitro cultivation of human tumors: establishment of cell lines derived from a series of solid tumors, J. Natl Cancer Inst. 51 (5) (1973) 1417-1423.
73. HudsonM.J.H. , JonesM.N. , The preparation and characterisation of immunoliposomes with surface-bound placental alkaline phosphate antibody, Colloids Surf., B. 1 (1993) 157-166.
74. T. Völke, P. Hölig, T. Merdan, R. Müller, R.E. Kontermann, Targeting of immunoliposomes to endothelial cells using a single-chain Fv fragment directed against human endoglin (CD105), Biochim. Biophys. Acta 1663 (1-2) (2004) 158-166. (Pubitemid 38625590)
75. L. Zhang, H. Gao, L. Chen, B. Wu, Y. Zheng, R. Liao, Y. Jiang, F. He, Tumor targeting of vincristine by mBAFF-modified PEG liposomes in B lymphoma cells, Cancer Lett. 269 (1) (2008) 26-36.
76. M. Singh, A.J. Ferdous, N. Kanikkannan, G. Faulkner, Stealth monensin immunoliposomes as potentiator of immunotoxins in vitro, Eur. J. Pharm. Biopharm. 52 (1) (2001) 13-20. (Pubitemid 32594785)
77. C.J.F. Böttcher, C.M. van Gent, C. Pries, A rapid and sensitive sub-micro phosphorus determination, Anal. Chim. Acta 24 (1961) 203-204.
78. G.A. Koning, H.W. Morselt, M.J. Velinova, J. Donga, A. Gorter, T.M. Allen, S. Zalipsky, J.A.A.M. Kamps, G.L. Scherphof, Selective transfer of a lipophilic prodrug of 5-fluorodeoxyuridine (FUdR) from immunoliposomes to colon cancer cells, Biochim. Biophys. Acta 1420 (1999) 153-167.
79. J.A. Harding, C.M. Engbers, M.S. Newman, N.I. Goldstein, S. Zalipsky, Immunogenicity and pharmacokinetic attributes of poly (ethylene glycol)-grafted immunoliposomes, Biochim. Biophys. Acta 1327 (2) (1997) 181-192.
80. S. Kessner, A. Krause, U. Rothe, G. Bendas, Investigation of the cellular uptake of E-Selectin-targeted immunoliposomes by activated human endothelial cells, Biochim. Biophys. Acta 1514 (2001) 177-190.
81. G. Bendas, A. Krause, U. Bakowsky, J. Vogel, U. Rothe, Targetability of novel immunoliposomes prepared by a new antibody conjugation technique, Int. J. Pharm. 181 (1999) 79-93.
82. K.-Y. Ng, L. Zhao, Y. Liu, M. Mahapatro, The effects of polyethyleneglycol (PEG)-derived lipid on the activity of target-sensitive immunoliposomes, Int. J. Pharm. 193 (2) (2000) 157-166.
83. P. Pinnaduwage, L. Huang, Stable target-sensitive immunoliposomes, Biochem. 31 (1992) 2850-2855.
84. X. Pan, R.J. Lee, Construction of anti-EGFR immunoliposomes via folate-folate binding protein affinity, Int. J. Pharm. 336 (2007) 276-283.
85. T.A. Elbayoumi, V.P. Torchilin, Enhanced cytotoxicity of monoclonal anticancer antibody 2C5-modified doxorubicin-loaded PEGylated liposomes against various tumor cell lines, Eur. J. Pharm. Sci. 32 (3) (2007) 159-168. (Pubitemid 47532709)
86. A.N. Lukyanov, T.A. Elbayoumi, A.R. Chakilam, V.P. Torchilin, Tumor-targeted liposomes: doxorubicin-loaded long-circulating liposomes modified with anti-cancer antibody, J. Control. Rel. 100 (1) (2004) 135-144.
87. V.P. Torchilin, T.S. Levchenko, A.N. Lukyanov, B.A. Khaw, A.L. Klibanov, R. Rammohan, G.P. Samokhin, K.R. Whiteman, p-Nitrophenylcarbonyl-PEG-PE- liposomes: fast and simple attachment of specific ligands, including monoclonal antibodies, to distal ends of PEG chains via p-nitrophenylcarbonyl groups, Biochim. Biophys. Acta 1511 (2) (2001) 397-411. (Pubitemid 32250227)
88. T. Steenpaß, A. Lung, R. Schubert, Tresylated PEG-sterols for coupling of proteins to preformed plain or PEGylated liposomes, Biochim. Biophys. Acta 1758 (1) (2006) 20-28.
89. P. Sapra, T.M. Allen, Ligand-targeted liposomal anticancer drugs, Prog. Lipid Res. 42 (2003) 439-462.
90. S. Matzku, H. Krempel, H.P. Weckenmann, V. Schirrmacher, H. Sinn, H. Stricker, Tumour targeting with antibody-coupled liposomes: failure to achieve accumulation in xenografts and spontaneous liver metastases, Cancer Immunol. Immunother. 31 (5) (1990) 285-291.
91. R) liposomes, J. Liposome Res. 4 (1) (1994) 1-25.
92. G.T. Hermanson, Bioconjugate Techniques, Second ed, Academic press, USA, 2008, pp. 613-614.
93. E.A. Bayer, H. Ben-Hur, M. Wilchek, Enzyme-based detection of glycoproteins on blot transfers using avidin-biotin technology, Anal. Biochem. 161 (1987) 123-131.
94. D. Rideout, Self-assembling cytotoxins, Science 233 (1986) 561-563. (Pubitemid 16019912)
95. D. Rideout, Self-assembling drugs: a new approach to biochemical modulation in cancer chemotherapy, Cancer Invest. 12 (1994) 189-202. (Pubitemid 24120468)
96. D. Rideout, T. Calogeropoulou, J. Jaworski, M. McCarthy, Synergism through direct covalent bonding between agents: a strategy for rational design of chemotherapeutic combinations, Biopolymers 29 (1990) 247-262. (Pubitemid 20055820)
97. J.M. Rothenberg, M. Wilchek, p-Diazobenzoyl-biocytin: a new biotinylating reagent for DNA, Nucleic Acids Res. 16 (1988) 7197-7198.
98. A. Chouai, E.E. Simanek, Kilogram-scale synthesis of a second-generation dendrimer based on 1, 3, 5-triazine using green and industrially compatible methods with a single chromatographic step, J. Org. Chem. 73 (2008) 2357-2366.
99. K. Rydzynski, R. Jedrychowski, Sensory irritating properties of cyanuric chloride as revealed with plethysmographic method, Int. J. Occup. Med. Environ. Health 7 (1994) 149-154. (Pubitemid 24293404)
100. K. Wyszynska, B. Przybojewska, E. Spiechowicz, W.C. Liro, E. Dziubaltowska, E. Rydzynski, Cyanuric chloride has no genotoxic andmutagenic properties in bacteria and bone marrow cells, Int. J. Occup. Med. Environ. Health 7 (1994) 281-289. (Pubitemid 24374401)
101. S.C. Kinsky, K.Hashimoto, J.E. Loader, A.L. Benson, Synthesis of N-hydroxysuccinimide esters of phosphatidylethanolamine and some properties of liposomes containing these derivatives, Biochim. Biophys. Acta 769 (3) (1984) 543-550.
102. V.T. Kung, C.T. Redeman, Synthesis of carboxyacyl derivatives of phosphatidylethanolamine and use as an efficient method for conjugation of protein to liposomes, Biochim. Biophys. Acta 862 (2) (1986) 435-439.
103. V.K. Jonsons, P.L. Mallet, Targeted liposomes: a method for preparation and analysis, Anal. Biochem. 111 (1) (1980) 54-59.
104. V.K. Jonsons, Liposome Technology, CRC Press, Florida, 1984, p. 63.
105. N.E. Weisser, J.C. Hall, Applications of single-chain variable fragment antibodies in therapeutics and diagnostics, Biotechnol. Adv. 27 (2009) 502-520.
106. J. Maynard, G. Georgiou, Antibody engineering, Annu. Rev. Biomed. Eng. 2 (2000) 339-376.
107. J.S. Huston, D. Levinson, M.M. Hunter, J.T.-S. Novotny, M.N. Margolies, R.J. Ridge, R.E. Bruccoleri, E. Haber, R. Crea, Protein engineering of antibody binding sites: recovery of specific activity in an anti-digoxin single-chain Fv analogue produced in Escherichia coli, Proc. Natl Acad. Sci. USA 85 (1988) 5879-5883.
108. R.E. Bird, K.D. Hardman, J.W. Jacobsen, S. Johnson, B.M. Kaufman, S.M. Lee, T. Lee, S.H. Pope, G.S. Riordan, M. Whitlow, Single-chain antigen-binding proteins, Science 242 (1988) 423-426.
109. A. Todorovska, R.C. Roovers, O. Dolezal, A.A. Kortt, H.R. Hoogenboom, P.J. Hudson, Design and application of diabodies, triabodies and tetrabodies for cancer targeting, J. Immunol. Meth. 248 (2001) 47-66. (Pubitemid 32167024)
110. P. Holliger, T. Prospero, G. Winter, "Diabodies": small bivalent and bispecific antibody fragments, Proc. Natl Acad. Sci. USA 90 (1993) 6444-6448.
111. P. Iliades, A.A. Kortt, P.J. Hudson, Triabodies: single chain Fv fragments without a linker form trivalent trimers, FEBS Lett. 409 (1997) 437-441. (Pubitemid 27285901)
112. O. Dolezal, D. Gori, M. Walter, L. Doughty, M. Hattarki, P.J. Hudson, A.A. Kortt, Single-chain Fv multimers of the anti-neuraminidase antibody NC10: the residue at position 15 in the VL domain of the scFv (VL-VH) molecule is primarily responsible for formation of a tetramer-trimer equilibrium, Protein Eng. 16 (2003) 47-56. (Pubitemid 36407064)
113. T. Olafsen, C.W. Cheung, P.J. Yazaki, L. Li, G. Sundaresan, S.S. Gambhir, M.A. Sherman, L.E. Williams, J.E. Shively, A.A. Raubitschek, A.M. Wu1, Covalent disulfide-linked anti-CEA diabody allows site-specific conjugation and radiolabeling for tumor targeting applications, Protein Eng. Des. Sel. 17 (2004) 21-27. (Pubitemid 38173165)
114. W.W. Cheng, T.M. Allen, Targeted delivery of anti-CD19 liposomal doxorubicin in B-cell lymphoma: a comparison of whole monoclonal antibody, Fab′ fragments and single chain Fv, J. Control. Rel. 126 (1) (2008) 50-58.
115. S.M. Kipriyanov, G. Moldenhauer, M, Little, High level production of soluble single chain antibodies in small-scale Escherichia coli cultures, J. Immunol. Meth. 200 (1-2) (1997) 69-77.
116. A. Pini, L. Bracci, Phage display of antibody fragments, Curr. Protein Pept. Sci. 1 (2) (2000) 155-169.
117. P. Lindner, K. Bauer, A. Krebber, L. Nieba, E. Kremmer, C. Krebber, A. Honegger, B. Klinger, R. Mocikat, A. Plückthun, Specific detection of his-tagged proteins with recombinant anti-His tag scFv-phosphatase or scFv-phage fusions, Biotechniques 22 (1) (1997) 140-149. (Pubitemid 27036427)
118. G. Pavlinkova, D. Colcher, B.J. Booth, A. Goel, U.A. Wittel, S.K. Batra, Effects of humanization and gene shuffling on immunogenicity and antigen binding of anti-TAG-72 single-chain Fvs, Int. J. Cancer 94 (2001) 717-726. (Pubitemid 33035693)
119. R.E. Kontermann, Immunoliposomes for cancer therapy, Curr. Opin. Mol. Ther. 8 (1) (2006) 39-45. (Pubitemid 43230899)
120. C. Marty, Z.L. Machova, S. Sigrist, H. Schott, R.A. Schwendener, K.B. Hofer, Isolation and characterization of a scFv antibody specific for tumor endothelial marker 1 (TEM1), a new reagent for targeted tumor therapy, Cancer Lett. 235 (2006) 298-308.
121. C. Mamot, D.C. Drummond, U. Greiser, K. Hong, D.B. Kirpotin, J.D. Marks, J.W. Par, Epidermal growth factor receptor (EGFR)-targeted immunoliposomes mediate specific and efficient drug delivery to EGFR and EGFRvIII-overexpressing tumor cells, Cancer Res. 63 (12) (2003) 3154-3161. (Pubitemid 36735867)
122. L. Xu, C.C. Huang, W. Huang, W.H. Tang, A. Rait, Y.Z. Yin, I. Cruz, L.M. Xiang, K.F. Pirollo, E.H. Chang, Systemic tumor-targeted gene delivery by anti-transferrin receptor scFv-immunoliposomes, Mol. Cancer Ther. 1 (5) (2002) 337-346.
123. C. Marty, B. Odermatt, H. Schott, D. Neri, K.B. Hofer, R. Klemenz, R.A. Schwendener, Cytotoxic targeting of F9 teratocarcinoma tumours with anti-ED-B fibronectin scFv antibody modified liposomes, Br. J. Cancer 87 (1) (2002) 106-112.
124. R. Ruger, D. Muller, A. Fahr, R.E. Kontermann, Generation of immunoliposomes using recombinant single-chain Fv fragments bound to Ni-NTA-liposomes, J. Drug Target. 13 (7) (2005) 399-406. (Pubitemid 43084540)
125. S.K.E. Messerschmidt, A. Kolbe, D. Müller, M. Knoll, J. Pleiss, R.E. Kontermann, Novel single-chain Fv′ formats for the generation of immunoliposomes by sitedirected coupling, Bioconj. Chem. 19 (2008) 362-369.
126. B. Ramakrishnan, E. Boeggeman, M. Manzoni, Z. Zhu, K. Loomis, A. Puri, D.S. Dimitrov, P.K. Qasba, Multiple site-specific in vitro labeling of single-chain antibody, Bioconj. Chem. 20 (2009) 1383-1389.
127. K. Loomis, B. Smith, Y. Feng, H. Garg, A. Yavlovich, R.C. Massa, D.S. Dimitrov, R. Blumenthal, X. Xiao, A. Puri, Specific targeting to B cells by lipid-based nanoparticles conjugated with a novel CD22-ScFv, Exp. Mol. Pathol. 88 (2010) 238-249.
128. H. Hu, D. Chen, Y. Liu, Y. Deng, S. Yang, M. Qiao, J. Zhao, X. Zhao, Target ability and therapy efficacy of immunoliposomes using a humanized antihepatoma disulfide-stabilized Fv fragment on tumor cells, J. Pharm. Sci. 95 (1) (2006) 192-199.
129. D. Müller, G. Trunk, A. Sichelstiel, K.A. Zettlitz, M. Quintanilla, R.E. Kontermann, Murine endoglin-specific single-chain Fv fragments for the analysis of vascular targeting strategies in mice, J. Immunol. Meth. 339 (2008) 90-98.
130. A. Puri, K. Loomis, B. Smith, J.H. Lee, A. Yavlovich, E. Heldman, R. Blumenthal, Lipid-based nanoparticles as pharmaceutical drug carriers: from concepts to clinic, Crit. Rev. Ther. Drug Carrier Syst. 26 (6) (2009) 523-580.
131. F. Alexis, P. Basto, E.L. Nissenbaum, A.F. Radovic-Moreno, L. Zhang, E. Pridgen, A.Z. Wang, S.L. Marein, K. Westerhof, L.K. Molnar, O.C. Farokhzad, HER-2-targeted nanoparticle-affibody bioconjugates for cancer therapy, Chem. MedChem. 3 (12) (2008) 1839-1843.
132. M. Wikman, A.C. Steffen, E. Gunneriusson, V. Tolmachev, G.P. Adams, J. Carlsson, S. Ståhl, Selection and characterization of HER2/neu-binding affibody ligands, Protein Eng. Des. Sel. 17 (5) (2004) 455-462. (Pubitemid 39294720)
133. V. Tolmachev, A. Orlova, R. Pehrson, J. Galli, B. Baastrup, K. Andersson, M. Sandström, D. Rosik, J. Carlsson, H. Lundqvist, A. Wennborg, F.Y. Nilsson, Radionuclide therapy of HER2-positive microxenografts using a 177Lu-labeled HER2-specific affibody molecule, Cancer Res. 67 (6) (2007) 2773-2782. (Pubitemid 46548966)
134. S.B. Lee, M. Hassan, R. Fisher, O. Chertov, V. Chernomordik, G.K. Marek, A. Gandjbakhche, J. Capala, Affibody molecules for in vivo characterization of HER2-positive tumors by near-infrared imaging, Clin. Cancer Res. 14 (12) (2008) 3840-3849.
135. N. Belousova, G. Mikheeva, J. Gelovani, V. Krasnykh, Modification of adenovirus capsid with a designed protein ligand yields a gene vector targeted to a major molecular marker of cancer, J. Virol. 82 (2) (2008) 630-637.
136. A. Puri, G.M. Kramer, R.M. Campbell, A. Yavlovich, S.C. Tele, S.B. Lee, J.D. Clogston, A.K. Patri, R. Blumenthal, J. Capala, HER2-specific affibody-conjugated thermosensitive liposomes (Affisomes) for improved delivery of anticancer agents, J. Liposome Res. 18 (4) (2008) 293-307.
137. J. Beuttler, M. Rothdiener, D. Muller, F.Y. Frejd, R.E. Kontermann, Targeting of epidermal growth factor receptor (EGFR)-expressing tumor cells with sterically stabilized affibody liposomes (SAL), Bioconj. Chem. 20 (6) (2009) 1201-1208.
138. Y. Matsumura, M. Gotoh, K. Muro, Y. Yamada, K. Shirao, Y. Shimada, M. Okuwa, S. Matsumoto, Y. Miyata, H. Ohkura, K. Chin, S. Baba, T. Yamao, A. Kannami, Y. Takamatsu, K. Ito, K. Takahashi, Phase I and pharmacokinetic study of MCC-465, a doxorubicin (DXR) encapsulated in PEG immunoliposome, in patients with metastatic stomach cancer, Ann. Oncol. 15 (2004) 517-525. (Pubitemid 38444560)
139. R. Suzuki, T. Takizawa, Y. Kuwata, M. Mutoh, N. Ishiguro, N. Utoguchi, A. Shinohara, M. Eriguchi, H. Yanagie, K. Maruyama, Effective anti-tumor activity of oxaliplatin encapsulated in transferrin-PEG-liposome, Int. J. Pharm. 346 (2008) 143-150.
140. D.B. Kirpotin, D.C. Drummond, Y. Shao, M.R. Shalaby, K. Hong, U.B. Nielsen, J.D. Marks, C.C. Benz, J.W. Park, Antibody targeting of long-circulating lipidic nanoparticles does not increase tumor localization but does increase internalization in animal models, Cancer Res. 66 (2006) 6732-6740. (Pubitemid 44085631)
141. J.W. Park, K. Hong, D.B. Kirpotin, G. Colbern, R. Shalaby, J. Baselga, Y. Shao, U.B. Nielsen, J.D. Marks, D. Moore, D. Papahadjopoulos, C.C. Benz, Anti-HER2 immunoliposomes: enhanced efficacy attributable to targeted delivery, Clin. Cancer Res. 8 (2002) 1172-1181.
142. C. Mamot, D.C. Drummond, C.O. Noble, V. Kallab, Z. Guo, K. Hong, D.B. Kirpotin, J. W. Park, Epidermal growth factor receptor-targeted immunoliposomes significantly enhance the efficacy of multiple anticancer drugs in vivo, Cancer Res. 65 (2005) 11631-11638. (Pubitemid 41821723)
143. H. Hatakeyama, H. Akita, E. Ishida, K. Hashimoto, H. Kobayashi, T. Aoki, J. Yasuda, K. Obata, H. Kikuchi, T. Ishida, H. Kiwada, H. Harashima, Tumor targeting of doxorubicin by anti-MT1-MMP antibody-modified PEG liposomes, Int. J. Pharm. 342 (2007) 194-200.
144. S. Gosk, T. Moos, C. Gottstein, G. Bendas, VCAM-1 directed immunoliposomes selectively target tumor vasculature in vivo, Biochim. Biophys. Acta 1778 (2008) 854-863.
145. F. Pastorino, C. Brignole, D. Marimpietri, M. Cilli, C. Gambini, D. Ribatti, R. Longhi, T.M. Allen, A. Corti, M. Ponzoni, Vascular damage and anti-angiogenic effects of tumor vessel-targeted liposomal chemotherapy, Cancer Res. 63 (2003) 7400-7409. (Pubitemid 37413482)
146. M.L. Krieger, N. Eckstein, V. Schneider, M. Koch, H.D. Royer, U. Jaehde, G. Bendas, Overcoming cisplatin resistance of ovarian cancer cells by targeted liposomes in vitro, Int. J. Pharm. 389 (2010) 10-17.
147. X. Ying, H. Wen, W.L. Lu, J. Dua, J. Guo, W. Tian, Y. Men, Y. Zhang, R.J. Li, T.Y. Yang, D.W. Hang, J.N. Lou, L.R. Zhang, Q. Zhang, Dual-targeting daunorubicin liposomes improve the therapeutic efficacy of brain glioma in animals, J. Control. Release 141 (2010) 183-192.
148. A. Gabizon, A.T. Horowitz, D. Goren, D. Tzemach, H. Shmeeda, S. Zalipsky, In vivo fate of folate-targeted polyethylene-glycol liposomes in tumor-bearing mice, Clin. Cancer Res. 9 (2003) 6551-6559.
149. R.E. Eliaz, S. Nir, C. Marty, F.C. Szoka Jr., Determination and modeling of kinetics of cancer cell killing by doxorubicin and doxorubicin encapsulated in targeted liposomes, Cancer Res. 64 (2004) 711-718. (Pubitemid 38120914)
150. X.B. Xiong, Y. Huang, W.L. Lu, X. Zhang, H. Zhang, T. Nagai, Q. Zhang, Intracellular delivery of doxorubicin with RGD-modified sterically stabilized liposomes for an improved antitumor efficacy: in vitro and in vivo, J. Pharm. Sci. 94 (2005) 1782-1793.
151. M. Kondo, T. Asai, Y. Katanasaka, Y. Sadzuka, H. Tsukada, K. Ogino, T. Taki, K. Baba, N. Oku, Anti-neovascular therapy by liposomal drug targeted to membrane type-1 matrix metalloproteinase, Int. J. Cancer 108 (2004) 301-306. (Pubitemid 37541787)
152. M. Mitra, A.K. Mandal, T.K. Chatterjee, N. Das, Targeting of mannosylated liposome incorporated benzyl derivative of Penicillium nigricans derived compound MT81 to reticuloendothelial systems for the treatment of visceral leishmaniasis, J. Drug Target. 13 (2005) 285-293. (Pubitemid 41283162)
153. P. Ghosh, B.K. Bachhawat, Grafting of different glycosides on the surface of liposomes and its effect on the tissue distribution of 125I-labelled gammaglobulin encapsulated in liposomes, Biochim. Biophys. Acta 632 (1980) 562-572.