Synthesis and biological evaluation of immunoconjugates of adriamycin and a human IgM linked by poly[N5-(2-hydroxyethyl)-L-glutamine]

Journal of Controlled Release

Volumn 38, Issue 2-3, 1996, Pages 245-266

  Hoes, C J T ^a   Ankone M ^a   Grootoonk, J ^a   Feijen, J ^a   Van Der Struik, E ^b   Van Doornmalen, A ^b   Pham, D ^b   De Man, A ^b   Van Ettekoven, A ^b   Schlachter, I ^b   Boon, P J ^b   Kaspersen, F ^b   Bos, E S ^b  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b NV ORGANON   (Netherlands)

Author keywords

Adriamycin; Antibody; Biodegradable polymer; Drug targeting; Poly N5 (2 hydroxyethyl) L glutamine

Indexed keywords

DOXORUBICIN; DOXORUBICIN DERIVATIVE; DRUG CARRIER; IMMUNOGLOBULIN M; IODINE 125; IODINE 131; MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY 16 88; POLY[N5 (2 HYDROXYETHYL)GLUTAMINE]; POLYMER; TUMOR ANTIGEN; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER GRAFT; CANCER INHIBITION; COLON TUMOR; CONTROLLED STUDY; CYTOTOXICITY; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG PURIFICATION; DRUG RELEASE; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IMMUNOREACTIVITY; INTRAVENOUS DRUG ADMINISTRATION; MOUSE; NONHUMAN; OVARY TUMOR; PRIORITY JOURNAL; TUMOR CELL LINE;

EID: 0029872673     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/0168-3659(95)00126-3     Document Type: Review

References (34)

1. E.S. Bos, P. Boon, F. Kaspersen and R. McCabe, Passive immunotherapy of cancer: perspectives and problems. J. Control. Release 16 (1991) 101-112.
2. For a survey, see Abstracts from the Sixth International Conference on Monoclonal Antibody Immunoconjugates for Cancer, February 27-March 2, 1991, San Diego, USA, Antibody, Immunoconj. Radiopharm. (1991) 201-239.
3. Y. Kato, N. Umemoto, Y. Kayama, H. Fukushima, Y. Takeda, T. Hara and Y. Tsukada, A novel method of conjugation of daunomycin with antibody with a poly-L-glutamic acid derivative as intermediate drug carrier. An anti-α-fetoprotein antibody-daunomycin conjugate, J. Med. Chem. 27 (1984) 1602-1607.
4. R.G. Steis, J.A. Carrasquillo, R.P. McCabe, M.A. Bookman, J.C. Reynolds, S. Larson, J.W. Smith, J.W. Clark, V. Dailey, S. Del Vecchio, N. Shuke, C.M. Pinsky, W.J. Urba, M. Haspel, P. Perentesis, B. Paris, D.L. Longo and M.G. Hanna Jr., Toxicity, immunogenicity and tumour radioimmunodetecting ability of two human monoclonal antibodies in patients with metastatic colorectal carcinoma, J. Clin. Oncol. 8 (1990) 476-490.
5. H.J. Haisma, M.A.P. Kessel, C. Silva, M. van Muijen, J.C. Roos, H. Bril. H.J.M. Martens, R. McCabe and E. Boven, Human IgM monoclonal antibody 16.88: pharmacokinetics and distribution in mouse and man, Br. J. Cancer 62, Suppl. X (1990) 40-43.
6. 131I-labelled human IgM monoclonal antibody 16.88 in advanced colorectal cancer patients, Eur. J. Cancer 27 (1991) 1430-1436.
7. R. De Jager, H. Abdel-Nabi, A. Serafini, A. Pecking, J.L. Klein and M.G. Hanna Jr, Current status of cancer immunodetection with radiolabeled human monoclonal antibodies, Sem. Nucl. Med. 23 (1993) 165-179.
8. N. Pomato, J.H. Murray, E. Bos, M.V. Haspel, R.P. McCabe and M.G. Hanna, Identification and characterization of a human colon tumor-associated antigen, CTAA 16-88, recognized by a human monoclonal antibody, in: R.S. Metzger and M.S. Mitchell (Eds), Human Tumor Antigens and Specific Tumor Therapy, A.R. Liss, New York, 1989, pp. 127-136.
9. C.J.T. Hoes and J. Feijen, The application of drug-polymer conjugates in chemotherapy, in: F.H.D. Roerdink and A.M. Kroon (Eds), Drug Carrier Systems. Wiley & Sons Ltd., Chichester, 1989, pp. 57-109.
10. C.J.T. Hoes, J. Grootoonk, J. Feijen, P.J. Boon, F. Kaspersen, P. Loeffen, I. Schlachter, M. Winters and E.S. Bos, Synthesis and biodistribution of immunoconjugates of a human IgM and polymeric drug carriers, J. Control. Release 19 (1992) 59-76.
11. European Patent 495265; US Patent 5306809.
12. P. Boon, E. Bos, F. Kaspersen, A. de Man, A. van Ettekoven, P. Loeffen, D. Pham and R. McCabe, Novel, acid sensitive linker structures: design, synthesis and application in the preparation of adriamycin immunoconjugates. Antibody, Immunoconj. Radiopharm. 5 (1992) 118.
13. St. Guttmann and R.A. Boissonnas, Synthèse du N-acétyl-L-séryl-L-tyrosyl-L-séryl-L-méthionyl- γ-L-glutamate de benzyle et des peptides apparantés, Helv. Chim. Acta 41 (1958) 1852.
14. C.J.T. Hoes, J. Grootoonk, R. Duncan, I.C. Hume, M. Bhakoo, J.M.W. Bouma and J. Feijen, Biological properties of adriamycin bound to biodegradable polymeric carriers, J. Control. Release 23 (1993) 37-54.
15. J. Barnett, Analogs of pantothenic acid. III. Preparation of growth-inhibiting analogs related to N-pantoyltaurine, J. Chem. Soc. (1944) 5-8.
16. G.L. Ellman, Tissue sulfhydryl groups. Arch. Biochem. Biophys. 82 (1959) 70-77.
17. D.R. Grassetti and J.F. Murray, Determination of sulfhydryl groups with 2,2′-or 4,4′-dithiopyridine, Arch. Biochem. Biophys. 119 (1967) 41-49.
18. H. Towbin, T. Shaehelin and J. Gordon, Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedures and some applications, Proc. Natl. Acad. Sci. USA 76 (1979) 4350-4354.
19. α-tert-Butoxycarbonyl α,ω-alkanediamine hydrochlorides from amino alcohols, Synthesis April (1990) 366-368.
20. P.J. Boon et al., in preparation.
21. D.A. Scudiero, R.H. Shoemaker, K.D. Paull, A. Monks, S. Tierney, T.H. Nofziger. M.J. Currens, D. Seniff and M.R. Boyd, Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines, Cancer Res. 48 (1988) 4827-4833.
22. E. Boven, Human ovarian cancer xenografts in nude mice. Application of a new model in the selection of novel agents for ovarian cancer, Ph.D. thesis, Free University of Amsterdam, 1986.
23. K. Nilsson, O. Norrlöw and K. Mosbach, p-Toluenesulfonyl chloride as an activating agent of agarose for the preparation of immobilized affinity ligands and proteins. Optimization of conditions for activation and coupling, Acta Chem. Scand. B 35 (1981) 19-27.
24. K. Nilsson and K. Mosbach, Immobilization of ligands with organic sulfonyl chlorides, Methods Enzymol. 104 (1984) 56-69.
25. A. Lääne, M. Haga, A. Aaviksaar, V. Chytry and J. Kopecek, Activation of poly[N-(2-hydroxypropyl)methacrylamide] for the binding of bioactive molecules. I, Makromol. Chem. 184 (1983) 1339-1344.
26. E. Schacht, J. Vermeersch, F. Vandoorne, R. Vercauteren and J.P. Remon, Synthesis and characterization of some modified polysaccharides containing drug moieties, J. Control. Release 2 (1985) 245-256.
27. W.A.R. van Heeswijk, C.J.T. Hoes, T. Stoffer, M.J.D. Eenink, W. Potman and J. Feijen, The synthesis and characterization of polypeptide-adriamycin conjugates and its complexes with adriamycin. I, J. Control. Release 1 (1985) 301-315.
28. J. Gerber and H.G. Elias, Multimerisation: Association and aggregation. VII. Poly-γ-benzyl-L-glutamat in reinen Lösungsmitteln, Makromol. Chem. 112 (1968) 142-159.
29. W. Bushuk and H. Benoit, Light-scattering studies of copolymers. I. Effect of heterogeneity of chain composition on the molecular weight. Can. J. Chem. 36 (1958) 1616-1626.
30. H. Tanimori, T. Kitagawa, T. Tsunoda and R. Tsuchiya. Enzyme immunoassay of neocarzinostatin using β-galactosidase as a label, J. Pharm. Dyn. 4 (1981) 812-819.
31. M.D. Partis, D.G. Griffiths, G.C. Roberts and R.B. Beechey, Cross-linking of protein by ω-maleimido alkanoyl N-hydroxysuccinimido esters, J. Protein Chem. 2 (1983) 263-277.
32. S. Yoshitake, M. Imagawa, E. Ishikawa, Y. Niitsu, I. Urushizaki, M. Nishiura, R. Kanazawa, H. Kurosaki, S. Tachibana, N. Nakazawa and H. Ogawa, Mild and efficient conjugation of rabbit Fab′ and horseradish peroxidase using a maleimide compound and its use for enzyme immunoassay, J. Biochem. 92 (1982) 1413-1424.
33. M. Nukui, K. Hoes, H. van den Berg and J. Feijen, Association of macromolecular prodrugs consisting of adriamycin bound to poly(L-glutamic acid), Makromol. Chem. 192 (1991) 2925-2942.
34. W.-C. Shen and H.J.-P. Ryser, cis-Aconityl spacer between daunomycin and macromolecular carriers: a model of pH-sensitive linkage releasing drug from a lysosomotropic conjugate, Biochem. Biophys. Res. Commun. 102 (1981) 1048-1054.