Synthesis of doxorubicin conjugates through hydrazone bonds to melanotransferrin p97

Synthetic Communications

Volumn 33, Issue 14, 2003, Pages 2377-2390

  Chen, Qingqi ^a   Sowa, Damian A ^a   Cai, Jianlin ^a   Gabathuler, Reinhard ^a  

^a BIOMARIN PHARMACEUTICAL INC   (United States)

Author keywords

Anticancer drug; Bioconjugate; Blood brain barrier; Brain tumor; Cross linking; Doxorubicin; Drug delivery; Hydrazone linker; Protein carrier

Indexed keywords

4 (4 N MALEIMIDOPHENYL)BUTYRIC ACID HYDRAZINE; ADIPIC ACID MONOHYDRAZINE; ADIPIC DIHYDRAZINE; DOXORUBICIN; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; LINK PROTEIN; MELANOTRANSFERRIN P97; TRANSFERRIN; UNCLASSIFIED DRUG;

ARTICLE; BRAIN TUMOR; CHEMICAL BOND; CONJUGATION; DRUG SYNTHESIS; HUMAN;

EID: 0043065558     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120021827     Document Type: Article

References (27)

1. Arcamone, F. Doxrubicin Anticancer Antibiotics; Academic Press: New York, 1981, chapter 2.
2. Wiernik, P.H. In Anthracyclines. Current Status and New Developments; Crooke, S.T., Reich, S.D., Eds; Academic Press: New York, 1980; 273-294.
3. Dorr, R.T.; Von Hoff, D.D. Cancer Chemotherapy Handbook, 2nd Ed.; Appleton and Lange: New York, 1994.
4. Begley, D.J.; Bradbury, M.W.; Kreuter, J. The Blood-Brain Barrier and Drug Delivery to the CNS; Marcel Dekker Inc.: New York, 2000.
5. (a) Fratz, F.; Beyer, U.; Roth, T.; Tarasova, N.; Collery, P.; Lechenault, F.; Cazabat, A.; Schumacher, P.; Unger, C.; Falken, U. Transferrin conjugates of dooxorubicin: synthesis, characterization, cellular uptake. J. Pharm. Sci. 1998, 87 (3), 338-346;
6. (b) King, D.H.; Yurgaitis, D.; Willner, D.; Firestone, R.A.; Yang, M.B.; Lasch, S.J.; Hellstron, K.E.; Trail, P.A. Monoclonal antibody conjugates of doxorubicin prepared with branched linkers: a novel method for increasing the potency of doxorubicin immunoconjugates. Bioconjugate Chem. 1999, 10 (2), 279-288.
7. (a) Lau, A.; Berube, G.; Ford, C.H.J. Conjugation of doxorubicin to monoclonal anticarcinoembryonic antigen antibody via novel thio-directed cross-linking reagents. Bioorg. Med. Chem. 1995, 3 (10), 1299-1304;
8. (b) Froesch, B.A.; Stahel, R.A.; Zangemeister-Wittke, U. Preparation and funtional evaluation of new doxorubicin immunoconjugates containing and acid-senstitive linker on small-cell lung cancer cells. Cancer Immunol. Immunother. 1996, 42 (1), 55-63.
9. (a) Godwin, A.; Hartenstein, M.; Muller, A.H.E.; Brocchini, S. Narrow molecular weight distribution precursors for polymer-drug conjugates. Angew. Chem. Int. Ed. 2001, 40 (3), 594-597;
10. (b) Yokoyama, M.; Fukushima, S.; Uehara, R.; Okamoto, K.; Kataoka, K.; Sakurai, Y.; Okano, T. Characterization of physical entrapment and chemcial conjugation of adriamycin in polymeric micelles and their design for in vivo delivery to a solid tumor. J. Control. Release 1998, 50 (1), 79-92;
11. (c) Nogusa, H.; Yano, T.; Kashima, N.; Yamamoto, K.; Okuno, S.; Hamana, H. Structure-activity relationships of carboxymethylpullulan-peptide-doxorubicin conjugates - systematic modification of peptide spacer. Bioorg. Med. Chem. Lett. 2000, 10 (3), 227-230;
12. (d) Dvorak, M.; Kopeckova, P.; Kopecek, J. High-molecular weight HMPA copolymer-adriamycin conjugates. J. Control. Release 1999, 60 (2-3), 321-332;
13. (e) Rodrigues, P.C.A.; Beyer, U.; Schumacher, P.; Roth, T.; Fiebig, H.H.; Unger, C.; Messori, L.; Orioli, P.; Paper, D.H.; Mulhaupt, R.; Kratz, F. Acid-sensitive polyethylene glycol conjugates of doxorubicin: preparation, in vitro efficacy and intracellular distribution. Bioorg. Med. Chem. 1999, 7 (11), 2517-2524.
14. (a) Dubowchik, G.M.; Firestone, R.A. Capthepsin B-sensitive dipeptide prodrugs. 1. A model study of structural requirements for efficient release of doxorubicin. Bioorg. Med. Chem. Lett. 1998, 8 (23), 3341-3346;
15. (b) Dubowchik, G.M.; Mosure, K.; Knipe, J.O.; Firestone, R.A. Capthepsin B-sensitive dipeptide prodrugs. 2. Models of anticancer drugs pacitaxel (taxol), mitomycin c and doxorubicin. Bioorg. Med. Chem. Lett. 1998, 8 (23), 3347-3352.
16. Garnett, M.C. Targeted drug conjugates: principales and progress. Adv. Drug Delivery Rev. 2001, 53 (2), 171-216.
17. (a) Rousselle, C.; Clair, P.; Lefauconnier, J.-M.; Kaczorek, M.; Scherrmann, J.-M. Temsamani, J. New advances in the transport of doxorubicin through the blood-brain barrier by a peptide vector-mediated strategy. Mol. Pharmacol. 2000, 57 (4), 679-686;
18. (b) Remsen, L.G.; Trail, P.A.; Hellstrom, I.; Hellstrom, K.E.; Neuwelt, E.A. Enhanced delivery improves the efficacy of a tumor-specific doxorubicin immunoconjugate in a human brain tumor xenograft model. Neurosurgery 2000, 46 (3), 704-709.
19. (a) Yamada, T.; Tsujioka, Y.; Taguchi, J.; Takahashi, M.; Tsuboi, Y.; Moroo, I.; Yang, J.; Jefferies, W.A. Brain Research 1999, 845, 1-5;
20. (b) Rothenberger, S.; Food, M.R.; Gabthuler, R.; Kennard, M.L.; Yamada, T.; Yasuhara, O.; McGeer, P.L.; Jefferies, W.A. Brain Research 1996, 7 (12), 117-121.
21. (a) Kruger, M.; Beyer, U.; Schumacher, P.; Unger, C.; Zahn, H.; Kratz, F. Synthesis and stability of four maleimide derivatives of the anticancer drug doxorubicin for the preparation of chemoimmunoconjugates. Chem. Pharm. Bull. 1997, 45 (2), 399-401;
22. (b) Thottathil, J.K.; Gadamasetti, K.G.; Li, W.-S.; Mueller, R.H. Method for Preparing Thioether Conjugates. European Patent 665,020, January 27, 1995.
23. (a) Staros, J.V.; Wright, R.W.; Swingle, D.M. Enhancement by N-hydroxysulfosuccinimide of water-soluble carbodiimide-mediated coupling reactions. Anal. Biochem. 1986, 156 (1), 220-222;
24. (b) Grabarek, Z.; Gergely, J. Zero-length cross-linking procedure with the use of active esters. Anal. Biochem. 1990, 185 (1), 131-135.
25. Chen, Q.; Sowa, D.; Cai, J.; Gabathuler, R. Efficient one-pot synthesis of doxorubicin conjugates through its amino group to melano-transferrin p97. Synth. Commun. 2003, 33 (14), 2399-2419.
26. 1H nuclear magnetic resonance spectrum in various solvents. Can. J. Chem. 1987, 65 (10), 2405-2410;
27. (b) Arnone, A.; Fronza, G.; Mondelli, R. Tetrahedron Lett. 1976, 37 (3), 248-250.