Synthesis of a lipophilic daunorubicin derivative and its incorporation into lipidic carriers developed for LDL receptor-mediated tumor therapy

Pharmaceutical Research

Volumn 15, Issue 4, 1998, Pages 531-537

  Versluis, A Jenny ^a   Rump, Erik T ^a   Rensen, Patrick C N ^a   Van Berkel, Theo J C ^a   Bijsterbosch, Martin K ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Daunorubicin derivative; Drug carrier; Low density lipoprotein receptor; Tumor therapy

Indexed keywords

CHOLESTEROL OLEATE; DAUNORUBICIN DERIVATIVE; DRUG CARRIER; LIPOSOME; LOW DENSITY LIPOPROTEIN RECEPTOR;

ARTICLE; CANCER CHEMOTHERAPY; CANCER THERAPY; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG SYNTHESIS; LIPOPHILICITY; NONHUMAN; PRIORITY JOURNAL;

ANTIBIOTICS, ANTINEOPLASTIC; CHOLESTEROL ESTERS; CHOLIC ACIDS; DAUNORUBICIN; DRUG CARRIERS; EMULSIONS; HUMANS; LIPOSOMES; OLIGOPEPTIDES; PRODRUGS; RECEPTORS, LDL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0031925731     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1011917508056     Document Type: Article

References (30)

1. R. A. Firestone. Low-density lipoprotein as a vehicle for targeting antitumor compounds to cancer cells. Bioconjugate Chem. 5:105-113 (1994).
2. M. S. Brown and J. L. Goldstein. A receptor-mediated pathway for cholesterol homeostasis. Science 232:34-47 (1986).
3. P.C. De Smidt and Th. J. C. Van Berkel. Prolonged serum half-life of antineoplastic drugs by incorporation into the low density lipoprotein. Cancer Res. 50:7476-7482 (1990).
4. M. Masquelier, S. Vitols, and C. Peterson. Low-density lipoprotein as a carrier of antitumoral drugs: In vivo fate of drug-human low-density lipoprotein complexes in mice. Canc. Res. 46:3842-3847 (1986).
5. G. S. Ginsburg, D. M. Small, and D. Atkinson. Microemulsions of phospholipids and cholesterol esters: protein-free models of low density lipoprotein. J. Biol. Chem. 257:8216-8227 (1982).
6. G. S. Ginsburg, M. T. Walsh, D. M. Small, and D. Atkinson. Reassembled plasma low density lipoproteins: Phospholipid-cholesterol ester-apoprotein B complexes. J. Biol. Chem. 259:6667-6673 (1984).
7. B. Lundberg, K. Hong, and D. Papahadjopoulos. Conjugation of apolipoprotein B with liposomes and targeting to cells in culture. Biochim. Biophys. Acta 1149:305-312 (1993).
8. R.C. Maranhão, T. B. Cesar, S. R. Pedroso-Mariani, M. H. Hirata, and C. H. Mesquita. Metabolic behaviour in rats of a nonprotein microemulsion resembling low-density lipoprotein. Lipids 28:691-696 (1993).
9. R. C. Maranhão, B. Garicochea, E. L. Silva, P. Dorlhiac-Llacer, S. M. S. Cadena, I. J. C. Coelho, J. C. Meneghetti, F. J. C. Pileggi, and D. A. F. Chamone. Plasma kinetics and biodistribution of a lipid emulsion resembling low-density lipoprotein in patients with acute leukemia. Cancer Res. 54:4660-4666 (1994).
10. P. C. N. Rensen, R. M. Schiffelers, A. J. Versluis, M. K. Bijsterbosch, M. E. M. J. Meuwissen, and Th. J. C. Van Berkel. Human recombinant apolipoprotein E-enriched liposomes can mimic low density lipoproteins as carriers for the site-specific delivery of anti-tumour agents. Mol. Pharmacol. 52:445-455 (1997).
11. P. C. N. Rensen, N. Herijgers, M. H. Netscher, S. C. J. Meskers, M. Van Eck, and Th. J. C. Van Berkel. Particle size determines the specificity of apoE-containing triglyceride-rich emulsions for the LDL receptor versus hepatic remnant receptor in vivo. J. Lipid Res. 38:1070-1084 (1997).
12. T. L. Innerarity, R. E. Pitas, and R. W. Mahley. Binding of arginine-rich (E) apolipoprotein after recombination with phospholipid vesicles to the low density lipoprotein receptors of fibroblasts. J. Biol. Chem. 254:4186-4190 (1979).
13. R. E. Pitas, T. L. Innerarity, and R. W. Mahley. Cell surface receptor binding of phospholipid protein complexes containing different ratios of receptor-active and -inactive E apolipoprotein. J. Biol. Chem. 255:5454-5460 (1980).
14. c. Proc. Natl. Acad. Sci. USA 76:2311-2315 (1979).
15. T. Funahashi, S. Yokoyama, and A. Yamamoto. Association of apolipoprotein E with the low density lipoprotein receptor: demonstration of its co-operativity on lipid microemulsion particles. J. Biochem. 105:582-587 (1989).
16. D. W. Henry. Adriamycin (NCS-123127) and its analogs. Cancer Chemother. Rep. - Part 2 4:5-9 (1974).
17. A. Trouet, D. Deprez-De Campeneere, C. de Duve. Chemotherapy through lysosomes with a DNA-daunorubicin complex. Nature, New Biol. 239:110-112 (1972).
18. A. Di Marco, F. Zunino, R. Silvestrini, C. Gambarucci, and R. A. Gambetta. Interaction of some daunomycin derivatives with deoxyribonucleic acid and their biological activity. Biochem. Pharmacol. 20:1323-1328 (1971).
19. A. Trouet, M. Masquelier, R. Baurain, D. A Deprez-De Campeneere. Covalent linkage between daunorubicin and proteins that is stable in serum and reversible by lyosomal hydrolases, as required for a lysosomotropic drug-carrier conjugate: in vitro and in vivo studies. Proc. Natl. Acad. Sci. USA 79:626-629 (1982).
20. N. Umemoto, Y. Kato, N. Endo, Y. Takeda, and T. Hara. Preparation and in vitro cytotoxicity of a methotrexate-anti-MM46 monoclonal antibody conjugate via an oligopeptide spacer. Int. J. Cancer 43:677-684 (1989).
21. J. J. Fitzpatrick and M. C. Garnett. Design, synthesis and in vitro testing of methotrexate carrier conjugates linked via oligopeptide spacers. Anti-Cancer Drug Design 10:1-9 (1995).
22. K. L. Law, K. E. Studtmann, R. E. Carlson, T. A. Swanson, A. W. Buirge, and A. Ahmad. Tumor reactive cis-aconitylated monoclonal antibodies coupled to daunorubicin through a peptide spacer are unable to kill tumor cells. Anticancer Res. 10:845-852 (1990).
23. T. G. Redgrave, D. C. K. Roberts, and C. E. West. Separation of plasma lipoproteins by density-gradient ultracentrifugation. Anal. Biochem. 65:42-49 (1975).
24. R. R. C. New. Liposomes: a practical approach, IRL Press, Oxford, 1990.
25. S. Vitols, G. Gahrton, and C. Peterson. Significance of the low-density lipoprotein (LDL) receptor pathway for the in vitro accumulation of AD-32 incorporated into LDL in normal and leukemic white blood cells. Canc. treat Rep. 68:515-520 (1984).
26. S. G. Vitols, M. Masquelier, and C. O. Peterson. Selective uptake of a toxic lipophilic anthracycline derivative by the low-density lipoprotein receptor pathway in cultured fibroblasts. J. Med. Chem. 28:451-454 (1985).
27. P. C. De Smidt, T. Le Doan, S. De Falco, and Th. J. C. Van Berkel. Association of antisense oligonucleotides with lipoproteins prolongs the plasma half-life and modifies the tissue distribution. Nucleic Acids Res. 19:4695-4700 (1991).
28. P. C. De Smidt, A. J. Versluis, and Th. J. C. Van Berkel. Properties of incorporation, redistribution and integrity of phorphyrin-LDL complexes. Biochem. 32:2916-2922 (1993).
29. Y. Oschry and S. Eisenberg. Rat plasma lipoproteins: re-evaluation of a lipoprotein system in an animal devoid of cholesteryl ester transfer activity. J. Lipid Res. 23:1099-1106 (1982).
30. P. J. Barter and J. I. Lally. The activity of an estrified cholesterol transferring factor in human and rat serum. Biochim. Biophys. Acta 531:233-236 (1978).