Drug delivery systems employing 1,4- or 1,6-elimination: Poly(ethylene glycol) prodrugs of amine-containing compounds

Journal of Medicinal Chemistry

Volumn 42, Issue 18, 1999, Pages 3657-3667

  Greenwald, Richard B ^a   Pendri, Annapurna ^a   Conover, Charles D ^a   Zhao, Hong ^a   Choe, Yun H ^a   Martinez, Anthony ^a   Shum, Kwok ^a   Guan, Shuiyun ^a  

^a Enzon Incorporated   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DAUNORUBICIN; MACROGOL DERIVATIVE; PRODRUG;

ANIMAL EXPERIMENT; ARTICLE; CANCER INHIBITION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG DISCRIMINATION; DRUG HALF LIFE; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HYDROLYSIS; MOUSE; NONHUMAN; SOLUBILIZATION; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

AMINES; ANIMALS; ANTINEOPLASTIC AGENTS; CARBAMATES; CARBONATES; CELL DIVISION; DAUNORUBICIN; DRUG DELIVERY SYSTEMS; ESTERS; HYDROLYSIS; MICE; MICE, INBRED STRAINS; POLYETHYLENE GLYCOLS; PRODRUGS; RATS; RATS, INBRED STRAINS; SOLUBILITY; TUMOR CELLS, CULTURED;

EID: 0033539039     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990166e     Document Type: Article

References (42)

1. Wakselman, M. 1,4-And 1,6-Eliminations From Hydroxy And Amino-Substituted Benzyl Systems: Chemical And Biochemical Applications. Nouv. J. Chem. 1983, 7, 439-447.
2. (a) Wakselman, M.; Guibe-Jampel, E. J. An Alkali-labile Benyloxycarbonyl Amino-protecting Group. J. Chem. Soc., Chem. Commun. 1973, 593-594.
3. (b) Le Corre, G.; Guibe-Jampel, E.; Wakselman, M. Groupements Protecteurs Benzyloxycarbonyles Substitues Alcalinolabiles. Tetrahedron 1978, 34, 3105-3112.
4. (c) Guibe-Jampel, E.; Wakselman, M. Selective Cleavage of p-Nitrobenzyl Esters With Sodium Dithionite. Synth. Commun. 1982,12, 219-223.
5. Kemp, D. S.; Hoyng, C. F. New Protecting Groups For Peptide Synthesis-I. The BIC Group Base And Solvent Lability of 5-Benzisoxylmethyleneoxycarbonylamino Function. Tetrahedron Lett. 1975, 4625-4628.
6. Taylor, L. D.; Grasshoff, M.; Pluhar, M. Use of o-and p-Hydroxybenzyl Functions as Blocking Groups Which Are Removable with Base. J. Org. Chem. 1978, 43, 1197-1200.
7. (a) Cain, B. F. 2-Acyloxymethylbenzoic Acids. Novel Amine Protective Functions Providing Amides With the Lability of Esters. J. Org. Chem. 1976, 41, 2029-2031.
8. (b) Bundgaard, H. The Double Prodrug Concept and Its Applications. Adv. Drug Delivery Rev. 1989, 3, 39-65.
9. Carl, P. L.; Chakravarty, P. K; Katzenellenbogen, J. A. A Novel Connector Linkage Applicable in Prodrug Design. J. Med. Chem. 1981, 24, 479-480.
10. Senter, P. D.; Pearce, W. E.; Greenfield, W. E. Development of a Drug-Release Strategy Based on the Reductive Fragmentation of Benzyl Carbamate Disulfides. J. Org. Chem. 1990, 55, 2975-2978.
11. Mauger, A. B.; Burke, P. J.; Somani, H. H.; Friedlos, F.; Knox, R. J. Self-Immolative Prodrugs: Candidates for Antibody-Directed Enzyme Prodrug Therapy in Conjunction with a Nitroreductase Enzyme. J. Med. Chem. 1994, 37, 3452-3458.
12. Hay, M. P.; Wilson, W. R.; Denny, W. A. A Novel Enediyne Prodrug For Antibody Directed Enzyme Prodrug Therapy (ADEPT) Using E. Coli B Nitroreductase. Bioorg. Med. Chem. Lett. 1995, 5, 2829-2834.
13. Lee, M.; Simpson, J. E.; Woo, S.; Kaenzig, C.; Anlezark, G. M.; Eno-Amoquaye, E.; Burke, P. J. Synthesis of an Aminopropyl Analogue of the Experimental Anticancer Drug Tallmustine, and Activation of its 4-Nitrobenzylcarbamoyl Prodrug By Nitrorectuctase and NADH. Bioorg. Med. Chem. Lett. 1997, 7, 1065-1070.
14. (a) Andrianomenjanahary, S.; Dong, X.; Florent, J.-C.; Gaudel, G.; Gesson, P.-P.; Jacquesy, J.-C.; Koch, M.; Mondon, M.; Pettit, P.; Renoux, B.; Tillequin, F. Synthesis of Novel Targeted Pro-Prodrugs of Anthracyclines Potentially Activated by a Monoclonal Antibody Galactosidase Conjugate. Bioorg. Med. Chem. Lett. 1992, 2, 1093.
15. (b) Gesson, J.-P.; Jacquesy, J.-C.; Mondon, P.; Petit, P.; Renoux, S.; Andrianomenjanahary, H.; Dufat-Trinh, V.; Koch, M.; Bosslet, K.; Czech, J.; Hoffman, D. Prodrugs of Anthracyclines for Chemotherapy Via Enzyme-Monoclonal Antibody Conjugates. Anti-Cancer Drug Des. 1994, 9, 409-423.
16. (c) Azoulay, M.; Florent, J.-C.; Moneret, C.; Gesson, J. P.; Jacquesy, J.-C.; Tillequin, F.; Koch, M.; Bosslet, K.; Czech, J.; Hoffman, D. Prodrugs of Anthracycline Antibiotics Suited for Tumor-Specific Activation Anti-Cancer Drug Des. 1995, 10, 441-450.
17. (d) Florent, J.-C.; et al. Prodrugs of Anthracyclines for Use in Antibody-Directed Enzyme Prodrug Therapy. J. Med. Chem. 1998, 41, 3572-3581.
18. (a) Leenders, R. G. G.; Gerrits, K A. A.; Ruijtenbeek, R.; Scheeren, H. W.; Haisma, H. J.; Boven, E. β-Glucuronyl Carbamate Based Pro-Moieties Designed for Prodrugs in ADEPT. Tetrahedron Lett. 1995, 36, 1701-1704.
19. (b) Houba, P. H. J.; Leenders, R. G. G.; Boven, E.; Scheeren, J. W.; Pinedo, H. M.; Haisma, H. J. Characterization of Novel Anthracycline Prodrugs Activated by Human β-Glucuronidase for Use in Antibody-Directed Enzyme Prodrug Therapy. Biochem. Pharmacol. 1996, 52, 455-463.
20. Nagele, E.; Schelhaas, M.; Kuder, N.; Waldmann, H. Chemoenzymatic Synthesis of N-Ras Lipopeptides. J. Am. Chem. Soc. 1998, 120, 6889-6902.
21. Trouet, A. Increased Selectivity of Drugs by Linking to Carriers. Eur. J. Cancer 1978, 14, 105-111.
22. Gardner, C. R. Potential and Limitations of Drug Targeting: An Overview. Biomaterials 1985, 6, 153-160.
23. Maeda, H.; Seymour, L. W.; Miyamoto, Y. Conjugates of Anti-cancer Agents and Polymers: Advantages of Macromolecular Therapeutics in Vivo. Bioconjugate Chem. 1992, 3, 351-362.
24. Jungheim, L. N.; Shepard, T. A. Design of Antitumor Prodrugs: Substrates for Antibody Targeted Enzymes. Chem, Rev. 1994, 94, 1553-1566.
25. Kearny, A. S. Prodrugs and Targeted Drug Delivery. Adv. Drug Delivery Rev. 1996, 19, 225-239.
26. Greenwald, R. B. Drug Delivery Systems: Anticancer Prodrugs and Their Polymeric Conjugates. Exp. Opin. Ther. Patents 1997, 7, 601-609.
27. Denny, W. A.; Wilson, W. R. The Design of Selectively-Activated Anti-Cancer Prodrugs for Use in Antibody-Directed and Gene-Directed Enzyme-Prodrug Therapies. J. Pharm. Pharmacol. 1998, 50, 387-394.
28. Chakravarty, P. K.; Carl, P. L.; Weber, M. J.; Katzenellenbogen, J. A. Plasmin-Activated Prodrugs for Cancer Chemotherapy. 2. Synthesis and Biological Activity of Peptidyl Derivatives of Doxorubicin. J. Med. Chem. 1983, 26, 638-644 and references cited.
29. Greenwald, R. B.; Gilbert, C. W.; Pendri, A.; Conover, C. D.; Xia, J.; Martinez, A. Drug Delivery Systems: Water Soluble Taxol 2′-Poly(ethylene glycol) Ester Prodrugs-Design and In Vivo Effectiveness. J. Med. Chem. 1996, 39, 424-431.
30. Greenwald, R. B.; Pendri, A.; Conover, C.; Gilbert, C.; Yang, R.; Xia, J. Drug Delivery Systems. 2. Camptothecin 20-O-Poly-(ethylene glycol) Ester Transport Forms. J. Med. Chem. 1996, 33, 1938-1940.
31. Greenwald, R. B.; Pendri, A.; Martinez, A.; Gilbert, C.; Bradley, P. PEG Thiazolidine-2-thione, a Novel Reagent for Facile Protein Modification of Bovine Hemoglobin. Bioconjugate Chem. 1996, 7, 638-641.
32. Plusquella, D.; Boczko, K. Sugar Chemistry Without Protecting Groups: A Novel Regioselective Synthesis of 6-0-Acyl-D-Glucopyranoses And Methyl-6-α-D-Glucopyranosides. Tetrahedron Lett. 1987, 28, 3809-3812.
33. Yamada, S. Highly Selective Acylation of Di-and Polyhydroxyl Compounds by 3-Acylthiazolidine-2-thiones. J. Org. Chem. 1992, 57, 1591-1592.
34. Greenwald, R. B.; Pendri, A.; Bolikal, D. Highly Water Soluble Taxol Derivatives: 7-Polyethylene Glycol Carbamates and Carbonates. J. Org. Chem. 1995, 60, 331-336.
35. More detailed chemical and biological experimental results will be presented in a subsequent publication.
36. Miron, T.; Wilchek, M. A. Simplified Method for the Preparation of Succinimidyl Carbonate Polyethylene Glycol for Coupling to Proteins. Bioconjugate Chem. 1993, 4, 568-569.
37. Rose, W. C. Evaluation of Madison 109 Lung Carcinoma as a Model for Screening Antitumor Drugs. Cancer Treat. Rep. 1981, 65, 299-312.
38. Greenwald, R. B.; Pendri, A.; Conover, C. D.; Lee, C.; Choe, Y. H.; Gilbert, C.; Martinez, A.; Xia, J.; Wu, D.; Hsue, M. Camptothecin-20-PEG Ester Transport Forms: The Effect of Spacer Groups on Antitumor Activity. Bioorg. Med. Chem. 1998, 6, 551-562.
39. Murakami, Y.; Tabata, Y.; Ikada, Y. Tumor Accumulation of Poly (Ethylene Glycol) with Different Molecular Weights After Intravenous Injection. Drug Delivery 1997, 4, 23-31.
40. Kopecek, J. Controlled Biodegradability of Polymers-a Key to Drug Delivery Systems. Biomaterials 1984, 5, 119-125 and references cited.
41. Bolton, J. L.; Turnipseed, S. B.; Thompson, J. A. Influence of Quinone Methide Reactivity on the Alkylation of Thiol and Amino Groups in Proteins: Studies Utilizing Amino Acids and Peptide Models. Chem.-Biol. Interact. 1997, 107, 185-200.
42. Corbett, T. T.; et al. Discovery of Solid Tumor Active Agents Using a Soft-Agar-Colony Formation Disk-Diffusion-Assay. In Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery and Development; Valeriote, F., Corbett, T., Baker, L., Eds.; Kluwer Academic: Boston, 1992; pp 35-87.