Camptothecin delivery systems: Enhanced efficacy and tumor accumulation of camptothecin following its conjugation to polyethylene glycol via a glycine linker

Cancer Chemotherapy and Pharmacology

Volumn 42, Issue 5, 1998, Pages 407-414

  Conover, Charles D ^a   Greenwald, Richard B ^a   Pendri, Annapurna ^a   Gilbert, Carl W ^a   Shum, Kwok L ^a  

^a Enzon Incorporated   (United States)

Author keywords

Biodistribution; Camptothecin; Polyethylene glycol; Prodrug; Xenograft

Indexed keywords

CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; FLUOROURACIL; MACROGOL; TOPOTECAN; TRITIUM;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; COLORECTAL CARCINOMA; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACCUMULATION; DRUG BIOAVAILABILITY; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG EFFICACY; FEMALE; HUMAN; HUMAN CELL; INTRAPERITONEAL DRUG ADMINISTRATION; INTRAVENOUS DRUG ADMINISTRATION; ISOTOPE LABELING; MOUSE; NONHUMAN; PRIORITY JOURNAL; XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; COLORECTAL NEOPLASMS; DRUG CARRIERS; GLYCINE; HUMANS; INJECTIONS, INTRAPERITONEAL; INJECTIONS, INTRAVENOUS; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; POLYETHYLENE GLYCOLS; PRODRUGS; TISSUE DISTRIBUTION; TRITIUM;

EID: 0031657330     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002800050837     Document Type: Article

References (34)

1. Allen T (1989) Stealth liposomes: avoiding reticuloendothelial uptake. In: Lopez-Berestein G, Fidler I (eds) Liposomes in the therapy of infectious diseases and cancer. Alan R. Liss, New York, p 405
2. Baurain R, Masquelier M, Deprez-De Campeneere D, Trouet A (1980) Amino acid and dipeptide derivatives of daunorubicin. 2. Cellular pharmacology and antitumor activity on L1210 leukemia cells in vitro and in vivo. J Med Chem 23: 1171
3. Bundgaard H (1986) Bioreversible derivatization of peptides. In: Davis S, Illum E, Tomlinson E (eds) Delivery systems for peptide drugs. Plenum Press, New York, p 49
4. Carl P, Chakravarty P, Katzenellenbogen J (1981) A novel connector linkage applicable in prodrug design. J Med Chem 24: 479
5. Conover C, Pendri A, Lee C, Gilbert C, Shum K, Oreenwald R (1997) Camptothecin delivery systems: the antitumor activity of a camptothecin-20′-O-polyethylene glycol ester transport form. Anticancer Res 17: 3361
6. Corbett T, Valeriote F, Polin L, Panchapor C, Pygh S, White K. Lowichik N, Knight J, Bissery M, Wizniak A, LoRusso P, Biernat L, Polin D, Knight L, Biggar S, Looney D, Demchik L, Jones J, Jones L, Blair S, Palmer K, Essenmacher S, Lisow L, Mattles K, Cavanaugh P, Rake J, Baker L (1992) Discovery of solid tumor active agents using a soft-agar-colony formation disk-diffusion-assay. In: Valeriote F, Corbett T, Baker L (eds) Cytotoxic anticancer drugs: models and concepts for drug discovery and development. Kluwer Academic, Boston Dordrecht London, p 77
7. Dvorak H, Nagy J, Dvorak J, Dvorak A (1988) Identification and characterization of the blood vessels of solid tumors that are leaky to circulating macromolecules. Am J Pathol 138: 95
8. Emerson D, Besterman J, Brown H, Evans M, Leitner P, Luzzio M, Shaffer J, Sternbach D, Uehling D, Vuong A (1995) In vivo antitumor activity of two new seven-substituted water-soluble camptothecin analogues. Cancer Res 55: 603
9. Eno-Amooquaye E, Searle F, Boden J, Sharma S, Burke P (1996) Altered biodistribution of an antibody-enzyme conjugate modified with polyethylene glycol. Br J Cancer 73: 1323
10. Fogler W, Wade R, Brundish D, Fidler I (1985) Distribution and fate of free and liposome-encapsulated [3H]normuramyl dipeptide and [3H]muramyl tripeptide phosphatidylethanolamine in mice. J Immunol 135: 1372
11. Giovanella B, Stehlin J, Wall M, Wani M, Nicholas A, Liu L, Silber R, Potmesil M (1989) DNA topoisomerase I-target chemotherapy of human colon cancer in xenografts. Science 246: 1046
12. Giovanella B, Hinz H, Kozielski A, Stehlin J, Silber R. Potmesil M (1991) Complete growth inhibition of human cancer xenograft in nude mice by treatment with 20-(S)-camptothecin. Cancer Res 51: 3052
13. Greenwald R (1997) Drug delivery systems: anticancer prodrugs and their polymeric conjugates. Exp Opin Ther Patents 7: 601
14. Greenwald R, Pendri A, Bolikal D. Gilbert C (1994) Highly water soluble taxol derivatives: 2′-polyethylene glycol esters as potential prodrugs. Bioorg Med Chem Lett 4: 2465
15. Greenwald R, Pendri A, Conover C, Gilbert C, Yang R, Xia J (1996) Drug delivery systems. 2. Camptothecin-20-O-poly(ethylene glycol) ester transport forms. J Med Chem 39: 1938
16. Greenwald R, Pendri A, Conover C, Lee C, Choe Y, Gilbert C, Martinez A, Xia J, Wu D, Hsue M (1998) Camptothecin-20-PEG ester transport forms: the effect of spacer groups on antitumor acitivity. Bioorg Med Chem 6: 551
17. Hertzberg R, Caranfa M, Holden K, Jakaa D, Gallagher G, Mattern M, Mong S, Bartus J, Johnson R, Kingsbury W (1989) Modification of the hydroxy lactone ring of camptothecin: inhibition of mammalian topoisomerase I and biological activity. J Med Chem 32: 715
18. H-labeled camptothecins. J Labeled Compounds Radiopharm 38: 733
19. Jaxel C, Kohn K, Wani M, Wall M, Pommier Y (1989) Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: evidence for a specific receptor site and a relation to antitumor activity. Cancer Res 49: 1465
20. Kingsbury W, Boehm J, Jakas D, Holden K, Hecht S, Gallagher G, Caranfa M, McCabe F, Faucette L, Johnson R, Hertzberg R (1991) Synthesis of water-soluble (aminoalkyl)camptothecin analogues: inhibition of topoisomerase I and antitumor activity. J Med Chem 34: 98
21. Maeda H, Seymour L, Miyamota Y (1992) Conjugates of anticancer agents and polymers: advantages of macromolecular therapeutics in vivo. Bioconjug Chem 3: 351
22. Murakami Y, Tabata Y, Ikada Y (1997) Tumor accumulation of poly(ethylene glycol) with different molecular weights after intravenous injection. Drug Delivery 4: 23
23. Oliyai R, Stella V (1993) Prodrugs of peptides and proteins for improved formulation and delivery. Annu Rev Pharmacol Toxicol 32: 521
24. Pantazis P (1995) Preclinical studies of water-insoluble camptothecin congeners: Cytotoxicity, development of resistance, and combination treatments. Clin Cancer Res 1: 1235
25. Pendley R, Boden J, Boden R, Begent R, Turner A, Haines A, King D (1994) The potential for enhanced tumour localisation of poly(ethylene glycol) modification of anti-CEA antibody. Br J Cancer 70: 1126
26. Potmesil M (1994) Camptothecins: from bench research to hospital wards. Cancer Res 54: 1431
27. Sawada S, Okajima S, Aiyama R, Nokata K, Furuta T, Yokokura T, Sugino E, Yamaguchi K, Miyasaka T (1991) Synthesis and antitumor activity of 20(S)-camptothecin derivatives: carbamate-linked, water-soluble derivatives of 7-ethyl-10-hydroxycamptothecin. Chem Pharm Bull 10: 1451
28. Schappei U, Fleischman R, Cooney D (1974) Toxicity of camptothecin (NSC-100800). Cancer Chemother Rep 5: 25
29. Senter P, Svensson H, Schreiber G, Rodriguez J, Vrudhula Y (1995) Poly(ethylene glycol)-doxorubicin conjugates containing β-lactamase-sensitive linkers. Bioconjug Chem 6: 389
30. Seymour L (1992) Passive tumour-targeting of soluble macromolecules and drug conjugates. Crit Rev Ther Drug Carrier Syst 9: 135
31. Stella V, Charman W, Naringrekar V (1985) Prodrugs: do they have advantages in clinical practice? Drugs 29: 455
32. Tannock I, Rotin D (1989) Acid pH in tumors and its potential for therapeutic exploitation. Cancer Res 49: 4373
33. Trouet A (1978) Increased selectivity of drugs by linking to carriers. Eur J Cancer 14: 105
34. Yamaoka T, Tabata Y, Ikada Y (1994) Distribution and tissue uptake of polyethylene glycol with different molecular weights after intravenous administration to mice. J Pharm Sci 83: 601