journal article·1996-04

PEG Modified Anticancer Drugs: Synthesis and Biological Activity

Annapurna Pendri, Carl W. Gilbert, Soundara Soundararajan, Durgadas Bolikal, Robert G. L. Shorr, Richard B. Greenwald

Publisher page

Abstract

Three well known anticancer drugs, doxorubicin, methotrexate and paclitaxel (taxol), have been modified by the permanent attachment of poly(ethylene glycol)(PEG) and evaluated for in vitro cytotoxic activity against murine leukemias P388 and L1210. The relative potencies of the PEG derivatives suggest that modification of antitumor agents with this type of polymer yields compounds that are highly water soluble but less cytotoxic.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Cancer Treatment and Pharmacology · Nanoparticle-Based Drug Delivery · HER2/EGFR in Cancer Research

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Enzon Inc., Piscataway, NJ 08854

References (58)

Show source-provided references
1. 1. All polyethylene glycol derivatives discussed in this paper are terminated on one end of the polymer with a methyl group. The IUPAC nomenclature for the general polymer is α-hydroxy-ω-methyl-poly(oxy-1 2-ethanediyl). We find it more convenient to refer to this material as PEG.
2. 10.1016/S0960-894X(01)80411-X10.1016/S0960-894X(01)80411-X ↗
3. 10.1007/978-1-4899-0703-510.1007/978-1-4899-0703-5 ↗
4. (b) Delgado, C., G. E. Francis and D. Fisher. 1992. Critical Revs. in Therap. Drug Carrier Systems, 9:249-304;
5. 10.1080/0736657850808196010.1080/07366578508081960 ↗
6. 10.1016/0169-409X(91)90037-D10.1016/0169-409X(91)90037-D ↗
7. 10.1016/0169-409X(93)90005-O10.1016/0169-409X(93)90005-O ↗
8. 10.1002/jps.260083043210.1002/jps.2600830432 ↗
9. 10.1021/bc00032a00210.1021/bc00032a002 ↗
10. 6. Dreborg, S. and Akerblom,, E. B. 1990. Crit. Rev. Ther Drug Carrier Syst., 6:315-365.
11. 7. Kitamira, K., T. K. Takahashi, T. Yamaguchi, A. Noguchi, K. I. Takashina, H. Tsurumi, M. Inagake, T. Toyokunti and S. I. Hakomori. 1991. Cancer Res., 51:4310-4315.
12. 8. Francis, G. E., C. Delgado and D. Fisher. 1991. "PEG Modified Proteins," in Pharmaceutical Biotechnology, Vol. 3, in vivo Pathways of Degradation and Strategies for Stabilisation, T. J. Ahern and M. Manning, eds., New York, NY: Plenum Press, pp. 235-263.
13. 10.1038/255066a010.1038/255066a0 ↗
14. 10.1038/263696a010.1038/263696a0 ↗
15. 10.1128/AEM.57.5.1516-1522.199110.1128/AEM.57.5.1516-1522.1991 ↗
16. 10.1021/jm00036a00910.1021/jm00036a009 ↗
17. 10.7326/0003-4819-111-4-27310.7326/0003-4819-111-4-273 ↗
18. 10.1007/BF0019454610.1007/BF00194546 ↗
19. (d) Rowinsky, E. K., N. Onetto, R. M. Canetta and S. G. Arbuck. 1992. Seminars Oncol., 19:646-662;
20. 10.1002/cncr.282071044210.1002/cncr.2820710442 ↗
21. (f) Suffness, M. 1993. "Taxol: From Discovery to Therapeutic Use," in Annual Reports in Medicinal Chemistry, Vol. 28, J. A. Bristol, ed., San Diego: Academic Press, Chapter 32, pp. 305-314.
22. 12. (a) Arbuck, S. G., R. Canetta, N. Onetto and M. C. Christian. 1993. Seminars in Oncology, 20:31-39;
23. (b) Chervinsky, D. S., M. L. Brecher and M. J. Hoelcle. 1993. Anticancer Research, 13:93-96.
24. 10.1093/oxfordjournals.annonc.a05859910.1093/oxfordjournals.annonc.a058599 ↗
25. 10.1016/0140-6736(93)92789-V10.1016/0140-6736(93)92789-V ↗
26. 10.1200/JCO.1990.8.7.126310.1200/JCO.1990.8.7.1263 ↗
27. 15. (a) Seidman, A. D. 1993. Stony Brook Symposium on Taxol and Taxotere, May 14-15, Stony Brook, NY, Abstracts, pp. 14-16;
28. (b) Horowitz, S. B. Ibid., May 14-15, Stony Brook, NY, Abstracts, pp. 23-24;
29. 10.1007/BF0068555710.1007/BF00685557 ↗
30. 10.1093/jnci/85.6.47810.1093/jnci/85.6.478 ↗
31. 10.1146/annurev.bi.62.070193.00212510.1146/annurev.bi.62.070193.002125 ↗
32. 10.1021/jo00107a01010.1021/jo00107a010 ↗
33. 17. These aspects of MTX are reviewed in: (a) Albrecht, A. M. and J. M. Beilder. 1982. Folate Antagonists Ther Agents, Vol. 1, F. M. Sirotnak, J. J. Burchall, W. D. Ensminger and J. A. Montgomery, eds., Orlando, FL: Academic, pp. 317-353.
34. Ensminger, W. D. Ibid., Vol. 2, pp. 133-189;
35. (b) Bertino, J. R. 1979. Cancer Res., 39:293.
36. 18. (a) Sirotnak, F. M., D. M. Moccio, L. J. Goutas, L. E. Kelleher and J. A. Montgomery. 1982. Cancer Res., 42:924-928;
37. (b) Henderson, G. B. and B. P. Strauss. 1990. Cancer Res., 50:1709-1714;
38. (c) Westerhof, G. R., G. Jansen, N. van Emmeric, I. Kathmann, G. Rijksen, A. L. Jackman and J. H. Schornagel. 1991. Cancer Res., 51:5507-5513.
39. 19. Greenfield, R. S., T. Kaneko, T., A. Daues, M. A. Edson, K. A. Fitzgerald, L. J. Olech, J. A. Grattan, G. L. Spitalny and G. R. Braslawsky. 1990. Cancer Res., 50:6600-6607.
40. 10.1177/08839115880030010210.1177/088391158800300102 ↗
41. 10.1016/0141-8130(88)90013-X10.1016/0141-8130(88)90013-X ↗
42. (c) Hurwitz, E., M. Wilchek and J. Pitha. 1980. J. Appl. Biochem., 2:25;
43. 10.1177/08839115950100010610.1177/088391159501000106 ↗
44. 10.1002/macp.1985.02009198512510.1002/macp.1985.020091985125 ↗
45. 10.1177/08839115940090030110.1177/088391159400900301 ↗
46. (g) Calceti, P., C. Monfardini, L. Sartore, O. Schiavon, F. Bacchichetti, F. Carlassare, M. F. Veronese. 1993. Il Farmaco, 48(7):919-932.
47. 10.1002/pol.1984.17022020710.1002/pol.1984.170220207 ↗
48. 22. The stability of this compound at various pH was not explored. We found that at pH 5-7 the PEG-Dox conjugate 6 was unstable due to hydrolysis of the ester bond.
49. 23. Embelton, M. J. and M. C. Garnett. 1985. "Antibody Targeting of Anticancer Agents," in Monoclonal Antibodies for Cancer Detection and Therapy, R. W. Baldwin and V. S. Byers, eds., London: Academic Press, 317-344;
50. 10.1002/art.178031030110.1002/art.1780310301 ↗
51. 10.1111/j.1749-6632.1971.tb46953.x10.1111/j.1749-6632.1971.tb46953.x ↗
52. 10.1021/jm00202a01310.1021/jm00202a013 ↗
53. (c) Piper, J. R. and J. A. Montgomery. 1979. In Chemistry and Biology of Pteridines, R. L. Kisliuk and G. M. Brown, eds., New York: Elsevier/North Holland, pp. 261-265.
54. 10.1021/jm00144a01610.1021/jm00144a016 ↗
55. 10.1021/bk-1991-0469.ch00910.1021/bk-1991-0469.ch009 ↗
56. 10.1021/jm950475e10.1021/jm950475e ↗
57. 10.1021/bc00009a00110.1021/bc00009a001 ↗
58. 28. Zalipsky S. 1992. U.S. Patent 5 122 614