Antibody-directed enzyme prodrug therapy: A promising approach for a selective treatment of cancer based on prodrugs and monoclonal antibodies

Chemical Biology and Drug Design

Volumn 74, Issue 3, 2009, Pages 205-211

  Tietze, Lutz F ^a   Krewer, Birgit ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Antibody directed enzyme prodrug therapy; Anticancer agents; CC 1065; Duocarmycins; Glycosides; Prodrugs

Indexed keywords

BETA GALACTOSIDASE; CARMUSTINE; DOXORUBICIN; DUOCARMYCIN A; MELPHALAN; MONOCLONAL ANTIBODY; PRODRUG; RACHELMYCIN;

ANTIBODY DIRECTED ENZYME PRODRUG THERAPY; CELL SURFACE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG SCREENING; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IC 50; IMMUNOGENICITY; MOLECULAR WEIGHT; NEOPLASM; PRIORITY JOURNAL; REVIEW;

ANTIBODIES, MONOCLONAL; ANTINEOPLASTIC AGENTS; BETA-GALACTOSIDASE; CELL LINE, TUMOR; DRUG DESIGN; GLYCOSIDES; HUMANS; INDOLES; NEOPLASMS; PRODRUGS; PYRROLES; STEREOISOMERISM;

EID: 68949213822     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00856.x     Document Type: Review

References (46)

1. Parkin D.M., Bray F., Ferlay J., Pisani P. (2001) Estimating the world cancer burden: globocan 2000. Int J Cancer 94 : 153 156.
2. Kratz F., Müller I.A., Ryppa C., Warnecke A. (2008) Prodrug strategies in anticancer chemotherapy. Chem Med Chem 3 : 20 53.
3. Rautio J., Kumpulainen H., Heimbach T., Oliyai R., Oh D., Järvinen T., Savolainen J. (2008) Prodrugs: design and clinical applications. Nat Rev Drug Discov 7 : 255 270.
4. Shukla G.S., Krag D.N. (2006) Selective delivery of therapeutic agents for the diagnosis and treatment of cancer. Expert Opin Biol Ther 6 : 39 54.
5. de Albuquerque S.A.T., Chung M.C., Castro L.F., Carvalho G.R.V., Ferriera E.I. (2005) Advances in prodrug design. Mini Rev Med Chem 5 : 893 914.
6. Yoon K.J., Potter P.M., Danks M.K. (2005) Development of prodrugs for enzyme-mediated, tumor-selective therapy. Curr Med Chem Anticancer Agents 5 : 107 113.
7. Jiang T., Olsen E.S., Quyen T.N., Roy M., Jennings P.A., Tsien R.Y. (2004) Tumor imaging by means of proteolytic activation of cell-penetrating peptides. Proc Natl Acad Sci USA 101 : 17867 17872.
8. Han H.K., Amidon G.L. (2000) Targeted prodrug design to optimize drug delivery. AAPS PharmSci 2 : E6.
9. Chari R.V.J. (1998) Targeted delivery of chemotherapeutics: tumour-activated prodrug therapy. Adv Drug Deliv Rev 31 : 89 104.
10. Bagshawe K.D. (2006) Antibody-directed enzyme prodrug therapy (ADEPT) of cancer. Expert Rev Anticancer Ther 6 : 1421 1431.
11. Sharma S.K., Bagshawe K.D., Begent R.H. (2005) Advances in antibody-directed enzyme prodrug therapy. Curr Opin Investig Drugs 6 : 611 615.
12. Tietze L.F., Feuerstein T. (2003) Enzyme and proton-activated prodrugs for a selective cancer therapy. Curr Pharm Des 9 : 2155 2175.
13. Tietze L.F., Feuerstein T. (2003) Highly selective compounds for the antibody-directed enzyme prodrug therapy of cancer. Aust J Chem 56 : 841 854.
14. Nishi Y. (2003) Enzyme/abzyme prodrug activation systems: potential use in clinical oncology. Curr Pharm Des 9 : 2113 2130.
15. Jung M. (2001) Antibody directed enzyme prodrug therapy (ADEPT) and related approaches for anticancer therapy. Mini Rev Med Chem 1 : 399 407.
16. Xu G., McLeod H.L. (2001) Strategies for enzyme/prodrug cancer therapy. Clin Cancer Res 7 : 3314 3324.
17. Senter P.D., Springer C.J. (2001) Selective activation of anticancer prodrugs by monoclonal antibody-enzyme conjugates. Adv Drug Deliv Rev 53 : 247 264.
18. Syrigos K.N., Epenetos A.A. (1999) Antibody directed enzyme prodrug therapy (ADEPT): a review of the experimental and clinical considerations. Anticancer Res 19 : 605 613.
19. Senter P.D., Saulnier M.G., Schreiber G.J., Hirschberg D.L., Brown J.P., Hellström I., Hellström K.E. (1988) Anti-tumor effects of antibody-alkaline phosphatase conjugates in combination with etoposide phosphate. Proc Natl Acad Sci USA 85 : 4842 4846.
20. Bagshawe K.D. (1987) Antibody directed enzymes revive anti-cancer prodrugs concept. Br J Cancer 56 : 531 532.
21. Cheng T.L., Wei S.L., Chern B.M., Wu M.F., Liu P.W., Roffler S.R. (1999) Bystander killing of tumour cells by antibody-targeted enzymatic activation of a glucuronide prodrug. Br J Cancer 79 : 1378 1385.
22. Prescott D.M., Charles H.C., Poulson J.M., Page R.L., Thrall D.E., Vujaskovic Z., Dewhirst M.W. (2000) The relationship between intracellular and extracellular pH in spontaneous canine tumors. Cancer Res 6 : 2501 2505.
23. Kratz F., Beyer U., Schütte M.T. (1999) Drug-polymer conjugates containing acid-cleavable bonds. Crit Rev Ther Drug Carrier Syst 16 : 245 288.
24. Vol'pin M., Levitin E., Osinski S. (1996) New course in the search for antitumor agents: the use of pH-dependent sources of reactive radicals. Angew Chem Int Ed Engl 35 : 2395 2396.
25. Tietze L.F., Beller M. (1990) Development of selective anticancer agents. Synthesis of acetal β-glucosides from cytotoxic alcohols. Liebigs Ann Chem 6 : 587 591.
26. Tietze L.F., Beller M., Fischer R., Lögers M., Jähde E., Glüsenkamp K., Rajewsky M.F. (1990) Development of custom-made, acid-catalytically activatable cytostatics for selective tumor therapy. Angew Chem Int Ed Engl 29 : 782 783.
27. Tannock I.F., Rotin D. (1989) Acid pH in tumors and its potential for therapeutic exploitation. Cancer Res 49 : 4373 4384.
28. Tietze L.F., Fischer R. (1981) Stereoselective synthesis of β-glucosides with 1,1′-diacetal structure. Angew Chem Int Ed Engl 20 : 696 970.
29. Warburg O. (1956) On respiratory impairment in cancer cells. Science 124 : 269 270.
30. Martin D.G., Biles C., Gerpheide S.A., Hanka L.J., Krueger W.C., McGovren J.P., Mizsak S.A., Neil G.L., Stewart J.C., Visser J. (1981) CC-1065 (NSC 298223), a potent new antitumor agent improved production and isolation, characterization and antitumor activity. J Antibiot 34 : 1119 1125.
31. Ichimura M., Ogawa T., Takahashi K., Kobayashi E., Kawamoto I., Yasuzawa T., Takahashi I., Nakano H. (1990) Duocarmycin, a new antitumor antibiotic from streptomyces sp. J Antibiot 43 : 1037 1038.
32. Tietze L.F., Krewer B., Frauendorf H., Major F., Schuberth I. (2006) Investigation of reactivity and selectivity of DNA-alkylating duocarmycin analogues by high-resolution mass spectrometry. Angew Chem 118 : 6720 6724
33. Angew Chem Int Ed Engl;45:6570-6574.
34. Boger D.L., Johnson D.S. (1996) CC-1065 and the duocarmycins: understanding their biological function through mechanistic studies. Angew Chem Int Ed Engl 35 : 1438 1474.
35. Tietze L.F., Schuster H., Krewer B., Schuberth I. (2009) Synthesis and biological studies of different duocarmycin based glycosidic prodrugs for their use in the antibody-directed enzyme prodrug therapy. J Med Chem 52 : 537 543.
36. Tietze L.F., von Hof J.M., Krewer B., Müller M., Major F., Schuster H.J., Schuberth I., Alves F. (2008) Asymmetric synthesis and biological evaluation of new glycosidic prodrugs for a selective cancer therapy. ChemMedChem 3 : 1946 1955.
37. Tietze L.F., Schuster H.J., Schmuck K., Schuberth I., Alves F. (2008) Duocarmycin-based prodrugs for cancer prodrug monotherapy. Bioorg Med Chem 16 : 6312 6318.
38. Tietze L.F., Panknin O., Krewer B., Major F. (2008) Synthesis and biological evaluation of a novel pentagastrin-toxin conjugate designed for a targeted prodrug monotherapy of cancer. Int J Mol Sci 9 : 821 837.
39. Tietze L.F., Major F., Schuberth I., Spiegl D.A., Krewer B., Maksimenka K., Bringmann G., Magull J. (2007) Selective treatment of cancer: synthesis, biological evaluation and structural elucidation of novel analogues of the antibiotic CC-1065 and the duocarmycins. Chem Eur J 13 : 4396 4409.
40. Tietze L.F., Major F., Schuberth I. (2006) Antitumor agents: development of highly potent glycosidic duocarmycin analogues for selective cancer therapy. Angew Chem 118 : 6724 6727
41. Angew Chem Int Ed Engl;45:6574-6577.
42. Tietze L.F., Schuster H.J., Hampel S.M., Rühl S., Pfoh R. (2008) Enantio- and diastereoselective synthesis of duocarmycin-based prodrugs for a selective treatment of cancer by epoxide opening. Chem Eur J 14 : 895 901.
43. Tietze L.F., Major F. (2006) Synthesis of new water-soluble DNA-binding subunits for analogues of the cytotoxic antibiotic CC-1065 and their prodrugs. Eur J Org Chem 10 : 2314 2321.
44. Tietze L.F., Krewer B., Frauendorf H. (in press) Investigation of the transformations of a novel anticancer agent combining HPLC, HPLC-MS and direct ESI-HRMS analyses. Anal Bioanal Chem.
45. Milbank J.B.J., Tercel M., Atwell G.J., Wilson W.R., Hogg A., Denny W.A. (1999) Synthesis of 1-substituted 3-(chloromethyl)-6-aminoindoline (6-amino-seco-CI) DNA minor groove alkylating agents and structure-activity relationships for their cytotoxicity. J Med Chem 42 : 649 658.
46. Zientkowska M. (2007) Evaluierung des Antibody Directed Enzyme Prodrug Therapy-Konzeptes im Mammakarzinom- und Lymphom-Mausmodell. PhD Thesis, Göttingen.