Enzyme and proton-activated prodrugs for a selective cancer therapy

Current Pharmaceutical Design

Volumn 9, Issue 26, 2003, Pages 2155-2175

  Tietze, L F ^a   Feuerstein, T ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

ADEPT; Antitumor agents; Cancer therapy; Enzymes; Glycosides; Monoclonal antibodies; Prodrugs

Indexed keywords

ALKYLATING AGENT; ANTINEOPLASTIC AGENT; ASCORBIC ACID DERIVATIVE; CALICHEAMICIN; CAMPTOTHECIN; CARBOXYPEPTIDASE A; CARBOXYPEPTIDASE G2; CHLORMETHINE; CISPLATIN; CYCLOPHOSPHAMIDE; CYTOTOXIC AGENT; DOCETAXEL; DOXORUBICIN; ETOPOSIDE; FLOXURIDINE; FLUOROURACIL; FLUOROURIDINE; GLYCOSIDE; HAPTEN ANTIBODY; MITOMYCIN; MONOCLONAL ANTIBODY; PHOSPHORAMIDE MUSTARD; PRODRUG; RACHELMYCIN; TUMOR ANTIGEN; UNINDEXED DRUG; VINCA ALKALOID; ZINOSTATIN;

ANTIBODY DIRECTED ENZYME PRODRUG THERAPY; ANTINEOPLASTIC ACTIVITY; CANCER CHEMOTHERAPY; CANCER TISSUE; CATALYSIS; CONCENTRATION (PARAMETERS); DRUG ACTIVATION; DRUG CONJUGATION; DRUG DEGRADATION; DRUG DESIGN; DRUG HYDROLYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HYPERGLYCEMIA; NONHUMAN; PRIORITY JOURNAL; RETROSPECTIVE STUDY; REVIEW;

ANIMALS; ANTIBODIES, MONOCLONAL; ANTIGENS, NEOPLASM; CELL SURVIVAL; ENZYMES; HUMANS; NEOPLASMS; PRODRUGS; PROTONS; TUMOR CELLS, CULTURED;

EID: 0141538127     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/1381612033454072     Document Type: Review

References (97)

1. Chen W, Metha SC, Lu DR, Adv Drug Delivery Rev 1997; 26: 231-247.
2. Tietze LF, Bothe U, Griesbach U, Nakaichi M, Hasegawa T, et al. Chem Bio Chem 2001; 2: 326-334.
3. Tietze LF, Bothe U, Griesbach U, Nakaichi M, Hasegawa T, Nakamura H, et al. Bioorg Med Chem 2001; 9: 1747-1752.
4. Awada A, Piccart M. Curr Opin Oncol 2000; 12: 289-296, cit lit.
5. Danesi R, De Braud F, Fogli S, Di Palo A, Del Tacca, M. Trends Pharmacol Sci 2001; 22: 420-426, cit. lit.
6. Boon T, Coulie PG, Van den Eynde B. Immunology Today 1997; 18: 267-268.
7. Cander PC. Nutr Rev 1998; 56, 70-83.
8. Schott ME, Schlom J, Siler K, Milenic DE, Eggensperger D, Cheng R, et al. Cancer 1994; 73: 993-998.
9. Safa M, Foon KA. Semin Oncol 2001; 28: 68-92.
10. Warburg O. The Metabolism of Tumors, Constable London, 1930.
11. Mazurek S, Grimm H, Wilker S, Leib S, Eigenbrodt E. Anticancer Res 1998; 18: 3275-3282.
12. Schneider F. Naturwissenschaften 1981; 68: 20.
13. Tannock IF, Rotin D. Cancer Res 1989; 49: 4373-4384.
14. Jähde E, Rajewsky MF.Cancer Res 1982; 42: 1505-1512.
15. Montcourrier P, Silver I, Farnoud R, Bird I, Rochefort H. Clin Exp Metastasis 1997; 15: 382-392.
16. Tietze LF, Keim H. Angew Chem 1997; 109: 1704-1706 Angew Chem Int Ed Engl 1997; 36: 1615-1617.
17. Tietze LF, Keim H, Janßen CO, Tappertzhofen C, Olschimke J. Chem Eur J 2000; 6: 2801-2808.
18. Kawashima I, Kotani M, Ozawa H, Suzuki M, Tai T. Int J Cancer 1994; 58: 263-268.
19. Hakamori S-I. Cancer Res 1996; 56: 5309-5318.
20. Hakomori S-I, Zhang Y. Chem Biol 1997; 4: 79-90.
21. Hakomori S-I, Yamamura S, Handa KK. Annu New York Acad Sci 1998; 845: 1-10.
22. Jungheim LN, Shepherd TA. Chem Rev 1994; 94: 1553-1566.
23. Springer CJ, Niculescu-Duvaz I. Adv Drug Deliv Rev 1997; 26: 151-172.
24. Syrigos KN, Epenetos AA. AntiCancer Res 1999; 19: 605-614.
25. Dubowchik GM, Walker MA. Pharmacol Ther 1999; 83: 67-123.
26. Denny WA. Eur J Med 2001; 36: 577-95.
27. Tietze LF. in E. Borowski D. Shugar (Hrsg.): Molecular Aspects of Chemotherapy, Pergamon Press, Oxford 1990.
28. Tietze LF, Nachr Chem Tech Lab 1988; 36: 728-737.
29. de Groot ACW, de Bart JH, Verheijen HW. Scheeren J. Med Chem 1999; 42: 5277-5283.
30. Trouet A, Passioukov A, Van Derpoorten K, Fernandez A-M, Abarca-Quinones J, Baurain R, et al. Cancer Res 2001; 61: 2843-2846.
31. Prescott D, Charles HC, Poulson JM, Page RL, Thrall DE, Vujaskovic Z, et al. Clinical Cancer Res 2000; 6: 2501-2505.
32. Osinsky S, Bubnovskaja L, Sergienko T. AntiCancer Res 1987; 7: 199-201.
33. Kozin SV, Shkarin P, Gerweck LE. Cancer Res 2001; 61: 4740-4743 and cited papers therein.
34. Yamagata M, Tannock IF. Br J Cancer 1996; 73: 1328-1334.
35. Schulze W, Horn H. Arzneim Forsch 1970; 20: 329-335.
36. Riley PA. Chem Biol Interactions 1980; 31: 73-80.
37. Hohorst H-J, Bielicki L, Voelcker The enzymatic basis of cyclophosphamide specifity, G. Weber (Hrsg.), Advances in Enzyme Regulation 25, 1986; 99.
38. Tietze LF, Fischer R. Angew Chem 1981; 93: 1002; Angew Chem Int Ed Engl 1981; 20: 969-970.
39. Tietze LF, Fischer R, Guder H-J. Synthesis 1982; 946-948.
40. Tietze LF, Beller M, Liebigs Ann Chem 1990; 587-591.
41. Tietze LF, Neumann M, Möllers T, Fischer R, Glüsenkamp K-H, Rajewsky ME, et al. Cancer Research 1989; 49: 4179-4184.
42. Tietze LF, Fischer-Beller A. Carbohydrate Research 1994; 254: 169-182.
43. Tietze LF, Beller M, Fischer R, Lögers M, Jähde E, Glüsenkamp KH, et al. Angew Chem 1990; 102: 812-813; Angew Chem Int Ed Engl 1990; 29: 782-783.
44. Tietze LF, Jähde E, Rajewski MF, unpublished results.
45. Chabner BA, Collins JM. Cancer Chemotherapy: Prinziples and Practice, JB. Lippincott Co, Philadelphia 1990.
46. Rutman RJ,Cantarow A, Paschkis KE. Cancer Res 1954; 14: 119.
47. Walliser S,Redmann K. Cancer Res 1978; 38: 3555-3559.
48. Tietze LF, Lögers M, unpublished results.
49. Vol'pin M, Levitin I, Osinsky S. Angew Chem 1996; 108: 2516-2518; Angew Chem Int Ed 1996; 35: 2395-2396.
50. Sperker B, Backman JT, Kroemer HK. Clin Pharmacokinet 1997; 33: 18-31.
51. Yamashita Y-I, Ogawa M. Int J Oncol 1997; 10; 807-813.
52. Ruening U, Magdolen V, Wilhelm O, Fischer K, Lutz V, Graeff H, et al. Int J Oncol 1998; 13: 893-906.
53. Andreasen PA, Kjøller L, Christensen L, Duffy MJ. Int J Cancer 1997; 72: 1-22.
54. Duffy MJ. Adv Clin Chem 1996; 32: 136-166.
55. Leenders RGG, Damen FWP, Bijsterfeld EJA, Scheeren HWP, Houba HJ. Bioorganic & Medicinal Chemistry 1999; 7: 1597-1610.
56. de Groot FMH, de Bart ACW, Verheijen JH, Scheeren HW. J Med Chem 1999; 42: 5277-5283.
57. Trouet A, Passioukov A, Van derpoorten K, Fernandez A-M, Abarca-Quinones J, Baurain R, et al. Cancer Research 2001; 61: 2843-2846.
58. Wick B, Groner B. Cancer Lett 1997; 118: 161-172.
59. Buchsbaum DJ, Lawrence TS. Targeted Diagn Ther 1990; 3: 215-255.
60. Bagshawe KD. Br J Cancer 1987; 56: 531-532.
61. Engert A, Diehl V. Der Internist 2001; 42: 801-802, and whole issue.
62. Napier MP, Sharma SK, Springer CJ, Bagshawe KD, Green AJ, Martin J, et al. Clinical Cancer Research 2000; 6: 765-772.
63. Martin J,Stribbling SM, Poon GK, Begent RHJ, Napier M, Sharma SK, et al. Cancer Chemother Pharmacol 1997; 40: 189-201.
64. Springer CJ, Dowell R, Burke PJ, Hadley E, Davis DH, Blakey DC, et al. Med Chem 1995; 38: 5051-5065.
65. Blakey DC, Burke PJ, Davies DH, Dowell RI, East SJ, Eckersley KP, et al. Cancer Res 1996; 56: 3287-3292.
66. Pedley RB, Sharma SK, Boxer GM, Boden R, Stribbling SM, Davies L, et al. Cancer Research 1999; 59: 3998-4003.
67. Khan TH, Eno-Amooquave EA, Searle F, Browne PJ, Osborn HMI, Burke PJ. J Med Chem 1999; 42: 951-956.
68. Wentworth P, Datta A, Blakey D, Boyle T, Partridge LJ, Blackburn GM. Proc Natl Acad Sci USA 1996; 93: 799-803.
69. Rosenblum JS, Lo L-C, Li T, Janda KD, Lerner RA, Angew Chem 1995; 107: 2448-2450; Angew Chem Int Ed Engl 1995; 34: 2275-2277.
70. Svensson HP, Kadow JF, Vrudhula VM, Wallace PM, Senter PD. Bioconjug Chem 1992; 3: 176-181.
71. Leu YL, Roffler SR, Chern J-W. J Med Chem 1999; 42: 3623-3628.
72. Madec-Lougerstay R, Florent J-C, Monneret C. J Chem Soc Perkin Trans 1 1999, 1369-1375.
73. Florent J-C, Dong X, Gaudel G, Mitaku S, Monneret C, Gesson J-P, et al. J Med Chem 1998; 41: 3572-3581.
74. Syrigos KN, Rowlinson-Busza G, Epenetos A. A Int J Cancer 1998; 78: 712-719.
75. Reviews: Boger DL, Johnson DS. Angew Chem 1996; 108: 1542-1580; Angew Chem Int Ed Engl 1996; 35: 1438-1474.
76. Boger DL, Garbaccio RM. Acc Chem Res 1999; 32: 1043-1052.
77. Ichimura M, Ogawa T, Takahashi K, Kobayashi E, Kawamoto I, Yasuzawa T, et al. Antibiot 1990; 43: 1037-1038.
78. Tietze LF, Hannemann R, Buhr W, Lögers M, Menningen P, Lieb M, et al. Angew Chem 1996; 108: 2840-2842; Angew Chem Int Ed Engl 1996; 35: 2674-2677.
79. Schmidt RR. Angew Chem 1986; 98: 213-236; Angew Chem Int Ed Engl 1986; 25: 212-235.
80. Dullenkopf W, Castro-Palomino JC, Manzoni L, Schmidt RR. Carbohydr Research 1996; 296: 135-147.
81. Appel R. Angew Chem 1975; 87: 863-874; Angew Chem Int Ed Engl 1975; 15: 801-812.
82. Tietze LF, Lieb M, Herzig T, Haunert F, Schuberth I. Bioorg Med Chem 2001; 9: 1929-1939.
83. Sakamoto T, Kondo Y, Uchiyama M, Yamanaka H. J Chem Soc Perkin Trans I 1993; 1941-1942.
84. Boger DL, Boyce CW, Garbaccio RM, Goldberg JA. Chem Rev 1997; 97: 787-828.
85. Boger DL, Boyce SW, Garbaccio RM, Searcey M, Jin Q. Synthesis 1999; 1505-1509.
86. Warpehoski MA. Tetrahedron Lett 1986; 27: 4103-4106.
87. Rajeswari S, Adesomoju AA, Cava MPJ. Heterocycl Chem 1989; 20: 557-564.
88. Boger DL, Yun W, Han N. Bioorg Med Chem 1995; 3: 1429-1453.
89. Tietze LF, Herzig T, Fecher A, Haunert F. Schuberth I. ChemBioChem 2001; 758-765.
90. Tietze LF, Herzig T, unpublisched results.
91. Tietze LF, Feuerstein T, Fecher A, Haunert F, Panknin O, Borchers U, et al. Angew Chem 2002; 114: 785-787; Angew Chem Int Ed Engl 2002; 41: 759-761.
92. Alves F, Borchers U, Pladge B, Augustin H, Nebendahl K, Klöppel G, et al. Cancer Letters 2001; 165: 161-170.
93. Denny WA, Curr Med Chem 2001; 8: 533-544.
94. de Graaf M, Boven F, Scheeren HW, Haisma HJ, Pinedo HM. Beta-glucuronidase-mediated drug release. Curr Pharm Des 2002; 8(15): 1391-403.
95. Jackson DY. Alpha 4 integrin antagonists. Curr Pharm Des 2002; 8(14): 1229-53.
96. Jones GB, Fouad FS. Designed enediyne antitumor agents. Curr Pharm Des 2002; 8(27): 2415-40.
97. Wardman P. Indole-3-acetic acids and horseradish peroxidase: a new prodrug/enzyme combination for targeted cancer therapy. Curr Pharm Des 2002; 8(15): 1363-74.