Estramustine in malignant glioma

Journal of Neuro-Oncology

Volumn 30, Issue 1, 1996, Pages 81-89

  Bergenheim, A Tommy ^a   Henriksson, Roger ^a   Piepmeier, Joseph M ^b   Yoshida, Daizo ^c  

^a UMEÅ UNIVERSITY   (Sweden)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c NIPPON MEDICAL SCHOOL   (Japan)

Author keywords

Astrocytoma; Carbamate ester; Chemotherapy; Estramustine; Glioma

Indexed keywords

ANTINEOPLASTIC AGENT; ESTRAMUSTINE;

ADVANCED CANCER; ANIMAL EXPERIMENT; ANIMAL MODEL; APOPTOSIS; ASTROCYTOSIS; BIOACCUMULATION; CELL CULTURE; CONCENTRATION RESPONSE; DNA SYNTHESIS; DRUG BINDING SITE; GLIOBLASTOMA; GLIOMA CELL; HUMAN; HUMAN CELL; MITOSIS; NONHUMAN; PROSTATE CARCINOMA; REVIEW; UROGENITAL TRACT DISEASE; VEIN THROMBOSIS;

EID: 0029834460     PISSN: 0167594X     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00177446     Document Type: Review

References (79)

1. Sheline GE: Radiotherapy for high grade gliomas. Int J Radiation Oncology Biol Phys 18: 793-803, 1990
2. Salford LG, Brun A, Nirfalk S: Ten-year survival among patients with supratentorial astrocytomas grade III and IV. J Neurosurg 69: 506-509, 1988
3. Stenning SP, Freedman LS, Bleehen NM: An overview of published results from randomized studies of nitrosoureas in primary high grade malignant glioma. Br J Cancer 56: 89-90, 1987
4. Kornblith PL, Walker M: Chemotherapy for malignant gliomas. J Neurosurg 68: 1-17, 1988
5. Fine HA: The basis for current treatment recommendations for malignant gliomas. J Neuro-Oncol 20: 111-120, 1994
6. von Schoultz E, Lundblad D, Bergh J, Grankvist K, Henriksson R: Estramustine binding protein and anti-proliferative effect of estramustine in human glioma cell lines. Br J Cancer 58: 326-329, 1988
7. von Schoultz E: Malignant glioma. Experimental studies with an estrogen-linked cytostatic. Doctoral dissertation, Umeȧ University, 1990
8. Piepmeier JM, Keefe DL, Weinstein MA, Yoshida D, Zielinski J, Lin TT, Chen Z, Naftolin F: Estramustine and estrone analogs rapidly and reversibly inhibit deoxyribonucleic acid synthesis and alter morphology in cultured human glioblastoma cells. Neurosurg 32: 422-431, 1993
9. Bergenheim AT: Estramustine-binding protein and cytotoxic effect of estramustine in glioma. Doctorial dissertation, Umeȧ University, 1994
10. Bergenheim AT, Elfverson J, Gunnarsson PO, Hartman M, Henriksson R: Cytotoxic effect and uptake of estramustine in a rat glioma model. Int J Oncol 5: 293-299, 1994
11. von Schoultz E, Bergenheim T, Grankvist K, Björk P, Henriksson R: Estramustine binding protein in human brain tumor tissue. J Neurosurg 74: 962-964, 1991
12. Bergenheim AT, Björk P. Bergh J, von Schoultz E, Svedberg H, Hendriksson R: Estramustine-binding protein and specific binding of estramustine in astrocytoma. Cancer Res 54: 4974-4979, 1994
13. Bergenheim AT, Gunnarsson PO, Edman K, von Schoultz E, Hariz MI, Henriksson R: Uptake and retention of estramustine and the presence of estramustine-binding protein in malignant brain tumors in humans. Br J Cancer 67: 358-361, 1993
14. Bergenheim AT, Zackrisson B, Elfverson J, Henriksson R: Synergism between estramustine and radiotherapy in a rat glioma model. (Abstract) J Neuro-Oncol (Suppl) 15: S3, 1993
15. Yoshida D, Piepmeier J, Weinstein M: Estramustine sensitizes human glioblastoma cells to irradiation. Cancer Res 54: 1415-1417, 1994
16. Bergenheim AT, Zackrisson B, Elfverson J, Henriksson R: Radiosensitizing effect of estramustine in gliomas in vitro and in vivo. J Neuro-Oncol 23: 191-200, 1995
17. Folca PJ, Glascock RF, Irvine WT: Studies with tritium-la-belled hexoestrol in advanced breast cancer. Lancet 2: 796, 1961
18. Fex H, Högberg B, Könyves I: Estramustine phosphate - historical review. J Urol 23: 4-5, 1984
19. Groupe European du Cancer du Sein: Essai clinique du phénol bis(2-chloroéthyl)carbamate d'oestradiol dans le cancer mammaire en phase avancée. Eur J Cancer 5: 1-4, 1969
20. Plym-Forshell G, Nilsson H: The distribution of radioactivity after administration of labelled estramustine phosphate (Estracyt), estradio-17β-phosphate and estradiol to rats. Acta Pharmacol Toxicol 35 (Suppl 1): 28, 1974
21. Jönsson G: Cytotoxic agents in the treatment of prostatic carcinoma. Life Sci Monogr 1: 145-159, 1969
22. Klein D: Behandlung mit estramustinphosphat bei fortgeschrittenen Prostatacarcinomen. Wiener Medizinische Wochenschrift 122: 458-460, 1971
23. Lindberg B: Treatment of rapidly progressing prostatic carcinoma with estracyt. J Urol 108: 303-306, 1972
24. Forsgren B, Björk P, Carlström K, Gustafsson J-Ȧ, Pousette Ȧ, Högberg B: Purification and distribution of a major protein in rat prostate that binds estramustine, a nitrogen mus-tard derivate of estradiol-17β. Proc Natl Acad Sci 76: 3149-3153, 1979
25. Björk P, Forsgren B, Gustafsson J-Ȧ, Pousette Ȧ Högberg B: Partial characterization and 'quantitation' of a human prostatic estramustine binding protein. Cancer Res 42: 1935-1942, 1982
26. Forsgren B, Björk P: Specific binding of estramustine to prostatic proteins. Urology 23 (suppl 6): 34-38, 1984
27. Tew K, Hartley-Asp B: Cytotoxic properties of estramustine unrelated to alkylating and steroid constituents. J Urol 23: 28-33, 1984
28. Tew KD, Stearns ME: Hormone-independent, non-alkylating mechanism of cytotoxicity for estramustine. Urol Res 15: 155-160, 1987
29. Dixon R, Brooks M, Gill G: Estramustine phosphate: plasma concentrations of its metabolites following oral administration to man, rat, and dog. Res Comm Chem Pathol Pharmacol 27: 17-29, 1980
30. Andersson SB. Gunnarsson PO, Nilsson T, Plym-Foshell G: Metabolism of estramustine phosphate in patients with prostatic carcinoma. Eur J Drug Metab Pharmacoki 6: 149-154, 1981
31. Gunnarsson P-O, Plym-Forshell G, Fritjofsson Ȧ, Norlén BJ: Plasma concentrations of estramustine phosphate and its major metabolites in patients with prostatic carcinoma treated with different doses of estramustine phosphate (Estracyt®). Scand J Urol Nephrol 15: 201-206, 1981
32. Gunnarsson PO, Andersson S-B, Johansson S-A, Nilsson T, Plym-Forshell G: Pharmacokinetics of estramustine phosphate (Estracyt®) in prostatic cancer patients. Eur J Clin Pharmacol 26: 113-119, 1984
33. Gunnarsson PO, Davidsson T, Andersson S-B, Johansson S-A: Impairment of estramustine phosphate absorption by concurrent milk and food intake. Eur J Clin Pharmacol 38: 189-193, 1990
34. Björk P, Fritjofsson Ȧ, Hartley-Asp B: Uptake and binding of estramustine and estromustine, metabolites of estramustine phosphate (Estracyt), in the human prolate, and new aspects on the cytotoxic activity of estramustine phosphate in vitro. In: Harzmann R (ed) Experimentelle Urologie. Springer-Verlag, Berlin-Heidelberg, 1985, pp 341-353
35. Björk P, Flücher S, Neide H: Estramustine-binding protein - a marker for effect of therapy in prostatic carcinoma? Scand J Urol Nephrol Suppl 107: 59-64, 1988
36. Kruse E, Hartley-Asp B: Uptake and metabolism of estramustine in the Dunning R3327H tumor. In vivo 2: 371-376, 1988
37. Norlén BJ, Andersson S-B, Björk P, Gunnarsson PO, Fritjofsson A: Uptake of estramustine phosphate (Estracyt) metabolites in prostatic cancer. J Urology 140: 1058-1062, 1988
38. Flüchter SH, Neide HJ, Björk P, Müntzing J, Bichler K-H: Effect of treatment on the expression of estramustine-binding protein (EMBP) in prostatic cancer patients: An immunohistochemical study. Prostate 14: 27-43, 1989
39. Forsgren B, Gustafsson J-A, Pousette Ȧ, Hogberg B: Bind-ing characteristics of a major protein in rat ventral prostate cytosol that interacts with estramustine, a nitrogen mustard derivate of 17β-estradiol. Cancer Res 39: 5155-5164, 1979
40. Högberg B, Björk P, Carlström K, Forsgren B, Gustafsson J-Ȧ, Hökfelt T, Pousette A: The interaction of steroidal alkylating agents with binding components in the soluble fraction of the prostate. In: Prostate cancer and hormone receptors. Alan R. Liss Inc, 1979, pp 181-199
41. Stearns M, Tew K: Antimicrotubule effects of estramustine, an antiprostatic tumor drug. Cancer Res 45: 3891-3897, 1985
42. Wallin M, Deinum J, Hartley-Asp B: Estramustine phosphate inhibits microtubule assembly by binding to the microtubule-associated proteins. Ann NY Acad Sci 466: 423-425, 1986
43. Stearns M, Tew K: Estramustine binds to MAP-2 to inhibit microtubule assembly in vitro. J Cell Sci 89: 331-342, 1988
44. Moraga D, Rivas-Berrios A, Farìas G, Wallin M, Maccioni RB: Estramustine-phosphate binds to a tubulin binding domain on microtubule-associated proteins MAP-2 and TAU. Biochem Biophys Acta 1121: 97-103, 1992
45. Dahllöf B, Billström A, Cabral F, Hartley-Asp B: Estramustine depolymerizes microtubules by binding to tubulin. Cancer Res 53: 4573-4581, 1993
46. von Schoultz E, Lundgren E, Hendriksson R: Effects of estramustine and its constituents on human malignant glioma cells. Anticancer Res 10: 693-696, 1990
47. von Schoultz E, Grankvist K, Gustavsson H, Henriksson R: Effects of estramustine on DNA and cell membrane in malignant glioma cells. Acta Oncol 30: 719-723, 1991
48. Engström KG, Grankvist K, Henriksson R: Early morphological detection of estramustine cytotoxicity measured as alteration in cell size and shape by a new technique of microperifusion. Eur J Cancer 27: 1288-1295, 1991
49. Henriksson R, Bjermer L, von Schoultz E, Grankvist K: The effect of estramustine on microtubuli is different from the direct action via oxygen radicals on DNA and cell membrane. Anticancer Res 10: 303-310, 1990
50. Vallbo C, Bergenheim T, Bergh A, Grankvist K, Henriksson R: DNA fragmentation induced by the antimitotic drug estramustine in malignant rat glioma but not in normal brain - suggesting an apoptotic cell death. Br J Cancer 71: 717-720, 1995
51. Sandström PE, Jonsson Ö, Grankvist K, Henriksson R: Identification of potassium flux pathways and their role in the cytotoxicity of estramustine in human malignant glioma, prostatic carcinoma, and pulmonary carcinoma cell lines. Eur J Cancer 12: 1822-1826, 1994
52. von Schoultz E, Gunnarsson PO, Henriksson R: Uptake, metabolism and proliferative effect of estramustine phosphate in human glioma cell lines. Anticancer Res 9: 1713-1716, 1989
53. Yoshida D, Cornell-Bell A, Piepmeier JM: Selective antimitotic effects of estramustine correlate with its antimicrotubule properties on glioblastoma and astrocytes. Neurosurgery 34: 863-868, 1994
54. Hartley-Asp B, Gunnarsson PO: Growth and cell survival following treatment with estramustine, nor-nitrogen mustard, estradiol and testosterone of a human prostatic cancer cell line (DU 145). J Urol 127: 818-822, 1982
55. Piepmeier JM, Pedersen PE, Greer CA: Immunohistochemical analysis of estramustine binding protein in astrocytes and glioblastoma. (Abstract). J Neuro-Oncol 19: 179, 1994
56. Heyns W, Peeters B, Mous J, Rombauts W, De Moor P: Purification and characterisation of prostatic binding protein and its subunits. Eur J Biochem 89: 181-186, 1978
57. Eklöv S, Larsson A, Björk P, Nilsson S: The expression of estramustine-binding protein in the human prostatic cancer cell line DU 145 is not androgen dependent. Scand J Urol Nephrol 26: 119-125, 1992
58. Bergenheim AT, Hartman M, Bergh J, Ridderheim P-Ȧ, Henriksson R: Expression of estramustine-binding protein in ependymomas and in human and developing rat ependymal cells. J Neuro-Oncol 22: 45-53, 1994
59. Bergenheim AT, Karlsson AE, Stȧhl A, Sandström J, Hartman M, Henriksson R: Prognostic implication of estramustine-binding protein in astrocytoma. Int J Oncol 7: 349-352, 1995
60. Sinclair WK, Morton RA: X-ray sensitivity during the cell generation cycle of cultured Chinese hamster cells. Radiat Res 29: 450-474, 1966
61. Kim JH, Khil MS, Kim SH, Ryu S, Gabel M: Clinical and biological studies of estramustine as a novel radiation sensitizer. Int J Radiat Oncol Biol Phys 29: 555-557, 1994
62. Ruy S, Gabel M, Khil MS, Lee YJ, Kim SH, Kim JH: Estramustine: a novel radiation enhancer in human carcinoma cells. Int J Radiat Oncol Biol Phys 30: 99-104, 1994
63. Widmark A, Bergh A, Damber J-E, Henriksson R: Estramustin potentierar strȧleffekten av prostatacancer hos rȧtta. (Abstract) Swedish Medical Society Annual Meeting, 1991, p 268
64. Ekläv S, Essand M, Carlsson J, Nilsson S: Radiation sensitization by estramustine. Studies in cultured human prostatic cancer cells. The Prostate 21: 287-295, 1992
65. Widmark A, Damber J-E, Bergh A, Henriksson R: Estramustine potentiates the effects of irradiation on the Dunning (R3327) rat prostatic adenocarcinoma. Prostate 24: 79-83, 1994
66. Littbrand B, Révész L: The effect of oxygen on cellular survival and recovery after radiation. Br J Radiol 42: 914-924, 1969
67. Grankvist K, von Schoultz E, Henriksson R: New aspects on the cytotoxicity of estramustine-involvement of free-oxygen radicals. Int J Exp Clin Chemother 1: 37-42, 1988
68. Gupta R: Cross-resistance of nocodazole-resistant mutants of CHO cells toward other microtubule inhibitors: Similar mode of action of benzimidazole carbamate derivatives and NSC 181928 and TN-16. Molec Pharmacol 30: 142-148, 1986
69. McMillin JM, Seal US, Doe RP: Effect of oral estramustine phosphate on pituitary, gonodal, and adrenal function in the green monkey. Invest Urol 15: 151-154, 1977
70. Küss R, Khoury S, Richard F, Fourcade F, Frantz P, Capelle JP: Estramustine phosphate in the treatment of advanced prostatic cancer. Br J Urol 52: 29-33, 1980
71. Lerclercq G, Heuson J-C: Biochemical assays for the selection of cytotoxic-linked estrogens with potential therapeutic activity. Cancer Treat Rep 62: 1255-1257, 1978
72. Korfsmeier K-H, Schulte-Fischediek R: Effects of estramustin phosphate on hypothalamus and hypophysis of the rat. Abstract. Acta Anatomica 111: 78, 1981
73. Müntzing J, Gunnarsson K: Preclmical pharmacology and toxicology of estramustine phosphate. Urology 23 (suppl 6): 6-10, 1984
74. Slack NH, Murphy GP: Clinical toxicity and long-term results of Emcyt therapy for prostatic cancer. Urology (Suppl) 23: 73-77, 1984
75. Blombäck M, Hedlund PO, Säwe U: Thrombosis Res 49: 11-121, 1988
76. Sawaya R, Zuccarello M, Elkalliny M, Nishiyama H: Post-operative venous thromboembolism and brain tumors: part I. Clinical profile. J Neuro-Oncol 14: 119-125, 1992
77. Kjaer TB, Nilsson T, Madson PO: Effect of estramustine phosphate on plasma testosterone during treatment of carcinoma of the prostate. Urology 5: 802-804, 1975
78. Sumi N, Yoshida H, Nakai K, Fujimoto S, Kameyama K, Nishiguchi Y, Tawaratani T, Yanagawa H, Nagasawa H, Enomoto H: Estramustine phosphate disodium (EMP). Oyo Yakuri 20: 757-802, 1980
79. Sumi N, Kameyama K, Nishiguchi Y, Fujimoto S, Tawaratani T, Nagasawa H, Enomoto H: Estramustine phosphate disodium (EMP). Oyo Yakuri 21: 549-586, 1981