Hypoxia-specific cytotoxins in cancer therapy

Seminars in Radiation Oncology

Volumn 6, Issue 1, 1996, Pages 22-36

  Brown, J M ^a   Siim, B G ^a  

^a STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 BROMOETHYLAMINO) 3 (2 NITRO 1 IMIDAZOLYL) 2 PROPANOL; 1 AZIRIDINO 3 (2 NITRO 1 IMIDAZOLYL) 2 PROPANOL; 5 (1 AZIRIDINYL) 3 HYDROXYMETHYL 2 (3 HYDROXY 1 PROPENYL) 1 METHYL 4,7 INDOLEDIONE; AROMATIC NITRO COMPOUND; CYTOTOXIN; MITOMYCIN C; PORFIROMYCIN; TIRAPAZAMINE;

ANTINEOPLASTIC ACTIVITY; CANCER THERAPY; HYPOXIA; MULTIMODALITY CANCER THERAPY; NONHUMAN; PRIORITY JOURNAL; RADIATION DOSE; REVIEW; SOLID TUMOR; TUMOR BLOOD FLOW;

EID: 0030028884     PISSN: 10534296     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1053-4296(96)80033-6     Document Type: Article

References (116)

1. Brown JM Koong A Therapeutic advantage of hypoxic cells in tumors: A theoretical study J Natl Cancer Inst 83 1991 178 185
2. Brown JM Giaccia AJ Tumour hypoxia: The picture has changed in the 1990s Int J Radiat Biol 65 1994 95 102
3. Brown JM Evidence for acutely hypoxic cells in mouse tumours, and a possible mechanism of reoxygenation Br J Radiol 52 1979 650 656
4. Kim IH Brown JM Reoxygenation and rehypoxiation in the SCGVII mouse tumor Int J Radiat Oncol Biol Phys 29 1994 493 497
5. Haffty BG Son YH Sasaki CT Mitomycin C as an adjunct to postoperative radiation therapy in squamous cell carcinoma of the head and neck: Results from two randomized clinical trials Int J Radiat Oncol Biol Phys 27 1993 241 250
6. Weissberg JB Son YH Papae RJ Randomized clinical trial of mitomycin C as an adjunct to radiotherapy in head and neck cancer Int J Radiat Oncol Biol Phys 17 1989 3 9
7. Brown JM Lemmon MJ Potentiation by the hypoxic cytotoxin SR 4233 of cell killing produced by fractionated irradiation of mouse tumors Cancer Res 50 1990 7745 7749
8. Dorie MJ Menke D Brown JM Comparison of the enhancement of tumor responses to fractionated irradiation by SR 4233 (tirapazamine) and by nicotinamide with carbogen Int J Radiat Oncol Biol Phys 28 1994 145 150
9. Sebolt-Leopold JS Elliott WL Showalter HD Rationale for selection of PD 144872, the R isomer of RB 6145, for clinical development as a radiosensitizer Proc Amer Assoc Cancer Res 34 1993 362
10. Hill RP Sensitizers and radiation dose fractionation: Results and interpretations Int J Radiat Oncol Biol Phys 12 1986 1049 1054
11. Brown JM Lemmon MJ Fractionation increases the antitumor effect of adding a hypoxic cytotoxin to irradiation Dewey WC Radiation Research a Twentieth Century Perspective 1992 Academic San Diego, CA 807 812
12. Crooke ST Bradner WT Mitomycin C A review Cancer Treat Rev 3 1976 121 139
13. Rauth AM Marshall RS Kuchl BL Cellular approaches to bioreductive drug mechanisms Cancer Metastasis Rev 12 1993 153 164
14. Rockwell S Sartorelli AC Tomasz M Cellular pharmacology of quinone bioreductive alkylating agents Cancer Metastasis Rev 12 1993 165 176
15. Fracasso PM Sartorelli AC Cytotoxicity and DNA lesions produced by mitomycin C and porfiromycin in hypoxic and aerobic EMT6 and Chinese hamster ovary cells Cancer Res 46 1986 3939 3944
16. Ludwig CU Peng YM Beaudry JN Cytotoxicity of mitomycin C on clonogenic human carcinoma cells is not enhanced by hypoxia Cancer Chemother Pharmacol 12 1984 146 150
17. Rockwell S Kennedy KA Sartorelli AC Mitomycin-C as a prototype bioreductive alkylating agent: in vitro studies of metabolism and cytotoxicity Int J Radiat Oncol Biol Phys 8 1982 753 755
18. Rauth AM Mohindra JK Tannock IF Activity of mitomycin C for aerobic and hypoxic cells in vitro and in vivo Cancer Res 43 1983 4154 4158
19. Marshall RS Paterson MC Rauth AM Deficient activation by a human cell strain leads to mitomycin resistance under aerobic but not hypoxic conditions Br J Cancer 59 1989 341 346
20. Marshall RS Rauth AM Oxygen and exposure kinetics as factors influencing the cytotoxicity of porfiromycin, a mitomycin C analogue in Chinese hamster ovary cells Cancer Res 48 1988 5655 5659
21. Rockwell S Kennedy KA Combination therapy with radiation and mitomycin C: Preliminary results with EMT6 tumor cells in vitro and in vivo Int J Radiat Oncol Biol Phys 5 1979 1673 1676
22. Adams GE Stratford IJ Edwards HS Bioreductive drugs as post-irradiation sensitizers: Comparison of dual function agents with SR 4233 and the mitomycin C analogue E09 Int J Radiat Oncol Biol Phys 22 1992 717 720
23. Rockwell S Keyes SR Sartorelli AC Modulation of the antineoplastic efficacy of mitomycin C by dicoumarol in vivo Cancer Chemother Pharmacol 24 1989 349 353
24. Keyes SR Rockwell S Sartorelli AC Porfiromycin as a bioreductive alkylating agent with selective toxicity to hypoxic EMT6 tumor cells in vivo and in vitro Cancer Res 45 1985 3642 3645
25. Rockwell S Keyes SR Sartorelli AC Preclinical studies of porfiromycin as an adjunct to radiotherapy Radiat Res 116 1988 100 113
26. Hendriks HR Pizao PE Berger DP E09: A novel bioreductive alkylating indoloquinone with preferential solid tumour activity and lack of bone marrow toxicity in preclinical models Eur J Cancer 29A 1993 897 906
27. Workman P Walton MI Enzyme-directed bioreductive drug development Adams GE Breccia A Fielden EM Selective activation of drugs by redox processes 1990 Plenum New York, NY 173 191
28. Walton MI Smith PJ Workman P The role of NAD(P)H: quinone reductase (EC 1.6.99.2, DT-diaphorase) in the reductive bioactivation of the novel indoloquinone antitumor agent E09 Cancer Commun 3 1991 199 206
29. Walton MI Bibby MC Double JA DT-diaphorase activity correlates with sensitivity to the indoloquinone E09 in mouse and human colon carcinomas Eur J Cancer 28A 1992 1597 1600
30. Robertson N Haigh A Adams GE Factors affecting sensitivity to E09 in rodent and human tumour cells in vitro: DT-diaphorase activity and hypoxia Eur J Cancer 30A 1994 1013 1019
31. Plumb JA Gerritsen M Milroy R Relative importance of DT-diaphorase and hypoxia in the bioactivation of E09 by human lung tumor cell lines Int J Radiat Oncol Biol Phys 29 1994 295 299
32. Adams GE Cooke MS Electron-affinic sensitization. I. A structural basis for chemical radiosensitizers in bacteria Int J Radiat Biol 15 1969 457 471
33. Adams GE Flockhart IR Smithen CE Electron-affinic sensitization. VII. A correlation between structures, oneelectron reduction potentials, and efficiencies of nitroimidazoles as hypoxic cell radiosensitizers Radiat Res 67 1976 9 20
34. Hall EJ Roizin-Towle L Hypoxic sensitizers: radiobiological studies at the cellular level Radiology 117 1975 453 457
35. Mohindra JK Rauth AM Increased cell killing by metronidazole and nitrofurazone of hypoxic compared to aerobic mammalian cells Cancer Res 36 1976 930 936
36. Brown JM Cytotoxic effects of the hypoxic cell radiosensitizer Ro 7-0582 to tumor cells in vivo Radiat Res 72 1977 469 486
37. Denekamp J McNally NJ The magnitude of hypoxic cell cytotoxicity of misonidazole in human tumours Br J Radiol 51 1978 747 748
38. Mason RP Holtzman JL The mechanism of microsomal and mitochondrial nitroreductase. Electron spin resonance evidence for nitroaromatic free radical intermediates Biochemistry 14 1975 1626 1632
39. Josephy PD Palcic B Skarsgard LD In vitro metabolism of misonidazole Br J Cancer 43 1981 443 450
40. Adams GE Clarke ED Jacobs RS Mammalian cell toxicity of nitro compounds: Dependence upon reduction potential Biochem Biophys Res Commun 72 1976 824 829
41. Adams GE Ahmed I Sheldon PW RSU 1069, a 2-nitroimidazole containing an alkylating group: High efficiency as a radio- and chemosensitizer in vitro and in vivo Int J Radiat Oncol Biol Phys 10 1984 1653 1656
42. Chaplin DJ Durand RE Stratford IJ The radiosensitizing and toxic effects of RSU-1069 on hypoxic cells in a murine tumor Int J Radiat Oncol Biol Phys 12 1986 1091 1095
43. Hill RP Gulyas S Whitmore GF Studies of the in vivo and in vitro cytotoxicity of the drug RSU-1069 Br J Cancer 53 1986 743 751
44. Whitmore GF Gulyas S Studies on the toxicity of RSU-1069 Int J Radiat Oncol Biol Phys 12 1986 1219 1222
45. Wong KH Koch CJ Wallen CA Pharmacokinetics and cytotoxicity of RSU-1069 in subcutancous 9L tumours under oxic and hypoxic conditions Br J Cancer 63 1991 484 488
46. Silver AR O'Neill P Interaction of the aziridine moiety of RSU-1069 with nucleotides and inorganic phosphate. Implications for alkylation of DNA Biochem Pharmacol 35 1986 1107 1112
47. Silver AR O'Neill P Jenkins TC Induction of DNA strand breaks by RSU-1069, a nitroimidazole-aziridine radiosensitizer. Role of binding of both unreduced and radiation-reduced forms to DNA, in vitro Biochem Pharmacol 34 1985 3537 3542
48. O'Neill P McNeil SS Jenkins TC Induction of DNA crosslinks in vitro upon reduction of the nitroimidazole-aziridines RSU-1069 and RSU-1131 Biochem Pharmacol 36 1987 1787 1792
49. Olive PL Detection of hypoxia by measurement of DNA damage in individual cells from spheroids and murine tumours exposed to bioreductive drugs. II. RSU 1069 Br J Cancer 71 1995 537 542
50. Horwich A Holliday SB Deacon JM A toxicity and pharmacokinetic study in man of the hypoxic-cell radiosensitiser RSU-1069 Br J Radiol 59 1986 1238 1240
51. Ahmed I Jenkins TC Walling JM Analogues of RSU-1069: Radiosensitization and toxicity in vitro and in vivo Int J Radiat Oncol Biol Phys 12 1986 1079 1081
52. Wilson WR Denny WA Twigden SJ Selective toxicity of nitracrine to hypoxic mammalian cells Br J Cancer 49 1984 215 223
53. Wilson WR Denny WA Stewart GM Reductive metabolism and hypoxia-selective toxicity of nitracrine Int J Radiat Oncol Biol Phys 12 1986 1235 1238
54. Roberts PB Denny WA Wakelin LP Radiosensitization of mammalian cells in vitro by nitroacridines Radiat Res 123 1990 153 164
55. Denny WA Roberts PB Anderson RF NLA-1: a 2-nitroimidazole radiosensitizer targeted to DNA by intercalation Int J Radiat Oncol Biol Phys 22 1992 553 556
56. Panicucci R Heal R Laderoute K NLP-1: A DNA intercalating hypoxic cell radiosensitizer and cytotoxin Int J Radiat Oncol Biol Phys 16 1989 1039 1043
57. Cowan DS Kanagasabapathy VM McClelland RA Mechanistic studies of enhanced in vitro radiosensitization and hypoxic cell cytotoxicity by targeting radiosensitizers to DNA via intercalation Int J Radiat Oncol Biol Phys 22 1992 541 544
58. Cowan DSM Matejovic JF McClelland RA DNA-targeted 2-nitroimidazoles: in vitro and in vivo studies Br J Cancer 70 1994 1067 1074
59. Papadopoulou MV Epperly MW Shields DS Radiosensitization and hypoxic cell toxicity of NLA-1 and NLA-2, two new bioreductive compounds Jpn J Cancer Res 83 1992 410 414
60. Gniazdowski M Filipski J Chorazy M Nitracrine Hahn Antibiotics V/Part 2 1978 Springer-Verlag Berlin, Germany 275 297
61. Wilson WR Anderson RF Denny WA Hypoxia-selective antitumour agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine J Med Chem 32 1989 23 30
62. Wilson WR Thompson LH Anderson RF Hypoxia-selective antitumour agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives J Med Chem 32 1989 31 38
63. Cobb LM Connors TA Elson LA 2,4-Dinitro-5-ethyleneiminobenzamide (CB 1954): A potent and selective inhibitor of the growth of the Walker carcinoma 256 Biochem Pharmacol 18 1969 1519 1527
64. Khan AH Ross WCJ Tumour growth inhibitory nitrophenyl aziridines and related compounds: Structure-activity relationships Chem Biol Interact 1 1969/1970 27 47
65. Roberts JJ Friedlos F Knox RJ CB 1954 (2,4-dinitro-5-aziridinyl benzamide) becomes a DNA interstrand crosslinking agent in Walker tumour cells Biochem Biophys Res Commun 140 1986 1073 1078
66. Workman P Morgan JE Talbot K CB 1954 revisited II. Toxicity and antitumour activity Cancer Chemother Pharmacol 16 1986 9 14
67. Palmer BD Wilson WR Cliffe S Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells J Med Chem 35 1992 3214 3222
68. Denny WA Wilson WR Bioreducible mustards: a paradigm for hypoxia-selective prodrugs of diffusible cytotoxins (HPDCs) Cancer Metastasis Rev 12 1993 135 151
69. Anlezark GM Melton RG Sherwood RF The bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954)-I Purification and properties of a nitroreductase enzyme from Escherichia Coli-A potential enzyme for antibody-directed enzyme prodrug therapy (ADEPT) Biochem Pharmacol 44 1992 2289 2295
70. Knox RJ Friedlos F Boland MP The bioactivation of CB 1954 and its use as a prodrug in antibody-directed enzyme prodrug therapy (ADEPT) Cancer Metastasis Rev 12 1993 195 212
71. Bagshawe KD Towards generating cytotoxic agents at cancer sites Br J Cancer 60 1989 275 281
72. Senter PD Wallace PM Svensson HP Activation of prodrugs by antibody-enzyme conjugates Adv Exp Med Biol 303 1991 97 105
73. Cliffe S Taylor ML Rutland M Combining bioreductive drugs (SR 4233 or SN 23862) with the vasoactive agents flavone acetic acid or 5,6-dimethylxanthenone acetic acid Int J Radiat Oncol Biol Phys 29 1994 373 377
74. Palmer BD Wilson WR Atwell GJ Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide J Med Chem 37 1994 2175 2184
75. Zeman EM Brown JM Lemmon MJ SR-4233: A new bioreductive agent with high selective toxicity for hypoxic mammalian cells Int J Radiat Oncol Biol Phys 12 1986 1239 1242
76. Brown JM SR 4233 (tirapazamine): A new anticancer drug exploiting hypoxia in solid tumours Br J Cancer 67 1993 1163 1170
77. Siemann DW In vitro cytotoxicity and chemosensitizing activity of the dual function nitroimidazole RB 6145 Int J Radiat Oncol Biol Phys 29 1994 301 306
78. Siim BG, van Zijl PL, Brown JM: Tirapazamine-induced DNA damage measured using the comet assay correlates with cytotoxicity towards hypoxic tumour cells in vitro. Br J Cancer (in press)
79. Koch CJ Unusual oxygen concentration dependence of toxicity of SR-4233, a hypoxic cell toxin Cancer Res 53 1993 3992 3997
80. Baker MA Zeman EM Hirst VK Metabolism of SR 4233 by Chinese hamster ovary cells: Basis of selective hypoxic cytotoxicity Cancer Res 48 1988 5947 5952
81. Brown JM Redox activation of benzotriazine N-oxides: Mechanisms and potential as anticancer drugs Adams GE Breccia A Fielden EM Selective Activation of Drugs by Redox Processes 1990 Plenum New York, NY 137 148
82. Lloyd RV Duling DR Rumyantseva GV Microsomal reduction of 3-amino-1,2,4-benzotriazine 1,4-dioxide to a free radical Mol Pharmacol 40 1991 440 445
83. Biedermann KA Wang J Graham RP SR 4233 cytotoxicity and metabolism in DNA repair-competent and repair-deficient cell cultures Br J Cancer 63 1991 358 362
84. Wang J Biedermann KA Wolf CR Metabolism of the bioreductive cytotoxin SR 4233 by tumour cells: Enzymatic studies Br J Cancer 67 1993 321 325
85. Barham HM Patterson A Chinje EC Sensitivity to tirapazamine (SR 4233) is determined by P450 reductase activity in human breast but not lung cancer cell lines Br J Cancer 71 Suppl XXIV 1995 20
86. Zeman EM Hirst VK Lemmon MJ Enhancement of radiation-induced tumor cell killing by the hypoxic cell toxin SR 4233 Radiother Oncol 12 1988 209 218
87. Zeman EM Brown JM Pre- and post-irradiation radiosensitization by SR 4233 Int J Rad Oncol Biol Phys 16 1989 967 971
88. Dorie MJ Brown JM Tumor-specific, schedule-dependent interaction between tirapazamine (SR 4233) and cisplatin Cancer Res 53 1993 4633 4636
89. Durand RE The influence of microenvironmental factors during cancer therapy In Vivo 8 1994 691 702
90. Patterson LH Rationale for the use of aliphatic N-oxides of cytotoxic anthraquinones as prodrug DNA binding agents: A new class of bioreductive agent Cancer Metastasis Rev 12 1993 119 134
91. McKeown SR Hejmadi MV McIntyre IA AQ4N: an alkylaminoanthraquinone N-oxide showing bioreductive potential and positive interaction with radiation in vivo Br J Cancer 72 1995 76 81
92. Wilson WR van Zijl PI Denny WA Bis-bioreductive agents as hypoxia-selective cytotoxins: Nitracrine N-oxide Int J Radiat Oncol Biol Phys 22 1992 693 696
93. Hay MP Wilson WR Moselen JW Hypoxia-selective antitumor agents. 8. Bis(nitroimidazolyl)alkanecarboxamides: A new class of hypoxia-selective cytotoxins and hypoxic cell radiosensitizers J Med Chem 37 1994 381 391
94. Hay MP Lee HH Wilson WR Hypoxia-selective antitumor agents. 10. Bis-(nitroimidazoles) and related bis-(nitroheterocycles): Development of derivatives with higher rates of metabolic activation under hypoxia and improved aqueous solubility J Med Chem 38 1995 1928 1941
95. Moselen JW Hay MP Denny WA N-[2-(2-Methyl-5-nitroimidazolyl)ethyl]-4-(2-nitroimidazolyl)butanamide (NSC 639862), a bis-nitroimidazole with enhanced selectivity as a bioreductive drug Cancer Res 55 1995 574 580
96. Ware DC Palmer BD Wilson WR Hypoxia-selective antitumor agents. 7. Metal complexes of aliphatic mustards as a new class of hypoxia selective cytotoxins. Synthesis and evaluation of cobalt(III) complexes of bidentate mustards J Med Chem 36 1993 1839 1846
97. Wilson WR Moselen JW Cliffe S Exploiting tumor hypoxia through bioreductive release of diffusible cytotoxins: The cobalt(III)-nitrogen mustard complex SN 24771 Int J Radiat Oncol Biol Phys 29 1994 323 327
98. Tercel M Wilson WR Denny WA Nitrobenzyl mustard quaternary salts: A new class of hypoxia selective cytotoxins showing very high in vitro selectivity J Med Chem 36 1993 2578 2579
99. Denny WA Wilson WR Tercel M Nitrobenzyl mustard quaternary salts: A new class of hypoxia-selective cytotoxins capable of releasing diffusible cytotoxins on bioreduction Int J Radiat Oncol Biol Phys 29 1994 317 321
100. Lin AJ Cosby LA Shansky CW Potential bioreductive alkylating agents. 1. Benzoquinone derivatives J Med Chem 15 1972 1247 1252
101. Brown JM Lemmon MJ Tumor hypoxia can be exploited to preferentially sensitize tumors to fractionated irradiation Int J Radiat Oncol Biol Phys 20 1991 457 461
102. Brown JM Lemmon MJ SR 4233: A tumor specific radiosensitizer active in fractionated radiation regimes Radiother Oncol 20 1991 151 156
103. Tannock IF In vivo interaction of anti-cancer drugs with misonidazole or metronidazole: Methotrexate, 5-fluorouracil and adriamycin Br J Cancer 42 1980 861 870
104. Siemann DW Modification of chemotherapy by nitroimidazoles Int J Radiat Oncol Biol Phys 10 1984 1585 1594
105. Murray D Meyn RE Enhancement of the DNA cross-linking activity of melphalan by misonidazole in vivo Br J Cancer 47 1983 195 203
106. Taylor YC Evans JW Brown JM Mechanism of sensitization of Chinese hamster ovary cells to melphalan by hypoxic treatment with misonidazole Cancer Res 43 1983 3175 3181
107. Langmuir VK Rooker JA Osen M Synergistic interaction between tirapazamine and cyclophosphamide in human breast cancer xenografts Cancer Res 54 1994 2845 2847
108. Cater DB Grigson CMB Watkinson DA Changes of oxygen tension in tumors induced by vasoconstrictor and vasodilator drugs Acta Radiol 58 1962 401 408
109. Voorhees WDI Babbs CF Hydralazine-enhanced selective heating of transmissible veneral tumor implants in dogs Eur J Cancer Clin Oncol 18 1982 1027 1033
110. Zwi LJ Baguley BC Gavin JB Blood flow failure as a major determinant in the anti-tumor action of flavone acetic acid J Natl Cancer Inst 81 1989 1005 1013
111. Chaplin DJ Acker B The effect of hydralazine on the tumor cytotoxicity of the hypoxic cell cytotoxin RSU-1069: Evidence for therapeutic gain Int J Radiat Oncol Biol Phys 13 1987 579 585
112. Bremner JC Stratford IJ Bowler J Bioreductive drugs and the selective induction of tumour hypoxia Br J Cancer 61 1990 717 721
113. Brown JM Exploitation of bioreductive agents with vasoactive drugs Fielden EM Fowler JF Hendry JH Radiation Research vol 2 1987 Taylor & Francis London, UK 719 724
114. Sun JR Brown JM Enhancement of the antitumor effect of flavone acetic acid by the bioreductive cytotoxic drug SR 4233 in a murine carcinoma Cancer Res 49 1989 5664 5670
115. G-nitro-L-arginine Cancer Res 54 1994 6458 6463
116. Dorie MJ Brown JM Potentiation of the anticancer effect of cisplatin by the hypoxic cytotoxin tirapazamine Vaupel PW Kelleher DK Günderoth M Tumor Oxygenation 1995 Fischer-Verlag Stuttgart, Germany 125 135