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 Diaziquone

diaziquone is a synthetic bifunctional quinone derivative with potential antineoplastic activity. Diaziquone alkylates and cross-links DNA during all phases of the cell cycle, resulting in disruption of DNA function, cell cycle arrest, and apoptosis. This agent can also form free radicals, thereby initiating DNA damage via DNA strand breaks. Due to its lipophilicity, diaziquone readily crosses the blood brain barrier. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)

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19: Li B, Blough NV, Gutierrez PL. Trace detection of hydroxyl radicals during the redox cycling of low concentrations of diaziquone: a new approach. Free Radic Biol Med. 2000 Sep 15;29(6):548-56. PubMed PMID: 11025198.

20: Byrd JC, Dodge RK, Carroll A, Baer MR, Edwards C, Stamberg J, Qumsiyeh M, Moore JO, Mayer RJ, Davey F, Schiffer CA, Bloomfield CD. Patients with t(8;21)(q22;q22) and acute myeloid leukemia have superior failure-free and overall survival when repetitive cycles of high-dose cytarabine are administered. J Clin Oncol. 1999 Dec;17(12):3767-75. PubMed PMID: 10577848.

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27: Lee EJ, George SL, Amrein PC, Paciucci PA, Allen SL, Schiffer CA. An evaluation of combinations of diaziquone, etoposide and mitoxantrone in the treatment of adults with relapsed or refractory acute myeloid leukemia: results of 8722, a randomized phase II study conducted by Cancer and Leukemia Group B. Leukemia. 1998 Feb;12(2):139-43. PubMed PMID: 9519774.

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35: Powis G, Gasdaska PY, Gallegos A, Sherrill K, Goodman D. Over-expression of DT-diaphorase in transfected NIH 3T3 cells does not lead to increased anticancer quinone drug sensitivity: a questionable role for the enzyme as a target for bioreductively activated anticancer drugs. Anticancer Res. 1995 Jul-Aug;15(4):1141-5. PubMed PMID: 7653992.

36: Gutierrez PL, Siva S. Diaziquone-glutathione conjugates: characterization and mechanisms of formation. Chem Res Toxicol. 1995 Apr-May;8(3):455-64. PubMed PMID: 7578933.

37: Hartmann LC, Ames MM, Reid JM, Richardson RL. Phase I trial of diaziquone (AZQ) plus GM-CSF. Invest New Drugs. 1995;13(2):175-6. PubMed PMID: 8617583.

38: White L, Sterling-Levis K, Fisher R, Tobias V. Response of brain tumors to chemotherapy, evaluated in a clinically relevant xenograft model. J Neurooncol. 1995;25(1):39-47. PubMed PMID: 8523088.

39: Alley SC, Hopkins PB. DNA-DNA interstrand cross-linking by 2,5-bis(1-aziridinyl)-3,6-bis(carbethoxyamino)-1,4-benzoquinone: covalent structure of the dG-to-dG cross-links in calf thymus DNA and a synthetic DNA duplex. Chem Res Toxicol. 1994 Sep-Oct;7(5):666-72. PubMed PMID: 7841346.

40: Beall HD, Mulcahy RT, Siegel D, Traver RD, Gibson NW, Ross D. Metabolism of bioreductive antitumor compounds by purified rat and human DT-diaphorases. Cancer Res. 1994 Jun 15;54(12):3196-201. PubMed PMID: 8205540.

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45: Kimler BF. The 9L rat brain tumor model for pre-clinical investigation of radiation-chemotherapy interactions. J Neurooncol. 1994;20(2):103-9. PubMed PMID: 7528789.

46: Fisher GR, Patterson LH, Gutierrez PL. A comparison of free radical formation by quinone antitumour agents in MCF-7 cells and the role of NAD(P)H (quinone-acceptor) oxidoreductase (DT-diaphorase). Chem Biol Interact. 1993 Sep;88(2-3):137-53. PubMed PMID: 8403076.

47: Halperin EC, Gaspar L, Imperato J, Salter M, Herndon J 2nd, Dowling S. An analysis of radiotherapy data from the CNS cancer consortium's randomized prospective trial comparing AZQ to BCNU in the treatment of patients with primary malignant brain tumors. The CNS cancer consortium. Am J Clin Oncol. 1993 Aug;16(4):277-83. PubMed PMID: 8392285.

48: Devine SM, Geller RB, Holland HK, Wingard JR, Saral R. New preparative regimens with diaziquone or cytarabine in combination with busulfan and cyclophosphamide. Semin Oncol. 1993 Aug;20(4 Suppl 4):56-63; quiz 64. Review. PubMed PMID: 8342077.

49: Huang ZD, Chen YN, Menon K, Teicher BA. Synthesis and evaluation of the antitumor activity of 4,5-diamino-substituted 1,2-benzoquinones. J Med Chem. 1993 Jun 25;36(13):1797-801. PubMed PMID: 8515418.

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51: Belinsky M, Jaiswal AK. NAD(P)H:quinone oxidoreductase1 (DT-diaphorase) expression in normal and tumor tissues. Cancer Metastasis Rev. 1993 Jun;12(2):103-17. Review. PubMed PMID: 8375015.

52: Berardini MD, Souhami RL, Lee CS, Gibson NW, Butler J, Hartley JA. Two structurally related diaziridinylbenzoquinones preferentially cross-link DNA at different sites upon reduction with DT-diaphorase. Biochemistry. 1993 Apr 6;32(13):3306-12. PubMed PMID: 8461296.

53: Schlager JJ, Hoerl BJ, Riebow J, Scott DP, Gasdaska P, Scott RE, Powis G. Increased NAD(P)H:(quinone-acceptor)oxidoreductase activity is associated with density-dependent growth inhibition of normal but not transformed cells. Cancer Res. 1993 Mar 15;53(6):1338-42. PubMed PMID: 8443814.

54: Schold SC Jr, Herndon JE, Burger PC, Halperin EC, Vick NA, Cairncross JG, Macdonald DR, Dropcho EJ, Morawetz R, Bigner DD, et al. Randomized comparison of diaziquone and carmustine in the treatment of adults with anaplastic glioma. J Clin Oncol. 1993 Jan;11(1):77-83. PubMed PMID: 8418246.

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58: Fisher GR, Donis J, Gutierrez PL. Reductive metabolism of diaziquone (AZQ) in the S9 fraction of MCF-7 cells. II. Enhancement of the alkylating activity of AZQ by NAD(P)H: quinone-acceptor oxidoreductase (DT-diaphorase). Biochem Pharmacol. 1992 Oct 20;44(8):1625-35. PubMed PMID: 1301071.

59: Weiss RB. Hypersensitivity reactions. Semin Oncol. 1992 Oct;19(5):458-77. Review. PubMed PMID: 1384149.

60: Ordoñez ID, Cadenas E. Thiol oxidation coupled to DT-diaphorase-catalysed reduction of diaziquone. Reductive and oxidative pathways of diaziquone semiquinone modulated by glutathione and superoxide dismutase. Biochem J. 1992 Sep 1;286 ( Pt 2):481-90. PubMed PMID: 1530580; PubMed Central PMCID: PMC1132923.

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62: al-Nabulsi I, Gutierrez PL. Photosensitization of MCF-7 cells with diaziquone using visible light: correlation with DNA strand breaks and free radical production. Photochem Photobiol. 1992 Aug;56(2):201-9. PubMed PMID: 1502264.

63: Riley RJ, Workman P. DT-diaphorase and cancer chemotherapy. Biochem Pharmacol. 1992 Apr 15;43(8):1657-69. Review. PubMed PMID: 1575764.

64: Mau BL, Powis G. Inhibition of cellular thioredoxin reductase by diaziquone and doxorubicin. Relationship to the inhibition of cell proliferation and decreased ribonucleotide reductase activity. Biochem Pharmacol. 1992 Apr 1;43(7):1621-7. PubMed PMID: 1567483.

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76: Preusch PC, Siegel D, Gibson NW, Ross D. A note on the inhibition of DT-diaphorase by dicoumarol. Free Radic Biol Med. 1991;11(1):77-80. Review. PubMed PMID: 1718826.

77: Fisher GR, Gutierrez PL. Free radical formation and DNA strand breakage during metabolism of diaziquone by NAD(P)H quinone-acceptor oxidoreductase (DT-diaphorase) and NADPH cytochrome c reductase. Free Radic Biol Med. 1991;11(6):597-607. PubMed PMID: 1663902.

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82: Amrein PC, Davis RB, Mayer RJ, Schiffer CA. Treatment of relapsed and refractory acute myeloid leukemia with diaziquone and mitoxantrone: a CALGB phase I study. Am J Hematol. 1990 Oct;35(2):80-3. PubMed PMID: 2399909.

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89: Lee EJ, Reck K, Schiffer CA. Continuous infusion diaziquone and etoposide: a phase I study in adult patients with acute leukemia. Leukemia. 1990 Mar;4(3):189-92. PubMed PMID: 2314118.

90: O'Brien PJ, Kaul HK, Rauth AM. Differential cytotoxicity of diaziquone toward Chinese hamster ovary cells under hypoxic and aerobic exposure conditions. Cancer Res. 1990 Mar 1;50(5):1516-20. PubMed PMID: 2302714.

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97: Ross D, Siegel D, Gibson NW, Pacheco D, Thomas DJ, Reasor M, Wierda D. Activation and deactivation of quinones catalyzed by DT-diaphorase. Evidence for bioreductive activation of diaziquone (AZQ) in human tumor cells and detoxification of benzene metabolites in bone marrow stroma. Free Radic Res Commun. 1990;8(4-6):373-81. PubMed PMID: 2113030.

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101: Silva JM, O'Brien PJ. Diaziquone-induced cytotoxicity in isolated rat hepatocytes. Cancer Res. 1989 Oct 15;49(20):5550-4. PubMed PMID: 2790779.

102: Yung WK, Harris MI, Bruner JM, Feun LG. Intravenous BCNU and AZQ in patients with recurrent malignant gliomas. J Neurooncol. 1989 Sep;7(3):237-40. PubMed PMID: 2795118.

103: Stewart DJ. The role of chemotherapy in the treatment of gliomas in adults. Cancer Treat Rev. 1989 Sep;16(3):129-60. Review. PubMed PMID: 2695239.

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