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).
1: Ewald JA, Jarrard DF. Decreased skp2 expression is necessary but not sufficient for therapy-induced senescence in prostate cancer. Transl Oncol. 2012 Aug;5(4):278-87. Epub 2012 Aug 1. PubMed PMID: 22937180; PubMed Central PMCID: PMC3431038.
2: Smejkal K, Svacinová J, Slapetová T, Schneiderová K, Dall'acqua S, Innocenti G, Závalová V, Kollár P, Chudík S, Marek R, Julínek O, Urbanová M, Kartal M, Csöllei M, Dolezal K. Cytotoxic activities of several geranyl-substituted flavanones. J Nat Prod. 2010 Apr 23;73(4):568-72. doi: 10.1021/np900681y. PubMed PMID: 20192247.
3: Peng YC, Kuo HS, Tsai HD, Yang YP, Lin YL. The lethal effect of bis-type azridinylnaphthoquinone derivative on oral cancer cells (OEC-M1) associated with anti-apoptotic protein bcl-2. Bioorg Med Chem. 2006 Jan 1;14(1):263-72. Epub 2005 Oct 5. PubMed PMID: 16213738.
4: Alegria AE, Sanchez-Cruz P, Lopez-Colon D. Sonochemically induced covalent binding of calf thymus DNA by aziridinylquinones. Radiat Res. 2005 Oct;164(4 Pt 1):446-52. PubMed PMID: 16187747.
5: Marcucci G, Mrózek K, Ruppert AS, Maharry K, Kolitz JE, Moore JO, Mayer RJ, Pettenati MJ, Powell BL, Edwards CG, Sterling LJ, Vardiman JW, Schiffer CA, Carroll AJ, Larson RA, Bloomfield CD. Prognostic factors and outcome of core binding factor acute myeloid leukemia patients with t(8;21) differ from those of patients with inv(16): a Cancer and Leukemia Group B study. J Clin Oncol. 2005 Aug 20;23(24):5705-17. PubMed PMID: 16110030.
6: Smith WE, Hubert DD, Yazdi E, Holiat SM, Bissell EC, Watts LM, Baylouny RA, Sobel HJ. Complete remissions in chemotherapy of lung cancer models induced in mice by asbestos. Mt Sinai J Med. 2005 Jan;72(1):23-32. PubMed PMID: 15682259.
7: Fleischhack G, Jaehde U, Bode U. Pharmacokinetics following intraventricular administration of chemotherapy in patients with neoplastic meningitis. Clin Pharmacokinet. 2005;44(1):1-31. Review. PubMed PMID: 15634030.
8: Moore JO, George SL, Dodge RK, Amrein PC, Powell BL, Kolitz JE, Baer MR, Davey FR, Bloomfield CD, Larson RA, Schiffer CA. Sequential multiagent chemotherapy is not superior to high-dose cytarabine alone as postremission intensification therapy for acute myeloid leukemia in adults under 60 years of age: Cancer and Leukemia Group B Study 9222. Blood. 2005 May 1;105(9):3420-7. Epub 2004 Nov 30. PubMed PMID: 15572587; PubMed Central PMCID: PMC1895015.
9: Farag SS, Ruppert AS, Mrózek K, Mayer RJ, Stone RM, Carroll AJ, Powell BL, Moore JO, Pettenati MJ, Koduru PR, Stamberg J, Baer MR, Block AW, Vardiman JW, Kolitz JE, Schiffer CA, Larson RA, Bloomfield CD. Outcome of induction and postremission therapy in younger adults with acute myeloid leukemia with normal karyotype: a cancer and leukemia group B study. J Clin Oncol. 2005 Jan 20;23(3):482-93. Epub 2004 Nov 8. PubMed PMID: 15534356.
10: Lopez-Colón D, Alegría AE. Sonochemistry of antitumor quinones in argon-saturated aqueous solutions: enhanced ferricytochrome c reduction. Ultrason Sonochem. 2004 Jul;11(5):311-6. PubMed PMID: 15157861.
2: Smejkal K, Svacinová J, Slapetová T, Schneiderová K, Dall'acqua S, Innocenti G, Závalová V, Kollár P, Chudík S, Marek R, Julínek O, Urbanová M, Kartal M, Csöllei M, Dolezal K. Cytotoxic activities of several geranyl-substituted flavanones. J Nat Prod. 2010 Apr 23;73(4):568-72. doi: 10.1021/np900681y. PubMed PMID: 20192247.
3: Peng YC, Kuo HS, Tsai HD, Yang YP, Lin YL. The lethal effect of bis-type azridinylnaphthoquinone derivative on oral cancer cells (OEC-M1) associated with anti-apoptotic protein bcl-2. Bioorg Med Chem. 2006 Jan 1;14(1):263-72. Epub 2005 Oct 5. PubMed PMID: 16213738.
4: Alegria AE, Sanchez-Cruz P, Lopez-Colon D. Sonochemically induced covalent binding of calf thymus DNA by aziridinylquinones. Radiat Res. 2005 Oct;164(4 Pt 1):446-52. PubMed PMID: 16187747.
5: Marcucci G, Mrózek K, Ruppert AS, Maharry K, Kolitz JE, Moore JO, Mayer RJ, Pettenati MJ, Powell BL, Edwards CG, Sterling LJ, Vardiman JW, Schiffer CA, Carroll AJ, Larson RA, Bloomfield CD. Prognostic factors and outcome of core binding factor acute myeloid leukemia patients with t(8;21) differ from those of patients with inv(16): a Cancer and Leukemia Group B study. J Clin Oncol. 2005 Aug 20;23(24):5705-17. PubMed PMID: 16110030.
6: Smith WE, Hubert DD, Yazdi E, Holiat SM, Bissell EC, Watts LM, Baylouny RA, Sobel HJ. Complete remissions in chemotherapy of lung cancer models induced in mice by asbestos. Mt Sinai J Med. 2005 Jan;72(1):23-32. PubMed PMID: 15682259.
7: Fleischhack G, Jaehde U, Bode U. Pharmacokinetics following intraventricular administration of chemotherapy in patients with neoplastic meningitis. Clin Pharmacokinet. 2005;44(1):1-31. Review. PubMed PMID: 15634030.
8: Moore JO, George SL, Dodge RK, Amrein PC, Powell BL, Kolitz JE, Baer MR, Davey FR, Bloomfield CD, Larson RA, Schiffer CA. Sequential multiagent chemotherapy is not superior to high-dose cytarabine alone as postremission intensification therapy for acute myeloid leukemia in adults under 60 years of age: Cancer and Leukemia Group B Study 9222. Blood. 2005 May 1;105(9):3420-7. Epub 2004 Nov 30. PubMed PMID: 15572587; PubMed Central PMCID: PMC1895015.
9: Farag SS, Ruppert AS, Mrózek K, Mayer RJ, Stone RM, Carroll AJ, Powell BL, Moore JO, Pettenati MJ, Koduru PR, Stamberg J, Baer MR, Block AW, Vardiman JW, Kolitz JE, Schiffer CA, Larson RA, Bloomfield CD. Outcome of induction and postremission therapy in younger adults with acute myeloid leukemia with normal karyotype: a cancer and leukemia group B study. J Clin Oncol. 2005 Jan 20;23(3):482-93. Epub 2004 Nov 8. PubMed PMID: 15534356.
10: Lopez-Colón D, Alegría AE. Sonochemistry of antitumor quinones in argon-saturated aqueous solutions: enhanced ferricytochrome c reduction. Ultrason Sonochem. 2004 Jul;11(5):311-6. PubMed PMID: 15157861.
| Chemical | |
|---|---|
| CAS Num | 57998-68-2 |
| Chemical Formula | C16H20N4O6 |
| Molecular Weight | 364.35 |
| IUPAC Chemical Name | diethyl (2,5-di(aziridin-1-yl)-3,6-dioxocyclohexa-1,4-diene-1,4-diyl)dicarbamate |
| Exact Mass | 364.13828 |
| Elemental Analysis | C, 52.74; H, 5.53; N, 15.38; O, 26.35 |
| Synonym | Aziridinyl Benzoquinone; aziridinylbenzoquinone; Aziridinylbenzoquinone carbamic acid. Abbreviation |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | O=C(C(NC(OCC)=O)=C1N2CC2)C(N3CC3)=C(NC(OCC)=O)C1=O |
| Biological | |
| Targets and Effects | N/A |
| Pathways | alkylating agent, Apoptosis |
| Physical | |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >2 years if stored properly |
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