5-(1-aziridinyl)-2,4-dinitrobenzamide
Tretazicar
CAS: 21919-05-1
Molecular Formula: C9H8N4O5
5-(1-aziridinyl)-2,4-dinitrobenzamide - Names and Identifiers
5-(1-aziridinyl)-2,4-dinitrobenzamide - Physico-chemical Properties
| Molecular Formula | C9H8N4O5 |
| Molar Mass | 252.18 |
| Density | 1.671±0.06 g/cm3(Predicted) |
| Melting Point | 173 °C |
| Boling Point | 427.2±45.0 °C(Predicted) |
| Solubility | Soluble in DMSO, not in water |
| Appearance | solid |
| Color | Yellow to Dark Yellow |
| pKa | 14.23±0.50(Predicted) |
| Storage Condition | -20°C |
| Use | Tretazicar (CB 1954) is an anti-tumor prodrug with high potency and selectivity to Walker 256 rat tumor cell lines. Tretazicar enzymatic activation results in a bifunctional reagent, which can form DNA-DNA interchain crosslinking. Tretazicar in rat cells involves the reduction of their 4-nitro to 4-hydroxyamine by the enzyme NAD(P)H: quinone oxidoreductase 1 (NQO1). |
| In vitro study | Overexpression of NOR1 converts the single-function alkylating agent CB1954 to its toxic form. Cytotoxic CB1954 enhances cell killing of the NPC cell line cne1. The NOR1 gene can enhance the cytotoxicity mediated by CB1954 in HepG2 cells by up-regulating the expression of Grb2 and activating MAPK signal transduction. |
| In vivo study | The NTR/CB1954 system was used in vivo for cell-specific ablation experiments. This induced ablation system has a dose-dependent effect. This process does not require cell proliferation, and activated CB1954 cross-links with DNA, causing an apoptotic cascade that leads to rapid cell death. Specific cell ablation induced by the NTR-CB1954 system does not require a functional p53 pathway. |
5-(1-aziridinyl)-2,4-dinitrobenzamide - Risk and Safety
| WGK Germany | 3 |
5-(1-aziridinyl)-2,4-dinitrobenzamide - Reference
| Reference Show more | 1: Prosser GA, Copp JN, Mowday AM, Guise CP, Syddall SP, Williams EM, Horvat CN, Swe PM, Ashoorzadeh A, Denny WA, Smaill JB, Patterson AV, Ackerley DF. Creation and screening of a multi-family bacterial oxidoreductase library to discover novel nitroreductases that efficiently activate the bioreductive prodrugs CB1954 and PR-104A. Biochem Pharmacol. 2013 Apr 15;85(8):1091-103. doi: 10.1016/j.bcp.2013.01.029. Epub 2013 Feb 8. PubMed PMID: 23399641. 2: Swe PM, Copp JN, Green LK, Guise CP, Mowday AM, Smaill JB, Patterson AV, Ackerley DF. Targeted mutagenesis of the Vibrio fischeri flavin reductase FRase I to improve activation of the anticancer prodrug CB1954. Biochem Pharmacol. 2012 Sep 15;84(6):775-83. doi: 10.1016/j.bcp.2012.07.002. Epub 2012 Jul 14. PubMed PMID: 22796568. 3: Prosser GA, Patterson AV, Ackerley DF. uvrB gene deletion enhances SOS chromotest sensitivity for nitroreductases that preferentially generate the 4-hydroxylamine metabolite of the anti-cancer prodrug CB1954. J Biotechnol. 2010 Oct 1;150(1):190-4. doi: 10.1016/j.jbiotec.2010.08.007. Epub 2010 Aug 19. PubMed PMID: 20727918. 4: Prosser GA, Copp JN, Syddall SP, Williams EM, Smaill JB, Wilson WR, Patterson AV, Ackerley DF. Discovery and evaluation of Escherichia coli nitroreductases that activate the anti-cancer prodrug CB1954. Biochem Pharmacol. 2010 Mar 1;79(5):678-87. doi: 10.1016/j.bcp.2009.10.008. Epub 2009 Oct 21. PubMed PMID: 19852945. |
5-(1-aziridinyl)-2,4-dinitrobenzamide - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 3.965 ml | 19.827 ml | 39.654 ml |
| 5 mM | 0.793 ml | 3.965 ml | 7.931 ml |
| 10 mM | 0.397 ml | 1.983 ml | 3.965 ml |
| 5 mM | 0.079 ml | 0.397 ml | 0.793 ml |
Last Update：2024-01-02 23:10:35
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