Tretazicar

Tretazicar (CB 1954), an antitumor proagent, is highly selective against the Walker 256 rat tumour line. Tretazicar is enzymatically activated to generate a bifunctional agent, which can form DNA-DNA interstrand cross-links. Tretazicar in rat cells involves the reduction of its 4-nitro group to a 4-hydroxylamine by the enzyme NAD (P) H:quinone oxidoreductase 1 (NQO1) [1][2].

Product Specifications

CAS Number

[21919-05-1]

Product Name Alternative

CB 1954

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

DNA Alkylator/Crosslinker; Quinone Reductase

Type

Reference compound

Related Pathways

Cell Cycle/DNA Damage; Metabolic Enzyme/Protease

Applications

Neuroscience-Neuromodulation

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/tretazicar.html

Purity

99.65

Solubility

DMSO : 125 mg/mL (ultrasonic)

Smiles

O=C(N)C1=CC(N2CC2)=C([N+]([O-])=O)C=C1[N+]([O-])=O

Molecular Formula

C9H8N4O5

Molecular Weight

252.18

Precautions

H302, H315, H319, H335

References & Citations

[1]Knox RJ, et al. Bioactivation of 5- (aziridin-1-yl) -2,4-dinitrobenzamide (CB 1954) by human NAD (P) H quinone oxidoreductase 2: a novel co-substrate-mediated antitumor prodrug therapy. Cancer Res. 2000 Aug 1;60 (15) :4179-86.|[2]Knox RJ, et al. CB 1954: from the Walker tumor to NQO2 and VDEPT. Curr Pharm Des. 2003;9 (26) :2091-104.|[3]Green NK, et al. Immune enhancement of nitroreductase-induced cytotoxicity: studies using a bicistronicadenovirus vector. Int J Cancer. 2003 Mar 10;104 (1) :104-12.|[4]Drabek D, et al. The expression of bacterial nitroreductase in transgenic mice results in specific cell killing by the prodrug CB1954. Gene Ther. 1997 Feb;4 (2) :93-100.