C2235
CB 1954
solid
Synonym(s):
5-(1-Aziridinyl)-2,4-dinitrobenzamide, 5-(Aziridin-1-yl)-2,4-dinitrobenzamide
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About This Item
CAS Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32
Recommended Products
Assay
≥94% (HPLC)
Quality Level
form
solid
storage temp.
−20°C
SMILES string
NC(=O)c1cc(N2CC2)c(cc1[N+]([O-])=O)[N+]([O-])=O
InChI
1S/C9H8N4O5/c10-9(14)5-3-7(11-1-2-11)8(13(17)18)4-6(5)12(15)16/h3-4H,1-2H2,(H2,10,14)
InChI key
WOCXQMCIOTUMJV-UHFFFAOYSA-N
Application
CB 1954 has been used in drug-induced ablation studies.
Biochem/physiol Actions
CB 1954 is an anticancer prodrug used in gene therapy research; activated by NAD(P)H quinone oxidoreductase 2.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Corbeaux T, et al.
Proceedings of the National Academy of Sciences of the USA, 1-6 (2010)
Gareth A Prosser et al.
Biochemical pharmacology, 85(8), 1091-1103 (2013-02-13)
Two potentially complementary approaches to improve the anti-cancer strategy gene-directed enzyme prodrug therapy (GDEPT) are discovery of more efficient prodrug-activating enzymes, and development of more effective prodrugs. Here we demonstrate the utility of a flexible screening system based on the
Andrew Christofferson et al.
Biochemical Society transactions, 37(Pt 2), 413-418 (2009-03-18)
NTR (nitroreductase NfsB from Escherichia coli) is a flavoprotein with broad substrate specificity, reducing nitroaromatics and quinones using either NADPH or NADH. One of its substrates is the prodrug CB1954 (5-[aziridin-1-yl]-2,4-dinitrobenzamide), which is converted into a cytotoxic agent; so NTR/CB1954
Validation of nitroreductase, a prodrug-activating enzyme, mediated cell death in embryonic zebrafish (Danio rerio)
Pisharath H
Comparative Medicine, 57(3), 241-246 (2007)
David Jarrom et al.
Biochemistry, 48(32), 7665-7672 (2009-07-08)
The enzyme nitroreductase, NfsB, from Escherichia coli has entered clinical trials for cancer gene therapy with the prodrug CB1954 [5-(aziridin-1-yl)-2,4-dinitrobenzamide]. However, CB1954 is a poor substrate for the enzyme. Previously we made several NfsB mutants that show better activity with
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