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C2235

Sigma-Aldrich

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:
21919-05-1
MDL number:
MFCD00869490
UNSPSC Code:
12352204
PubChem Substance ID:
24278301
NACRES:
NA.32

Assay

≥94% (HPLC)

Quality Level

200

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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Thymopoiesis in mice depends on a Foxn1-positive thymic epithelial cell lineage
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
Mayumi Hirakawa et al.
Scientific reports, 8(1), 11095-11095 (2018-07-25)
The numbers of thymic epithelial cells (TECs) and thymocytes steadily increase during embryogenesis. To examine this dynamic, we generated several TEC-specific transgenic mouse lines, which express fluorescent proteins in the nucleus, the cytosol and in the membranes under the control
Karine Reybier et al.
Free radical research, 45(10), 1184-1195 (2011-07-19)
NRH:quinone oxidoreductase 2 (QR2) is a cytosolic enzyme that catalyzes the reduction of quinones, such as menadione and co-enzymes Q. With the aim of understanding better the mechanisms of action of QR2, we approached this enzyme catalysis via electron paramagnetic
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