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I4659

Sigma-Aldrich

ICRF-193

apoptosis inducer, arabinosidase substrate

Sinónimos:

meso-4,4′-(3,2-Butanediyl)-bis(2,6-piperazinedione)

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About This Item

Fórmula empírica (notación de Hill):
C12H18N4O4
Número de CAS:
21416-88-6
Peso molecular:
282.30
Número MDL:
MFCD01702964
Código UNSPSC:
12352204
ID de la sustancia en PubChem:
24896062
NACRES:
NA.77

origen biológico

synthetic (organic)

Ensayo

≥95%

Formulario

powder or flakes
solid

solubilidad

DMSO: 4 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

C[C@@H]([C@@H](C)N1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2

InChI

1S/C12H18N4O4/c1-7(15-3-9(17)13-10(18)4-15)8(2)16-5-11(19)14-12(20)6-16/h7-8H,3-6H2,1-2H3,(H,13,17,18)(H,14,19,20)/t7-,8+

Clave InChI

OBYGAPWKTPDTAS-OCAPTIKFSA-N

Descripción general

ICRF-193 is a bisdiopiperazine derivative. It inhibits topoisomerase II by forming a non-cleavable complex.

Aplicación

ICRF-193 has been used as a topoisomerase II (TOP2) inhibitor to treat mouse oocytes to investigate the role of TOP2 in meiosis.

Acciones bioquímicas o fisiológicas

ICRF-193 helps in the enhancement of cell cycle without chromosome segregation. It is considered as an important drug for chemo-differentiation therapy against acute promyelocytic leukemia (APL). ICRF-193 serves as an inducer of differentiation between anticancer drugs.
ICRF-193 induces a G2 checkpoint that is associated with an ATR-dependent inhibition of polo-like kinase 1 (plk1) activity and a decrease in cyclin B1 phosphorylation. Induces apoptosis in several cell lines including K562 and Molt-4 cells., ICRF-193 is a topoisomerase II inhibitor, more potent against topoisomerase II-β than topoisomerase II-α, and may in addition cause DNA strand breaks.

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H301,H317

Clasificaciones de peligro

Acute Tox. 3 Oral - Skin Sens. 1

Código de clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
SLCL7373
SLCJ1721
SLCG1862
SLCD9267
SLCC8904

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ICRF-193, a catalytic inhibitor of DNA topoisomerase II, delays the cell cycle progression from metaphase, but not from anaphase to the G1 phase in mammalian cells
Iwai M, et al.
Febs Letters, 406(3), 267-270 (1997)
N Hajji et al.
Mutation research, 530(1-2), 35-46 (2003-10-18)
The bis-dioxopiperazine ICRF-193 has long time been considered as a pure topoisomerase II catalytic inhibitor able to exert its inhibitory effect on the enzyme without stabilization of the so-called cleavable complex formed by DNA covalently bound to topoisomerase II. In
The catalytic DNA topoisomerase II inhibitor ICRF-193 and all-trans retinoic acid cooperatively induce granulocytic differentiation of acute promyelocytic leukemia cells: candidate drugs for chemo-differentiation therapy against acute promyelocytic leukemia
Niitsu,
Experimental Hematology, 30(11), 1273-1282 (2002)
K C Huang et al.
The Journal of biological chemistry, 276(48), 44488-44494 (2001-09-29)
Antineoplastic bis(dioxopiperazine)s, such as meso-2,3-bis(2,6-dioxopiperazin-4-yl)butane (ICRF-193), are widely believed to be only catalytic inhibitors of topoisomerase II. However, topoisomerase inhibitors have little or no antineoplastic activity unless they are topoisomerase poisons, a special subclass of topoisomerase-targeting drugs that stabilize topoisomerase-DNA
Sílvia Dyson et al.
The EMBO journal, 40(1), e105393-e105393 (2020-11-07)
The juxtaposition of intracellular DNA segments, together with the DNA-passage activity of topoisomerase II, leads to the formation of DNA knots and interlinks, which jeopardize chromatin structure and gene expression. Recent studies in budding yeast have shown that some mechanism
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