I4659
ICRF-193
synthetic (organic), ≥95%, topoisomerase II inhibitor, solid,powder or flakes
Synonym(s):
meso-4,4′-(3,2-Butanediyl)-bis(2,6-piperazinedione)
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About This Item
Empirical Formula (Hill Notation):
C12H18N4O4
CAS Number:
Molecular Weight:
282.30
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
ICRF-193, apoptosis inducer, arabinosidase substrate
biological source
synthetic (organic)
Quality Level
assay
≥95%
form
powder or flakes, solid
solubility
DMSO: 4 mg/mL
storage temp.
−20°C
SMILES string
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+
InChI key
OBYGAPWKTPDTAS-OCAPTIKFSA-N
General description
ICRF-193 is a bisdiopiperazine derivative. It inhibits topoisomerase II by forming a non-cleavable complex.
Application
ICRF-193 has been used as a topoisomerase II (TOP2) inhibitor to treat mouse oocytes to investigate the role of TOP2 in meiosis.
Biochem/physiol Actions
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Skin Sens. 1
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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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)