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 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.
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.
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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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
B B Hasinoff et al.
Molecular pharmacology, 59(3), 453-461 (2001-02-17)
The bisdioxopiperazines ICRF-187 (dexrazoxane), ICRF-193, and ICRF-154 are catalytic noncleavable complex-forming inhibitors of DNA topoisomerase II that do not produce protein-linked DNA strand breaks. In this study, we showed that bisdioxopiperazines induced erythroid differentiation, inhibited human leukemia K562 cell growth