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I4659

Sigma-Aldrich

ICRF-193

apoptosis inducer, arabinosidase substrate

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C12H18N4O4
CAS-Nummer:
21416-88-6
Molekulargewicht:
282.30
MDL-Nummer:
MFCD01702964
UNSPSC-Code:
12352204
PubChem Substanz-ID:
24896062
NACRES:
NA.77

Biologische Quelle

synthetic (organic)

Qualitätsniveau

200

Assay

≥95%

Form

powder or flakes
solid

Löslichkeit

DMSO: 4 mg/mL

Lagertemp.

−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+

InChIKey

OBYGAPWKTPDTAS-OCAPTIKFSA-N

Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H301,H317

Gefahreneinstufungen

Acute Tox. 3 Oral - Skin Sens. 1

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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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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