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I4659

Sigma-Aldrich

ICRF-193

apoptosis inducer, arabinosidase substrate

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:
21416-88-6
Molecular Weight:
282.30
MDL number:
MFCD01702964
UNSPSC Code:
12352204
PubChem Substance ID:
24896062
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301,H317

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

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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
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
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
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 Iguchi et al.
Biochemical pharmacology, 57(10), 1105-1111 (2001-03-07)
As many antitumor drugs can kill tumors through the induction of apoptosis, the effect of these drugs presumably would be enhanced if they were used in combination with other drugs that interact with apoptotic processes. To clarify the biological events
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