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I4659

Sigma-Aldrich

ICRF-193

apoptosis inducer, arabinosidase substrate

Sinônimo(s):

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

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About This Item

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

fonte biológica

synthetic (organic)

Ensaio

≥95%

forma

powder or flakes
solid

solubilidade

DMSO: 4 mg/mL

temperatura de armazenamento

−20°C

cadeia de caracteres 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+

chave InChI

OBYGAPWKTPDTAS-OCAPTIKFSA-N

Descrição geral

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

Aplicação

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

Ações bioquímicas/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

Palavra indicadora

Danger

Frases de perigo

H301,H317

Declarações de precaução

P280 - P301 + P310 + P330 - P302 + P352

Classificações de perigo

Acute Tox. 3 Oral - Skin Sens. 1

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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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
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 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
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
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