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Merck
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Key Documents

Altri documenti

M2070

Sigma-Aldrich

Merbarone

≥98% (HPLC), solid

Sinonimo/i:

5-(N-Phenylcarbamoyl)-2-thiobarbituric acid, NSC-336628

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About This Item

Formula empirica (notazione di Hill):
C11H9N3O3S
Numero CAS:
97534-21-9
Peso molecolare:
263.27
Numero MDL:
MFCD00866337
Codice UNSPSC:
12352200
ID PubChem:
24724534
NACRES:
NA.77

Saggio

≥98% (HPLC)

Forma fisica

solid

Controllo stupefacenti

regulated under CDSA - not available from Sigma-Aldrich Canada

Solubilità

DMSO: >5 mg/mL

Temperatura di conservazione

2-8°C

Stringa SMILE

O=C1NC(=S)NC(=O)C1C(=O)Nc2ccccc2

InChI

1S/C11H9N3O3S/c15-8(12-6-4-2-1-3-5-6)7-9(16)13-11(18)14-10(7)17/h1-5,7H,(H,12,15)(H2,13,14,16,17,18)
JARCFMKMOFFIGZ-UHFFFAOYSA-N

Applicazioni

Merbarone has been used to study its effect on the occurrence of DNA lesions.

Azioni biochim/fisiol

Thiobarbituric acid with aniline joined by an amide linkage forms merbarone. It is known to prolong cell cycle progression by inducing DNA double strand breaks, retarding S phase and arresting G2 phase. This delays cell entry into mitosis. Merbarone possesses cytotoxic and genotoxic action and promotes endoreduplication. Merbarone has mild antitumor action and is also found to nephrotoxic.
Selective topoisomerase II inhibitor. Blocks topo II-mediated DNA cleavage without stabilizing DNA-topo II-cleavable complexes. Induces apoptosis in CEM cells via caspase 3 dependent mechanism.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Christy R Hagan et al.
Genes, chromosomes & cancer, 46(3), 248-260 (2006-12-16)
Among the cellular responses observed following treatment with DNA-damaging agents is the activation of Short Interspersed Elements (SINEs; retrotransposable genetic elements that comprise over 10% of the human genome). By placing a human SINE (the Alu element) into murine cells
Alexei Mikhailov et al.
The Journal of cell biology, 166(4), 517-526 (2004-08-11)
When early prophase PtK(1) or Indian muntjac cells are exposed to topoisomerase II (topo II) inhibitors that induce little if any DNA damage, they are delayed from entering mitosis. We show that this delay is overridden by inhibiting the p38
B B Hasinoff et al.
Biochemical pharmacology, 53(12), 1843-1853 (1997-06-15)
A Chinese hamster ovary (CHO) cell line highly resistant to the non-cleavable complex-forming topoisomerase II inhibitor dexrazoxane (ICRF-187, Zinecard) was selected. The resistant cell line (DZR) was 1500-fold resistant (IC50 = 2800 vs 1.8 microM) to continuous dexrazoxane exposure. DZR
Y Y Mo et al.
Molecular pharmacology, 55(2), 216-222 (1999-02-03)
Many anticancer agents exert their cytotoxicity through DNA damage and induction of apoptosis. Fas ligand (FasL), a key component of T lymphocytes, has been shown to be induced by some of those agents. To address what is an early signal
Novel mechanisms of resistance to inhibitors of DNA topoisomerases.
W T Beck et al.
Advances in enzyme regulation, 37, 17-26 (1997-01-01)
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