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M2070

Sigma-Aldrich

Merbarone

≥98% (HPLC), solid

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C11H9N3O3S
Numéro CAS:
97534-21-9
Poids moléculaire :
263.27
Numéro MDL:
MFCD00866337
Code UNSPSC :
12352200
ID de substance PubChem :
24724534
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

solid

Contrôle du médicament

regulated under CDSA - not available from Sigma-Aldrich Canada

Solubilité

DMSO: >5 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

JARCFMKMOFFIGZ-UHFFFAOYSA-N

Application

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Ling Wang et al.
Mutation research, 616(1-2), 70-82 (2006-12-19)
Merbarone, a topoisomerase II (topo II) inhibitor which, in contrast to etoposide, does not stabilize topo II-DNA cleavable complexes, was previously shown to be a potent clastogen in vitro and in vivo. To investigate the possible mechanisms, we compared the
U R Malik et al.
Medical oncology (Northwood, London, England), 14(3-4), 159-162 (1998-02-19)
The standard treatment for patients with primary malignant glioma includes surgical resection, radiotherapy, and nitrosourea. Despite this multimodality approach, adults with newly diagnosed glioblastoma multiforme (GBM) and high-grade astrocytoma have a median survival duration of 50 weeks and 150 weeks
Y Y Mo et al.
Cancer research, 57(22), 5004-5008 (1997-11-26)
DNA topoisomerase II (topo II) is a target for many clinically useful anticancer drugs. However, a major concern in the use of these drugs is the development of resistance, often manifested by reduced drug accumulation or reduced topo IIalpha activity
Nuria Pastor et al.
Mutation research, 738-739, 45-51 (2012-08-28)
In the last years a number of reports have shown that the so-called topoisomerase II (topo II) catalytic inhibitors are able to induce DNA and chromosome damage, an unexpected result taking into account that they do not stabilize topo II-DNA
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
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Articles

Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

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