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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

CHF 145.00

Spedizione prevista il26 maggio 2025

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Saggio

≥98% (HPLC)

Stato

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

Categorie correlate

Applicazioni

Merbarone has been used to study its effect on the occurrence of DNA lesions.[1]

Azioni biochim/fisiol

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.
Thiobarbituric acid with aniline joined by an amide linkage forms merbarone.[2] It is known to prolong cell cycle progression by inducing DNA double strand breaks, retarding S phase and arresting G2 phase.[3][4] This delays cell entry into mitosis.[3] Merbarone possesses cytotoxic and genotoxic action and promotes endoreduplication.[4] Merbarone has mild antitumor action and is also found to nephrotoxic.[2]

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)

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Certificati d'analisi (COA)

Lot/Batch Number
0000412102
0000412102
0000135487
0000119683
0000100639

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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
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
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
J M Fortune et al.
The Journal of biological chemistry, 273(28), 17643-17650 (1998-07-04)
Merbarone is a catalytic inhibitor of topoisomerase II that is in clinical trials as an anticancer agent. Despite the potential therapeutic value of this drug, the mechanism by which it blocks topoisomerase II activity has not been delineated. Therefore, to
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Articoli

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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