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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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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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