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Merck

M2070

Merbarone

≥98% (HPLC), solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C11H9N3O3S
CAS Number:
97534-21-9
Molecular Weight:
263.27
NACRES:
NA.77
PubChem Substance ID:
24724534
UNSPSC Code:
12352200
MDL number:
MFCD00866337
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
200

Key Documents

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Quality Level

200

assay

≥98% (HPLC)

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

solubility

DMSO: >5 mg/mL

storage temp.

2-8°C

SMILES string

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)

InChI key

JARCFMKMOFFIGZ-UHFFFAOYSA-N

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Application

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

Biochem/physiol Actions

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000444198
0000444198
0000412102
0000412102
0000135487

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Yoko Otake et al.
Molecular pharmacology, 69(4), 1477-1485 (2006-01-26)
Studies were carried out to address possible cellular mechanisms by which merbarone, a catalytic inhibitor of DNA topoisomerase II, can block tumor cell growth without inducing extensive DNA cleavage. Merbarone induced the release of high molecular weight DNA fragments from
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
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
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
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
View All Related Papers

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