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M2070

Sigma-Aldrich

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
MDL number:
MFCD00866337
UNSPSC Code:
12352200
PubChem Substance ID:
24724534
NACRES:
NA.77

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Frontiers in Anti-Cancer Drug Discovery, 3, 21-21 (2014)
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
Multi-Targeted Approach to Treatment of Cancer, 616, 328-328 (2015)
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