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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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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
DNA breaks and chromatin structural changes enhance the transcription of Autoimmune Regulator target genes
Guha M, et al.
The Journal of Biological Chemistry, 292(16), 6542-6554 (2017)
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
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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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

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