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Merck

M8515

Monastrol

≥98% (HPLC), Mitosis inhibitor, solid

Synonym(s):

4-(3-Hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-4H-pyrimidin-5-carboxylic Acid Ethyl Ester

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About This Item

Empirical Formula (Hill Notation):
C14H16N2O3S
CAS Number:
254753-54-3
Molecular Weight:
292.35
UNSPSC Code:
12352200
PubChem Substance ID:
24897267
NACRES:
NA.77
MDL number:
MFCD00813077

Key Documents

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Product Name

Monastrol, ≥98% (HPLC), solid

SMILES string

CCOC(=O)C1=C(C)NC(=S)NC1c2cccc(O)c2

InChI

1S/C14H16N2O3S/c1-3-19-13(18)11-8(2)15-14(20)16-12(11)9-5-4-6-10(17)7-9/h4-7,12,17H,3H2,1-2H3,(H2,15,16,20)

InChI key

LOBCDGHHHHGHFA-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

solid

storage condition

protect from light

color

white to off-white

mp

185-185.9 °C (lit.)

solubility

DMSO: >5 mg/mL

storage temp.

2-8°C

Quality Level

100

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Application

Monastrol has been used:
  • to treat MDA-MB-231 cells as a non-microtubule-targeting agent
  • as a antineoplastic agent, to treat mouse myeloma cell line SP 2/0, to induce apoptosis and to elucidate the role of metabotropic glutamate receptor 3 (Grm3) in apoptosis
  • as an inhibitor of pteridine reductase in GFP-transfected promastigotes infected macrophages for flow cytometer-based growth inhibition assay and to evaluate anti-leishmanial activity of Leishmania donovani hamster model in vivo

Biochem/physiol Actions

Monastrol is a potent, cell-permeant inhibitor of mitosis. Monastrol arrested cells are characterized by monopolar spindles. This phenotype is induced through specific disruption of mitotic molecular motor kinesin Eg5 with IC50 at 14 μM. No effect on other motor proteins and tubulin.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Packaging

Packaged under inert gas.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

M8515-IP: + M8515-BULK: + M8515-1MG: + M8515-VAR: + M8515-5MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000388644
0000331148
0000331149
0000388644
0000331149

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Rebecca A Holton et al.
Biology of reproduction, 103(1), 24-35 (2020-03-29)
The number and quality of oocytes, as well as the decline in both of these parameters with age, determines reproductive potential in women. However, the underlying mechanisms of this diminution are incompletely understood. Previously, we identified novel roles for CHTF18
Metabotropic glutamate receptor 3 is involved in B-cell-related tumor apoptosis
Liu X, et al.
International journal of oncology, 49(4), 1469-1478 (2016)
M410, a combretastatin A4 analogue, disrupts microtubules and inhibits HIF-1 alpha in human breast cancer cells
Yang H, et al.
Oncology Reports, 34(1), 334-340 (2015)
Steven Haney et al.
PloS one, 8(6), e64946-e64946 (2013-07-11)
Genome-wide association (GWA) studies have described a large number of new candidate genes that contribute to of Type 2 Diabetes (T2D). In some cases, small clusters of genes are implicated, rather than a single gene, and in all cases, the
T U Mayer et al.
Science (New York, N.Y.), 286(5441), 971-974 (1999-11-05)
Small molecules that perturb specific protein functions are valuable tools for dissecting complex processes in mammalian cells. A combination of two phenotype-based screens, one based on a specific posttranslational modification, the other visualizing microtubules and chromatin, was used to identify
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Articles

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Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

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