M8515

Monastrol

Name: Monastrol
Brand: SIGMA

≥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

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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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)

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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)

Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen.

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

Targeting Aurora B to the equatorial cortex by MKlp2 is required for cytokinesis.

Mayumi Kitagawa et al.

PloS one, 8(6), e64826-e64826 (2013-06-12)

Although Aurora B is important in cleavage furrow ingression and completion during cytokinesis, the mechanism by which kinase activity is targeted to the cleavage furrow and the molecule(s) responsible for this process have remained elusive. Here, we demonstrate that an

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)

CHTF18 ensures the quantity and quality of the ovarian reserve†.

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

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Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

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