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M8515

Sigma-Aldrich

Monastrol

≥98% (HPLC), 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
MDL number:
MFCD00813077
UNSPSC Code:
12352200
PubChem Substance ID:
24897267
NACRES:
NA.77

Quality Level

100

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

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

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 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

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.

JAN Code

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

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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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)
Renske van Leuken et al.
PloS one, 4(4), e5282-e5282 (2009-04-25)
Polo-like kinase-1 (Plk1) is activated before mitosis by Aurora A and its cofactor Bora. In mitosis, Bora is degraded in a manner dependent on Plk1 kinase activity and the E3 ubiquitin ligase SCF-betaTrCP. Here, we show that Plk1 is also
Jun Takagi et al.
Scientific reports, 3, 2808-2808 (2013-10-01)
The chromosome alignment is mediated by polar ejection and poleward forces acting on the chromosome arm and kinetochores, respectively. Although components of the motile machinery such as chromokinesin have been characterized, their dynamics within the spindle is poorly understood. Here
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
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