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Monastrol

Names

[ CAS No. ]:
329689-23-8

[ Name ]:
Monastrol

[Synonym ]:
ethyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(3-hydroxyphenyl)-6-methyl-2-thioxo-, ethyl ester
Ethyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate
5-pyrimidinecarboxylic acid, 1,6-dihydro-6-(3-hydroxyphenyl)-2-mercapto-4-methyl-, ethyl ester
4-(3-Hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-4H-pyrimidin-5-carboxylic acid ethyl ester
Ethyl 6-(3-hydroxyphenyl)-4-methyl-2-sulfanyl-1,6-dihydropyrimidine-5-carboxylate
Monastrol

Biological Activity

[Description]:

Monastrol is a potent and cell-permeable inhibitor of the mitotic kinesin Eg5 with an IC50 value of 14 μM.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Kinesin
Signaling Pathways >> Cytoskeleton >> Kinesin
Research Areas >> Cancer

[Target]

Eg5:14 μM (IC50)


[In Vitro]

Monastrol is a small, cell-permeable molecule that arrests cells in mitosis by specifically inhibiting Eg5, a member of the Kinesin-5 family. Monastrol treatment of dividing cells results in spindle collapse and cell cycle arrest with a monoastral spindle, which is similar to the phenotype observed when Eg5 is inhibited by anti-Eg5 antibodies[1]. Monastrol is an allosteric inhibitor of the mitotic kinesin Eg5 that exhibits an antiproliferative effect against several cell lines. Monastrol treatment can decrease cell viability in MCF-7 tumor cells. Real-time cell growth kinetic analysis showed a decrease in the proliferation of MCF-7 cells exposed to monastrol[2].

[Cell Assay]

The cytotoxicity assay is performed with MTT. Cells are seeded in 96-well culture plates (5000 cells/well) and incubated for 24 h for stabilization. After this period, the following treatments are administered for 24 and 48 h: vehicle control (0.5 % DMSO); 1 μM doxorubicin and monastrol at 5, 25, 50, 75, and 100 μM. After each time of treatment, the medium is withdrawn, serum-free media containing 0.5 mg/mL MTT salt is added and incubated for 4 h, and formazan crystal products are diluted[2].

[References]

[1]. Cochran JC, et al. Monastrol inhibition of the mitotic kinesin Eg5. J BiolChem. 2005 Apr 1;280(13):12658-67.

[2]. Marques LA, et al. Antiproliferative activity of monastrol in human adenocarcinoma (MCF-7) and non-tumor (HB4a) breast cells. Naunyn Schmiedebergs Arch Pharmacol. 2016 Dec;389(12):1279-1288.

[3]. Mayer TU, et al. Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. Science. 1999 Oct 29;286(5441):971-4.


[Related Small Molecules]

ARRY-520 | GSK-923295 | Ispinesib | Kif15-IN-1 | Kif15-IN-2 | Litronesib | CW-069 | K 858 | SB743921 | AZ82 | Eg5 Inhibitor V, trans-24 | EMD534085 | Paprotrain

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
441.3±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C14H16N2O3S

[ Molecular Weight ]:
292.353

[ Flash Point ]:
220.7±31.5 °C

[ Exact Mass ]:
292.088165

[ PSA ]:
109.72000

[ LogP ]:
2.18

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.648

[ Storage condition ]:
-20℃

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds