| Identification | More | [Name]
MONASTROL | [CAS]
254753-54-3 | [Synonyms]
CS-2432
Monastrol - CAS 254753-54-3 - Calbiochem
6-METHYL-4-(3-HYDROXYPHENYL)-2-THIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-CARBOXYLATE
1,2,3,4-TETRAHYDRO-4-(3-HYDROXYPHENYL)-6-METHYL-2-THIOXO-5-PYRIMIDINECARBOXYLIC ACID, ETHYL ESTER
4-(3-HYDROXYPHENYL)-6-METHYL-2-THIOXO-1,2,3,4-TETRAHYDRO-4H-PYRIMIDIN-5-CARBOXYLIC ACID ETHYL ESTER
5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-4-(3-hydroxyphenyl)-6-methyl-2-thioxo-, ethyl ester, (4S)- | [Molecular Formula]
C14H16N2O3S | [MDL Number]
MFCD00813077 | [Molecular Weight]
292.35 | [MOL File]
254753-54-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
185-185.9 °C(lit.) | [Boiling point ]
441.3±55.0 °C(Predicted) | [density ]
1.34±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: 100 mg/mL
| [form ]
White solid | [pka]
9.63±0.10(Predicted) | [color ]
white to off-white | [Usage]
A cell-permeablesmall molecule inhibitor of the mitotic kinesin, Eg5, arrests cells in mitosis with monoastral spindles | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. | [CAS DataBase Reference]
254753-54-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
|
| Hazard Information | Back Directory | [Description]
Monastrol (254753-54-3) is a potent, cell-permeable, small molecule inhibitor of mitosis. Monastrol-arrested cells are characterized by monopolar spindles.1?Does not affect other motor proteins or tubulin. Specifically inhibits the mitotic molecular motor kinesin Eg5, a motor protein required for spindle formation (IC50?= 14 μM).2?Mimics the effect of amyloid β on long term potentiation in a cellular model of learning and memory.3?Enhances regeneration of adult axons.4 | [Chemical Properties]
Crystalline Solid | [Uses]
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
| [Uses]
A cell-permeablesmall molecule inhibitor of the mitotic kinesin, Eg5, arrests cells in mitosis with monoastral spindles | [Uses]
Inhibitor of mammalian cell mitosis. | [Definition]
ChEBI: Monastrol is a racemate comprising equimolar amounts of R- and S-monastrol. It has a role as an antineoplastic agent, an EC 3.5.1.5 (urease) inhibitor, an antileishmanial agent and an antimitotic. It contains a (R)-monastrol and a (S)-monastrol. | [Biological Activity]
Potent, cell-permeable, small molecule mitosis inhibitor that does not interact with tubulin. Arrests cells in mitosis and specifically inhibits the motility of the mitotic kinesin Eg5, a motor protein required for mitotic spindle formation and maintenance (IC 50 = 14 μ M). | [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. | [storage]
Store at RT | [References]
1) Mayer?et al. (1999), Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen; Science,?286?971
2) Kapoor?et al.?(2000),?Probing spindle assembly mechanisms with monastrol, a small molecule inhibitor of mitotic kinesin, Eg5; J. Cell Biol.,?150?975
3) Ari?et al.?(2014),?Alzheimer amyloid beta inhibition of Eg5/kinesin 5 reduces neurotrophin and/or transmitter receptor function; Neurobiol. Aging,?35?1839
4) Lin?et al. (2011),?Inhibition of Kinesin-5, a microtubule-based motor protein, as a strategy for enhancing regeneration of adult axons; Traffic,?12?269 |
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| Company Name: |
Sigma-Aldrich
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021-61415566 800-8193336 |
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https://www.sigmaaldrich.cn |
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