MONASTROL
Synonym(s):4-(3-Hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-4H-pyrimidin-5-carboxylic Acid Ethyl Ester, Eg5 Inhibitor I;Monastrol - CAS 254753-54-3 - Calbiochem
- CAS NO.:254753-54-3
- Empirical Formula: C14H16N2O3S
- Molecular Weight: 292.35
- MDL number: MFCD11978057
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-30 15:45:59
What is MONASTROL?
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
The Uses of MONASTROL
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
The Uses of MONASTROL
A cell-permeablesmall molecule inhibitor of the mitotic kinesin, Eg5, arrests cells in mitosis with monoastral spindles
The Uses of MONASTROL
Inhibitor of mammalian cell mitosis.
What are the applications of Application
Monastrol is a kinesin Eg5 inhibitor which arrests cells in 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
Properties of MONASTROL
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 |
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 information for MONASTROL
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for MONASTROL
New Products
Tert-butyl bis(2-chloroethyl)carbamate (S)-3-Aminobutanenitrile hydrochloride N-Boc-D-alaninol N-BOC-D/L-ALANINOL N-octanoyl benzotriazole 3,4-Dibenzyloxybenzaldehyde 4-Hydrazinobenzoic acid 1,1’-CARBONYLDIIMIDAZOLE R-2-BENZYLOXY PROPIONIC ACID 3-NITRO-2-METHYL ANILINE 4-IODO BENZOIC ACID 4-HYDROXY BENZYL ALCOHOL 4-(3-chloropropyl)morpholine phenylhydrazine hydrochloride (2-Hydroxyphenyl)acetonitrile 4-Bromopyrazole 5-BROMO-2CYANO PYRIDINE 5,6-Dimethoxyindanone 5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine 4-methoxy-3,5-dinitropyridine 2-(Cyanocyclohexyl)acetic acid 2-aminopropyl benzoate hydrochloride 1-(4-(aminomethyl)benzyl)urea hydrochloride tert-butyl 4- (ureidomethyl)benzylcarbamateRelated products of tetrahydrofuran
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