MONASTROL

Product NameMONASTROL
CAS254753-54-3
MFC14H16N2O3S
MW292.35
EINECS
MOL File254753-54-3.mol

Chemical Properties

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.
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)
InChIKey	LOBCDGHHHHGHFA-UHFFFAOYSA-N
SMILES	CCOC(=O)C1=C(C)NC(=S)NC1c2cccc(O)c2
CAS DataBase Reference	254753-54-3(CAS DataBase Reference)

Safety Information

Safety Statements	22-24/25
WGK Germany	3
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

Monastrol (254753-54-3) is a potent, cell-permeable, small molecule inhibitor of mitosis. Monastrol-arrested cells are characterized by monopolar spindles.1Does 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).2Mimics the effect of amyloid β on long term potentiation in a cellular model of learning and memory.3Enhances 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] MAKOTO KINOSHITA Naoki W. [Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen].[J]. Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme, 2007, 52 13 Suppl: 1796-1799.
[2] T M KAPOOR. Probing spindle assembly mechanisms with monastrol, a small molecule inhibitor of the mitotic kinesin, Eg5.[J]. Journal of Cell Biology, 2000, 150 5: 975-988. DOI:10.1083/jcb.150.5.975
[3] CSILLA ARI . Alzheimer amyloid beta inhibition of Eg5/kinesin 5 reduces neurotrophin and/or transmitter receptor function[J]. Neurobiology of Aging, 2014, 35 8: Pages 1839-1849. DOI:10.1016/j.neurobiolaging.2014.02.006
[4] SHEN LIN. Inhibition of Kinesin-5, a microtubule-based motor protein, as a strategy for enhancing regeneration of adult axons.[J]. Traffic (Copenhagen, Denmark), 2011: 269-286. DOI:10.1111/j.1600-0854.2010.01152.x

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