Monastrol

Names

[ Name ]:
Monastrol

[Synonym ]:
F3284-6466
MFCD00813077
monastrol

Biological Activity

[Description]:

(S)-Monastrol ((+)-Monastrol) is an allosteric inhibitor of the mitotic kinesin Eg5 that exhibits an antiproliferative effect against several cancer cell lines. (S)-Monastrol arrests mammalian cells in mitosis with monopolar spindles[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Kinesin

Signaling Pathways >> Cytoskeleton >> Kinesin

[References]

[1]. 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.

[2]. 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.

Chemical & Physical Properties

[ Density]:
1.34g/cm3

[ Boiling Point ]:
441.3ºC at 760mmHg

[ Melting Point ]:
185-185.9ºC(lit.)

[ Molecular Formula ]:
C₁₄H₁₆N₂O₃S

[ Molecular Weight ]:
292.35

[ Flash Point ]:
220.7ºC

[ Exact Mass ]:
292.08800

[ PSA ]:
109.72000

[ LogP ]:
1.92380

[ Vapour Pressure ]:
2.13E-08mmHg at 25°C

[ Index of Refraction ]:
1.648

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: 100 mg/mL

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Cytokinetic Failure-induced Tetraploidy Develops into Aneuploidy, Triggering Skin Aging in Phosphovimentin-deficient Mice.

J. Biol. Chem. 290 , 12984-98, (2015)

Tetraploidy, a state in which cells have doubled chromosomal sets, is observed in ∼20% of solid tumors and is considered to frequently precede aneuploidy in carcinogenesis. Tetraploidy is also detecte...

Loop 5-directed compounds inhibit chimeric kinesin-5 motors: implications for conserved allosteric mechanisms.

J. Thorac. Cardiovasc. Surg. 286 , 6201-10, (2011)

The human Eg5 (HsEg5) protein is unique in its sensitivity to allosteric agents even among phylogenetic kin. For example, S-trityl-l-cysteine (STC) and monastrol are HsEg5 inhibitors that bind to a su...

A sensitised RNAi screen reveals a ch-TOG genetic interaction network required for spindle assembly.

Sci. Rep. 5 , 10564, (2015)

How multiple spindle assembly pathways are integrated to drive bipolar spindle assembly is poorly understood. We performed an image-based double RNAi screen to identify genes encoding Microtubule-Asso...