B0560

(−)-Blebbistatin

Name: (−)-Blebbistatin
Brand: SIGMA

≥98% (HPLC), solid, cell cycle inhibitor

Synonym(s):

1-Phenyl-1,2,3,4-tetrahydro-4-hydroxypyrrolo[2.3-b]-7-methylquinolin-4-one

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₁₆N₂O₂

CAS Number:

856925-71-8

Molecular Weight:

292.33

UNSPSC Code:

12352200

PubChem Substance ID:

329773119

NACRES:

NA.77

MDL number:

MFCD08460907

Product Name

(−)-Blebbistatin, solid, synthetic

SMILES string

Cc1ccc2N=C3N(CC[C@@]3(O)C(=O)c2c1)c4ccccc4

InChI key

LZAXPYOBKSJSEX-GOSISDBHSA-N

InChI

1S/C18H16N2O2/c1-12-7-8-15-14(11-12)16(21)18(22)9-10-20(17(18)19-15)13-5-3-2-4-6-13/h2-8,11,22H,9-10H2,1H3/t18-/m1/s1

form

solid

solubility

DMSO: 5 mg/mL
chloroform: soluble(lit.)
ethyl acetate: soluble(lit.)
methanol: soluble(lit.)
methylene chloride: soluble(lit.)

storage temp.

−20°C

Quality Level

200

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

(−)-Blebbistatin has been used to investigate the effect on cardiac contractility and effect of thrombin on actomyosin contractility

Biochem/physiol Actions

(-)-Blebbistatin is a cell cycle inhibitor; selective inhibitor of non-muscle myosin II.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

General description

(-)-Blebbistatin, a bioactive small molecule, is a selective inhibitor of skeletal muscle and non-muscle myosin II isoforms.The mechanism of action of blebbistatin, a myosin II ATPase inhibitor, does not influence other members of the myosin superfamily, such as I, V, and X.Blebbistatin is highly light sensitive, and photobleaching can reverse its effect completely. Blebbistatin is a commonly used as excitation-contraction uncoupling agent in cardiovascular physiology. Blebbistatin controls the inhibitory effect of thrombin on intercellular Ca₂⁺ wave propagation. Blebbistatin reduces cardiac contractility by stabilizing the OFF state of the thick filament.Blebbistatin’s selectivity and affinity for multiple class II myoisin make it an attractive candidate for use in cell motility research and muscle physiology.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

WXBF7940V

0000509842

0000500504

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Blebbistatin: use as inhibitor of muscle contraction

Farman GP, et al.

Pflugers Archiv : European Journal of Physiology, 455(6), 995-1005 (2008)

The myosin II ATPase inhibitor blebbistatin prevents thrombin-induced inhibition of intercellular calcium wave propagation in corneal endothelial cells

Ponsaerts R, et al.

Investigative Ophthalmology & Visual Science, 49(11), 4816-4827 (2008)

Extracellular Matrix Geometry and Initial Adhesive Position Determine Stress Fiber Network Organization during Cell Spreading.

Elena Kassianidou et al.

Cell reports, 27(6), 1897-1909 (2019-05-09)

Three-dimensional matrices often contain highly structured adhesive tracks that require cells to turn corners and bridge non-adhesive areas. Here, we investigate these complex processes using micropatterned cell adhesive frames. Spreading kinetics on these matrices depend strongly on initial adhesive position

Roles of formin nodes and myosin motor activity in Mid1p-dependent contractile-ring assembly during fission yeast cytokinesis.

Valerie C Coffman et al.

Molecular biology of the cell, 20(24), 5195-5210 (2009-10-30)

Two prevailing models have emerged to explain the mechanism of contractile-ring assembly during cytokinesis in the fission yeast Schizosaccharomyces pombe: the spot/leading cable model and the search, capture, pull, and release (SCPR) model. We tested some of the basic assumptions

Omecamtiv mercabil and blebbistatin modulate cardiac contractility by perturbing the regulatory state of the myosin filament

Kampourakis T, et al.

The Journal of Physiology, 596(1), 31-46 (2018)

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