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

Key Documents

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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

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This Item	203390	203391	203895
Sigma-Aldrich B0560 (−)-Blebbistatin	Sigma-Aldrich 203390 (Â±)-Blebbistatin	Sigma-Aldrich 203391 (-)-Blebbistatin	Sigma-Aldrich 203895 BTS
form solid	form solid	form solid	form crystalline solid
Quality Level 200	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. 2-8°C
solubility DMSO: 5 mg/mL, ethyl acetate: soluble(lit.), methylene chloride: soluble(lit.), chloroform: soluble(lit.), methanol: soluble(lit.)	solubility methanol: 1.5 mg/mL, 100% DMSO: 100 mg/mL, 90% DMSO: 75 mg/mL	solubility methanol: 1.5 mg/mL, 100% DMSO: 100 mg/mL, 90% DMSO: 75 mg/mL	solubility DMSO: 200 mg/mL

Application

(−)-Blebbistatin has been used to investigate the effect on cardiac contractility [1] and effect of thrombin on actomyosin contractility[2]

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.[3]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,[4] and photobleaching can reverse its effect completely.[5] Blebbistatin is a commonly used as excitation-contraction uncoupling agent in cardiovascular physiology.[4][5] Blebbistatin controls the inhibitory effect of thrombin on intercellular Ca₂⁺ wave propagation.[2] Blebbistatin reduces cardiac contractility by stabilizing the OFF state of the thick filament.[1]Blebbistatin’s selectivity and affinity for multiple class II myoisin make it an attractive candidate for use in cell motility research and muscle physiology.[3]

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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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)

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

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)

Epac and phospholipase Cepsilon regulate Ca2+ release in the heart by activation of protein kinase Cepsilon and calcium-calmodulin kinase II.

Emily A Oestreich et al.

The Journal of biological chemistry, 284(3), 1514-1522 (2008-10-30)

Recently, we identified a novel signaling pathway involving Epac, Rap, and phospholipase C (PLC)epsilon that plays a critical role in maximal beta-adrenergic receptor (betaAR) stimulation of Ca2+-induced Ca2+ release (CICR) in cardiac myocytes. Here we demonstrate that PLCepsilon phosphatidylinositol 4,5-bisphosphate

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