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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

MDL number:

MFCD08460907

UNSPSC Code:

12352200

PubChem Substance ID:

329773119

NACRES:

NA.77

product name

(−)-Blebbistatin, solid, synthetic

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

SMILES string

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

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

InChI key

LZAXPYOBKSJSEX-GOSISDBHSA-N

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

M1404

Nocodazole

Sigma-Aldrich

B0753

2,3-Butanedione monoxime

Application of blebbistatin as an excitation-contraction uncoupler for electrophysiologic study of rat and rabbit hearts

Fedorov VV, et al.

Heart Rhythm : the Official Journal of the Heart Rhythm Society, 4(5), 619-626 (2007)

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)

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

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)

Blebbistatin: use as inhibitor of muscle contraction

Farman GP, et al.

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

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