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B0560

(−)-Blebbistatin

≥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
Form:
solid
Quality level:
200
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Product Name

(−)-Blebbistatin, solid, synthetic

Quality Level

200

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.[1]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.[1]

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.

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This Item
203390203895D5919
(−)-Blebbistatin solid, synthetic

Sigma-Aldrich

B0560

(−)-Blebbistatin

(±)-Blebbistatin (±)-Blebbistatin, CAS 674289-55-5, is a cell-permeable, selective, and reversible inhibitor of nonmuscle myosin II. Blocks cell blebbing and disrupts cell migration & cytoKinesis in vertebrate cells.

Sigma-Aldrich

203390

(±)-Blebbistatin

BTS A potent inhibitor of Ca2+-stimulated myosin S1 ATPase (IC50 = ~ 5 µM) and reversibly blocks the gliding motility.

Sigma-Aldrich

203895

BTS

Diacylglycerol Kinase Inhibitor I solid

Sigma-Aldrich

D5919

Diacylglycerol Kinase Inhibitor I

form

solid

form

solid

form

crystalline solid

form

solid

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°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

DMSO: 200 mg/mL

solubility

0.1 M HCl: slightly soluble, 0.1 M NaOH: slightly soluble, DMSO: soluble, H2O: insoluble, ethanol: soluble, ethyl acetate: soluble

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Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
0000561082
0000529978
0000529978
0000561082
WXBF7940V

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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
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)
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Global Trade Item Number

SKUGTIN
B0560-5MG04061833419939
B0560-1MG04061833419922

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