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(-)-Blebbistatin (856925-71-8)

(-)-Blebbistatin is a cell-permeable inhibitor for non muscle myosin II ATPase with IC50 of ~2 μM, does not inhibit myosin light chain kinase, inhibits contraction of the cleavage furrow without disrupting mitosis or contractile ring assembly…

Not Intended for Therapeutic Use. For research use only.

CAS: 856925-71-8 Category

(-)-Blebbistatin (856925-71-8) Description:

(-)-Blebbistatin is a myosin II inhibitor. Blebbistatin stabilizes the super-relaxed state in skeletal muscle. Blebbistatin exert antitumorigenic properties in human hepatocellular carcinoma cells by interfering with intracellular HuR trafficking. Blebbistatin is phototoxic to human cancer cells under exposure to blue light. Blebbistatin suppresses Ca(2+)-induced and “sensitized”-contraction of skinned tracheal muscles from guinea pig. (-)-Blebbistatin, a myosin II inhibitor, suppresses contraction and disrupts contractile filaments organization of skinned taenia cecum from guinea pig.

(-)-Blebbistatin potently inhibits several striated muscle myosins as well as vertebrate nonmuscle myosin IIA and IIB with IC50 values ranging from 0.5 to 5 μM. Smooth muscle myosin is only poorly inhibited (IC50=80 μM)[1]. Blebbistatin does not compete with nucleotide binding to the skeletal muscle myosin subfragment-1. The inhibitor preferentially binds to the ATPase intermediate with ADP and phosphate bound at the active site, and it slows down phosphate release. It blocks the myosin heads in a products complex with low actin affinity[2]. In culture-activated hepatic stellate cells, blebbistatin is found to change both cell morphology and function. Stellate cells become smaller, acquire a dendritic morphology and have less myosin IIA-containing stress fibres and vinculin-containing focal adhesions. Blebbistatin impairs silicone wrinkle formation, reduces collagen gel contraction and blocks endothelin-1-induced intracellular Ca2+ release. It promotes wound-induced cell migration

(-)-Blebbistatin (856925-71-8) Specifications:

Product Name (-)-Blebbistatin
Synonym Blebbistatin; (S)-Blebbistatin.
Chemical Name 1,2,3,3a-tetrahydro-3aS-hydroxy-6-methyl-1-phenyl-4H-Pyrrolo[2,3-b]quinolin-4-one
Drug Class Inhibitor
Purity ≥98% (HPLC)
CAS Number 856925-71-8
Molecular Formula C18H16N2O2
Molecular Weight 292.338
Monoisotopic Mass 292.12118 g/mol
MDL number MFCD08460907
InChIKey LZAXPYOBKSJSEX-GOSISDBHSA-N
InChi Code 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
SMILES CC1=CC2=C(C=C1)N=C3C(C2=O)(CCN3C4=CC=CC=C4)O
Form Solid Powder
Color Yellow
Solubility  Soluble in methanol (1.5 mg/ml), DMSO (100 mM), Dichloromethane, ethyl acetate, chloroform, methylene chloride, DMF (~12.5 mg/ml), 1:1 solution of DMF:PBS (pH 7.2) (~0.5 mg/ml), and water (0.5 mg/ml at 25° C).
Storage Temp.  -20°C
Shelf life >2 years if stored properly
Handling Protect from air and moisture
Application An inhibitor of myosin II

 


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RIDADR NONH for all modes of transport

References:

[1]. Boberg L, Rahman A, Poljakovic M, Arner A. Protein kinase C activation of a blebbistatin sensitive contractile component in the wall of hypertrophying mouse urinary bladder. Neurourol Urodyn. 2015 Feb;34(2):196-202. doi: 10.1002/nau.22531. Epub 2013 Nov 26. PubMed PMID: 25794194.

[2]. Wang X, Chong M, Wang X, Wang H, Zhang J, Xu H, Zhang J, Liu D. Block the function of nonmuscle myosin II by blebbistatin induces zebrafish embryo cardia bifida. In Vitro Cell Dev Biol Anim. 2015 Mar;51(3):211-7. doi: 10.1007/s11626-014-9836-0. Epub 2014 Nov 18. PubMed PMID: 25403653.

[3]. Wilson C, Naber N, Pate E, Cooke R. The myosin inhibitor blebbistatin stabilizes the super-relaxed state in skeletal muscle. Biophys J. 2014 Oct 7;107(7):1637-46. doi: 10.1016/j.bpj.2014.07.075. PubMed PMID: 25296316; PubMed Central PMCID: PMC4190596.

[4]. Lv Y, Lu S, Lu T, Kou J, Yu B. Homology model of nonmuscle myosin heavy chain IIA and binding mode analysis with its inhibitor blebbistatin. J Mol Model. 2013 Apr;19(4):1801-10. doi: 10.1007/s00894-012-1750-3. Epub 2013 Jan 13. PubMed PMID: 23315199.

[5]. Brack KE, Narang R, Winter J, Ng GA. The mechanical uncoupler blebbistatin is associated with significant electrophysiological effects in the isolated rabbit heart. Exp Physiol. 2013 May;98(5):1009-27. doi: 10.1113/expphysiol.2012.069369. Epub 2013 Jan 4. PubMed PMID: 23291912; PubMed Central PMCID: PMC3734628.