856925-71-8

Basic information

• Product Name: (-)-Blebbistatin
• Synonyms: (+/-)-BLEBBISTATIN;(S)-(-)-BLEBBISTATIN;4H-Pyrrolo[2,3-b]quinolin-4-one, 1,2,3,3a-tetrahydro-3a-hydroxy-6-methyl-1-phenyl-, (3aS)-;3a-Hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (-)-Blebbistatin;3a-Hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one 1,2,3,3atetrahydro3ahydroxy6methyl1phenyl4Hpyrrolo[2,3b]quinolin4one;(S)-3a-Hydroxy-6-methyl-1-phenyl-3,3a-dihydro-1H-pyrrolo[2,3-b]quinolin-4(2H)-one;(-)-Blebbistatin *CAS#: 856925-71-8*
• CAS NO: 856925-71-8
• Molecular Formula: C18H16N2O2
• Molecular Weight: 292.336
• Product Categories: Caspases/Apoptosis;Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 856925-71-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 210-212°C
• Boiling Point: 507.3±60.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• Storage Temp.: Desiccate at +4°C
• Solubility: DMSO: soluble5mg/mL
• PKA: 11.15±0.20(Predicted)
• CAS DataBase Reference: (-)-Blebbistatin(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Blebbistatin(856925-71-8)
• EPA Substance Registry System: (-)-Blebbistatin(856925-71-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 856925-71-8(Hazardous Substances Data)

Usage

Description

(-)-Blebbistatin is a small molecule inhibitor that specifically targets myosin II, a motor protein involved in various cellular processes. It has the ability to rapidly and reversibly block cell blebbing, a phenomenon where cells shed membrane protrusions. This property makes (-)-Blebbistatin a valuable tool in studying the role of myosin II in cell biology.

Uses

Used in Cell Biology Research:
(-)-Blebbistatin is used as a research tool for investigating the role of myosin II in various cell processes, such as cell blebbing, directed cell migration, and cytokinesis in vertebrate cells. It is particularly useful for studying the effects of myosin II inhibition on these processes, as it can block both blebbing and cytokinesis at concentrations of 50-100μM.
Used in Cardiac Contractility Studies:
(-)-Blebbistatin has been used to explore its effects on cardiac contractility, providing insights into the role of myosin II in heart function. This application helps researchers understand the mechanisms underlying heart contractions and the potential therapeutic targets for treating cardiac diseases.
Used in Actomyosin Contractility Research:
(-)-Blebbistatin has also been employed to study the effects of thrombin on actomyosin contractility. Thrombin is an enzyme involved in blood clotting, and its interaction with actomyosin can have implications for various physiological processes. By using (-)-Blebbistatin, researchers can better understand the role of myosin II in these interactions and their consequences.

Biological Activity

Selective inhibitor of myosin II ATPase activity (IC 50 ~0.5-5 μ M); active enantiomer of (±)-blebbistatin ((?-1,2,3,3a-Tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one ). Inhibits contraction of the cleavage furrow without disrupting mitosis or contractile ring assembly. Rapidly and reversibly blocks cell blebbing, and disrupts directed cell migration and cytokinesis in vertebrate cells.

Biochem/physiol Actions

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

references

[1]. straight af, cheung a, limouze j, et al. dissecting temporal and spatial control of cytokinesis with a myosin ii inhibitor. science, 2003, 299:1743–1747.[2]. kovacs m, toth j, hetenyi c, malnasi-csizmadia a, sellers jr. mechanism of blebbistatin inhibition of myosin ii. j biol chem, 2004, 279:35557–35563.[3]. limouze j, straight af, mitchison t, sellers jr. specificity of blebbistatin, an inhibitor of myosin ii. j muscle res cell motil, 2004, 25:337–341.[4]. miguel vicente-manzanares, xuefei ma, robert s. adelstein,alan rick horwitz. non-muscle myosin ii takes centre stage in cell adhesion and migration.nat rev mol cell biol, 2009 nov, 10(11): 778–790.[5]. burt ra, joseph je, milliken s, collinge je, kile bt. description of a novel mutation leading to myh9-related disease. thrombosis research, 2008, 122(6): 861-863.[6]. butcher dt, alliston t, weaver vm. a tense situation: forcing tumour progression. nature reviews cancer, 2009 feb, 9(2):108-122.[7]. chen y, boukour s, milloud r, favier r, saposnik b, schlegel n, et al. the abnormal proplatelet formation in myh9-related macrothrombocytopenia results from an increased actomyosin contractility and is rescued by myosin iia inhibition. journal of thrombosis and haemostasis : jth , 2013, 11:2163-2175.[8]. fedorov vv, lozinsky it, sosunov ea, anyukhovsky ep, rosen mr, balke cw, et al. application of blebbistatin as an excitation-contraction uncoupler for electrophysiologic study of rat and rabbit hearts. heart rhythm: the official journal of the heart rhythm society, 2007, 4:619-626.[9]. zhang x-h, aydin m, kuppam d, melman a, disanto me. in vitro and in vivo relaxation of corpus cavernosum smooth muscle by the selective myosin ii inhibitor, blebbistatin. the journal of sexual medicine, 2009, 6:2661-2671.[10]. zhang m, rao pv. blebbistatin, a novel inhibitor of myosin ii atpase activity, increases aqueous humor outflow facility in perfused enucleated porcine eyes. investigative ophthalmology & visual science, 2005, 46:4130-4138.[11]. lucas-lopez c, allingham js, lebl t, lawson cp, brenk r, sellers jr, et al. the small molecule tool (s)-(-)-blebbistatin: novel insights of relevance to myosin inhibitor design. organic & biomolecular chemistry, 2008, 6:2076-2084.

Upstream product

• 18595-16-9 2-amino-5-methylbenzoic acid methyl ester 
• 7661-32-7 1-(4-bromophenyl)pyrrolidin-2-one 
• 4641-57-0 1-phenylpyrrolidin-2-one 
• 856925-76-3 1-(4-bromophenyl)-6-methyl-1,2,3,9-tetrahydropyrrolo[2,3-b]quinolin-4-one 
• 856925-74-1 1-(4-bromophenyl)-3a-hydroxy-6-methyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]quinolin-4-one 
• 856925-72-9 6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one 
• 591-50-4 iodobenzene 
• 2941-78-8 2-Amino-5-methylbenzoic acid 

Downstream Products

• 1621326-35-9 para-chloroblebbistatin 

Relevant articles and documents

Discovery of Selective Inhibitors forIn VitroandIn VivoInterrogation of Skeletal Myosin II

Myosin IIs, actin-based motors that utilize the chemical energy of adenosine 5′-triphosphate (ATP) to generate force, have potential as therapeutic targets. Their heavy chains differentiate the family into muscle (skeletal [SkMII], cardiac, smooth) and nonmuscle myosin IIs. Despite the therapeutic potential for muscle disorders, SkMII-specific inhibitors have not been reported and characterized. Here, we present the discovery, synthesis, and characterization of “skeletostatins,” novel derivatives of the pan-myosin II inhibitor blebbistatin, with selectivity 40- to 170-fold for SkMII over all other myosin II family members. In addition, the skeletostatins bear improved potency, solubility, and photostability, without cytotoxicity. Based on its optimalin vitroprofile, MT-134’sin vivotolerability, efficacy, and pharmacokinetics were determined. MT-134 was well-tolerated in mice, impaired motor performance, and had excellent exposure in muscles. Skeletostatins are useful probes for basic research and a strong starting point for drug development.

Improved synthesis and comparative analysis of the tool properties of new and existing D-ring modified (S)-blebbistatin analogs

(S)-Blebbistatin is a widely used research tool to study myosin II, an important regulator of many motility based diseases. Its potency is too low to be of clinical relevance, but identification of analogs with enhanced potency could deliver leads for tar