| Identification | Back Directory | [Name]
(-)-Blebbistatin | [CAS]
856925-71-8 | [Synonyms]
CS-978
(-)-BLEBBISTATIN
(-)-Blebbistcitin
(+/-)-BLEBBISTATIN
(S)-(-)-BLEBBISTATIN
Blebbistatin S enantiomer
(-)-Blebbistatin USP/EP/BP
(-)-Blebbistatin *CAS#: 856925-71-8*
(-)-BLEBBISTATIN;(S)-(-)-BLEBBISTATIN
(-)-Blebbistatin - CAS 856925-71-8 - Calbiochem
(3aS)-3a-hydroxy-6-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one
(S)-3a-Hydroxy-6-methyl-1-phenyl-3,3a-dihydro-1H-pyrrolo[2,3-b]quinolin-4(2H)-one
(S)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one
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 | [Molecular Formula]
C18H16N2O2 | [MDL Number]
MFCD08460907 | [MOL File]
856925-71-8.mol | [Molecular Weight]
292.33 |
| Chemical Properties | Back Directory | [Melting point ]
210-212°C | [Boiling point ]
507.3±60.0 °C(Predicted) | [density ]
1.31±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO: soluble5mg/mL | [form ]
Yellow solid | [pka]
11.15±0.20(Predicted) | [color ]
Light Yellow to Yellow | [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 | [InChIKey]
LZAXPYOBKSJSEX-GOSISDBHSA-N | [SMILES]
Cc1ccc2N=C3N(CC[C@@]3(O)C(=O)c2c1)c4ccccc4 |
| Hazard Information | Back Directory | [Chemical Properties]
Bright Yellow Solid | [Uses]
Blebbistatin blocked myosin II-dependent cell processes. It blocks cell blebbing rapidly and reversibly. Also rapidly disrupted directed cell migration and cytokinesis in vertebrate cell. It blocks both blebbing and cytokinesis at 50-100μM.
[a]D= -103 | [Definition]
ChEBI: (S)-blebbistatin is the (S)-enantiomer of blebbistatin. It is a blebbistatin and a tertiary alpha-hydroxy ketone. | [General Description]
(?)-Blebbistatin, a myosin II ATPase inhibitor, does not affect other members of myosin superfamily like 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. | [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. | [storage]
Store at +4°C | [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. |
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Sigma-Aldrich
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