(+/-)-BLEBBISTATIN

(+/-)-BLEBBISTATIN Basic information
Product Name:(+/-)-BLEBBISTATIN
Synonyms:(R)-(+)-BLEBBISTATIN;(3AS)-(-)-1,2,3,3A-TETRAHYDRO-3A-HYDROXY-6-METHYL-1-PHENYL-4H-PYRROLO[2,3-B]QUINOLIN-4-ONE;(+/-)-1-PHENYL-1,2,3,4-TETRAHYDRO-4-HYDROXYPYRROLO[2,3-B]-7-METHYLQUINOLIN-4-ONE;(+/-)-1,2,3,3A-TETRAHYDRO-3A-HYDROXY-6-METHYL-1-PHENYL-4H-PYRROLO[2,3-B]QUINOLIN-4-ONE;(+/-)-1-Phenyl-1,2,3,4-tetrahydro-4-hydroxypyrrolo[2,3-β]-7-methylquinolin-4-one;1,2,3,3a-Tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-β]quinolin-4-one;(3aS)-1,2,3,3a-Tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-β]quinolin-4-one;(3aR)-1,2,3,3a-Tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-β]quinolin-4-one
CAS:674289-55-5
MF:C18H16N2O2
MW:292.33
EINECS:
Product Categories:Caspases/Apoptosis;Chiral Reagents;All Inhibitors;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:674289-55-5.mol
(+/-)-BLEBBISTATIN Structure
(+/-)-BLEBBISTATIN Chemical Properties
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 Chloroform (Slightly), Dichloromethane, DMSO, Ethyl Acetate, Methanol
form Bright yellow solid.
pka11.15±0.20(Predicted)
color Yellow
CAS DataBase Reference674289-55-5
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36/37
MSDS Information
(+/-)-BLEBBISTATIN Usage And Synthesis
Description(±)-Blebbistatin is a racemic mixture of (–)-blebbistatin and (+)-blebbistatin , the active and inactive forms, respectively. (–)-Blebbistatin is a selective cell-permeable inhibitor of non-muscle myosin II ATPases. (–)-Blebbistatin rapidly and reversibly inhibits Mg-ATPase activity and in vitro motility of non-muscle myosin IIA and IIB for several species (IC50s = 0.5-5 μM), while poorly inhibiting smooth muscle myosin (IC50 = 8 μM). Through these effects, (–)-blebbistatin blocks apoptosis-related bleb formation, directed cell migration, and cytokinesis in vertebrate cells. However, prolonged exposure to blue light (450-490 nm) results in degradation of blebbistatin to an inactive product via cytotoxic intermediates, which may be problematic for its use in fluorescent live cell imaging applications. (S)-nitro-Blebbistatin and (R)-nitro-blebbistatin are more stable forms of (–)-blebbistatin and (+)-blebbistatin, respectively. The addition of a nitro group stabilizes the molecules to circumvent their degradation by prolonged blue light exposure. (S)-nitro-Blebbistatin and (R)-nitro-blebbistatin have the same stereochemistry of the active and inactive enantiomers, respectively.
Chemical PropertiesBright Yellow Solid
UsesBlebbistatin 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. (±)-1-Phenyl-1,2,3,4-tetrahydro-4-hydroxypyrrolo[2,3-b]-7-methylquinolin-4-one Selective inhibitor of nonmuscle myosin II; 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.
Uses(±)-Blebbistatin is a selective cell-permeable inhibitor of non-muscle myosin II ATPases. It rapidly and reversibly inhibits Mg-ATPase activity and in vitro motility of non-muscle myosin IIA and IIB for several species (IC50 = 0.5-5.0 μM), while poorly inhibiting smooth muscle myosin (IC50 = 80 μM). Through these effects, blebbistatin blocks apoptosis-related bleb formation, directed cell migration and cytokinesis in vertebrate cells. Blebbistatin is inactivated by UV light, which may be particularly important in fluorescent cell imaging applications. Purified enantiomers of Blebbistatin are also available from Cayman ((?)-Blebbistatin - ).
DefinitionChEBI: A pyrroloquinoline that is 1,2,3,3a-tetrahydro-H-pyrrolo[2,3-b]quinolin-4-one substituted by a hydroxy group at position 3a, a methyl group at position 6 and a phenyl group at position 1. It acts as an inhibitor of ATPase ac ivity of non-muscle myosin II.
Biological ActivitySelective inhibitor of myosin II ATPase activity; 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.
storageStore at +4°C
(+/-)-BLEBBISTATIN Preparation Products And Raw materials
(+/-)-BLEBBISTATIN 3-(3-METHYL-BENZYL)-PYRROLIDINE N-2,4-DIMETHYLPHENYL-N'-METHYLFORMAMIDINE 2-HYDROXY-2-METHYL-PROPIONAMIDINE (-)-Blebbistatin

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