(+/-)-BLEBBISTATIN

Product Name: (+/-)-BLEBBISTATIN
CAS No.: 674289-55-5
Chemical Name: (+/-)-BLEBBISTATIN
Synonyms: (±)Bebbistatin;(+/-)-BLEBBISTATIN;(R)-(+)-BLEBBISTATIN;E1249 (+/-)-Blebbi- Calbiochem;Blebbistatin,Inhibitor,Myosin,inhibit;3a-hydroxy-6-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one;3a-hydroxy-6-methyl-1-phenyl-3,3a-dihydro-1H-pyrrolo[2,3-b]quinolin-4(2H)-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-β]quinolin-4-one;(+/-)-1-Phenyl-1,2,3,4-tetrahydro-4-hydroxypyrrolo[2,3-β]-7-methylquinolin-4-one
CBNumber: CB0787697
Molecular Formula: C18H16N2O2
Formula Weight: 292.33
MOL File: 674289-55-5.mol

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(+/-)-BLEBBISTATIN Property

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.
pka: 11.15±0.20(Predicted)
color: Yellow
CAS DataBase Reference: 674289-55-5

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22-36/37/38
Safety Statements: 26-36/37

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 203390
Product name: (±)-Blebbistatin - CAS 674289-55-5 - Calbiochem
Packaging: 5mg
Price: $272
Updated: 2024/03/01

Cayman Chemical

Product number: 13186
Product name: (±)-Blebbistatin
Purity: ≥98%
Packaging: 5mg
Price: $86
Updated: 2024/03/01

Cayman Chemical

Product number: 13186
Product name: (±)-Blebbistatin
Purity: ≥98%
Packaging: 10mg
Price: $189
Updated: 2024/03/01

Cayman Chemical

Product number: 13186
Product name: (±)-Blebbistatin
Purity: ≥98%
Packaging: 25mg
Price: $336
Updated: 2024/03/01

Cayman Chemical

Product number: 13186
Product name: (±)-Blebbistatin
Purity: ≥98%
Packaging: 50mg
Price: $629
Updated: 2024/03/01

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(+/-)-BLEBBISTATIN Chemical Properties,Usage,Production

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 Properties

Bright Yellow Solid

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 - ).

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. (±)-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.

Definition

ChEBI: 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 Activity

Selective 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.

storage

Store at +4°C

(+/-)-BLEBBISTATIN Preparation Products And Raw materials

Raw materials

Preparation Products

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(+/-)-BLEBBISTATIN Suppliers

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674289-55-5, (+/-)-BLEBBISTATINRelated Search:

(-)-Blebbistatin (+/-)-BLEBBISTATIN N-2,4-DIMETHYLPHENYL-N'-METHYLFORMAMIDINE 2-HYDROXY-2-METHYL-PROPIONAMIDINE 3-(3-METHYL-BENZYL)-PYRROLIDINE

(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

(3aR)-1,2,3,3a-Tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one

(±)Bebbistatin

(+/-)-BLEBBISTATIN

4H-Pyrrolo[2,3-b]quinolin-4-one, 1,2,3,3a-tetrahydro-3a-hydroxy-6-Methyl-1-phenyl-

3a-hydroxy-6-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one

Blebbistatin,Inhibitor,Myosin,inhibit

3a-hydroxy-6-methyl-1-phenyl-3,3a-dihydro-1H-pyrrolo[2,3-b]quinolin-4(2H)-one

E1249 (+/-)-Blebbi- Calbiochem

3a-Hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one

674289-55-5

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