Blebbistatin

Base Information

• Chemical Name: Blebbistatin
• CAS No.: 674289-55-5
• Molecular Formula: C₁₈H₁₆N₂O₂
• Molecular Weight: 292.337
• UNII: 20WC4J7CQ6
• DSSTox Substance ID: DTXSID501017342
• Nikkaji Number: J1.888.295G
• Wikipedia: Blebbistatin
• Wikidata: Q27145262
• ChEMBL ID: CHEMBL1328324
• Mol file: 674289-55-5.mol

Synonyms:blebbistatin

Chemical Property of Blebbistatin

Chemical Property:

• Appearance/Colour: Bright Yellow Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 210-212°C
• Refractive Index: 1.681
• Boiling Point: 507.267 °C at 760 mmHg
• PKA: 11.15±0.20(Predicted)
• Flash Point: 260.586 °C
• PSA: 52.90000
• Density: 1.312 g/cm³
• LogP: 2.36330
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Dichloromethane, DMSO, Ethyl Acetate, Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 292.121177757
• Heavy Atom Count: 22
• Complexity: 497

Purity/Quality:

98%Min ^*data from raw suppliers

(+/-)-Blebbistatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)N=C3C(C2=O)(CCN3C4=CC=CC=C4)O
• 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.
• 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. (±)-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 - ).

Technology Process of Blebbistatin

There total 30 articles about Blebbistatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1-(4-bromophenyl)-3a-hydroxy-6-methyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]quinolin-4-one (856925-74-1) → (3aS)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; at 25 ℃; for 24h;

DOI:10.1002/ejoc.200500103

Reference yield: 37.0%

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (856925-72-9) → (3aR)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8) + (3aS)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8)

Guidance literature:

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

With (-)-(8,8-dichlorocamphorylsulfonyl)oxaziridine; In tetrahydrofuran; at -15 ℃; for 16h; Overall yield = 85%; Overall yield = 0.250 g; Inert atmosphere;

DOI:10.1039/c7ob00006e

Reference yield: 37.0%

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (856925-72-9) → (3aR)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8) + (3aS)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8)

Guidance literature:

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

With (-)-(8,8-dichlorocamphorylsulfonyl)oxaziridine; In tetrahydrofuran; at -15 ℃; for 16h; Overall yield = 85%; Overall yield = 0.250 g; Inert atmosphere;

DOI:10.1039/c7ob00006e

upstream raw materials:

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one

1-phenylpyrrolidin-2-one

2-amino-5-methylbenzoic acid methyl ester

2-Amino-5-methylbenzoic acid

Downstream raw materials:

para-chloroblebbistatin

Refernces

• 1、 Verhasselt, Sigrid,Roman, Bart I.,De Wever, Olivier,Van Hecke, Kristof,Van Deun, Rik,Bracke, Marc E.,Stevens, Christian V.. "Discovery of (S)-3′-hydroxyblebbistatin and (S)-3′-aminoblebbistatin: polar myosin II inhibitors with superior research tool properties". . p. 2104 - 2118. Retrieved 2017/03/11.
• 2、 Lucas-Lopez, Cristina,Patterson, Stephen,Blum, Till,Straight, Aaron F.,Toth, Judit,Slawin, Alexandra M. Z.,Mitchison, Timothy J.,Sellers, James R.,Westwood, Nicholas J.. "Absolute stereochemical assignment and fluorescence tuning of the small molecule tool, (-)-blebbistatin". . p. 1736 - 1740. Retrieved 2007/10/03.