CAS Number856925-71-8
Synonyms(3aS)-3a-Hydroxy-6-methyl-1-phenyl-1,2,3,3a,4a,8a-hexahydro-4H-pyrrolo[2,3-b]quinolin-4-one; (3aS)-3a-hydroxy-6-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one
Molecular FormulaC18H16N2O2
Molecular Weight292.33
Purity98.00%
Density1.3±0.1 g/cm3
Boiling Point486.7±55.0 °C at 760 mmHg
Melting Point210-212ºC
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 856925-71-8 |
| Catalog No. | 2A-1169036 |
| Chinese Name | (-)-II型肌球蛋白 |
| Synonyms | (3aS)-3a-Hydroxy-6-methyl-1-phenyl-1,2,3,3a,4a,8a-hexahydro-4H-pyrrolo[2,3-b]quinolin-4-one; (3aS)-3a-hydroxy-6-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one |
| Molecular Formula | C18H16N2O2 |
| Molecular Weight | 292.33 |
| Purity | 98.00 |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 486.7±55.0 °C at 760 mmHg |
| Melting Point | 210-212ºC |
| Appearance | powder |
| Water Solubility | DMSO: soluble5mg/mL |
| Storage Condition | Desiccate at +4°C |
| Application | (-)-Blebbistatin is the S enantiomer of blebbistatin. Blebbistatin is a potent and selective myosin II inhibitor with IC50 ranging from 0.5 to 5 μM. |
| PubChem ID | 855033 |
| SMILES | Cc1ccc2c(c1)C(=O)C1(O)CCN(c3ccccc3)C1=N2 |
| InChI | 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 |
| InChI Key | LZAXPYOBKSJSEX-GOSISDBHSA-N |
| Hazard Symbols | transportation |
| Bioactivity | (-)-Blebbistatin is an S enantiomer of blebbistatin. Blebbistatin is a potent and selective myosin II inhibitor with IC50s ranging from 0.5 to 5 μM. Related Catalog Signaling Pathways >> Cytoskeleton >> Myosin Research Areas >> Cardiovascular Disease Target IC50: 0.5 to 5 μM (myosin II)[1] In Vitro Blebbistatin potently inhibits several striated muscle myosins as well as vertebrate nonmuscle myosin IIA and IIB with IC50 values ranging from 0.5 to 5 μM. Smooth muscle myosin is only poorly inhibited (IC50=80 μM)[1]. Blebbistatin does not compete with nucleotide binding to the skeletal muscle myosin subfragment-1. The inhibitor preferentially binds to the ATPase intermediate with ADP and phosphate bound at the active site, and it slows down phosphate release. It blocks the myosin heads in a products complex with low actin affinity[2]. In culture-activated hepatic stellate cells, blebbistatin is found to change both cell morphology and function. Stellate cells become smaller, acquire a dendritic morphology and have less myosin IIA-containing stress fibres and vinculin-containing focal adhesions. Blebbistatin impairs silicone wrinkle formation, reduces collagen gel contraction and blocks endothelin-1-induced intracellular Ca2+ release. It promotes wound-induced cell migration[3]. In Vivo Blebbistatin dose-dependently and completely relax both KCl- and carbachol-induced rat detrusor and endothelin-1-induced human bladder contraction. Pre-incubation with 10 μM blebbistatin attenuates carbachol responsiveness by 65% while blocking electrical field stimulation-induced bladder contraction reaching 50% inhibition at 32 Hz[4]. Cell Assay Freshly isolated HSCs are replated on 96-well plate. At day 3, medium is replaced by serum-free medium and cells are starved overnight, treated with or without blebbistatin (25 μM) for 2 h followed by stimulation with platelet-derived growth factor-BB (20 ng/mL). After an overnight incubation, the WST-1 cell proliferation assay are performed[3]. References [1]. Limouze J, et al. Specificity of blebbistatin, an inhibitor of myosin II. J Muscle Res Cell Motil. 2004;25(4-5):337-41. [2]. Kovács M, et al. Mechanism of blebbistatin inhibition of myosin II. J Biol Chem. 2004 Aug 20;279(34):35557-63. [3]. Liu Z, et al. Blebbistatin inhibits contraction and accelerates migration in mouse hepatic stellate cells. Br J Pharmacol. 2010 Jan 1;159(2):304-15. [4]. Zhang X, et al. In vitro and in vivo relaxation of urinary bladder smooth muscle by the selective myosin IIinhibitor, blebbistatin. BJU Int. 2011 Jan;107(2):310-7. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 486.7±55.0 °C at 760 mmHg Melting Point 210-212ºC Molecular Formula C18H16N2O2 Molecular Weight 292.33 Flash Point 248.1±31.5 °C PSA 52.90000 LogP 0.93 Vapour Pressure 0.0±1.3 mmHg at 25°C Index of Refraction 1.681 InChIKey LZAXPYOBKSJSEX-GOSISDBHSA-N SMILES Cc1ccc2c(c1)C(=O)C1(O)CCN(c3ccccc3)C1=N2 Storage condition Desiccate at +4°C Water Solubility DMSO: soluble5mg/mL |
| Use of | (-)-Blebbistatin is an S enantiomer of blebbistatin. Blebbistatin is a potent and selective myosin II inhibitor with IC50s ranging from 0.5 to 5 μM. Properties Articles12 Name (S)-(-)-Blebbistatin Synonym More Synonyms (-)-Blebbistatin Biological Activity Description (-)-Blebbistatin is an S enantiomer of blebbistatin. Blebbistatin is a potent and selective myosin II inhibitor with IC50s ranging from 0.5 to 5 μM. Related Catalog Signaling Pathways >> Cytoskeleton >> Myosin Research Areas >> Cardiovascular Disease IC50: 0.5 to 5 μM (myosin II)[1] In Vitro Blebbistatin potently inhibits several striated muscle myosins as well as vertebrate nonmuscle myosin IIA and IIB with IC50 values ranging from 0.5 to 5 μM. Smooth muscle myosin is only poorly inhibited (IC50=80 μM)[1]. Blebbistatin does not compete with nucleotide binding to the skeletal muscle myosin subfragment-1. The inhibitor preferentially binds to the ATPase intermediate with ADP and phosphate bound at the active site, and it slows down phosphate release. It blocks the myosin heads in a products complex with low actin affinity[2]. In culture-activated hepatic stellate cells, blebbistatin is found to change both cell morphology and function. Stellate cells become smaller, acquire a dendritic morphology and have less myosin IIA-containing stress fibres and vinculin-containing focal adhesions. Blebbistatin impairs silicone wrinkle formation, reduces collagen gel contraction and blocks endothelin-1-induced intracellular Ca2+ release. It promotes wound-induced cell migration[3]. In Vivo Blebbistatin dose-dependently and completely relax both KCl- and carbachol-induced rat detrusor and endothelin-1-induced human bladder contraction. Pre-incubation with 10 μM blebbistatin attenuates carbachol responsiveness by 65% while blocking electrical field stimulation-induced bladder contraction reaching 50% inhibition at 32 Hz[4]. References [1]. Limouze J, et al. Specificity of blebbistatin, an inhibitor of myosin II. J Muscle Res Cell Motil. 2004;25(4-5):337-41. [2]. Kovács M, et al. Mechanism of blebbistatin inhibition of myosin II. J Biol Chem. 2004 Aug 20;279(34):35557-63. [3]. Liu Z, et al. Blebbistatin inhibits contraction and accelerates migration in mouse hepatic stellate cells. Br J Pharmacol. 2010 Jan 1;159(2):304-15. [4]. Zhang X, et al. In vitro and in vivo relaxation of urinary bladder smooth muscle by the selective myosin IIinhibitor, blebbistatin. BJU Int. 2011 Jan;107(2):310-7. Chemical & Physical Properties Molecular Formula C18H16N2O2 PSA 52.90000 Index of Refraction 1.681 InChIKey LZAXPYOBKSJSEX-GOSISDBHSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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