(-)-Blebbistatin - ≥98% , CAS No.856925-71-8

CAS: 856925-71-8 Cat. No.: B129580 Molecular Weight: 292.33 EC Number: 689-630-0 PubChem CID: 5287792

GRADE & PURITY ≥98%

Synonyms

8WII7624I5 | (-)Blebbistatin | (S)-blebbistatin | (S)-3a-hydroxy-6-methyl-1-phenyl-3,3a-dihydro-1H-pyrrolo[2,3-b]quinolin-4(2H)-one | (S)-(-)-Blebbistatin | Blebbistatin (S)-form [MI] | 1-Phenyl-1,2,3,4-tetrahydro-4-hydroxypyrrolo[2.3-b]-7-methylquinolin-

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

(-)-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.

Specifications

Synonyms

8WII7624I5 | (-)Blebbistatin | (S)-blebbistatin | (S)-3a-hydroxy-6-methyl-1-phenyl-3, 3a-dihydro-1H-pyrrolo[2, 3-b]quinolin-4(2H)-one | (S)-(-)-Blebbistatin | Blebbistatin (S)-form [MI] | 1-Phenyl-1, 2, 3, 4-tetrahydro-4-hydroxypyrrolo[2.3-b]-7-methylquinolin-

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Selective inhibitor of myosin II ATPase activity (IC50~0.5 - 5μM); active enantiomer of (±)-blebbistatin. Inhibits contraction of the cleavage furrow without disrupting mitosis or contractile ring assembly. Rapidly and reversibly blocks cell blebbing, and

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504763508
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763508
• Canonical Smiles: Cc1ccc2N=C3N(CC[C@@]3(O)C(=O)c2c1)c4ccccc4
• IUPAC Name: (3aS)-3a-hydroxy-6-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one
• InChIKey: LZAXPYOBKSJSEX-GOSISDBHSA-N
• 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
• Isomeric SMILES: CC1=CC2=C(C=C1)N=C3[C@](C2=O)(CCN3C4=CC=CC=C4)O
• WGK Germany: 3
• PubChem CID: 5287792
• Molecular Weight: 292.33

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Quinolines and derivatives
      • Subclass Pyrroloquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Quinolines and derivatives
• Subclass: Pyrroloquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrroloquinolines
• Alternative Parents: Phenylpyrrolidines Aminoquinolines and derivatives Aryl alkyl ketones Aniline and substituted anilines Imidolactams Tertiary alcohols Pyrroles Propargyl-type 1,3-dipolar organic compounds Carboxamidines Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pyrroloquinoline - Aminoquinoline - 1-phenylpyrrolidine - Aryl ketone - Aniline or substituted anilines - Aryl alkyl ketone - Monocyclic benzene moiety - Benzenoid - Imidolactam - Pyrrole - Pyrrolidine - Tertiary alcohol - Ketone - Amidine - Carboxylic acid amidine - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Azacycle - Hydrocarbon derivative - Organic nitrogen compound - Organic oxide - Alcohol - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrroloquinolines. These are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline.
• External Descriptors: blebbistatin

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

BXPC-3 (2997 Activities)

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DU-145 (51482 Activities)

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PANC-1 (6144 Activities)

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U-87 MG (3946 Activities)

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MIA PaCa-2 (5949 Activities)

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LNCaP (8286 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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Capan-2 (270 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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MYH2 Tbio Myosin-2 (5 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Dictyostelium discoideum (81 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Danio rerio (3092 Activities)

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FTL Ferritin light chain (43324 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 29.23, Max Conc. mM: 100
• Sensitivity: Light sensitive
• Molecular Weight: 292.300 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 292.121 Da
• Monoisotopic Mass: 292.121 Da
• Topological Polar Surface Area: 52.900 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 497.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yang Sihui, Wang Miao, Tian Dawei, Zhang Xiaoyu, Cui Kaiqing, Lü Shouqin, Wang Hong-hui, Long Mian, Nie Zhou.  (2024)  DNA-functionalized artificial mechanoreceptor for de novo force-responsive signaling.  Nature Chemical Biology,      [PMID:38448735] [10.1038/s41589-024-01572-x]