Structural Formula Vector Image
Title: Blebbistatin
CAS Registry Number: 674289-55-5
CAS Name: 1,2,3,3a-Tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one
Additional Names: 1-phenyl-1,2,3,4-tetrahydro-4-hydroxypyrrolo[2,3-b]-7-methylquinolin-4-one
Molecular Formula: C18H16N2O2
Molecular Weight: 292.33
Percent Composition: C 73.95%, H 5.52%, N 9.58%, O 10.95%
Literature References: Small molecule inhibitor of the ATPase activity of myosin II; affects cell blebbing during cell division. Prepn and inhibition of non-muscle myosin II: A. F. Straight et al., Science 299, 1743 (2003). Prepn and crystal structure of (-)-form: C. Lucas-Lopez et al., Eur. J. Org. Chem. 2005, 1736. Crystal structure in complex with myosin II: J. S. Allingham et al., Nat. Struct. Mol. Biol. 12, 378 (2005). Kinetics of non-muscle myosin IIB inhibition: B. Ramamurthy et al., Biochemistry 43, 14832 (2004). Mechanism of myosin II inhibition: M. Kovács et al., J. Biol. Chem. 279, 35557 (2004). Photochemistry studies: J. Kolega, Biochem. Biophys. Res. Commun. 320, 1020 (2004); T. Sakamoto et al., Biochemistry 44, 584 (2005).
Properties: Bright yellow solid, mp 192-193°. Absorption max (phosphate-buffered saline): 265, 430 nm.
Melting point: mp 192-193°
Absorption maximum: Absorption max (phosphate-buffered saline): 265, 430 nm
Derivative Type: (S)-Form
Additional Names: (-)-Blebbistatin
Properties: Crystals from acetonitrile, [a]D26 -464° (c = 0.2 in dichloromethane).
Optical Rotation: [a]D26 -464° (c = 0.2 in dichloromethane)
Use: In studies of cytoskeletal dynamics and the biological roles of class-II myosins.

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