1317. Blebbistatin

Nomenclature

CAS number: 674289-55-5
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.
C18H16N2O2; mol wt 292.33.
C 73.95%, H 5.52%, N 9.58%, O 10.95%.

Description and 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).

Chemical structure

Properties

Bright yellow solid, mp 192-193°. Absorption max (phosphate-buffered saline): 265, 430 nm.

Derivative

(S)-Form.

Nomenclature

(-)-Blebbistatin.

Properties

Crystals from acetonitrile, [α]D26 -464° (c = 0.2 in dichloromethane).

Use

In studies of cytoskeletal dynamics and the biological roles of class-II myosins.