(-)-Blebbistatin

(-)-Blebbistatin is a selective cell-permeable inhibitor of non-muscle myosin II ATPases and the active enantiomer of (+)-blebbistatin (Cay-13165). It 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 = 80 µM). Through these effects, it 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 (Cay-13891) is a more stable form of (-)-blebbistatin. The addition of a nitro group stabilizes the molecule to circumvent its degradation by prolonged blue light exposure. (S)-nitro-Blebbistatin has the same stereochemistry as the active (-)-blebbistatin enantiomer.Formal Name: 1,2,3,3a-tetrahydro-3aS-hydroxy-6-methyl-1-phenyl-4H-Pyrrolo[2,3-b]quinolin-4-one. CAS Number: 856925-71-8. Synonyms: (S)-Blebbistatin. Molecular Formula: C18H16N2O2. Formula Weight: 292.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 mg/ml, DMF:PBS (pH 7.2) (1:1): 0.5 mg/ml, DMSO: 12.5 mg/ml. lambdamax: 236, 270, 298, 418 nm. SMILES: CC1=CC2C(C=C1)N=C1N(CC[C@@]1(O)C2=O)c1ccccc1. InChi Code: 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.