(±)-Blebbistatin

(±)-Blebbistatin is a racemic mixture of (-)-blebbistatin (Cay-13013) and (+)-blebbistatin (Cay-13165), the active and inactive forms, respectively. (-)-Blebbistatin is a selective cell-permeable inhibitor of non-muscle myosin II ATPases. (-)-Blebbistatin 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 = 8 µM). Through these effects, (-)-blebbistatin 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) and (R)-nitro-blebbistatin (Cay-9001935) are more stable forms of (-)-blebbistatin and (+)-blebbistatin, respectively. The addition of a nitro group stabilizes the molecules to circumvent their degradation by prolonged blue light exposure. (S)-nitro-Blebbistatin and (R)-nitro-blebbistatin have the same stereochemistry of the active and inactive enantiomers, respectively.Formal Name: 1,2,3,3a-tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one. CAS Number: 674289-55-5. 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: 10 mg/ml. lambdamax: 236, 270, 298, 417 nm. SMILES: Cc1ccc2N=C3N(CCC3(O)C(=O)c2c1)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. InChi Key: LZAXPYOBKSJSEX-UHFFFAOYSA-N.