(S)-nitro-Blebbistatin

(S)-nitro-Blebbistatin is a more stable form of (-)-blebbistatin (Cay-13013), which 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 = 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. 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: (3aS)-1,2,3,3a-tetrahydro-3a-hydroxy-7-nitro-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one. CAS Number: 856925-75-2. Synonyms: S-(-)-7-Desmethyl-8-nitro Blebbistatin. Molecular Formula: C17H13N3O4. Formula Weight: 323.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 16 mg/ml, DMSO: 16 mg/ml, DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml. lambdamax: 234, 271, 315, 445 nm. SMILES: O=C1[C@@]2(O)C(N(C3=CC=CC=C3)CC2)=NC4=C1C=CC([N+]([O-])=O)=C4. InChi Code: InChI=1S/C17H13N3O4/c21-15-13-7-6-12(20(23)24)10-14(13)18-16-17(15,22)8-9-19(16)11-4-2-1-3-5-11/h1-7,10,22H,8-9H2/t17-/m1/s1. InChi Key: VIMYHNYWFMRDKQ-QGZVFWFLSA-N.