A cell-permeable inhibitor of non-muscle myosin II ATPases
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(–)-Blebbistatin

Item No. 13013

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 12.5 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    (–)-Blebbistatin is a selective cell-permeable inhibitor of non-muscle myosin II ATPases and the active enantiomer of (+)-blebbistatin (Item No. 13165).1,2 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).3 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.4,5 (S)-nitro-Blebbistatin (Item No. 13891) is a more stable form of (–)-blebbistatin.6 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Straight, A.F., Cheung, A., Limouze, J., et al. Dissecting temporal and spatial control of cytokinesis with a myosin II inhibitor. Science 299(5613), 1743-1747 (2003).

    2. Kovács, M., Tóth, J., Hetényi, C., et al. Mechanism of blebbistatin inhibition of myosin II. The Journal of Biological Chemisty 279(34), 35557-35563 (2004).

    3. Limouze, J., Straight, A.F., Mitchison, T., et al. Specificity of blebbistatin, an inhibitor of myosin II. J. Muscle Res. Cell Motil. 25(4-5), 337-341 (2004).

    4. Kolega, J. Phototoxicity and photoinactivation of blebbistatin in UV and visible light. Biochem. Biophys. Res. Commun. 320(3), 1020-1025 (2004).

    5. Sakamoto, T., Limouze, J., Combs, C.A., et al. Blebbistatin, a myosin II inhibitor, is photoinactivated by blue light. Biochemistry 44(2), 584-588 (2005).

    6. Lucas-Lopez, C., Patterson, S., Blum, T., et al. Absolute stereochemical assignment and fluorescence tuning of the small molecule tool, (−)-blebbistatin. European J. Org. Chem. 9, 1736-1740 (2005).