A more stable and less phototoxic form of (–)-blebbistatin
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(S)-4'-nitro-Blebbistatin

Item No. 24171

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3aS)-1,2,3,3a-tetrahydro-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-4H-pyrrolo[2,3-b]quinolin-4-one
CAS Number
1621326-32-6
Synonyms
  • (−)-4'-nitro-Blebbistatin
  • p-nitro-Blebbistatin
  • para-nitro-Blebbistatin
Molecular Formula
C18H15N3O4
Formula Weight
337.3
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 10 mg/ml
λmax
260, 414 nm
SMILES
O=C1[C@@]2(O)C(N(C3=CC=C([N+]([O-])=O)C=C3)CC2)=NC4=C1C=C(C)C=C4
InChi Code
InChI=1S/C18H15N3O4/c1-11-2-7-15-14(10-11)16(22)18(23)8-9-20(17(18)19-15)12-3-5-13(6-4-12)21(24)25/h2-7,10,23H,8-9H2,1H3/t18-/m1/s1
InChi Key
KAUXNLHXGQGFOS-GOSISDBHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $129

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    5 mg

    $510

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    10 mg

    $953

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    Product Description

    (S)-4'-nitro-Blebbistatin is a more stable and less phototoxic form of (–)-blebbistatin (Item No. 13013), which is a selective cell-permeable inhibitor of non-muscle myosin II ATPases.1,2 (–)-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).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 The addition of a 4’-nitro group decreases the inherent fluorescence, stabilizes the molecule to circumvent its degradation by prolonged blue light exposure, and decreases its phototoxicity while retaining the in vitro and in vivo activity of (–)-blebbistatin.6,7 (S)-4'-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. Képiró, M., Várkuti, B.H., Végner, L., et al. para-Nitroblebbistatin, the non-cytotoxic and photostable myosin II inhibitor. Angew. Chem. Int. Ed. Engl. 53(31), 8211-8215 (2014).

    7. Verhasselt, S., Roman, B.I., Bracke, M.E., et al. Improved synthesis and comparative analysis of the tool properties of new and existing D-ring modified (S)-blebbistatin analogs. Eur. J. Med. Chem. 136, 85-103 (2017).