A more stable form of (+)-blebbistatin
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(R)-nitro-Blebbistatin

Item No. 9001935

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3aR)-1,2,3,3a-tetrahydro-3a-hydroxy-7-nitro-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one
CAS Number
1217619-62-9
Synonyms
  • R-(−)-7-Desmethyl-8-nitro Blebbistatin
Molecular Formula
C17H13N3O4
Formula Weight
323.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 25 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
234, 270, 315, 350, 443 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-/m0/s1
InChi Key
VIMYHNYWFMRDKQ-KRWDZBQOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature 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

    $800

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    Product Description

    (R)-nitro-Blebbistatin is a more stable form of (+)-blebbistatin (Item No. 13165), which is the inactive form of (–)-blebbistatin (Item No. 13013). 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.1,2 The addition of a nitro group stabilizes the molecule to circumvent its degradation by prolonged blue light exposure.3 (R)-nitro-Blebbistatin has the same stereochemistry as the inactive (+)-blebbistatin enantiomer.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

    2. 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).

    3. 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).