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(+)-Blebbistatin

Item № 13165
CAS № 1177356-70-5
Purity ≥98%
product image
                (CAS 1177356-70-5)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $29.00 0.00
     5 mg $123.00 0.00
     10 mg $232.00 0.00
     25 mg $508.00 0.00

Pricing updated 2019-06-26. Prices are subject to change without notice.

Description
Synonyms
  • (R)-Blebbistatin

(+)-Blebbistatin is the inactive enantiomer of (–)-blebbistatin (Item No. 13013), which is a selective inhibitor of non-muscle myosin II ATPases.1,2 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.3,4 (R)-nitro-Blebbistatin (Item No. 9001935) is a more stable form of (+)-blebbistatin.5 The addition of a nitro group stabilizes the molecule to circumvent its degradation by prolonged blue light exposure. (R)-nitro-Blebbistatin has the same stereochemistry as the inactive (+)-blebbistatin enantiomer.

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Technical Information
Formal Name
1,2,3,3a-tetrahydro-3aR-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one
CAS Number
1177356-70-5
Synonyms
  • (R)-Blebbistatin
Molecular Formula
C18H16N2O2
Formula Weight
292.3
Purity
≥98%
Formulation
A crystalline solid
λmax
236, 270, 298, 418 nm
SMILES
Cc1ccc2N=C3N(CC[C@@]3(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/t18-/m0/s1
InChI Key
LZAXPYOBKSJSEX-SFHVURJKSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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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 J. Biol. Chem. 279(34), 35557-35563 (2004).

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

4. 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).

5. 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. 2005(9), 1736-1740 (2005).

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