We collect cookies for vital website function and to better serve our customers. By continuing to browse you agree to the storing of cookies on your device. See our privacy policy for details.

(–)-Blebbistatin

Item № 13013
CAS № 856925-71-8
Purity ≥98%
product image
                (CAS 856925-71-8)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $45.00 0.00
     5 mg $169.00 0.00
     10 mg $315.00 0.00
     25 mg $619.00 0.00

Pricing updated 2019-06-15. Prices are subject to change without notice.

Description
Synonyms
  • (S)-Blebbistatin

(–)-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. 13186) 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.

Recommended Products

Related Products
View Related Product Categories
View Screening Libraries with (–)-Blebbistatin
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
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

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
Downloads & Resources
Product Downloads

Download Product Insert

Download Safety Data Sheet (SDS)

Download free InChI Key generation software

Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

Get Batch-Specific Data and Documents by Batch Number

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data pack, and GC-MS data.

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

Technical Support
Contact Us
  • Toll Free Phone (USA and Canada Only): (888) 526-5351
  • Direct Phone: (734) 975-3888
Cayman Contract Services

We work with scientists to accelerate their research, drug discovery, and drug development needs through our expertise in the following areas:

Cayman Chemical

1180 East Ellsworth Road

Ann Arbor, Michigan 48108 USA

Toll Free: (800) 364-9897

(USA and Canada Only)

Fax: (734) 971-3640