Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H16N2O2 |
Molecular Weight | 292.3318 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C2N=C3N(CCC3(O)C(=O)C2=C1)C4=CC=CC=C4
InChI
InChIKey=LZAXPYOBKSJSEX-UHFFFAOYSA-N
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
Molecular Formula | C18H16N2O2 |
Molecular Weight | 292.3318 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Blebbistatin is a small molecule inhibitor discovered in a screen for inhibitors of nonmuscle myosin IIA. Blebbistatin potently inhibits several striated muscle myosins as well as vertebrate nonmuscle myosin IIA and IIB with IC50 values ranging from 0.5 to 5 microM. Interestingly, smooth muscle which is highly homologous to vertebrate nonmuscle myosin is only poorly inhibited (IC50=80 microM). The drug potently inhibits Dictyostelium myosin II, but poorly inhibits Acanthamoeba myosin II. Blebbistatin did not inhibit representative myosin superfamily members from classes I, V, and X. Blebbistatin blocks apoptosis-related bleb formation, directed cell migration and cytokinesis in vertebrate cells. Blebbistatin is inactivated by UV light, which may be particularly important in fluorescent cell imaging applications. Blebbistatin does not compete with nucleotide binding to the skeletal muscle myosin subfragment-1. The inhibitor preferentially binds to the ATPase intermediate with ADP and phosphate bound at the active site, and it slows down phosphate release. Blebbistatin interferes neither with binding of myosin to actin nor with ATP-induced actomyosin dissociation. Instead, it blocks the myosin heads in a products complex with low actin affinity. Blind docking molecular simulations indicate that the productive blebbistatin-binding site of the myosin head is within the aqueous cavity between the nucleotide pocket and the cleft of the actin-binding interface. The property that blebbistatin blocks myosin II in an actin-detached state makes the compound useful both in muscle physiology and in exploring the cellular function of cytoplasmic myosin II isoforms, whereas the stabilization of a specific myosin intermediate confers a great potential in structural studies. (–)-blebbistatin is the active species, with an inhibitory concentration for 50% inhibition (IC50) of 2 uM,
whereas (+)-blebbistatin is inactive.
CNS Activity
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Myosin II regulatory light chain is required for trafficking of bile salt export protein to the apical membrane in Madin-Darby canine kidney cells. | 2005 Jun 24 |
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Myosin 2 is a key Rho kinase target necessary for the local concentration of E-cadherin at cell-cell contacts. | 2005 Oct |
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Myosin light chain kinase plays a role in the regulation of epithelial cell survival. | 2006 Jun 1 |
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Extracellular matrix rigidity promotes invadopodia activity. | 2008 Sep 9 |
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Correlation of dysfunction of nonmuscle myosin IIA with increased induction of Cyp1a1 in Hepa-1 cells. | 2011 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20482706
Rats: 250 nmol of blebbistatin was instilled into the bladder of a normal
awake rat
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25598228
When 30 uM Blebbistatin was
added to the medium bathing of the rat neuronal culture, protrusion/
retraction cycles of lamellipodia could be observed but with a period
30–50% longer than in control condition and after 15 minutes
lamellipodia shrank. When a higher concentration
of Blebbistatin was used, such as 100 uM, lamellipodia shrank within
2–3 minutes and motility was completely suppressed.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:08:43 GMT 2023
by
admin
on
Sat Dec 16 10:08:43 GMT 2023
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Record UNII |
20WC4J7CQ6
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Record Status |
Validated (UNII)
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Record Version |
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-
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