| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
The primary target of S-(-)-7-Desmethyl-8-nitro blebbistatin is non-muscle myosin II (NMII). Myosin II is a motor protein that hydrolyzes ATP to generate force and movement along actin filaments. The compound binds to the myosin head domain and stabilizes a transient state in the ATP hydrolysis cycle, leading to a strong inhibition of the actin-stimulated myosin II ATPase activity. This effectively blocks myosin II's motor function. The compound is selective for non-muscle myosin II over other myosin classes (e.g., smooth muscle or skeletal muscle myosin).
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| ln Vitro |
In vitro, S-(-)-7-Desmethyl-8-nitro blebbistatin is an inhibitor of non-muscle myosin II ATPases. The parent compound, (-)-blebbistatin, inhibits the myosin II ATPase activity with an IC₅0 of approximately 0.5-5 uM. The 8-nitro substitution is a photo-protecting group that renders the compound inactive until irradiated with UV light. This photoactivatable version ("caged" blebbistatin) allows for precise spatial and temporal control of myosin II inhibition. Upon exposure to UV light (e.g., 365 nm), the photolabile 8-nitro group is released, generating the active inhibitor. This enables cell biologists to disrupt myosin II function with high precision.
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| ln Vivo |
In vivo, photoactivatable blebbistatin derivatives allow for non-invasive, spatiotemporally controlled studies of myosin II function in living organisms. For example, in a zebrafish model of heart development, the compound can be microinjected into the embryo, and then a specific region of the embryo can be irradiated with a focused UV laser. This selective uncaging would inhibit myosin II only in the irradiated area, allowing researchers to study the role of contractility in specific cell populations during embryogenesis. It is a chemical tool for dissecting cell migration and contractility.
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| Enzyme Assay |
Non-cellular (enzymatic) assays are used to measure the inhibition of myosin II ATPase activity. Purified non-muscle myosin IIA (e.g., 0.1 uM) is incubated with S-(-)-7-Desmethyl-8-nitro blebbistatin (0-100 uM) in an ATPase assay buffer (20 mM MOPS, pH 7.0, 50 mM KCl, 5 mM MgCl2). The reaction is initiated by the addition of 1 mM ATP and actin (0.5 uM). After a 20-minute incubation at 25degC, the amount of inorganic phosphate released is quantified using a colorimetric malachite green assay. The IC₅0 is calculated. The compound will show no activity in this assay unless it is first irradiated with UV light (365 nm) to remove the photo-protecting group.
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| Cell Assay |
S-(-)-7-Desmethyl-8-nitro blebbistatin is used in cell-based assays to study myosin II function. Cells (e.g., HeLa, NIH/3T3) are plated on coverslips and allowed to adhere overnight. The culture medium is replaced with medium containing 10-50 uM of the caged compound. Cells are maintained in the dark to prevent premature uncaging. A specific region of the coverslip is then irradiated with a 365 nm UV laser through the microscope objective. For wound healing assays, a scratch is made in a confluent monolayer, and the cells are treated with the caged compound. Unwounded cells in a specific area are irradiated to locally inhibit myosin II, and the migration speed of the cells is tracked by time-lapse microscopy.
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| Animal Protocol |
No direct in vivo animal experiments are reported for this specific compound. A typical photoactivation experiment in zebrafish: Zebrafish embryos at the one-cell stage are injected with 1 nL of a 50 uM solution of S-(-)-7-Desmethyl-8-nitro blebbistatin. After the embryos reach the desired stage (e.g., 24 hours post-fertilization), a specific region of the embryo (e.g., the developing heart or neural crest cells) is irradiated with a 365 nm UV laser. The embryos are then observed for phenotypic changes (e.g., defects in heart tube formation or neural crest migration). Control embryos are injected but not irradiated. The survival and developmental abnormalities are scored.
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| ADME/Pharmacokinetics |
S-(-)-7-Desmethyl-8-nitro blebbistatin (MW 323.30) is a solid powder with a predicted logP of approximately 3. It is soluble in DMSO (stock solution 10-50 mM). The compound is light-sensitive and must be handled and stored in the dark. For long-term storage, the powder should be kept at -20degC, protected from light. Solutions in DMSO should be stored at -80degC in amber vials. The compound is not intended for systemic use as a drug; it is a research chemical for optical control of myosin II.
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| Toxicity/Toxicokinetics |
The toxicological profile of this compound is not well-documented. The parent compound, blebbistatin, can be cytotoxic at high concentrations due to its disruption of essential myosin II functions (e.g., cytokinesis). As a research chemical, standard safety precautions apply: use in fume hood, wear gloves, lab coat, and goggles. Avoid exposure to light during handling. Not for human consumption.
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| References |
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| Additional Infomation |
S-(-)-7-Desmethyl-8-nitro blebbistatin (Compound 12, CAS 856925-75-2) is a derivative of the widely used myosin II inhibitor blebbistatin. The 8-nitro group serves as a photolabile protecting group that blocks the inhibitor's activity. Upon exposure to UV light, the nitro group is removed ("uncaging"), generating the active inhibitor. This provides spatiotemporal control of myosin II inhibition, allowing researchers to probe the role of contractility in dynamic cellular processes with unprecedented precision. It is a valuable tool for chemical biology and developmental biology. For research use only.
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| Molecular Formula |
C17H13N3O4
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|---|---|
| Molecular Weight |
323.30
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| Exact Mass |
323.091
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| CAS # |
856925-75-2
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| PubChem CID |
11738810
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
570.7±60.0 °C at 760 mmHg
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| Flash Point |
298.9±32.9 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.737
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| LogP |
0.92
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
24
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| Complexity |
581
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| Defined Atom Stereocenter Count |
1
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| SMILES |
N1C2=C(C=CC([N+]([O-])=O)=C2)C(=O)[C@]2(O)CCN(C3=CC=CC=C3)C=12
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| InChi Key |
VIMYHNYWFMRDKQ-QGZVFWFLSA-N
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| 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-/m1/s1
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| Chemical Name |
(3aS)-3a-hydroxy-7-nitro-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0931 mL | 15.4655 mL | 30.9310 mL | |
| 5 mM | 0.6186 mL | 3.0931 mL | 6.1862 mL | |
| 10 mM | 0.3093 mL | 1.5466 mL | 3.0931 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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