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Cytochalasin C

Cat No.:V31547 Purity: ≥98%
Cytochalasin C is a cell-penetrable mycotoxin that induces the formation of nuclear rods.
Cytochalasin C
Cytochalasin C Chemical Structure CAS No.: 22144-76-9
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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100mg
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Product Description
Cytochalasin C is a cell-penetrable mycotoxin that induces the formation of nuclear rods. Cytochalasin C is 10 times less toxic than Cytochalasin D in mice.
Cytochalasin C is a cell-permeable fungal metabolite and actin polymerization inhibitor isolated from Chaetomium globosum. With a molecular formula of C30H3₇NO₆ and a molecular weight of 507.62, it belongs to the cytochalasin family of mycotoxins. This compound is widely used in cell biology research to study cytoskeletal dynamics and actin-dependent cellular processes. Cytochalasin C induces the formation of nuclear rodlets and is cytotoxic to various cancer cell lines.
Biological Activity I Assay Protocols (From Reference)
Targets
Cytochalasin C targets actin filaments by binding to the barbed (fast-growing) ends of actin filaments. This binding inhibits actin polymerization and blocks the elongation of actin filaments. By disrupting actin filament dynamics, the compound interferes with cytoskeletal organization. One cytochalasin molecule binds to one actin filament, effectively capping the filament end and preventing further monomer addition. This mechanism of action affects multiple actin-dependent cellular processes.
ln Vitro
In vitro, Cytochalasin C inhibits actin polymerization at a concentration of 10 uM. It promotes rapid initial filament formation but ultimately reduces steady-state polymerization. The compound is cytotoxic to HeLa cells with an IC₅0 of less than 0.32 ug/ml. Previous studies have described the results of actin assembly assays in the presence of various cytochalasins. By disrupting actin dynamics, Cytochalasin C interferes with cell growth, movement, phagocytosis, degranulation, and secretion.
ln Vivo
In vivo studies of Cytochalasin C are limited, as it is primarily used as a research tool in cell-based assays. As a fungal metabolite and mycotoxin, it can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. The compound's ability to disrupt actin cytoskeleton makes it potentially useful for studying actin-related physiological processes in animal models. However, its in vivo applications are constrained by its cytotoxicity and lack of target specificity. Further studies are needed to evaluate its potential in vivo.
Enzyme Assay
For in vitro enzyme/receptor binding assays, Cytochalasin C is evaluated using actin polymerization assays. The compound is incubated with purified actin monomers (G-actin) at various concentrations in polymerization buffer containing salts and ATP. Actin polymerization is monitored by measuring the increase in fluorescence of pyrene-labeled actin or by following the increase in absorbance at 350 nm due to light scattering. The rate and extent of polymerization are measured to determine the inhibitory effect. IC₅0 values are calculated from dose-response curves. Standard assay conditions include physiological ionic strength and temperature.
Cell Assay
For in vitro cellular experiments, Cytochalasin C is tested in various cell lines to evaluate its effects on actin cytoskeleton and actin-dependent cellular functions. Cells are cultured in appropriate media and treated with various concentrations of the compound (typically ranging from nanomolar to micromolar). Actin filament organization is assessed by fluorescent staining with phalloidin and visualized by fluorescence microscopy. Cell morphology, migration, phagocytosis, and cytokinesis are evaluated. Cell viability is assessed using standard assays such as MTT. The compound's effects on actin dynamics and cellular processes are quantified.
Animal Protocol
For in vivo animal experiments, Cytochalasin C can be administered to animals via various routes including intraperitoneal injection or intravenous injection. However, as a cytotoxic fungal metabolite, its in vivo use is limited. The compound could be used in studies investigating the role of actin in physiological processes such as tissue development, wound healing, and immune cell function. Typical doses would need to be carefully determined to balance efficacy and toxicity. Animal studies should follow appropriate ethical guidelines. Further studies are needed to establish standardized protocols for in vivo administration.
ADME/Pharmacokinetics
Pharmacokinetic properties of Cytochalasin C are not extensively characterized in the literature. As a fungal metabolite with a molecular weight of 507.62, it is expected to have moderate lipophilicity and tissue distribution. The compound is cell-permeable, facilitating its uptake into cells. When administered systemically, it would likely be distributed to various tissues and metabolized by liver enzymes. Its half-life in circulation would depend on its stability and clearance mechanisms. Further pharmacokinetic studies would be needed to fully characterize its absorption, distribution, metabolism, and excretion profile in vivo.
Toxicity/Toxicokinetics
Toxicological data for Cytochalasin C indicate that it is cytotoxic to HeLa cells with an IC₅0 of less than 0.32 ug/ml. As a mycotoxin, it can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. The compound's toxicity is primarily attributed to its disruption of the actin cytoskeleton, which is essential for numerous cellular functions. Standard toxicological assessments would include cytotoxicity screening in various cell lines and acute toxicity studies in animal models. As with all research chemicals, appropriate safety precautions should be taken when handling Cytochalasin C.
References

[1]. Wide-ranging effects of eight cytochalasins and latrunculin A and B on intracellular motility and actin filament reorganization in characean internodal cells. Plant Cell Physiol. 2007 Apr;48(4):585-97.

[2]. Correlation between effects of 24 different cytochalasins on cellular structures and cellular eventsand those on actin in vitro. J Cell Biol. 1982 Jan;92(1):69-78.

[3]. Tolerated doses in zebrafish of cytochalasins and jasplakinolide for comparison with tolerateddoses in mice in the evaluation of pre-clinical activity of microfilament-directed agents in tumormodel systems in vivo. In Vivo. 2014 Nov-D.

Additional Infomation
Cytochalasin C is a research compound used to study actin polymerization and cytoskeletal dynamics. No clinical trials or regulatory approvals have been reported for this compound as a therapeutic agent. It is available from various chemical suppliers for research purposes only. The compound is a cell-permeable fungal metabolite that inhibits actin polymerization by binding to the barbed ends of actin filaments. It interferes with diverse cellular processes including cell growth, movement, phagocytosis, degranulation, and secretion. Cytochalasin C is widely used in cell biology research as a tool for studying actin-dependent processes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H37NO6
Molecular Weight
507.61788
Exact Mass
507.262
CAS #
22144-76-9
PubChem CID
5836594
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
714.3±60.0 °C at 760 mmHg
Melting Point
260-264ºC
Flash Point
385.8±32.9 °C
Vapour Pressure
0.0±2.4 mmHg at 25°C
Index of Refraction
1.602
LogP
2.2
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
4
Heavy Atom Count
37
Complexity
1020
Defined Atom Stereocenter Count
0
SMILES
C[C@@H]1CC=C[C@H]2[C@H](O)C(C)=C(C3[C@@H](NC([C@@]23[C@@H](OC(C)=O)C=C[C@](C1=O)(O)C)=O)CC4=CC=CC=C4)C
InChi Key
NAIODHJWOHMDJX-WISUYLHISA-N
InChi Code
InChI=1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17,22-26,33,36H,10,16H2,1-5H3,(H,31,35)/b13-9+,15-14-
Chemical Name
[(3Z,9E)-16-benzyl-5,12-dihydroxy-5,7,13,14-tetramethyl-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9,13-trien-2-yl] acetate
HS Tariff Code
2934.99.9001
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)
Solubility Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9700 mL 9.8499 mL 19.6998 mL
5 mM 0.3940 mL 1.9700 mL 3.9400 mL
10 mM 0.1970 mL 0.9850 mL 1.9700 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.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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