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Curvulin

Cat No.:V55251 Purity: ≥98%
Curvulin is a plant toxin that can inhibit microtubule assembly and iNOS expression.
Curvulin
Curvulin Chemical Structure CAS No.: 19054-27-4
Product category: Microtubule(Tubulin)
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
Other Sizes
Official Supplier of:
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Product Description
Curvulin is a plant toxin that can inhibit microtubule assembly and iNOS expression.
Curvulin (CAS 19054-27-4) is a phytotoxin first isolated from Paraphoma sp. VIZR 1.46. Its molecular formula is C12H14O5 with a molecular weight of 238.24 g/mol. Curvulin inhibits microtubule assembly and inhibits iNOS expression. The compound is also known as ethyl 2-(2-acetyl-3,5-dihydroxyphenyl)acetate and 2-acetyl-3,5-dihydroxybenzeneacetic acid ethyl ester. Curvulin is classified as a microtubule/tubulin inhibitor.
Biological Activity I Assay Protocols (From Reference)
Targets
Curvulin targets microtubules, the cytoskeletal structures essential for cell division, intracellular transport, and cellular morphology. The compound inhibits microtubule assembly, preventing the polymerization of tubulin into microtubules. Additionally, Curvulin inhibits the expression of inducible nitric oxide synthase (iNOS), an enzyme involved in inflammatory responses.
ln Vitro
In cell-free biochemical assays, Curvulin inhibits microtubule assembly. The compound prevents the polymerization of purified tubulin into microtubules in vitro. This activity is typically measured using turbidimetric assays that monitor the increase in absorbance as tubulin polymerizes into microtubules. The compound also inhibits iNOS expression in cell-based systems.
ln Vivo
In cell-based assays, Curvulin inhibits microtubule assembly, leading to disruption of the cellular microtubule network. The compound also inhibits iNOS expression, reducing nitric oxide production in cells. These activities contribute to the compound's effects on cell division, migration, and inflammatory responses. Curvulin is a phytotoxin that may have potential applications in studying microtubule biology and inflammation.
Enzyme Assay
The cell-free microtubule assembly assay involves incubation of purified tubulin with the compound at various concentrations in assembly buffer containing GTP. The reaction is incubated at 37°C, and microtubule polymerization is monitored by measuring absorbance at 340 nm. The IC50 for inhibition of microtubule assembly is determined from dose-response curves. The iNOS expression assay measures iNOS protein levels by Western blotting or activity by measuring nitrite production.
Cell Assay
Cell-based assays for Curvulin involve culturing mammalian cells and treating them with the compound at concentrations ranging from 0.1 to 100 μM. Cells are incubated for 24-72 hours, and the effect on microtubule assembly is assessed by immunofluorescence staining of tubulin. The effect on iNOS expression is assessed by Western blotting or by measuring nitric oxide production using the Griess assay.
Animal Protocol
There is no established animal experimental protocol for Curvulin specifically. As a phytotoxin and microtubule inhibitor, the compound could potentially be evaluated in animal models of cancer or inflammation. Typical protocols for microtubule inhibitors involve administration to tumor-bearing mice via intraperitoneal or intravenous routes. Toxicity and efficacy would need to be established in preclinical studies.
ADME/Pharmacokinetics
Pharmacokinetic properties of Curvulin have not been extensively reported in the literature. As a small molecule with molecular weight of 238.24 g/mol, the compound would be expected to have moderate oral bioavailability and reasonable tissue penetration. The compound is soluble in methanol, DMSO, or acetone. Further pharmacokinetic studies would be required to determine plasma half-life, clearance, and metabolic pathways.
Toxicity/Toxicokinetics
Toxicity data for Curvulin are not well documented in the available literature. As a phytotoxin, the compound may have toxic effects on cells and tissues. Microtubule inhibitors are typically toxic to rapidly dividing cells, which could translate to bone marrow suppression, gastrointestinal toxicity, and other effects. Standard toxicity studies would be required to determine the safety profile.
References

[1]. Curvulin and Phaeosphaeride A From Paraphoma Sp. VIZR 1.46 Isolated From Cirsium arvense as Potential Herbicides. Molecules. 2018 Oct 28;23(11):2795.

Additional Infomation
Curvulin is an aromatic ketone. Ethyl 2-(2-acetyl-3,5-dihydroxyphenyl) has been reported and data are available for its presence in the genera Curvularia, Curvularia lunata, and Curvularia pallescens.
Curvulin is a research compound used to study microtubule assembly and iNOS expression. It is a phytotoxin first isolated from Paraphoma sp. VIZR 1.46. The compound inhibits microtubule assembly and inhibits iNOS expression. It is not an approved pharmaceutical and has no clinical trial history. This product is intended for research use only and is not for human therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H14O5
Molecular Weight
238.2366
Exact Mass
238.084
CAS #
19054-27-4
PubChem CID
177045
Appearance
White to off-white solid powder
Density
1.273g/cm3
Boiling Point
404.8ºC at 760 mmHg
Flash Point
155.3ºC
Vapour Pressure
3.92E-07mmHg at 25°C
Index of Refraction
1.561
LogP
1.406
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
5
Heavy Atom Count
17
Complexity
289
Defined Atom Stereocenter Count
0
SMILES
O(C([H])([H])C([H])([H])[H])C(C([H])([H])C1C([H])=C(C([H])=C(C=1C(C([H])([H])[H])=O)O[H])O[H])=O
InChi Key
TURXCFUGBPBPRS-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H14O5/c1-3-17-11(16)5-8-4-9(14)6-10(15)12(8)7(2)13/h4,6,14-15H,3,5H2,1-2H3
Chemical Name
ethyl 2-(2-acetyl-3,5-dihydroxyphenyl)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 4.1974 mL 20.9872 mL 41.9745 mL
5 mM 0.8395 mL 4.1974 mL 8.3949 mL
10 mM 0.4197 mL 2.0987 mL 4.1974 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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