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Hymenidin

Cat No.:V21847 Purity: ≥98%
Hymenidin is a natural serotonergic receptor blocker (antagonist) and inhibitor of voltage-gated potassium channels.
Hymenidin
Hymenidin Chemical Structure CAS No.: 107019-95-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price
500mg
1g
Other Sizes
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Product Description
Hymenidin is a natural serotonergic receptor blocker (antagonist) and inhibitor of voltage-gated potassium channels. Hymenidin also causes apoptosis in cancer/tumor cells.
Hymenidin is a natural alkaloid isolated from the Okinawan marine sponge Hymeniacidon sp. with the molecular formula C11H12BrN5O and a molecular weight of 310.15 g/mol. It is a 5-hydroxytryptaminergic receptor antagonist and a voltage-gated potassium channel inhibitor. Hymenidin also induces apoptosis in cancer cells and has potential antiprotozoal effects. It selectively binds to FOXO1 DNA and reduces depolarization-induced elevation of cellular calcium.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary molecular targets of Hymenidin are serotonergic receptors and voltage-gated potassium channels. It acts as an antagonist at 5-hydroxytryptaminergic receptors, blocking serotonin-mediated signaling. Hymenidin also inhibits voltage-gated potassium channels, modulating membrane excitability. Additionally, it selectively binds to FOXO1 DNA, a transcription factor involved in apoptosis and cell cycle regulation.
ln Vitro
In vitro, Hymenidin is a natural antagonist of serotonergic receptors and an inhibitor of voltage-gated potassium channels. It reduces depolarization-induced elevation of cellular calcium. Hymenidin induces apoptosis in cancer cells. It selectively binds to FOXO1 DNA. Specific IC50 values for receptor antagonism and potassium channel inhibition have not been extensively reported.
ln Vivo
No dedicated in vivo efficacy studies have been published specifically for Hymenidin. As a natural marine alkaloid, its in vivo applications are primarily in preclinical models of cancer and parasitic infections. No pharmacokinetic parameters, maximum tolerated doses, or in vivo efficacy data are available in the published literature.
Enzyme Assay
Non-cell-based assays for Hymenidin use radioligand binding with [3H]serotonin or [125I]iodocyanopindolol in membrane preparations from cells expressing serotonergic receptors. Membranes are incubated with radioligand and increasing concentrations of Hymenidin in assay buffer. Bound radioligand is separated by rapid filtration, and radioactivity is quantified.
Cell Assay
Cell-based assays for Hymenidin use cancer cell lines or cells expressing voltage-gated potassium channels. Cells are cultured in standard medium and treated with Hymenidin at concentrations ranging from 0.1 to 100 μM. Cell viability is measured by MTT assay. Apoptosis is assessed by Annexin V/PI staining and caspase activity assays. Potassium currents are measured by patch-clamp electrophysiology.
Animal Protocol
No specific in vivo animal protocols have been established for Hymenidin. For potential evaluation, the compound could be administered in murine tumor xenograft models or parasite infection models. Doses would be determined from pharmacokinetic studies. Endpoints could include tumor growth inhibition or parasite burden.
References

[1]. A novel antagonist of serotonergic receptors, hymenidin, isolated from the Okinawan marine sponge Hymeniacidon sp. Experientia. 1986 Oct 15;42(10):1176-7.

[2]. Clathrodin, hymenidin and oroidin, and their synthetic analogues as inhibitors of the voltage-gated potassium channels. Eur J Med Chem. 2017 Oct 20;139:232-241.

[3]. Analogues of the marine alkaloids oroidin, clathrodin, and hymenidin induce apoptosis in human HepG2 and THP-1 cancer cells. MedChemComm. 2015, 6(1): 105-110.

Additional Infomation
Hymenidin has reportedly been found in Stylissa carteri, Agelas nakamurai, and other organisms with available data.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H12N5OBR
Molecular Weight
310.14988
Exact Mass
309.023
CAS #
107019-95-4
Related CAS #
107019-95-4 Hymenidin
PubChem CID
6439099
Appearance
Typically exists as solid at room temperature
Density
1.69g/cm3
Index of Refraction
1.742
Source
Marine naturally occuring products: Sponge
LogP
2.497
tPSA
99.59
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Heavy Atom Count
18
Complexity
325
Defined Atom Stereocenter Count
0
SMILES
NC1=NC=C(/C=C/CNC(C2=CC(Br)=CN2)=O)N1
InChi Key
KHJREOQCERRAME-OWOJBTEDSA-N
InChi Code
InChI=1S/C11H12BrN5O/c12-7-4-9(15-5-7)10(18)14-3-1-2-8-6-16-11(13)17-8/h1-2,4-6,15H,3H2,(H,14,18)(H3,13,16,17)/b2-1+
Chemical Name
N-[(E)-3-(2-amino-1H-imidazol-5-yl)prop-2-enyl]-4-bromo-1H-pyrrole-2-carboxamide
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 : 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).
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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 : PEG300:Tween 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 3.2242 mL 16.1212 mL 32.2425 mL
5 mM 0.6448 mL 3.2242 mL 6.4485 mL
10 mM 0.3224 mL 1.6121 mL 3.2242 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

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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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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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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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  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • 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:
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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.

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  • 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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