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Tigloylgomisin P (crotonylgomisin P)

Cat No.:V35196 Purity: ≥98%
Tigloylgomisin P is a lignin with anti-HIV (Human Immunodeficiency Virus) activity with EC50 of 37 μM.
Tigloylgomisin P (crotonylgomisin P)
Tigloylgomisin P (crotonylgomisin P) Chemical Structure CAS No.: 69176-51-8
Product category: HIV
This product is for research use only, not for human use. We do not sell to patients.
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5mg
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Product Description
Tigloylgomisin P is a lignin with anti-HIV (Human Immunodeficiency Virus) activity with EC50 of 37 μM. Tigloylgomisin P has potential anticancer/anti-tumor effects.
Tigloylgomisin P (crotonylgomisin P) (CAS#: 69176-51-8) is a naturally occurring lignin isolated from Schisandra species, such as Schisandra pubescens and Schisandra rubriflora. It exhibits anti-HIV (Human Immunodeficiency Virus) activity with an EC50 of 37 μM. Additionally, it has potential anticancer/anti-tumor effects. Tigloylgomisin P is a member of the dibenzocyclooctadiene lignan family and is known for its diverse biological activities, including cytotoxicity against certain cancer cell lines.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary biological targets of Tigloylgomisin P are not definitively established. It is known to have anti-HIV activity and potential anticancer effects. The compound exhibits cytotoxicity against A549 lung cancer cells and nasopharyngeal epidermoid carcinoma (KB) cells. Its mechanism of action may involve interaction with viral or cellular targets, but the specific molecular targets remain to be fully elucidated.
ln Vitro
Tigloylgomisin P exhibits a low level of cytotoxicity against A549 cells (GI50=18.77 μM) and nasopharyngeal epidermoid carcinoma (KB; GI50=13.91 μM)[1].
In vitro, Tigloylgomisin P exhibits a low level of cytotoxicity against A549 cells (GI50 = 18.77 μM) and nasopharyngeal epidermoid carcinoma (KB; GI50 = 13.91 μM). These data indicate that the compound has moderate cytotoxic activity against these cancer cell lines. The anti-HIV activity is characterized by an EC50 of 37 μM, suggesting that higher concentrations are required for antiviral effects compared to its cytotoxic activity.
ln Vivo
In vivo data for Tigloylgomisin P are not available in the literature. As a natural product with anti-HIV and anticancer potential, further studies would be needed to evaluate its efficacy and safety in animal models. The compound's pharmacokinetic properties and in vivo activity remain to be characterized, and it is currently in the early stages of research.
Enzyme Assay
Specific in vitro enzyme/receptor binding assay protocols for Tigloylgomisin P have not been reported. As a natural product with anti-HIV activity, its mechanism of action may involve inhibition of viral enzymes or interference with viral entry or replication. Standard antiviral assays, such as those measuring inhibition of HIV replication in infected cells, are typically used to assess its activity. Further biochemical studies are needed to identify its direct molecular targets.
Cell Assay
Cellular assays for Tigloylgomisin P are performed using cancer cell lines such as A549 (lung cancer) and KB (nasopharyngeal epidermoid carcinoma) cells. Cells are treated with various concentrations of the compound, and cell viability is assessed to determine GI50 values. Anti-HIV activity is evaluated using HIV-infected cell cultures, where the compound's ability to inhibit viral replication is measured. Standard cytotoxicity assays are also conducted to assess its safety profile.
Animal Protocol
In vivo animal protocols for Tigloylgomisin P are not available in the literature. As a natural product with potential therapeutic applications, it would typically be evaluated in mouse models of HIV infection or cancer. However, such studies have not been reported for this compound. Currently, Tigloylgomisin P remains at the in vitro research stage, and further studies are needed to explore its in vivo efficacy.
ADME/Pharmacokinetics
Pharmacokinetic (PK) properties of Tigloylgomisin P have not been characterized. As a natural lignan, its absorption, distribution, metabolism, and excretion (ADME) profile would need to be investigated to assess its drug-like properties. The compound is typically stored as a powder at -20°C and may be soluble in DMSO. Its solubility in aqueous media is limited, with a calculated value of 4.8E-3 g/L at 25°C.
Toxicity/Toxicokinetics
Toxicity data for Tigloylgomisin P are limited. It exhibits low-level cytotoxicity against A549 and KB cell lines, with GI50 values of 18.77 μM and 13.91 μM, respectively. These data suggest moderate cytotoxic potential. Comprehensive toxicological studies, including in vivo safety assessments, have not been conducted. The compound is intended for research use only and is not approved for human therapeutic use.
References

[1]. Cytotoxic and potential anticancer constituents from the stems of Schisandra pubescens. Pharm Biol. 2013 Sep;51(9):1204-7.

[2]. Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora. J Nat Prod. 2006 Dec;69(12):1697-701.

Additional Infomation
Schisandrin P has been reported to be present in Schisandra chinensis, Schisandra chinensis, and other organisms with relevant data.
See also: Schisandra chinensis fruit (partial).
Tigloylgomisin P is also known as crotonylgomisin P and is a natural lignin with anti-HIV and potential anticancer activities. It is isolated from Schisandra species and is a member of the dibenzocyclooctadiene lignan family. The compound is not currently in clinical trials and has not been approved for therapeutic use. Further research is needed to elucidate its mechanism of action and therapeutic potential.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C28H34O9
Molecular Weight
514.56
Exact Mass
514.22
CAS #
69176-51-8
PubChem CID
5318785
Appearance
White to off-white solid powder
LogP
4.61
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
7
Heavy Atom Count
37
Complexity
833
Defined Atom Stereocenter Count
3
SMILES
C/C=C(\C)/C(=O)O[C@@H]1C2=CC(=C(C(=C2C3=C(C4=C(C=C3C[C@@H]([C@@]1(C)O)C)OCO4)OC)OC)OC)OC
InChi Key
BKGUPIVDQHHVMV-TWJXSMCESA-N
InChi Code
InChI=1S/C28H34O9/c1-9-14(2)27(29)37-26-17-12-18(31-5)22(32-6)25(34-8)21(17)20-16(10-15(3)28(26,4)30)11-19-23(24(20)33-7)36-13-35-19/h9,11-12,15,26,30H,10,13H2,1-8H3/b14-9+/t15-,26+,28+/m0/s1
Chemical Name
[(8R,9R,10S)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl] (E)-2-methylbut-2-enoate
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 1.9434 mL 9.7170 mL 19.4341 mL
5 mM 0.3887 mL 1.9434 mL 3.8868 mL
10 mM 0.1943 mL 0.9717 mL 1.9434 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.

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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:
  • 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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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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