| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
Ajoene is an organic trisulphur originally isolated from garlic, it has an antimycotic activity which has been widely demonstrated both in vitro and in vivo.
| Targets |
Vimentin (covalent binding); multiple signaling pathways involved in apoptosis and metastasis.
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|---|---|
| ln Vitro |
Ajoene demonstrates cytotoxicity against B16/BL6, HT-29, A549, MDA-MB231, PANC-1, and SKBR-3 cells, with IC50s ranging from 7 to 41 uM[1].
Ajoene exerts its anti-cancer activity by covalently binding to vimentin, disrupting the vimentin network, and exerting anti-metastatic activity; it induces apoptosis in myeloid leukemia cells, accompanied by generation of reactive oxygen species (ROS) and activation of nuclear factor kappaB (NF-kappaB); it shows cytotoxic and anti-proliferative effects against various cancer cell lines, with selectivity for cancer cells over normal cells in some studies. |
| ln Vivo |
Ajoene reduces both primary tumor growth when administered intraperitoneally (i.p.) every other day from the day of inoculation until day 28 (25 μg/g body weight of Ajoene in 100 mL Intralipid)[1]. In the B16/BL6 melanoma tumor model in C57BL/6 mice, Ajoene (25, 15 or 5 μg/g body weight of Ajoene in 100 μL Intralipid; ip; every other day during 4 weeks) significantly suppresses lung metastasis[1].
In mouse skin tumor promotion models, ajoene exhibits anti-tumor effects; it reduces tumor incidence and multiplicity; it also shows potential in enhancing chemotherapy-induced apoptosis in resistant leukemia cells; specific in vivo efficacy data in other models (e.g., xenografts) are available but limited in open sources. |
| Enzyme Assay |
Not detailed in available sources; for S-thiolation assays, ajoene is incubated with purified target proteins (e.g., vimentin) in cell-free conditions, and the covalent adduct is detected by mass spectrometry or Western blot using thiol-specific probes; enzyme inhibition assays can also measure functional consequences.
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| Cell Assay |
Apoptosis is assessed in lymphoid leukemic or myeloid leukemia cells cultured in RPMI-1640 medium with 10% FBS; cells are treated with serial dilutions of ajoene (typically uM range) for 24-72 hours; apoptosis is measured by Annexin V-FITC/PI staining and flow cytometry; caspase activity is measured by fluorogenic substrates; ROS levels are measured using DCFH-DA probe.
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| Animal Protocol |
Mouse skin tumor promotion models: mice are initiated with a carcinogen (e.g., DMBA) followed by promotion with TPA; ajoene is applied topically or administered orally; endpoints include tumor incidence, multiplicity (number of tumors per mouse), and latency; skin samples are taken for histology and biomarker analysis.
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| ADME/Pharmacokinetics |
PK properties: ajoene is known to have limited bioavailability due to rapid metabolism and instability in blood; it undergoes S-thiolation reactions and is rapidly cleared; its development as a therapeutic is hampered by low systemic exposure; specific half-life, volume of distribution, and oral bioavailability are not fully characterized.
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| Toxicity/Toxicokinetics |
Toxicity: ajoene is generally considered to have low toxicity based on traditional use of garlic; however, concentrated formulations may cause gastrointestinal irritation; no formal toxicological studies (acute, sub-chronic, genotoxicity) are available in open sources; it is generally recognized as safe when consumed in dietary amounts.
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| References |
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| Additional Infomation |
(E)-Alliin is a sulfoxide. Alliin has been reported to exist in garlic (Allium sativum) and plants of the genus Allium, and relevant data are available.
Ajoene is a natural product and research tool compound derived from garlic; it is not an approved drug; no clinical trials have been conducted for ajoene as a therapeutic agent; it is used as a reference compound for studying organosulfur pharmacology, anti-cancer mechanisms (especially S-thiolation), and anti-metastatic activity; it has also been investigated for its antifungal and antibacterial properties. |
| Molecular Formula |
C9H14OS3
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|---|---|
| Molecular Weight |
234.40185880661
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| Exact Mass |
234.021
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| CAS # |
92284-99-6
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| Related CAS # |
Ajoene;92285-01-3
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| PubChem CID |
5386591
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.181±0.06 g/cm3 (20 °C, 760 mmHg)
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| Boiling Point |
376.0±42.0 °C (760 mmHg)
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| LogP |
3.867
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
13
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| Complexity |
199
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C=CCSSC=CCS(=O)CC=C
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| InChi Key |
IXELFRRANAOWSF-FNORWQNLSA-N
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| InChi Code |
InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5+
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| Chemical Name |
(E)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene
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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 | 4.2662 mL | 21.3311 mL | 42.6621 mL | |
| 5 mM | 0.8532 mL | 4.2662 mL | 8.5324 mL | |
| 10 mM | 0.4266 mL | 2.1331 mL | 4.2662 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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