| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| ln Vitro |
Pro-inflammatory gene expression in human and mouse macrophages can be inhibited by dihomo-γ-linolenic acid [2]. STAT1 serine 727 phosphorylation induced by IFN-γ is attenuated by dihomo-γ-linolenic acid (50 μM; 24 hours) [2]. When IL-1β and TNF-α are released into human macrophages, dihomo-γ-linolenic acid can reduce the expression of MCP-1 and ICAM-1 [2]. Chemokine-induced monocyte migration and macrophage foam cell formation are inhibited by dihomo-γ-linolenic acid [2]. The expression of CD36 and SR-A in human macrophages is attenuated by dihomo-γ-linolenic acid [2]. Dihomo-γ-linolenic acid controls the respiration of mitochondria [2]. Dihomo-γ-linolenic acid affects how VSMCs and endothelial cells behave [2].
|
|---|---|
| ln Vivo |
In mice with small xenograft tumors, diho-γ-linolenic acid (8 mg/mouse; injected twice weekly for 35 days) suppresses the development of human pancreatic cancer cells (BxPC-3) transfected with delta-5-desaturase shRNA [3].
|
| Cell Assay |
Western blot analysis [2]
Cell Types: THP-1 macrophages Tested Concentrations: 50 μM (pretreatment) Incubation Duration: 24 hrs (hours) Experimental Results: Attenuated IFN-γ-induced STAT1 phosphorylation on serine 727. |
| Animal Protocol |
Animal/Disease Models: Female nude mice (48, four weeks old) [3]
Doses: 8 mg/animal Route of Administration: po (oral gavage), twice a week for 35 days Experimental Results: Inhibited the metastasis potential of D5D-KD tumors. |
| References |
|
| Additional Infomation |
All-cis-icosa-8,11,14-trienoic acid is an icosatrienoic acid having three cis double bonds at positions 8, 11 and 14. It has a role as a nutraceutical, a human metabolite and a fungal metabolite. It is a fatty acid 20:3 and a long-chain fatty acid. It is a conjugate acid of an all-cis-icosa-8,11,14-trienoate.
A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5. Dihomo-gamma-linolenic acid has been reported in Mortierella hygrophila, Mortierella alpina, and other organisms with data available. Dihomo-gamma-linolenic Acid is a polyunsaturated long-chain fatty acid with a 20-carbon backbone and 3 double bonds, originating from the 6th, 9th and 12th positions from the methyl end, with all bonds in the cis- configuration. A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5. Drug Indication For nutritional supplementation, also for treating dietary shortage or imbalance Mechanism of Action DHLA (or DGLA) is a precursor in the synthesis of prostaglandin E1 (PGE1) as well as the series-3 prostaglandins. It also serves as a precursor in the synthesis of eicosapentaenoic acid (EPA). EPA is a precursor of the series-3 prostaglandins, the series-5 leukotrienes and the series-3 thromboxanes. These eicosanoids have anti-thrombogenic, anti-inflammatory and anti-atherogenic properties. PGE1 inhibits platelet aggregation and has a vasodilation action. DHLA has also been shown to reduce the production/activity of tumor necrosis factor alpha. Pharmacodynamics Dihomo gamma-linolenic acid or DHLA is an n-6 (omega-6) polyunsaturated fatty acid. It is comprised of 20 carbon atoms and three double bonds. DHLA is a byproduct of the 18 carbon gamma-linolenic acid (GLA). DHLA is then converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. |
| Molecular Formula |
C20H34O2
|
|---|---|
| Molecular Weight |
306.4828
|
| Exact Mass |
306.255
|
| CAS # |
1783-84-2
|
| PubChem CID |
5280581
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
0.917g/cm3
|
| Boiling Point |
437.984°C at 760 mmHg
|
| Flash Point |
334.667°C
|
| Vapour Pressure |
0.0±2.3 mmHg at 25°C
|
| Index of Refraction |
1.489
|
| LogP |
7.56
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
15
|
| Heavy Atom Count |
22
|
| Complexity |
327
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O([H])C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C(/[H])=C(/[H])\C([H])([H])/C(/[H])=C(/[H])\C([H])([H])/C(/[H])=C(/[H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
|
| InChi Key |
HOBAELRKJCKHQD-QNEBEIHSSA-N
|
| InChi Code |
InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
|
| Chemical Name |
(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
|
| 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 (In Vitro) |
DMSO : ~100 mg/mL (~326.29 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.16 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.16 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2629 mL | 16.3143 mL | 32.6286 mL | |
| 5 mM | 0.6526 mL | 3.2629 mL | 6.5257 mL | |
| 10 mM | 0.3263 mL | 1.6314 mL | 3.2629 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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