Eicosapentaenoic Acid (EPA)

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Tel.: +1 418 874.0054 / Fax: +1 418 874.0355 Toll Free: +1 877 745.4292 (North America Only) Email: [email protected]

Product Information Eicosapentaenoic acid (EPA)

Identification Product Number EPA-GP-xxx CAS Number 10417-94-4 EN Number N/A Common Name Eicosapentaenoic acid Systematic Name cis-5,8,11,14,17-Eicosapentaenoic acid 20:5(n-3); Icosapentaenoic acid; Alternative Names Timnodonic acid Storage Temperature -80°C or lower

Characteristics Specifications

Molecular Formula C20H30O2 Purity ≥ 99 % Molecular Weight 302.45 g/mol Form Liquid above -54°C Melting Point -54 to -53°C Color Clear, colorless Density 0.943 g/mL at 25°C (lit.)

Precautions & Disclaimer For laboratory use only. Not for use on humans. Not for drug, household or other uses.

Handling & Preparation Instructions

This purified fatty acid is liquid at room temperature (oil) and not soluble in water. It can be solubilized in undiluted serum or in ethanol or DMSO. Essential fatty acids are also soluble in chloroform or ether, however it is not recommended with the use of cells. After reconstitution, the product can be aliquoted and stored at -80°C. We recommend adding the essential fatty acids cocktail to the medium the day of use.

The concentration to add to the culture is to be determined by the user. As a starting point, we provide some references from the literature. Chen et al. treated primary microglial cells with 20 µM of EPA [1]. Hampel et al. treated human epithelial cells with 100 µM of EPA [2]. Tigistu-Sahle et al. used an intermediate concentration of 50 µM on bone marrow mesenchymal stromal cells [3]. With a molecular mass of 302.45 g/mol, the corresponding concentration (μg/mL or mg/L) should be between 6 and 30 mg/L.

Storage

Essential fatty acids are sensitive to oxidation, light and heat. The vacuum amber glass ampoule is optimal to prevent premature degradation. The product must be stored under -80°C and freeze-thaw cycles should be avoided. The product is stable in its ampoule at -80°C for at least 12 months.

About essential fatty acids and derivatives

Omega (ω) -3, and ω-6 fatty acids are essential to maintain the homeostasis of the human body. They have to be accumulated from food because mammals lack the appropriate enzyme to perform the carbon desaturation beyond carbon 9 and 10 to introduce a double bond. However, humans can synthesize long-chain (20 carbons or more) ω-6 fatty acids from the parent

Tel.: +1 418 874.0054 / Fax: +1 418 874.0355 Toll Free: +1 877 745.4292 (North America Only) Email: [email protected]

fatty acid Linoleic acid and long-chain ω-3 fatty acids from the parent fatty acid α-Linolenic acid

Fatty acids are the constituent of the hydrophobic tail of phospholipids that form the cell membrane. When polyunsaturated fatty acids (PUFAs) are used to form phospholipids, the curvature in their structure creates spacing between them, allowing the increase of lateral movements of transmembrane proteins. Movement of membrane proteins, such as receptors, integrins and ion channels, is fundamental to their function. PUFAs are also essential precursors of the eicosanoid family of hormones.

Supplementation with ω-3 fatty acids has been shown to reduce inflammation and increase microglial phagocytosis in a model of multiple sclerosis [1]; to suppress the pathological phenotype of human bronchial epithelial cells in a model of cystic fibrosis [4]; and to protect photoreceptors from oxidation-induced apoptosis in rat retinal neuron cells [5]. These in vitro studies demonstrate that various cell types do benefit from supplementation with essential fatty acids, not only adipocytes.

The beneficial effects of essential fatty acid supplementation have been well documented in vivo as well. For example, clinical studies have demonstrated that a diet rich in ω-3 fatty acids can reduce inflammation in obese pregnant women [6] and reduce the progression of Alzheimer’s disease [7].

About EPA

EPA is an ω-3 PUFA. It is a precursor for several eicosanoids including prostaglandin-E3, thromboxane-A3 and leukotriene-5. It also enters in competition with ω-6 fatty acids (Arachidonic acid) for the activity of the cyclooxygenase enzymes, resulting in a general anti-inflammatory effect.

EPA has been used as a cell culture supplement in several studies. Treatment of myelin-stimulated primary microglial cells with EPA has been shown to inhibit the release of nitric oxide and tumor necrosis factor-α, whilst enhancing myelin phagocytosis. Therefore, EPA was able to inhibit inflammation and enhance beneficial immune responses in this in vitro model of multiple sclerosis [1].

Bone marrow mesenchymal stromal cells (BMSCs) are well known for their use and potential in cell therapy due to their immunomodulatory capability. However, when extensively cultured in vitro, their cell membranes become deficient in ω-3 fatty acids, limiting their anti-inflammatory properties. Cultured-BMSCs were supplemented with different PUFA. Supplementation with EPA and DHA efficiently attenuated inflammatory signaling while supplementation with α-Linolenic acid did not [3], probably due to the low capability of BMSC to perform the desaturation steps necessary to convert α-Linolenic acid to EPA and DHA [8].

Thank you for choosing a SiliCycle product. Customer service is our priority and we give our best to answer your needs. If you have any questions or need further information, please contact us at [email protected] and our team of cell biologists will be delighted to respond quickly.

References

[1] Chen S, et al. (2014) n-3 PUFA supplementation benefits microglial responses to myelin pathology Sci Rep [2] Hampel U, et al. (2015) In vitro effects of docosahexaenoic and Eicosapentaenoic acid on human meibomian gland epithelial cells Exp Eye Res [3] Tigistu-Sahle F, et al. (2016) Metabolism and phospholipid assembly of polyunsaturated fatty acids in human bone marrow mesenchymal stromal cells J Lipid Res [4] Njoroge SW, et al. (2012) DHA and EPA reverse cystic fibrosis-related FA abnormalities by suppressing FA desaturase expression and activity J Lipid Res [5] Simon MV, et al. (2016) Synthesis of docosahexaenoic acid from Eicosapentaenoic acid in retina neurons protects photoreceptors from oxidative stress J Neurochem [6] Haghiac M, et al. (2015) Dietary Omega-3 Fatty Acid Supplementation Reduces Inflammation in Obese Pregnant Women: A Randomized Double-Blind Controlled Clinical Trial PLoS One [7] Wang X, et al. (2015) Effects of n-3 FA supplementation on the release of proresolving lipid mediators by blood mononuclear cells: the OmegAD study J Lipid Res [8] Grammatikos SI, et al. (1994) Diversity in the ability of cultured cells to elongate and desaturate essential (n-6 and n-3) fatty acids Ann N Y Acad Sci