Docosapentaenoic Acid (DPA)

2500, Parc-Technologique Blvd Quebec City (Quebec) G1P 4S6 CANADA

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

Product Information Docosapentaenoic acid (DPA)

Identification Product Number DPA-GP-xxx CAS Number 24880-45-3 EN Number N/A Common Name Docosapentaenoic acid Systematic Name (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid Alternative Names Clupanodonic acid, DPA, Cis-7,10,13,16,19-Docosapentaenoic acid Storage Temperature -80°C or lower

Characteristics Specifications

Molecular Formula C22H34O2 Purity ≥ 99 % Molecular Weight 330.51 g/mol Form Liquid at room temperature Melting Point -78°C Color Clear, colorless Density 0.932 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. The product is supplied sterile. It can be solubilized in undiluted serum or in ethanol or DMSO. The solubility of Docosapentaenoic acid in ethanol is approximately 100 mg/ml. To obtain an aqueous solution, Docosapentaenoic acid can be directly dissolved in 0.1 M Na2CO3 (1.7 mg/ml) and then diluted in PBS (pH 7.2) at the desired concentration. Essential fatty acids are also soluble in chloroform or ether. However those two organic solvents are 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. Docosapentaenoic acid has been shown to be a potent stimulator of endothelial cells migration in a dose-dependent fashion (0.01-10 μg/ml) [1].

Storage

Polyunsaturated 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 -20°C and freeze-thaw cycles should be avoided. The product is stable in its ampoule at -20°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 homoeostasis of the human body. Linoleic and α-Linolenic acids are considered the only two essential fatty acids because they cannot be synthetized by animals. Therefore, they have to be accumulated from food because mammals lack the appropriate enzyme to perform the carbon desaturation beyond carbons 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 fatty acid Linoleic acid and long-chain ω-3 fatty acids from the parent fatty acid α-Linolenic acid.

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

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 [2]; to suppress the pathological phenotype of human bronchial epithelial cells in a model of cystic fibrosis [3]; and to protect photoreceptors from oxidation-induced apoptosis in rats retinal neuron cells [4]. 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 [5] and reduce the progression of Alzheimer’s disease [6].

About Docosapentaenoic acid

Docosapentaenoic acid is an ω-3 fatty acid also known as the Clupanodonic acid. It is an intermediary between Eicosapentaenoic acid and Docosahexaenoic acid. Mammalian cells metabolize Docosapentaenoic acid to members of the specialized proresolving mediators class of PUFAs metabolites, including resolvins specialized pro-resolution mediators (SPM) that regulate key innate protective responses in the resolution of infectious inflammation, protectins and maresins [7-9]. There is also a significant association between DPA supplementation and reduced cardiovascular disease [10-12].

A study on the anti-tumorigenic effects of ω-3 fatty acids on colorectal cancer found anti-proliferative and pro-apoptotic effects for Docosapentaenoic acid in vitro and in vivo [13].

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] Kanayasu-Toyoda T, et al. (1996) Docosapentaenoic acid (22:5, n-3), an elongation metabolite of Eicosapentaenoic acid (20:5, n-3), is a potent stimulator of endothelial cell migration on pretreatment in vitro Prostaglandins Leukot Essent Fatty Acids [2] Chen S, et al. (2014) n-3 PUFA supplementation benefits microglial responses to myelin pathology Sci Rep [3] Njoroge SW, et al. (2012) DHA and EPA reverse cystic fibrosis-related FA abnormalities by suppressing FA desaturase expression and activity J Lipid Res [4] Simon MV, et al. (2016) Synthesis of docosahexaenoic acid from Eicosapentaenoic acid in retina neurons protects photoreceptors from oxidative stress J Neurochem [5] 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 [6] 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 [7] Dalli J, et al. (2015) Elucidation of novel 13-series resolvins that increase with atorvastatin and clear infections Nat Med [8] Yazdi PG (2013) A review of the biologic and pharmacologic role of Docosapentaenoic acid n-3 F1000Res [9] Weylandt KH (2016) Docosapentaenoic acid derived metabolites and mediators - The new world of lipid mediator medicine in a nutshell Eur J Pharmacol [10] Sun Q, et al. (2008) Blood concentrations of individual long-chain n-3 fatty acids and risk of nonfatal myocardial infarction Am J Clin Nutr [11] Simon JA, et al. (1995) Serum fatty acids and the risk of coronary heart disease Am J Epidemiol [12] Oda E, et al. (2005) A case-control pilot study on n-3 polyunsaturated fatty acid as a negative risk factor for myocardial infarction Int Heart J [13] Morin C, et al. (2013) Anti-proliferative effects of a new Docosapentaenoic acid monoacylglyceride in colorectal carcinoma cells Prostaglandins Leukot Essent Fatty Acids