Docosapentaenoic acid 22n-3 (Synonyms: DPA, n-3 DPA) |
| Katalog-Nr.GC31637 |
Ein Bestandteil von Phospholipiden, der in allen tierischen Zellmembranen vorkommt.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 24880-45-3
Sample solution is provided at 25 µL, 10mM.
Docosapentaenoic acid 22n-3 (n-3 DPA) is an elongated metabolite of EPA and is an intermediary product between eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)[1]. Docosapentaenoic acid 22n-3 is effective in the inhibition of aggregation in platelets and possesses greater endothelial cell migration ability than EPA. Docosapentaenoic acid 22n-3 also reduces the fatty acid synthase and malic enzyme activity levels, meanwhile having a role in attenuating age-related decrease in spatial learning and long-term potentiation[2].
In vitro experiments show Docosapentaenoic acid 22n-3 down-regulates the expression of genes involved in fat synthesis in liver cells (FAO cells; 50μM; 48h)[3]. Docosapentaenoic acid 22n-3 also acts as a potent stimulator of primary human endothelial cell migration (5mg/ml; 2 days)[4]. Moreover, docosapentaenoic acid 22n-3 decrease adrenal microsomal CYP21 activity and inhibit CYP17 activity (100μM; 10min)[5].
In vivo study shows that short-term Docosapentaenoic acid 22n-3 supplementation increases tissue docosapentaenoic acid, DHA, and EPA concentrations in male weanling Sprague–Dawley rats (50mg with food; 7d)[6]. Docosapentaenoic acid 22n-3 also decreased the hepatic TG levels compared to the control while EPA was most effective in reducing serum Triglycerides (TG) levels in C57BL/KsJ-db/db mice and C57BL/6J mice (1% [w/w] of trilinoleate in the control diet was replaced with n-3 DPA; 4 weeks)[7]. Docosapentaenoic acid 22n-3 exerts a protective effect in the hippocampus of the aged rat (200 mg/kg/day in laboratory chow; 56 days)[8].
References:
[1] Drouin, Gaetan et al. “The n-3 docosapentaenoic acid (DPA): A new player in the n-3 long chain polyunsaturated fatty acid family.” *Biochimie* vol. 159 (2019): 36-48. doi:10.1016/j.biochi.2019.01.022
[2] Kaur, Gunveen et al. “Docosapentaenoic acid (22:5n-3): a review of its biological effects.” *Progress in lipid research* vol. 50,1 (2011): 28-34. doi:10.1016/j.plipres.2010.07.004
[3] Kaur, Gunveen et al. “Docosapentaenoic acid (22:5n-3) down-regulates the expression of genes involved in fat synthesis in liver cells.” *Prostaglandins, leukotrienes, and essential fatty acids* vol. 85,3-4 (2011): 155-61. doi:10.1016/j.plefa.2011.06.002
[4] Kanayasu-Toyoda, T et al. “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, leukotrienes, and essential fatty acids* vol. 54,5 (1996): 319-25. doi:10.1016/s0952-3278(96)90045-9
[5] Xie, Xuemei et al. “Effect of n-3 and n-6 Polyunsaturated Fatty Acids on Microsomal P450 Steroidogenic Enzyme Activities and In Vitro Cortisol Production in Adrenal Tissue From Yorkshire Boars.” *Endocrinology* vol. 157,4 (2016): 1512-21. doi:10.1210/en.2015-1831
[6] Kaur, Gunveen et al. “Short-term docosapentaenoic acid (22:5 n-3) supplementation increases tissue docosapentaenoic acid, DHA and EPA concentrations in rats.” *The British journal of nutrition* vol. 103,1 (2010): 32-7. doi:10.1017/S0007114509991334
[7] Gotoh, Naohiro et al. “Effects of three different highly purified n-3 series highly unsaturated fatty acids on lipid metabolism in C57BL/KsJ-db/db mice.” *Journal of agricultural and food chemistry* vol. 57,22 (2009): 11047-54. doi:10.1021/jf9026553
Kelly, Laura et al. “The polyunsaturated fatty acids, EPA and DPA exert a protective effect in the hippocampus of the aged rat.” *Neurobiology of aging*vol. 32,12 (2011): 2318.e1-15. doi:10.1016/j.neurobiolaging.2010.04.001
| Cell experiment [1]: | |
Cell lines | FAO cells |
Preparation Method | FAO cells were treated with 50μM of EPA, DPA or DHA for 48h. 50μM OA was used as an unsaturated fatty acid control while ethanol (EC) (0.5%) was used as a vehicle control. Treatments were replenished after 24h. |
Reaction Conditions | 50μM, 48h |
Applications | Docosapentaenoic acid 22n-3 (50μM) incubation for 48h (like EPA and DHA) caused a significant decrease in the mRNA expression levels of SREBP-1c, 3-Hydroxy-3-Methyl-Glutaryl-Coenzyme A reductase (HMG-CoA reductase), Acetyl Coenzyme A Carboxylase (ACC-1) and Fatty Acid Synthase (FASn) compared with Oleic Acid (OA) and also a decrease in the protein levels of SREBP-1 and ACC-1. A time-course fatty acid analysis showed that Docosapentaenoic acid 22n-3 and EPA are interconvertable in the cells; however, after 8h of incubation with Docosapentaenoic acid 22n-3, the cell phospholipids contained mainly Docosapentaenoic acid 22n-3. |
| Animal experiment [2]: | |
Animal models | young (3–4 months) and aged (20–22 months) rats |
Preparation Method | rats treated with fatty acids received laboratory chow supplemented with either EPA or Docosapentaenoic acid 22n-3 (200mg/kg/day) and control rats received laboratory chow to which monounsaturated fatty acid was added to ensure isocaloric intake. The EPA preparation was 20:5n-3 ethyl-eicosapentaenoic acid (95% pure) to which 0.2% dl-tocopherol was added and the DPA preparation was Docosapentaenoic acid 22n-3. Food intake was measured for 1 week before the beginning of the experimental treatment to determine daily food intake and rats received their full daily allowance of freshly prepared chow each day. |
Dosage form | 200mg/kg/day in laboratory chow; 56 days |
Applications | Docosapentaenoic acid possesses neurorestorative effects and is capable of downregulating microglial activation. It also decreases the coupled activation of sphingomyelinase and caspase-3. |
References: | |
| Cas No. | 24880-45-3 | SDF | |
| Überlieferungen | DPA, n-3 DPA | ||
| Canonical SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(O)=O | ||
| Formula | C22H34O2 | M.Wt | 330.5 |
| Löslichkeit | 0.1 M Na2CO3: 1.7 mg/ml,DMF: >100 mg/ml,DMSO: >100 mg/ml,Ethanol: Miscible | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
||
| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 3.0257 mL | 15.1286 mL | 30.2572 mL |
| 5 mM | 0.6051 mL | 3.0257 mL | 6.0514 mL |
| 10 mM | 0.3026 mL | 1.5129 mL | 3.0257 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)
Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid 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 master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 35 reference(s) in Google Scholar.)
GLPBIO products are for RESEARCH USE ONLY. Please make sure your review or question is research based.
Required fields are marked with *