(±)13-HODE |
| Catalog No.GC19461 |
(±)13-HODE (13-hydroxyoctadecadienoic acid) is a racemic mixture of 13(S)-HODE and 13(R)-HODE, which is formed through the oxidation of linoleic acid by lipoxygenases or cyclooxygenases.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 18104-45-5
Sample solution is provided at 25 µL, 10mM.
_1-3.$$$39978408@51.jpg');)
_1-9.$$$38538795@65.jpg');)
_1-9.$$$39112701@51.jpg');)
_1-7.$$$37316672@70.jpg');)
_366-372.$$$36198801@70.jpg');)
.$$$38565142@65.jpg');)
_1867-1883.$$$33248023@67.jpg');)
_eads6055.$$$39977546@45.jpg');)
_eadm9805.$$$40080571@45.jpg');)
_eadj3020.$$$39666821@45.jpg');)
_1-20.$$$39757301@28.jpg');)
_1-24.$$$38898113@28.jpg');)
_273-287.$$$36806353@46.jpg');)
_1-16.$$$37156877@44.jpg');)
_1-19.$$$37460805@44.jpg');)
_1291-1307.$$$34518654@46.jpg');)
(±)13-HODE (13-hydroxyoctadecadienoic acid) is a racemic mixture of 13(S)-HODE and 13(R)-HODE, which is formed through the oxidation of linoleic acid by lipoxygenases or cyclooxygenases[1]. (±)13-HODE plays diverse roles in biological systems. In inflammation, (±)13-HODE can modulate the production of pro-and anti-inflammatory cytokines. (±)13-HODE can act on immune cells such as macrophages and lymphocytes, influencing their activation and function[2]. (±)13-HODE can either contribute to or alleviate oxidative damage depending on the cellular context. (±)13-HODE may induce the generation of reactive oxygen species (ROS), (±)13-HODE can upregulate antioxidant defense mechanisms[3]. (±)13-HODE can interact with specific receptors or intracellular signaling pathways. (±)13-HODE may activate protein kinase C (PKC) pathways, affecting cell proliferation, differentiation, and apoptosis[4].
In vitro, treatment of human umbilical vein endothelial cells (HUVEC) with (±)13-HODE (20-50µM) for 24 hours increased the expression of intercellular adhesion molecule-1 (ICAM-1), but had no significant effect on the expression of vascular cell adhesion molecule-1 (VCAM-1) and E-selectin[5]. In vitro, MDA-MB-231 cells were divided into two groups: FABP7-overexpressing cells (231-FABP7) and control cells (231-RFP). Both groups were treated with 12.5mM linoleic acid or vehicle for 72 hours. When 25nM (±)13-HODE was added to the linoleic acid-treated 231-FABP7 cells, the cell death was significantly alleviated[6].
In vivo, (±)13-HODE was administered at a dose of 8mg to low-density lipoprotein receptor knockout (LDL receptor knockout) mice for 13 weeks. (±)13-HODE led to an increase of over 100% in the aortic lesion area of the mice. (±)13-HODE also increased plasma total cholesterol and low-density lipoprotein cholesterol in the mice and enhanced oxidative stress[7].
References:
[1] Brash AR. Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate. J Biol Chem. 1999 Aug 20;274(34):23679-82.
[2] Serhan CN, Petasis NA. Resolvins and protectins in inflammation resolution. Chem Rev. 2011 Oct 12;111(10):5922-43.
[3] Buchanan MR, Horsewood P, Brister SJ. Regulation of endothelial cell and platelet receptor-ligand binding by the 12- and 15-lipoxygenase monohydroxides, 12-, 15-HETE and 13-HODE. Prostaglandins Leukot Essent Fatty Acids. 1998 May;58(5):339-46.
[4] Nishizuka Y. Intracellular signaling by hydrolysis of phospholipids and activation of protein kinase C. Science. 1992 Oct 23;258(5082):607-14.
[5] Friedrichs B, Toborek M, Hennig B, et al. 13-HPODE and 13-HODE modulate cytokine-induced expression of endothelial cell adhesion molecules differently. Biofactors. 1999;9(1):61-72.
[6] Kwong SC, Abd Jamil AH, Rhodes A, et al. Fatty acid binding protein 7 mediates linoleic acid-induced cell death in triple negative breast cancer cells by modulating 13-HODE. Biochimie. 2020 Dec;179:23-31.
[7] Khan-Merchant N, Penumetcha M, Meilhac O, et al. Oxidized fatty acids promote atherosclerosis only in the presence of dietary cholesterol in low-density lipoprotein receptor knockout mice. J Nutr. 2002 Nov;132(11):3256-62.
| Cell experiment [1]: | |
Cell lines | MC38 cells and HCA-7 cells |
Preparation Method | MC38 and HCA-7 cells were seeded into 96-well plates at a density of 1 × 104 cells per well in 200µL medium and cultured for 16 hours. The cells were then starved for 24 hours in medium containing 0.1% fetal bovine serum. Subsequently, various concentrations (0, 0.1, 1, 10µM) of (±)13-HODE were added to the wells for an additional 4 hours. BrdU solution was added to each well for 4 hours to measure cell proliferation. |
Reaction Conditions | 0, 0.1, 1, 10µM; 4h |
Applications | (±)13-HODE significantly inhibited the proliferation of both MC38 and HCA-7 colon cancer cells. |
| Animal experiment [2]: | |
Animal models | LDL receptor knockout mice |
Preparation Method | Mice were fed diets containing varying levels of fat and cholesterol, mice were fed a high-fat diet supplemented with 13-hydroxylinoleic acid (13-HODE) at a dose of 8mg for 13 weeks. |
Dosage form | 8mg of (±)13-HODE per diet for 13 weeks |
Applications | (±)13-HODE led to an increase of over 100% in the aortic lesion area of the mice, (±)13-HODE also increased plasma total cholesterol and low-density lipoprotein cholesterol in the mice and enhanced oxidative stress |
References: | |
| Cas No. | 18104-45-5 | SDF | |
| Chemical Name | (±)-13-hydroxy-9Z,11E-octadecadienoic acid | ||
| Canonical SMILES | CCCCCC(O)\C=C\C=C\CCCCCCCC(=O)O | ||
| Formula | C18H32O3 | M.Wt | 296.4 |
| Solubility | 50mg/mL in DMSO, 50mg/mL in DMF, 50mg/mL in Ethanol | Storage | Store at -20°C,protect from light |
| 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 | 3.3738 mL | 16.8691 mL | 33.7382 mL |
| 5 mM | 674.8 μL | 3.3738 mL | 6.7476 mL |
| 10 mM | 337.4 μL | 1.6869 mL | 3.3738 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 6 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 *