12 hete

Manufactured by Cayman Chemical

Sourced in United States

12-HETE is a biochemical product offered by Cayman Chemical. It is a hydroxyeicosatetraenoic acid, a class of oxygenated derivatives of arachidonic acid. 12-HETE is a chemical standard used for research purposes.

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Lab products found in correlation

11 protocols using 12 hete

Modulation of Lipid Mediators in Mice

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Exogenous 12-HETE and 15-HETE were purchased from Cayman Chemicals. PND1 and PND2 Alox15^−/− pups or adult mice were intranasally administered with vehicle, 12-HETE or 15-HETE (200 ng in 6 µl or 25 µl of PBS).
TG6-10-1 (5 mg kg^–1 in 25 µl or 100 µl of PBS) and LY255283 (5 mg kg^–1 in 25 µl or 100 µl of PBS) were purchased from Cayman Chemicals and intraperitoneally administered to pups (PND0, PND1 or PND2) or adult mice.
Isotype control (rat IgG2a) or anti-Ly6G (50 µg per mouse in 25 µl, both from BioLegend) were given intraperitoneally to PND0, PND1 and PND2 WT pups.
Isotype control (Armenian hamster IgG) or anti-FcεR1 (7 µl of a 100 µg solution per mouse, both from Life Technologies) were given intranasally to WT pups at PND1 and PND2.

Pernet E., Sun S., Sarden N., Gona S., Nguyen A., Khan N., Mawhinney M., Tran K.A., Chronopoulos J., Amberkar D., Sadeghi M., Grant A., Wali S., Prevel R., Ding J., Martin J.G., Thanabalasuriar A., Yipp B.G., Barreiro L.B, & Divangahi M. (2023). Neonatal imprinting of alveolar macrophages via neutrophil-derived 12-HETE. Nature, 614(7948), 530-538.

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Oxylipin Cytotoxicity in Glioma Cells

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Cells were seeded at 3 × 10³ for U251-MG and U87-MG and at 5 × 10³ for A172 in 96-well plates. After 24 h, cells were treated with 0.1 µM, 0.5 µM, and 1 µM of the following (S)-form oxylipins: 13-HODE, 9-HODE, 1 5-HETE, 5-HETE, 12-HETE, 8-HETE, 9-HETE, 20-HETE (all Cayman Chemical, USA) and 100% ethanol (control). At 24, 48, and 72 h of treatment, each well was incubated for 4 h with 0.25 mg/mL of tetrazolium at 37 °C in a humidified atmosphere with 5% CO₂. At the end of incubation, cells were washed with warm PBS and lysed with 100 µL of 0.04-M HCl in isopropanol to solubilize the formazan. The absorbance was read at 590 nm in an Epoch microplate reader (BIOTEK, Weinusky, VT, USA).

Souza F.D., Ferreira M.T, & Colquhoun A. (2020). Influence of Lipoxygenase Inhibition on Glioblastoma Cell Biology. International Journal of Molecular Sciences, 21(21), 8395.

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Quantification of Lipid Metabolites

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8-iso Prostaglandin F2α (8-iso-PGF_2α), 8-iso-PGF_2α-d₄, (±)5-hydroxyeicosatetraenoic acid (5-HETE), (±)12-HETE, 15(S)-HETE, 13(R,S)-hydroxy-9Z, 11E-octadecadienoic acid (13-(Z,E)-HODE), 9(R,S)-(Z,E)-HODE, and 13(R,S)-(Z,E)-HODE-d₄ were obtained from Cayman Chemical Company (MI, USA). 9(R,S)-(E,E)-HODE, 13(R,S)-(E,E)-HODE, 10(R,S)-(Z,E)-HODE, and 12(R,S)-(Z,E)-HODE were obtained from Larodan Fine Chemicals AB (Malmo, Sweden). Other materials were used at the highest grade that was commercially available.

Umeno A., Yoshino K., Hashimoto Y., Shichiri M., Kataoka M, & Yoshida Y. (2015). Multi-Biomarkers for Early Detection of Type 2 Diabetes, Including 10- and 12-(Z,E)-Hydroxyoctadecadienoic Acids, Insulin, Leptin, and Adiponectin. PLoS ONE, 10(7), e0130971.

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Lipidomics Sample Preparation Protocol

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AminoxyTMT sixplex Label Reagent Set was purchased from Thermo Fisher Scientific Inc. (Waltham, MA, USA). Phospholipid mixtures were obtained from Avanti Polar Lipids, Inc. (Alabaster, AL, USA). Lipid mediator standards, 12-HETE, 20-HETE, TXB₂, PGE₂, arachidonic acid, tetranor-PGDM, and 20-carboxy-LTB₄ were obtained from Cayman Chemical (Ann Arbor, MI, USA). LPA (16:0), LPA (18:1), and PA (36:2) were obtained from Avanti Polar Lipids (Alabaster, AL, USA). DMTMM and 4-methylmorpholine (NMM) were purchased from Sigma-Aldrich Co. (St. Louis, MO, USA). 1-Ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (EDC) was obtained from Fuji Film Wako Pure Chemical Co. (Osaka, Japan). Special grade reagents of ammonium bicarbonate, sodium chloride and 1-buthanol, and HPLC grade solvents of methanol, isopropanol and acetonitrile were purchased from Wako Pure Chemical Co. The authentic lipid standard stock solutions were 12-HETE (0.6 μg/mL), 20-HETE (0.6 μg/mL), TXB₂ (0.6 μg/mL), PGE₂ (0.6 μg/mL), AA (0.6 μg/mL), tetranor-PGDM (0.6 μg/mL), 20-carboxy-LTB₄ (0.6 μg/mL), LPA(16:0) (10 μM), LPA (18:1) (10 μM), PA (36:2) (5 μg/mL).

Tokuoka S.M., Kita Y., Sato M., Shimizu T., Yatomi Y, & Oda Y. (2020). Development of Tandem Mass Tag Labeling Method for Lipid Molecules Containing Carboxy and Phosphate Groups, and Their Stability in Human Serum. Metabolites, 11(1), 19.

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YAP1 Enhancer-Luciferase Assay

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Huh7 cells were transfected at 70% confluency in DMEM growth media containing 5% FBS with 8xGTIIC-Tead4-luciferase (Addgene), a 624b YAP1 enhancer-luciferase construct with or without the mutations in the first intronic TCF site^{7 (link)}, and renilla-luciferase plasmids (Addgene) using Biolab transfection reagent. After overnight, the cells were treated with 12(S)-HHTrE (50 nM, cat#34590),12-HETE (100 nM, cat#34570), Ozagrel (1 µM, cat#70515), LY255283 (10 µM, cat#70715) obtained from Cayman Chemical Company and the YAP-TEAD binding inhibitor Super-TDU (1-31) TFA (300 nM, MedChemexpress, cat#HY-P1728A) with respective vehicle controls in serum-free medium for 24 h. Protein concentrations were determined in cell lysates and equal amounts of proteins were analyzed for firefly and renilla luciferase activities using Dual-Glo Luciferase Assay Kit (Promega).

Sinha S., Aizawa S., Nakano Y., Rialdi A., Choi H.Y., Shrestha R., Pan S.Q., Chen Y., Li M., Kapelanski-Lamoureux A., Yochum G., Sher L., Monga S.P., Lazaris A., Machida K., Karin M., Guccione E, & Tsukamoto H. (2023). Hepatic stellate cell stearoyl co-A desaturase activates leukotriene B4 receptor 2 - β-catenin cascade to promote liver tumorigenesis. Nature Communications, 14, 2651.

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Quantifying Pulmonary Prostanoid Levels

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Immediately postmortem, the thoracic cavity was opened and the pulmonary vasculature flushed of blood with PBS via the right ventricle. The right atrium of the heart was then cannulated with PE10 tubing, secured with 5-0 silk, and the lung and heart were removed intact. The pulmonary vasculature was perfused via the right atrium with DMEM media at 37 °C for 20 minutes using a peristaltic pump at 50 μL/min and the venous outflow collected from the left atrium.
Levels of the prostacyclin breakdown product 6-keto PG F1_α (6-ketoPGF_1α), the thromboxane breakdown product thromboxane B₂, prostaglandin E₂, prostaglandin F_2α, prostaglandin D2, 12-HETE, and 15-HETE (Cayman Chemical) were measured in supernatants/plasma by commercial immunoassay. In some cases, tissue/vessel segments were weighed and prostanoid levels expressed relative to tissue mass.

Vinokurova M., Lopes-Pires M.E., Cypaite N., Shala F., Armstrong P.C., Ahmetaj-Shala B., Elghazouli Y., Nüsing R., Liu B., Zhou Y., Hao C.M., Herschman H.R., Mitchell J.A, & Kirkby N.S. (2023). Widening the Prostacyclin Paradigm: Tissue Fibroblasts Are a Critical Site of Production and Antithrombotic Protection. Arteriosclerosis, Thrombosis, and Vascular Biology, 44(1), 271-286.

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Modulating Immune Response with 12-HETE

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12-HETE (Cayman Chemicals) was administered to mice via alzet osmotic mini pumps (50ug/kg) for four weeks starting on the day of infection.

Mishra B.B., Lovewell R.R., Olive A.J., Zhang G., Wang W., Eugenin E., Smith C.M., Yao J.P., Long J.E., Dubuke M.L., Palace S.G., Goguen J.D., Baker R.E., Nambi S., Mishra R., Booty M.G., Baer C.E., Shaffer S.A., Dartois V., McCormick B., Chen X, & Sassetti C.M. (2017). Nitric oxide prevents a pathogen permissive granulocytic inflammation during tuberculosis. Nature microbiology, 2, 17072.

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Comprehensive Eicosanoid Analysis Protocol

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6-keto-prostaglandin F1α (6kPGF_1α), thromboxane B₂ (TXB₂), prostaglandin E₂ (PGE₂), prostaglandin A₁ (PGA₁), 8-iso prostaglandin A₂ (8-iso PGA₂), prostaglandin E₃ (PGE₃), 15-deoxy-Δ^12,14-prostaglandin J₂ (15d-PGJ₂), lipoxin A₄ (LxA₄), lipoxin B₄ (LxB₄), lipoxin A4 deuterated (LxA4-d5), resolvin D1 (RvD1), resolvin D2 (RvD2), 7-maresin (7-MaR1), leukotriene B₄ (LTB₄), leukotriene B₅ (LTB₅), leukotriene B₄ deuterated (LTB₄-d4), 10(S),17(S)-protectin (PDx), 18-hydroxyeicosapentaenoic acid (18-HEPE), dihydroxy-eicosatetraenoic acid (5,6-DiHETE), 15-hydroxyeicosatetraenoic acid (1 5-HETE) and 12-HETE, 8-HETE, 5-HETE, 5-HETE-d8, 17-hydroxy-docosahexaenoic acid (17-HDoHE) and 14-HDoHE, 14,15-epoxyeicosatrienoic acid (14,15-EET) and 11,12-EET, 8,9-EET, 5,6- EET, 5-oxoeicosatetraenoic acid (5-oxoETE) were purchased from Cayman Chemicals.

Bautzova T., Hockley J.R., Perez-Berezo T., Pujo J., Tranter M.M., Desormeaux C., Barbaro M.R., Basso L., Faouder P.L., Rolland C., Malapert P., Moqrich A., Eutamene H., Denadai-Souza A., Vergnolle N., Smith E.S., Hughes D.I., Barbara G., Dietrich G., Bulmer D.C, & Cenac N. (2018). 5-oxoETE triggers nociception in constipation-predominant irritable bowel syndrome through MAS-related G protein–coupled receptor D. Science signaling, 11(561), eaal2171.

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Modulating Immune Response with 12-HETE

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12-HETE (Cayman Chemicals) was administered to mice via alzet osmotic mini pumps (50ug/kg) for four weeks starting on the day of infection.

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Diabetic Retinopathy and Oxidative Stress

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Animals were used in accordance with the Association for Research in Vision and Ophthalmology (ARVO) Statement for the Use of Animals in Ophthalmic and Vision Research and all procedures were approved by the Institutional Animal Care and Use Committee (IACUC) of Augusta University. We used 8-week-old male wild-type (WT), 12/15-Lo knockout mice (12/15-Lo^−/−; B6.129S2-Alox15tm1Fun/^J; stock no: 002778, Jackson Laboratories, Bar Harbor, ME, USA), or Nox2-deficient mice (Nox2^−/−; B6.129S-Cybb^tm1Din/J; stock No: 002365, Jackson Laboratories) on C57BL/6J background. Diabetes was induced by intraperitoneal injection of streptozotocin (STZ) (Sigma, St Louis, MO, USA) at 50 mg/kg for 3–5 days until the mice developed diabetes (random blood glucose ≥ 13.9 mmol/l). Intravitreal injections were performed in non-diabetic mice as previously described using 12-HETE (Cayman Chemical, Ann Arbor, MI, USA) [25 (link), 26 (link)].

Elmasry K., Ibrahim A.S., Saleh H., Elsherbiny N., Elshafey S., Hussein K.A, & Al-Shabrawey M. (2018). Role of endoplasmic reticulum stress in 12/15-lipoxygenase-induced retinal microvascular dysfunction in a mouse model of diabetic retinopathy. Diabetologia, 61(5), 1220-1232.

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