- 日
- 関
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/07/24 17:22:14」(JST)
[Wiki en表示]
12-Hydroxyeicosatetraenoic acid |
|
IUPAC name
(5Z,8Z,10E,12S,14Z)-12-Hydroxyicosa-5,8,10,14-tetraenoic acid
|
|
Identifiers |
CAS number |
54397-83-0 |
PubChem |
5283155 |
ChemSpider |
4446279 Y |
ChEBI |
CHEBI:34146 Y |
Jmol-3D images |
Image 1
Image 2 |
-
CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)O
O=C(O)CCC\C=C/C/C=C\C=C\[C@@H](O)C\C=C/CCCCC
|
-
InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1 Y
Key: ZNHVWPKMFKADKW-LQWMCKPYSA-N Y
InChI=1/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1
Key: ZNHVWPKMFKADKW-LQWMCKPYBD
|
Properties |
Molecular formula |
C20H32O3 |
Molar mass |
320.47 g mol−1 |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
12-Hydroxyeicosatetraenoic acid (12-HETE) is an eicosanoid. It is a metabolite of arachidonic acid produced by the action of the enzyme arachidonate 12-lipoxygenase. 12-HETE is a highly selective ligand used to label mu opioid receptors.[1]
See also[edit]
- 5-Hydroxyeicosatetraenoic acid
References[edit]
- ^ 12-Hydroxy-5,8,10,14-eicosatetraenoic acid at PubChem
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Synthesis and Structure-Activity Relationship Studies of 4-((2-Hydroxy-3-methoxybenzyl)amino)benzenesulfonamide Derivatives as Potent and Selective Inhibitors of 12-Lipoxygenase.
- Luci DK1, Jameson JB 2nd, Yasgar A, Diaz G, Joshi N, Kantz A, Markham K, Perry S, Kuhn N, Yeung J, Kerns EH, Schultz L, Holinstat M, Nadler JL, Taylor-Fishwick DA, Jadhav A, Simeonov A, Holman TR, Maloney DJ.Author information 1National Center for Advancing Translational Sciences, National Institutes of Health , Rockville, Maryland, United States.AbstractHuman lipoxygenases (LOXs) are a family of iron-containing enzymes which catalyze the oxidation of polyunsaturated fatty acids to provide the corresponding bioactive hydroxyeicosatetraenoic acid (HETE) metabolites. These eicosanoid signaling molecules are involved in a number of physiologic responses such as platelet aggregation, inflammation, and cell proliferation. Our group has taken a particular interest in platelet-type 12-(S)-LOX (12-LOX) because of its demonstrated role in skin diseases, diabetes, platelet hemostasis, thrombosis, and cancer. Herein, we report the identification and medicinal chemistry optimization of a 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide-based scaffold. Top compounds, exemplified by 35 and 36, display nM potency against 12-LOX, excellent selectivity over related lipoxygenases and cyclooxygenases, and possess favorable ADME properties. In addition, both compounds inhibit PAR-4 induced aggregation and calcium mobilization in human platelets and reduce 12-HETE in β-cells.
- Journal of medicinal chemistry.J Med Chem.2014 Jan 23;57(2):495-506. doi: 10.1021/jm4016476. Epub 2014 Jan 6.
- Human lipoxygenases (LOXs) are a family of iron-containing enzymes which catalyze the oxidation of polyunsaturated fatty acids to provide the corresponding bioactive hydroxyeicosatetraenoic acid (HETE) metabolites. These eicosanoid signaling molecules are involved in a number of physiologic response
- PMID 24393039
- Serum levels of arachidonic acid metabolites change during prostate cancer progression.
- Rodríguez-Blanco G1, Burgers PC, Dekker LJ, Ijzermans JJ, Wildhagen MF, Schenk-Braat EA, Bangma CH, Jenster G, Luider TM.Author information 1Department of Neurology, Erasmus Medical Centre, Rotterdam, The Netherlands.AbstractBACKGROUND: Arachidonic acid (AA) pathway has been shown to play a role in the development and progression of prostate cancer (PCa). In this study we aimed to assess the changes in concentrations of hydroxyeicosatetraenoic acids (HETEs) in serum samples from patients diagnosed with PCa compared to controls.
- The Prostate.Prostate.2014 Jan 16. doi: 10.1002/pros.22779. [Epub ahead of print]
- BACKGROUND: Arachidonic acid (AA) pathway has been shown to play a role in the development and progression of prostate cancer (PCa). In this study we aimed to assess the changes in concentrations of hydroxyeicosatetraenoic acids (HETEs) in serum samples from patients diagnosed with PCa compared to c
- PMID 24435810
- Bioactive lipid mediators in polycystic kidney disease.
- Klawitter J1, Klawitter J, McFann K, Pennington AT, Abebe KZ, Brosnahan G, Cadnapaphornchai MA, Chonchol M, Gitomer B, Christians U, Schrier RW.Author information 1University of Colorado Denver, United States;AbstractInflammatory activity is evident in patients with chronic kidney disease with limited data available in ADPKD. We hypothesized that inflammation is an upstream event in the pathogenesis of ADPKD and may be a contributing factor in the disease severity and progression. Serum samples from 61 HALT study A group patients (early disease group with eGFR>60mL/min/1.73m2) were compared with samples from 49 patients from HALT study B group with moderately advanced disease (eGFR 25-60mL/min/1.73m2). Targeted mass spectrometry analysis of bioactive lipid mediators as markers of inflammation was performed and correlated with eGFR and total kidney volume (TKV) normalized to the body surface area (BSA) to assess if these markers are predictive of ADPKD severity. ADPKD patients with eGFR >60mL/min/1.73m2 showed higher levels of 5- and 12/15-lipoxygenase (LOX) and cycloxygenase (COX) generated hydroxy-octadecadienoic acids 9-HODE and 13-HODE and hydroxy-eicosatetraenoic acids 8-HETE, 11-HETE, 12-HETE and 15-HETE as compared to healthy subjects. Linear regression of 9-HODE and 13-HODE revealed significant relationship with eGFR and TKV, while 15-HETE significantly correlated with TKV/BSA. Production of 20-HETE, a P450-produced metabolite of arachidonic acid, was higher in ADPKD patients as compared to healthy subjects and significantly correlated with eGFR and TKV/BSA. Perturbation in fatty acid metabolism is evident early in ADPKD patients, even in those with preserved kidney function. Identified lipoxygenase pathways may be potential therapeutic targets for slowing down ADPKD progression.
- Journal of lipid research.J Lipid Res.2013 Dec 16. [Epub ahead of print]
- Inflammatory activity is evident in patients with chronic kidney disease with limited data available in ADPKD. We hypothesized that inflammation is an upstream event in the pathogenesis of ADPKD and may be a contributing factor in the disease severity and progression. Serum samples from 61 HALT stud
- PMID 24343898
Japanese Journal
- Enantioseparation of hydroxyeicosatetraenoic acids by hydroxypropyl-gamma-cyclodextrin-modified micellar electrokinetic chromatography
- Decreased hepatic phosphorylated p38 mitogen-activated protein kinase contributes to attenuation of thioacetamide-induced hepatic necrosis in diet-induced obese mice
- JJK694, a Synthesized Obovatol Derivative, Inhibits Platelet Activation by Suppressing Cyclooxygenase and Lipoxygenase Activities
- Bioscience, biotechnology, and biochemistry 76(11), 2038-2043, 2012-11-23
- NAID 10031126504
Related Links
- Treatment Mitochondria were treated with 12-HETE (3 or 5 nM) for 20 min at room temperature. Control samples were treated with equal volume of the vehicle (ethanol) under the same conditions. In order to inhibit mtNOS ...
- Buy (±)12-HETE (CAS 71030-37-0), an aggregator of neutrophils, from Santa Cruz Biotechnology. Molecular Formula: C20H32O3, Molecular Weight: 320.47 ... (±)12-HETE is one of the six monohydroxy fatty acids produced by the ...
Related Pictures
★リンクテーブル★
[★]
- 英
- 12-hydroxy-5,8,10,14-eicosatetraenoic acid、12-HETE
[★]
12-ヒドロキシ-5
- 関
- 12-HETE
[★]
- 同
- hydroxy-eicosatetraenoic acid