82200-87-1 Usage
Description
5(S),15(S)-DiHETE, also known as 5(S),15(S)-dihydroxy-6,8,11,13-eicosatetraenoic acid, is a bioactive eicosanoid synthesized by the enzyme 15-lipoxygenase (15-LO) from 5(S)-HETE. It plays a significant role in modulating immune responses and has been identified as a potentiator of degranulation in human polymorphonuclear leukocytes (PMNL) and a chemotactic agent for eosinophils.
Uses
Used in Immunology Research:
5(S),15(S)-DiHETE is used as a research tool in immunology for studying the mechanisms of neutrophil degranulation and eosinophil chemotaxis. Its ability to potentiate the degranulation of human PMNL in response to platelet-activating factor (PAF) makes it a valuable compound for investigating the signaling pathways and molecular interactions involved in immune cell activation.
Used in Drug Development:
5(S),15(S)-DiHETE is used as a lead compound in drug development for potential therapeutic applications in treating inflammatory and immune-related disorders. Its chemotactic properties for eosinophils and its role in neutrophil degranulation suggest that it may have potential as a modulator of immune responses, which could be harnessed for the development of new treatments for conditions such as asthma, allergies, and autoimmune diseases.
Used in Diagnostics:
5(S),15(S)-DiHETE can be used as a biomarker in diagnostic assays to assess the activity of immune cells and monitor the progression of inflammatory diseases. Its presence in biological samples can provide valuable information about the status of the immune system and the effectiveness of therapeutic interventions.
Check Digit Verification of cas no
The CAS Registry Mumber 82200-87-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,2,0 and 0 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 82200-87:
(7*8)+(6*2)+(5*2)+(4*0)+(3*0)+(2*8)+(1*7)=101
101 % 10 = 1
So 82200-87-1 is a valid CAS Registry Number.
InChI:InChI=1/C20H32O4/c1-2-3-9-13-18(21)14-10-7-5-4-6-8-11-15-19(22)16-12-17-20(23)24/h5-8,10-11,14-15,18-19,21-22H,2-4,9,12-13,16-17H2,1H3,(H,23,24)/b7-5-,8-6-,14-10+,15-11+/t18-,19+/m0/s1
82200-87-1Relevant articles and documents
Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5 S-HETE by native and aspirin-acetylated COX-2
Mulugeta, Surafel,Suzuki, Takashi,Hernandez, Noemi Tejera,Griesser, Markus,Boeglin, William E.,Schneider, Claus
experimental part, p. 575 - 585 (2010/09/04)
Biosynthesis of the prostaglandin endoperoxide by the cyclooxygenase (COX) enzymes is accompanied by formation of a small amount of 11 R- hydroxyeicosatetraenoic acid (HETE), 15 R-HETE, and 15 S-HETE as by-products. Acetylation of COX-2 by aspirin abrogates prostaglandin synthesis and triggers formation of 15 R-HETE as the sole product of oxygenation of arachidonic acid. Here, we investigated the formation of by-products of the transformation of 5 S-HETE by native COX-2 and by aspirin-acetylated COX-2 using HPLC-ultraviolet, GC-MS, and LC-MS analysis. 5 S,15 S-dihydroxy (di)HETE, 5 S,15 R-diHETE, and 5 S,11 R-diHETE were identified as by-products of native COX-2, in addition to the previously described di-endoperoxide (5 S,15 S-dihydroxy-9 S,11 R,8 S,12 S-diperoxy-6 E,13 E-eicosadienoic acid) as the major oxygenation product. 5 S,15 R-diHETE was the only product formed by aspirinacetylated COX-2. Both 5,15-diHETE and 5,11-diHETE were detected in CT26 mouse colon carcinoma cells as well as in lipopolysaccharide-activated RAW264.7 cells incubated with 5 S-HETE, and their formation was attenuated in the presence of the COX-2 specific inhibitor, NS-398. Aspirintreated CT26 cells gave 5,15-diHETE as the most prominent product formed from 5 S-HETE. 5 S,15 S-diHETE has been described as a product of the cross-over of 5-lipoxygenase (5-LOX) and 15-LOX activities in elicited rat mononuclear cells and human leukocytes, and our studies implicate crossover of the 5-LOX and COX-2 pathways as an additional biosynthetic route. Copyright
