146797-82-2

Basic information

• Product Name: ARACHIDONOYL THIO-PC
• Synonyms: 2-DEOXY-2-THIO ARACHIDONOYL PC;2-DEOXY-2-THIOARACHIDONOYLPHOSPHATIDYLCHOLINE;1-O-HEXADECYL-2-DEOXY-2-THIO-R-(5Z,8Z,11Z,14Z-EICOSATETRAENOYL)-SN-GLYCERYL-3-PHOSPHORYLCHOLINE;ARACHIDONOYL THIO-PC;1-hexadecyl-2-arachidonoylthio-2-deoxyglycero-3-phosphorylcholine;1-Hexadecyl-2-arachidonoylthio-2-deoxy-sn-glycero-3-phosphorylcholine;Thiopc;Arachidonoyl thio-PC (substrate)
• CAS NO: 146797-82-2
• Molecular Formula: C44H82NO6PS
• Molecular Weight: 784.16
• Mol File: 146797-82-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: ARACHIDONOYL THIO-PC(CAS DataBase Reference)
• NIST Chemistry Reference: ARACHIDONOYL THIO-PC(146797-82-2)
• EPA Substance Registry System: ARACHIDONOYL THIO-PC(146797-82-2)

Safety Data

• Hazardous Substances Data: 146797-82-2(Hazardous Substances Data)

Usage

Description

Arachidonoyl thio-PC, also known as arachidonoyl thio-phosphatidylcholine, is a synthetic substrate specifically designed for the assessment of phospholipase A2 (PLA2) activity. It is widely utilized in biochemical and pharmaceutical research due to its ability to mimic the natural phospholipids found in cell membranes. The unique feature of arachidonoyl thio-PC is the presence of a thiol group, which, upon cleavage by PLA2 enzymes, generates a free thiol that can be quantified using chromogenic reagents such as DTNB (Ellman's reagent) and DTP.

Uses

Used in Pharmaceutical Research:
Arachidonoyl thio-PC is used as a research tool for evaluating the activity of various PLA2 enzymes, including secretory PLA2 (sPLA2), cytosolic PLA2 (cPLA2), and calcium-independent PLA2 (iPLA2). The measurement of PLA2 activity is crucial in understanding the roles these enzymes play in various physiological processes and their potential as therapeutic targets for diseases such as inflammation, cancer, and neurological disorders.
Used in Biochemical Assays:
In the field of biochemistry, arachidonoyl thio-PC serves as a valuable substrate for the development and optimization of assays to measure isozyme-specific cPLA2 activity. By excluding or inhibiting the activities of sPLA2 and iPLA2 in the assay, researchers can accurately determine the activity of cPLA2, which is essential for studying its role in cellular signaling and membrane remodeling.
Used in Drug Discovery:
Arachidonoyl thio-PC is employed as a starting point for the development of novel inhibitors targeting PLA2 enzymes. These inhibitors have potential applications in the treatment of various diseases associated with dysregulated PLA2 activity, such as arthritis, asthma, and atherosclerosis. By using arachidonoyl thio-PC in high-throughput screening assays, researchers can identify and optimize potential drug candidates that selectively inhibit specific PLA2 isozymes.
Used in Cell Biology:
In cell biology, arachidonoyl thio-PC is utilized to study the mechanisms of PLA2-mediated phospholipid hydrolysis and the subsequent release of bioactive lipid mediators, such as arachidonic acid. These lipid mediators play crucial roles in cell signaling, membrane trafficking, and the regulation of various cellular processes. Understanding the role of PLA2 enzymes in these processes can provide insights into the development of targeted therapeutic strategies for a range of diseases.

InChI:InChI=1/C44H82NO6PS/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-44(46)53-43(42-51-52(47,48)50-40-38-45(3,4)5)41-49-39-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h14,16,20,22,24-25,29,31,43H,6-13,15,17-19,21,23,26-28,30,32-42H2,1-5H3/b16-14+,22-20+,25-24+,31-29+/t43-/m1/s1

Upstream product

• 20779-14-0 methanesulfonic acid hexadecyl ester 
• 146797-80-0 (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenethioic acid S-[(R)-1-hexadecyloxymethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl] ester 
• 146797-77-5 (S)-3-O-hexadecyl-2-O-(4-nitrobenzenesulfonyl)-1-O-tetrahydropyranylglycerol 
• 155100-89-3 (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenethioic acid S-((S)-2-hexadecyloxy-1-hydroxymethyl-ethyl) ester 
• 146923-48-0 (S)-2-O-benzyl-3-O-hexadecyl-1-O-tetrahydropyranylglycerol 
• 146797-78-6 (R)-1-O-hexadecyl-3-O-tetrahydropyranyl-2-thioacetyl-2-desoxyglycerol 
• 98186-50-6 (S)-3-O-hexadecyl-1-O-tetrahydropyranylglycerol 
• 155100-88-2 (R)-1-Hexadecyloxy-3-(tetrahydro-pyran-2-yloxy)-propane-2-thiol 
• 57959-37-2 3-O-hexadecyl-1,2-O-isopropylidene-sn-glycerol 
• 177167-83-8 1-O-hexadecyl-2-S-trityl-sn-2-thioglycero-3-O-phosphocholine 
• 177167-82-7 2-((R)-3-Hexadecyloxy-2-tritylsulfanyl-propoxy)-[1,3,2]dioxaphospholane 2-oxide 
• 92445-87-9 (S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-yl methanesulfonate 
• 177167-79-2 Thioacetic acid S-((R)-1-hexadecyloxymethyl-2-trityloxy-ethyl) ester 
• 177167-81-6 (S)-3-Hexadecyloxy-2-tritylsulfanyl-propan-1-ol 

Relevant articles and documents

A Stereoselective and Highly Practical Synthesis of Cytosolic Phospholipase A2 Substrate, 2-S-Arachidonoyl-1-O-hexadecyl-sn-2-thioglycero-3-O-phosphocholine

The substrate 1 of cytosolic phospholipase A2 (cPLA2) is an ether-type thiophospholipid with arachidonic acid at the C-2 position and is required for the chromogenic assay for reliable and convenient high throughput screening. The original method of synthesis of 1 has significant problems, resulting in extremely low overall yield and purity. We developed a novel and highly practical method of preparing sufficient quantities of pure 1 for assay. Our synthetic sequence is started with commercially available 1,2-O-isopropylidene-sn-grycerol (5) and is based on the following key steps: trityl migration reaction of 10 with boron trifluoride etherate to form 13, phosphocholine-forming reaction of 13 to yield 15, and efficient conversion of 15 into 1 by deprotection of a trityl group and condensation with arachidonic acid. Our method offers a practical means of large-scale production of 1 with excellent high chemical purity, because of the introduction of arachidonic acid at the last step of the synthetic sequence.