The importance of 8-Quinolineboronic acid
8-Quinolineboronic acid phosphorescent molecular switch (8-QBA-PMS) in the“off” state emitted weak room temperature phosphorescence (RTP) of 8 -QBA on the acetylcellulose membrane (ACM) with theperturbation of Pb2+. When 8-QBA-PMS was used to label concanavalin agglutinin (Con A) to form 8-QBA-PMS-Con A based on the reaction between -OH of 8-QBA-PMS and -C00H of Con A, 8-QBA-PMS turned “on” automatically due to its structure change, and RTP of the system increased 2.7 times. Besides, -NH2 of 8-QBA-PMS-Con A could carry out affinity adsorption (AA) reaction with the -C0OH of alpha-fetoprotein variant (AFP-V) to form the product Con A-AFP-V-Con A 8-QBA-PMS containing -NH-CO- bond, causing the RTP of the system to further increase. Thus, a new affinity sensitive adsorption solid substrate room temperature phosphorimetry using 8-QBA-PMS as labelling reagent (8-QBA-PMS- AASSRTP) for the determination of AFP-V was proposed with the detection limit (LD) of9x 10-15 g mL-1. It had been used to determine AFP-V in human serum with the results agreeing with enzyme-link immunoassay (ELISA), . showing promise for the prediction of PHC due to the intimate association between AFP-V and primary hepatocellular carcinoma (PHC).
How 8-Quinolineboronic acid was prepared?
Quinoline-8-boronic acid was prepared as follows: 8-bromoquinoline (2.08g, 10mmol) was dissolved in 30ml of THF, and then, at a temperature of -78°C, n-butyllithium (4mL, 2.5 M in hexane). One hour after the addition, at the same temperature, trimethyl borate (1.23 ml, 11 mmol) was added thereto. The resulting solution was stirred for 5 hours, and then 100 ml of 2M HCl was added to its Chemicalbook, and the extraction process was performed 3 times by using 60 ml of ethyl acetate. The obtained extracted parts are put together, then dehydrated by using anhydrous magnesium sulfate, and distilled under reduced pressure. The obtained compound was separated-purified by silica gel column chromatography to produce 1.30 g (yield: 75%) of quinoline-8-boronic acid in the form of a white solid. Confirm the obtained compound by LC-MS
8-Quinolineboronic acid applications:
-C-H and C-S bond activations
-Synthesis of pyridazine via sequential amination / Suzuki coupling / alkylation reactions
-Suzuki-Miyaura coupling reactions for synthesis of biaryl monophosphorus ligands, fused tricyclic oxa-quinolones, or substituted β-amino acids
-Copper-catalyzed azidation with sodium azide
-Studies of the affect of fluoride on the stability of boronic acids during click reactions
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