An acridinium sulphonylamide as a new chemiluminescent label for the determination of carboxylic acids in liquid chromatography.
The synthesis of a new acridinium sulphonylamide label for the liquid chromatographic determination of carboxylic acids is described. The label 10-methyl-N-(p-tolyl)-N-(p-iodoacetamidobenzenesulphonyl)-9-acr idi nium carboxamide iodide is synthesized from 9-acridine-carboxylic acid by a seven-step reaction. Ibuprofen, used as test compound, is coupled to the reactive iodoacetamide group of the label by means of an alkylation reaction in dry acetonitrile for 20 min at 50 degrees C in the presence of 18-crown-6 and potassium carbonate as base catalyst. The reaction mixture is injected into a liquid chromatographic system with chemiluminescence detection. Separation is performed on a Zorbax C18 column with acetonitrile-water-tetrahydrofuran (39:57:4, v/v/v) containing 10 mmol/L TBABr and 0.035% H2O2 as the mobile phase at a flow rate of 1.0 ml/min. Chemiluminescence detection is achieved by the post-column addition of 200 mmol/L potassium hydroxide dissolved in methanol-water (1:1, v/v) at a flow rate of 20 microL/min. The detection limit (S/N = 3) of derivatized ibuprofen is 60 pg (3 pg injected).
Steijger
O M
OM
Department of Analytical Chemistry, Free University, Amsterdam, The Netherlands.
Kamminga
D A
DA
Lingeman
H
H
Brinkman
U A
UA
D000166:Acridines / Q000138:chemical synthesis / Q000737:chemistry*; D002264:Carboxylic Acids / Q000032:analysis*; D002853:Chromatography, Liquid / Q000379:methods; D006878:Hydroxides / Q000737:chemistry; D007052:Ibuprofen / Q000032:analysis; D008163:Luminescent Measurements; D015335:Molecular Probes / Q000138:chemical synthesis / Q000737:chemistry*; D017680:Potassium Compounds / Q000737:chemistry; D012997:Solvents; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*
C113466:10-methyl-N-(p-tolyl)-N-(p-iodoacetamidobenzenesulfonyl)-9-acridinium carboxamide; D000166:Acridines; D002264:Carboxylic Acids; D006878:Hydroxides; D015335:Molecular Probes; D017680:Potassium Compounds; D012997:Solvents; D013449:Sulfonamides; D007052:Ibuprofen; C029943:potassium hydroxide